Science.gov

Sample records for acid 2-methyl methyl

  1. 2-Methyl-4-chlorophenoxyacetic acid (MCPA)

    Integrated Risk Information System (IRIS)

    2 - Methyl - 4 - chlorophenoxyacetic acid ( MCPA ) ; CASRN 94 - 74 - 6 Human health assessment information on a chemical substance is included in the IRIS database only after a comprehensive review of toxicity data , as outlined in the IRIS assessment development process . Sections I ( Health Hazard

  2. 2-Methyl-aspartic acid monohydrate.

    PubMed

    Brewer, Greg; Burton, Aaron S; Dworkin, Jason P; Butcher, Ray J

    2013-11-30

    The title compound, C5H9NO4·H2O, is an isomer of the α-amino acid glutamic acid that crystallizes from water in its zwitterionic form as a monohydrate. It is not one of the 20 proteinogenic α-amino acids that are used in living systems and differs from the natural amino acids in that it has an α-methyl group rather than an α-H atom. In the crystal, an O-H⋯O hydrogen bond is present between the acid and water mol-ecules while extensive N-H⋯O and O-H⋯O hydrogen bonds link the components into a three-dimensional array. PMID:24454270

  3. 2-(2-Methyl-4-chlorophenoxy)propionic acid (MCPP)

    Integrated Risk Information System (IRIS)

    2 - ( 2 - Methyl - 4 - chlorophenoxy ) propionic acid ( MCPP ) ; CASRN 93 - 65 - 2 Human health assessment information on a chemical substance is included in the IRIS database only after a comprehensive review of toxicity data , as outlined in the IRIS assessment development process . Sections I ( H

  4. 4-(2-Methyl-4-chlorophenoxy) butyric acid (MCPB)

    Integrated Risk Information System (IRIS)

    4 - ( 2 - Methyl - 4 - chlorophenoxy ) butyric acid ( MCPB ) ; CASRN 94 - 81 - 5 Human health assessment information on a chemical substance is included in the IRIS database only after a comprehensive review of toxicity data , as outlined in the IRIS assessment development process . Sections I ( Hea

  5. 40 CFR 721.10326 - 2-Propenoic acid, 2-methyl-, methyl ester, polymer with butyl 2-propenoate, ethyl 2-propenoate...

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... ester, polymer with butyl 2-propenoate, ethyl 2-propenoate, zinc 2-methyl-2-propenoate (1:2) and zinc 2... 2-Propenoic acid, 2-methyl-, methyl ester, polymer with butyl 2-propenoate, ethyl 2-propenoate, zinc 2-methyl-2-propenoate (1:2) and zinc 2-propenoate (1:2), 2,2'-(1,2-diazenediyl)bis - and...

  6. 40 CFR 721.10133 - 2-Propenoic acid, 2-methyl, 2-hydroxyethyl ester, homopolymer.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ...-hydroxyethyl ester, homopolymer. 721.10133 Section 721.10133 Protection of Environment ENVIRONMENTAL PROTECTION... New Uses for Specific Chemical Substances § 721.10133 2-Propenoic acid, 2-methyl, 2-hydroxyethyl ester... identified as 2-propenoic acid, 2-methyl, 2-hydroxyethyl ester, homopolymer (PMN P-07-401; CAS No....

  7. 40 CFR 721.10133 - 2-Propenoic acid, 2-methyl, 2-hydroxyethyl ester, homopolymer.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ...-hydroxyethyl ester, homopolymer. 721.10133 Section 721.10133 Protection of Environment ENVIRONMENTAL PROTECTION... New Uses for Specific Chemical Substances § 721.10133 2-Propenoic acid, 2-methyl, 2-hydroxyethyl ester... identified as 2-propenoic acid, 2-methyl, 2-hydroxyethyl ester, homopolymer (PMN P-07-401; CAS No....

  8. 40 CFR 721.10122 - 2-Propenoic acid, 2-methyl-, 1,1′-[2-ethyl-2-[[(2-methyl-1-oxo-2-propen-1-yl)oxy]methyl]- 1,3...

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ...- methyl]- 1,3-propanediyl] ester, polymer with 1,3-butadiene, ethenylbenzene and 2-hydroxyethyl 2-methyl-2..., polymer with 1,3-butadiene, ethenylbenzene and 2-hydroxyethyl 2-methyl-2-propenoate. (a) Chemical...-propenoic acid, 2-methyl-, 1,1′- methyl]- 1,3-propanediyl] ester, polymer with 1,3-butadiene,...

  9. 40 CFR 721.10122 - 2-Propenoic acid, 2-methyl-, 1,1′-[2-ethyl-2-[[(2-methyl-1-oxo-2-propen-1-yl)oxy]methyl]- 1,3...

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ...- methyl]- 1,3-propanediyl] ester, polymer with 1,3-butadiene, ethenylbenzene and 2-hydroxyethyl 2-methyl-2..., polymer with 1,3-butadiene, ethenylbenzene and 2-hydroxyethyl 2-methyl-2-propenoate. (a) Chemical...-propenoic acid, 2-methyl-, 1,1′- methyl]- 1,3-propanediyl] ester, polymer with 1,3-butadiene,...

  10. 40 CFR 721.10122 - 2-Propenoic acid, 2-methyl-, 1,1′-[2-ethyl-2-[[(2-methyl-1-oxo-2-propen-1-yl)oxy]methyl]- 1,3...

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ...- methyl]- 1,3-propanediyl] ester, polymer with 1,3-butadiene, ethenylbenzene and 2-hydroxyethyl 2-methyl-2..., polymer with 1,3-butadiene, ethenylbenzene and 2-hydroxyethyl 2-methyl-2-propenoate. (a) Chemical...-propenoic acid, 2-methyl-, 1,1′- methyl]- 1,3-propanediyl] ester, polymer with 1,3-butadiene,...

  11. 40 CFR 721.10122 - 2-Propenoic acid, 2-methyl-, 1,1′-[2-ethyl-2-[[(2-methyl-1-oxo-2-propen-1-yl)oxy]methyl]- 1,3...

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ...- methyl]- 1,3-propanediyl] ester, polymer with 1,3-butadiene, ethenylbenzene and 2-hydroxyethyl 2-methyl-2..., polymer with 1,3-butadiene, ethenylbenzene and 2-hydroxyethyl 2-methyl-2-propenoate. (a) Chemical...-propenoic acid, 2-methyl-, 1,1′- methyl]- 1,3-propanediyl] ester, polymer with 1,3-butadiene,...

  12. 40 CFR 180.318 - 4-(2-Methyl-4-chlorophenoxy) butyric acid; tolerance for residues.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ...)butanoic acid, and its metabolite MCPA, (4-chloro-2-methylphenoxy)acetic acid, in or on the following food... acid; tolerance for residues. 180.318 Section 180.318 Protection of Environment ENVIRONMENTAL... FOOD Specific Tolerances § 180.318 4-(2-Methyl-4-chlorophenoxy) butyric acid; tolerance for...

  13. Aplastic anaemia after exposure to a weed killer, 2-methyl-4-chlorphenoxyacetic acid.

    PubMed

    Palva, H L; Koivisto, O; Palva, I P

    1975-01-01

    A 64-year-old farmer developed aplastic anaemia after exposure to 2-methyl-4-chlorphenoxyactic acid while spraying weed killer. Muscular weakness, haemorrhagic gastritis and slight signs of liver damage occurred at the same time. All these symptoms, including blood dyscrasia , are consistent with those described as toxic effects of chlorphenoxyacetic acids in animal experiments. A causal relationship between aplastic anaemia and the 2-methyl-4-chlorphenoxyacetic acid thus seems probable. The anaemia was reversible, but the case serves as a warning that careful safety measures are required during the use of chlorphenoxyacetic acids and related compounds. PMID:804793

  14. 40 CFR 721.10122 - 2-Propenoic acid, 2-methyl-, 1,1′-[2-ethyl-2-[[(2-methyl-1-oxo-2-propen-1-yl)oxy]methyl]- 1,3...

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false 2-Propenoic acid, 2-methyl-, 1,1â²- methyl]- 1,3-propanediyl] ester, polymer with 1,3-butadiene, ethenylbenzene and 2-hydroxyethyl 2-methyl-2-propenoate. 721.10122 Section 721.10122 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL...

  15. Acute leukaemia after exposure to a weed killer, 2-methyl-4-chlorphenoxyacetic acid.

    PubMed

    Timonen, T T; Palva, I P

    1980-01-01

    Acute leukaemia is known to develop in many cases of benzene-induced pancytopenia [1]. This is a report of the development of acute leukaemia in a patient who had apparently recovered from pancytopenia after chronic exposure to a weed killer, 2-methyl-4-chlorphenoxyacetic acid. PMID:6769284

  16. 40 CFR 721.10326 - 2-Propenoic acid, 2-methyl-, methyl ester, polymer with butyl 2-propenoate, ethyl 2-propenoate...

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... ester, polymer with butyl 2-propenoate, ethyl 2-propenoate, zinc 2-methyl-2-propenoate (1:2) and zinc 2...-propenoate, zinc 2-methyl-2-propenoate (1:2) and zinc 2-propenoate (1:2), 2,2′-(1,2-diazenediyl)bis - and 2,2... butyl 2-propenoate, ethyl 2-propenoate, zinc 2-methyl-2-propenoate (1:2) and zinc 2-propenoate (1:2),...

  17. 40 CFR 721.10326 - 2-Propenoic acid, 2-methyl-, methyl ester, polymer with butyl 2-propenoate, ethyl 2-propenoate...

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... ester, polymer with butyl 2-propenoate, ethyl 2-propenoate, zinc 2-methyl-2-propenoate (1:2) and zinc 2...-propenoate, zinc 2-methyl-2-propenoate (1:2) and zinc 2-propenoate (1:2), 2,2′-(1,2-diazenediyl)bis - and 2,2... butyl 2-propenoate, ethyl 2-propenoate, zinc 2-methyl-2-propenoate (1:2) and zinc 2-propenoate (1:2),...

  18. 40 CFR 721.10136 - 2-Propenoic acid, 2-methyl-, 2-hydroxyethyl ester, reaction products with hexakis(alkoxyalkyl...

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ...-hydroxyethyl ester, reaction products with hexakis(alkoxyalkyl)melamine (generic). 721.10136 Section 721.10136... SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.10136 2-Propenoic acid, 2-methyl-, 2-hydroxyethyl ester, reaction products with...

  19. 40 CFR 721.10136 - 2-Propenoic acid, 2-methyl-, 2-hydroxyethyl ester, reaction products with hexakis(alkoxyalkyl...

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ...-hydroxyethyl ester, reaction products with hexakis(alkoxyalkyl)melamine (generic). 721.10136 Section 721.10136... SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.10136 2-Propenoic acid, 2-methyl-, 2-hydroxyethyl ester, reaction products with...

  20. 40 CFR 721.10363 - Alkenoic acid, 2-methyl-, 2-oxiranylmethyl ester, reaction products with 4,4′ -methylenebis...

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ...-oxiranylmethyl ester, reaction products with 4,4â² -methylenebis (cyclohexanamine) (generic). 721.10363 Section... CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.10363 Alkenoic acid, 2-methyl-, 2-oxiranylmethyl ester, reaction products with...

  1. 40 CFR 721.10363 - Alkenoic acid, 2-methyl-, 2-oxiranylmethyl ester, reaction products with 4,4′ -methylenebis...

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ...-oxiranylmethyl ester, reaction products with 4,4â² -methylenebis (cyclohexanamine) (generic). 721.10363 Section... CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.10363 Alkenoic acid, 2-methyl-, 2-oxiranylmethyl ester, reaction products with...

  2. 40 CFR 721.10136 - 2-Propenoic acid, 2-methyl-, 2-hydroxyethyl ester, reaction products with hexakis(alkoxyalkyl...

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ...-hydroxyethyl ester, reaction products with hexakis(alkoxyalkyl)melamine (generic). 721.10136 Section 721.10136... SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.10136 2-Propenoic acid, 2-methyl-, 2-hydroxyethyl ester, reaction products with...

  3. 40 CFR 721.10363 - Alkenoic acid, 2-methyl-, 2-oxiranylmethyl ester, reaction products with 4,4′ -methylenebis...

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ...-oxiranylmethyl ester, reaction products with 4,4â² -methylenebis (cyclohexanamine) (generic). 721.10363 Section... CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.10363 Alkenoic acid, 2-methyl-, 2-oxiranylmethyl ester, reaction products with...

  4. 40 CFR 721.10136 - 2-Propenoic acid, 2-methyl-, 2-hydroxyethyl ester, reaction products with hexakis(alkoxyalkyl...

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ...-hydroxyethyl ester, reaction products with hexakis(alkoxyalkyl)melamine (generic). 721.10136 Section 721.10136... SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.10136 2-Propenoic acid, 2-methyl-, 2-hydroxyethyl ester, reaction products with...

  5. 40 CFR 721.10136 - 2-Propenoic acid, 2-methyl-, 2-hydroxyethyl ester, reaction products with hexakis(alkoxyalkyl...

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ...-hydroxyethyl ester, reaction products with hexakis(alkoxyalkyl)melamine (generic). 721.10136 Section 721.10136... SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.10136 2-Propenoic acid, 2-methyl-, 2-hydroxyethyl ester, reaction products with...

  6. 40 CFR 721.4792 - 2-propenoic acid, 2-methyl-, C11-14-isoalkyl esters, C13-rich.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ...-isoalkyl esters, C13-rich. 721.4792 Section 721.4792 Protection of Environment ENVIRONMENTAL PROTECTION... esters, C13-rich. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as 2-propenoic acid, 2-methyl-, C11-14-isoalkyl esters, C13-rich (PMN P-99-1189; CAS...

  7. 40 CFR 721.4792 - 2-propenoic acid, 2-methyl-, C11-14-isoalkyl esters, C13-rich.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ...-isoalkyl esters, C13-rich. 721.4792 Section 721.4792 Protection of Environment ENVIRONMENTAL PROTECTION... esters, C13-rich. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as 2-propenoic acid, 2-methyl-, C11-14-isoalkyl esters, C13-rich (PMN P-99-1189; CAS...

  8. 40 CFR 721.8450 - 2-Propenoic acid, 2-methyl-, 2-[3-(2H-benzotriazol-2-yl)-4-hydroxyphenyl]ethyl ester.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... ester. 721.8450 Section 721.8450 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED... Specific Chemical Substances § 721.8450 2-Propenoic acid, 2-methyl-, 2- ethyl ester. (a) Chemical substance... acid, 2-methyl-, 2- ethyl ester, (PMN P-90-333) is subject to reporting under this section for...

  9. 40 CFR 721.10526 - 2-Propenoic acid, 2-methyl-, 2-hydroxyethyl ester, telomers with C18-26-alkyl acrylate, 1...

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false 2-Propenoic acid, 2-methyl-, 2-hydroxyethyl ester, telomers with C18-26-alkyl acrylate, 1-dodecanethiol, N-(hydroxymethyl)-2-methyl-2-propenamide, polyfluorooctyl methacrylate and vinylidene chloride, 2,2'- hydrochloride (1:2)-initiated (generic). 721.10526 Section 721.10526...

  10. 40 CFR 721.10526 - 2-Propenoic acid, 2-methyl-, 2-hydroxyethyl ester, telomers with C18-26-alkyl acrylate, 1...

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false 2-Propenoic acid, 2-methyl-, 2-hydroxyethyl ester, telomers with C18-26-alkyl acrylate, 1-dodecanethiol, N-(hydroxymethyl)-2-methyl-2-propenamide, polyfluorooctyl methacrylate and vinylidene chloride, 2,2'- hydrochloride (1:2)-initiated (generic). 721.10526 Section 721.10526...

  11. 75 FR 50926 - 2-propenoic acid, 2-methyl-, C12-16-alkyl esters, telomers with 1-dodecanethiol, polyethylene...

    Federal Register 2010, 2011, 2012, 2013, 2014

    2010-08-18

    ...This regulation establishes an exemption from the requirement of a tolerance for residues of 2-propenoic acid, 2-methyl-, C12-16- alkyl esters, telomers with 1-dodecanethiol, polyethylene-polypropylene glycol ether with propylene glycol monomethacrylate (1:1), and styrene 2,2'-(1,2-diazenediyl)bis[2-methylbutanenitrile]-initiated, number average molecular weight (in AMU) 4000; when used as an......

  12. Selectivity of substrate binding and ionization of 2-methyl-3-hydroxypyridine-5-carboxylic acid oxygenase.

    PubMed

    Luanloet, Thikumporn; Sucharitakul, Jeerus; Chaiyen, Pimchai

    2015-08-01

    2-Methyl-3-hydroxypyridine-5-carboxylic acid (MHPC) oxygenase (EC 1.14.12.4) from Pseudomonas sp. MA-1 is a flavin-dependent monooxygenase that catalyzes a hydroxylation and aromatic ring cleavage reaction. The functional roles of two residues, Tyr223 and Tyr82, located ~ 5 Å away from MHPC, were characterized using site-directed mutagenesis, along with ligand binding, product analysis and transient kinetic experiments. Mutation of Tyr223 resulted in enzyme variants that were impaired in their hydroxylation activity and had Kd values for substrate binding 5-10-fold greater than the wild-type enzyme. Because this residue is adjacent to the water molecule that is located next to the 3-hydroxy group of MHPC, the results indicate that the interaction between Tyr223, H2 O and the 3-hydroxyl group of MHPC are important for substrate binding and hydroxylation. By contrast, the Kd for substrate binding of Tyr82His and Tyr82Phe variants were similar to that of the wild-type enzyme. However, only ~ 40-50% of the substrate was hydroxylated in the reactions of both variants, whereas most of the substrate was hydroxylated in the wild-type enzyme reaction. In free solution, MHPC or 5-hydroxynicotinic acid exists in a mixture of monoanionic and tripolar ionic forms, whereas only the tripolar ionic form binds to the wild-type enzyme. The binding of tripolar ionic MHPC would allow efficient hydroxylation through an electrophilic aromatic substitution mechanism. For the Tyr82His and Tyr82Phe variants, both forms of substrates can bind to the enzymes, indicating that the mutation at Tyr82 abolished the selectivity of the enzyme towards the tripolar ionic form. Transient kinetic studies indicated that the hydroxylation rate constants of both Tyr82 variants are approximately two- to 2.5-fold higher than that of the wild-type enzyme. Altogether, our findings suggest that Tyr82 is important for the binding selectivity of MHPC oxygenase towards the tripolar ionic species, whereas the

  13. Vibrational spectra and natural bond orbital analysis of the herbicidal molecule 2(4-chlorophenoxy)-2-methyl propionic acid

    NASA Astrophysics Data System (ADS)

    Monicka, J. Clemy; James, C.

    2011-02-01

    The herbicide 2(4-chlorophenoxy)-2-methyl propionic acid (MCPP) has been subjected to NIR FT-Raman and infrared spectral studies. The optimized molecular structure, vibrational wavenumbers, IR intensities and Raman activities have been calculated by using density functional method (B3LYP) with the standard 6-31G(d) basis set. The calculated molecular geometry has been compared with the XRD data. The detailed assignments of the normal modes have been performed based on the potential energy distribution (PED) following the scaled quantum mechanical force field (SQMFF) methodology. The IR and Raman spectra have been plotted for the calculated wavenumbers. The simulated spectra satisfactorily coincide with the experimental spectra. The strong hyperconjugative interaction and charge delocalization that leads to the stability of the molecule have been investigated with the aid of natural bond orbital (NBO) analysis.

  14. An unusual case of non-fatal poisoning due to herbicide 4-chloro-2-methyl phenoxyacetic acid (MCPA).

    PubMed

    Tennakoon, D A S Sakunthala; Perera, K A P Bandumala; Hathurusinghe, L S

    2014-10-01

    MCPA (4-chloro-2-methyl phenoxyacetic acid) is a systemic hormone-type selective herbicide readily absorbed by leaves and roots. Use of MCPA for murder or attempted murder is very rare in Sri Lanka. However, a reported case of attempted murder by adding MCPA to water will be discussed in this paper. Three extraction methods were carried out with urine samples spiked with MCPA, namely liquid-liquid extraction with chloroform, solid phase extraction using C18 cartridges and vortex mixing with methanolic hydrochloric acid. Based on the recovery results, solid phase extraction was selected as the most suitable method and applied in the analysis of urine and water samples. Identification of MCPA in urine, water and the suspected poison bottle was carried out by HPLC and was confirmed by GC-MS. 4-chloro -2- methyl phenol metabolite was also identified and confirmed in the urine sample of the patient by GC-MS. Quantitative analysis of MCPA was carried out by HPLC using a validated method where Zorbax XDB-C18 column was used with photo diode array detector. In this case, presence of MCPA in one patient's urine sample collected four days after the incident was confirmed by GC-MS and found at a concentration of 0.83μg/ml. MCPA was not identified in the urine samples collected after 13 days in other three patients. The water sample taken from the suspected water storage tank found to contain 101μg/ml of MCPA. The results showed that HPLC combined with GC-MS is suitable for forensic analysis of MCPA in urine. PMID:24867053

  15. 40 CFR 721.1025 - Benzenamine, 4-chloro-2-methyl-; benzenamine, 4-chloro-2-methyl-, hydrochloride; and ben-zenamine...

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Benzenamine, 4-chloro-2-methyl-; benzenamine, 4-chloro-2-methyl-, hydrochloride; and ben-zenamine, 2-chloro-6-methyl-. 721.1025 Section 721... Benzenamine, 4-chloro-2-methyl-; benzenamine, 4-chloro-2-methyl-, hydrochloride; and ben-zenamine,...

  16. 40 CFR 721.1025 - Benzenamine, 4-chloro-2-methyl-; benzenamine, 4-chloro-2-methyl-, hydrochloride; and ben-zenamine...

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Benzenamine, 4-chloro-2-methyl-; benzenamine, 4-chloro-2-methyl-, hydrochloride; and ben-zenamine, 2-chloro-6-methyl-. 721.1025 Section 721... Benzenamine, 4-chloro-2-methyl-; benzenamine, 4-chloro-2-methyl-, hydrochloride; and ben-zenamine,...

  17. 2-Methyl-sulfonyl-4-(trifluoro-meth-yl)benzoic acid.

    PubMed

    Yao, Lin-Shan; We, Bo; Gao, Jin-Sheng

    2012-06-01

    In the title mol-ecule, C(9)H(7)F(3)O(4)S, the S and the methyl C atoms of the methyl-sulfonyl group deviate from the benzene ring plane by 0.185 (2) and -1.394 (3) Å, respectively. In the crystal, O-H⋯O hydrogen bonds link the mol-ecules into chains along [201]. Weak C-H⋯O inter-actions further link these chains into layers parallel to the ac plane. PMID:22719621

  18. The use of poly(2-acrylamido-2-methyl-1-propanesulfonic acid) polymers as spacers for isotachophoresis in sieving gel matrices.

    PubMed

    Bellini, M P; Manchester, K L

    1999-03-01

    The electric field strength gradients generated in isotachophoresis (ITP) may be used for the separation of biomolecules. Poly(2-acrylamido-2-methyl-1-propanesulfonic acid) (polyAMPS) polymers of a uniform distribution of molecular mass were synthesized and used as novel spacers in ITP. Since these polymeric spacers are strongly acidic species, their ionic charges remain constant over a wide pH range, so that their ionic mobilities are governed solely by their molecular masses and not by the pH of the milieu. A modification of ITP known as telescope electrophoresis was used to separate a number of acidic dyes of varying ionic mobility, using polyAMPS polymers as spacers. The resolution obtained was superior to that obtained by polyacrylamide gel electrophoresis (PAGE), due to the focusing effect of the electric field strength gradient. Since these novel polymeric spacers are designed to operate within sieving medium, it was decided to test their suitability for the separation of DNA molecules. DNA molecules up to 1000 bp long were successfully resolved, with a similar resolution to that obtained with conventional PAGE. PMID:10036157

  19. 40 CFR 721.8450 - 2-Propenoic acid, 2-methyl-, 2-[3-(2H-benzotriazol-2-yl)-4-hydroxyphenyl]ethyl ester.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false 2-Propenoic acid, 2-methyl-, 2- ethyl ester. 721.8450 Section 721.8450 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses...

  20. 40 CFR 721.8450 - 2-Propenoic acid, 2-methyl-, 2-[3-(2H-benzotriazol-2-yl)-4-hydroxyphenyl]ethyl ester.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false 2-Propenoic acid, 2-methyl-, 2- ethyl ester. 721.8450 Section 721.8450 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses...

  1. 40 CFR 721.8450 - 2-Propenoic acid, 2-methyl-, 2-[3-(2H-benzotriazol-2-yl)-4-hydroxyphenyl]ethyl ester.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false 2-Propenoic acid, 2-methyl-, 2- ethyl ester. 721.8450 Section 721.8450 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses...

  2. 40 CFR 721.8450 - 2-Propenoic acid, 2-methyl-, 2-[3-(2H-benzotriazol-2-yl)-4-hydroxyphenyl]ethyl ester.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false 2-Propenoic acid, 2-methyl-, 2- ethyl ester. 721.8450 Section 721.8450 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses...

  3. First European Report of Social Wasps Trapped in Response to Acetic acid, Isobutanol, 2-Methyl-2-propanol, and Heptyl butyrate in Tests Conducted in Hungary

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Five species of social wasps were captured in trapping tests in Hungary that evaluated the attractiveness of acetic acid, isobutanol, 2-methyl-2-propanol, and heptyl butyrate to social wasps. Both Vespula vulgaris (L.) and Vespula germanica (Fabr.), were captured in traps baited with isobutanol, t...

  4. 40 CFR 180.318 - 4-(2-Methyl-4-chlorophenoxy) butyric acid; tolerance for residues.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... established for the combined residues, free and conjugated, of the herbicide MCPB, 4-(4-chloro-2-methylphenoxy)butanoic acid, and its metabolite MCPA, (4-chloro-2-methylphenoxy)acetic acid, in or on the following...

  5. 1-Benzyl-2-methyl-3-indolylmethylene barbituric acid derivatives: Anti-cancer agents that target nucleophosmin 1 (NPM1).

    PubMed

    Penthala, Narsimha Reddy; Ketkar, Amit; Sekhar, Konjeti R; Freeman, Michael L; Eoff, Robert L; Balusu, Ramesh; Crooks, Peter A

    2015-11-15

    In the present study, we have designed and synthesized a series of 1-benzyl-2-methyl-3-indolylmethylene barbituric acid analogs (7a-7h) and 1-benzyl-2-methyl-3-indolylmethylene thiobarbituric acid analogs (7 i-7 l) as nucleophosmin 1 (NPM1) inhibitors and have evaluated them for their anti-cancer activity against a panel of 60 different human cancer cell lines. Among these analogs 7 i, 7 j, and 7 k demonstrated potent growth inhibitory effects in various cancer cell types with GI50 values <2 μM. Compound 7 k exhibited growth inhibitory effects on a sub-panel of six leukemia cell lines with GI50 values in the range 0.22-0.35 μM. Analog 7 i also exhibited GI50 values <0.35 μM against three of the leukemia cell lines in the sub-panel. Analogs 7 i, 7 j, 7 k and 7 l were also evaluated against the mutant NPM1 expressing OCI-AML3 cell line and compounds 7 k and 7 l were found to cause dose-dependent apoptosis (AP50 = 1.75 μM and 3.3 μM, respectively). Compound 7k also exhibited potent growth inhibition against a wide variety of solid tumor cell lines: that is, A498 renal cancer (GI50 = 0.19 μM), HOP-92 and NCI-H522 lung cancer (GI50 = 0.25 μM), COLO 205 and HCT-116 colon cancer (GI50 = 0.20 and 0.26 μM, respectively), CNS cancer SF-539 (GI50 = 0.22 μM), melanoma MDA-MB-435 (GI50 = 0.22 μM), and breast cancer HS 578T (GI50 = 0.22 μM) cell lines. Molecular docking studies suggest that compounds 7 k and 7 l exert their anti-leukemic activity by binding to a pocket in the central channel of the NPM1 pentameric structure. These results indicate that the small molecule inhibitors 7 i, 7 j, 7 k, and 7 l could be potentially developed into anti-NPM1 drugs for the treatment of a variety of hematologic malignancies and solid tumors. PMID:26602084

  6. Crystal structure of 3-acet-oxy-2-methyl-benzoic acid.

    PubMed

    Saranya, Matheswaran; Subashini, Annamalai; Arunagiri, Chidambaram; Muthiah, Packianathan Thomas

    2015-07-01

    In the title mol-ecule, C10H10O4, the carb-oxy-lic acid group is twisted by 11.37 (15)° from the plane of the benzene ring and the acet-oxy group is twisted from this plane by 86.60 (17)°. In the crystal, mol-ecules are linked by pairs of O-H⋯O hydrogen bonds, forming inversion dimers with the expected R 2 (2)(8) graph-set motif. PMID:26279915

  7. Crystal structure of (S)-2-amino-2-methyl­succinic acid

    PubMed Central

    Fujii, Isao

    2015-01-01

    The title compound, C5H9NO4, crystallized as a zwitterion. There is an intra­molecular N—H⋯O hydrogen bond involving the trans-succinic acid and the ammonium group, forming an S(6) ring motif. In the crystal, mol­ecules are linked by O—H⋯O hydrogen bonds, forming C(7) chains along the c-axis direction. The chains are linked by N—H⋯O and C—H⋯O hydrogen bonds, forming sheets parallel to the bc plane. Further N—H⋯O hydrogen bonds link the sheets to form a three-dimensional framework. PMID:26594447

  8. Structure of the PLP Degradative Enzyme 2-Methyl-3-hydroxypyridine-5-carboxylic Acid Oxygenase from Mesorhizobium loti MAFF303099 and Its Mechanistic Implications

    SciTech Connect

    McCulloch, Kathryn M.; Mukherjee, Tathagata; Begley, Tadhg P.; Ealick, Steven E.; Cornell

    2009-06-12

    A vitamin B{sub 6} degradative pathway has recently been identified and characterized in Mesorhizobium loti MAFF303099. One of the enzymes on this pathway, 2-methyl-3-hydroxypyridine-5-carboxylic acid oxygenase (MHPCO), is a flavin-dependent enzyme and catalyzes the oxidative ring-opening of 2-methyl-3-hydroxypyridine-5-carboxylic acid to form E-2-(acetamino-methylene)succinate. The gene for this enzyme has been cloned, and the corresponding protein has been overexpressed in Escherichia coli and purified. The crystal structure of MHPCO has been solved to 2.1 {angstrom} using SAD phasing with and without the substrate MHPC bound. These crystal structures provide insight into the reaction mechanism and suggest roles for active site residues in the catalysis of a novel oxidative ring-opening reaction.

  9. Evaluation of 2-methyl-3-hydroxy-4-pyridinecarboxylic acid as a possible chelating agent for iron and aluminium.

    PubMed

    Dean, Annalisa; Ferlin, Maria Grazia; Brun, Paola; Castagliuolo, Ignazio; Badocco, Denis; Pastore, Paolo; Venzo, Alfonso; Bombi, G Giorgio; Di Marco, Valerio B

    2008-04-01

    In view of a possible application to Fe and Al chelation therapy, 2-methyl-3-hydroxy-4-pyridinecarboxylic acid (DT2) was synthesised, and its complex formation, electrochemical and cytotoxic properties were studied. The complexing properties of DT2 towards Fe(III) and Al(III) were investigated in aqueous 0.6 m (Na)Cl at 25 degrees C by means of potentiometric titrations, UV-vis spectrophotometry, and 1H NMR spectroscopy. DT2 is a triprotic acid (H3L+) having pKa1 = 0.47, pKa2 = 5.64 and pKa3 = 11.18. The metal-ligand complexes observed in solution and their corresponding stability constants (log beta values) are the following: FeLH (19.38), FeL (16.01), FeLH(-1) (12.28), FeL2H2 (37.29), FeL3H3 (53.41), FeL3H2 (47.99), FeL3H (41.21) and FeL3 (34.1); AlLH (17.43), AlL2H2 (33.74), AlL2H (27.6), AlL3H3 (48.72), AlL3H2 (42.67), AlL3H (35.8) and AlL3 (27.92). The complex formation between DT2 and Fe(II) was studied by UV-vis: the weak complex FeLH (log beta = 15.8) was detected. DT2 shows a lower complexation efficiency with Fe(III) and Al(III) than that of other available chelators, but higher than that of its non-methylated analogue 3-hydroxy-4-pyridinecarboxylic acid (DT0). The electrochemical behaviour of DT2 was investigated by means of cyclic voltammetry, indicating that the oxidation of the ligand proceeds through a two electron process with a CECE mechanism. Voltammetric curves suggest that the oxidation or the reduction of DT2 in vivo is unlikely. According to the thermodynamic data, also the Fe(III)-DT2 complexes do not undergo redox cycling at physiological pH. Amperometric titrations of solutions containing Fe(III) and DT2 at pH = 5 indicated the same Fe(III) : ligand stoichiometric ratio as calculated from potentiometric data. The toxicity of DT2 and of other simple hydroxypyridinecarboxylic acids was investigated in vitro and no cytotoxic activity was observed (IC50 > 0.1 mM) on cancer cell lines and also on primary human cells, following a three day

  10. Experimental study of the removal of copper ions using hydrogels of xanthan, 2-acrylamido-2-methyl-1-propane sulfonic acid, montmorillonite: Kinetic and equilibrium study.

    PubMed

    Aflaki Jalali, Marzieh; Dadvand Koohi, Ahmad; Sheykhan, Mehdi

    2016-05-20

    In this paper, removal of copper ions from aqueous solution using novel xanthan gum (XG) hydrogel, xanthan gum-graft-2-acrylamido-2-methyl-1-propane sulfonic acid (XG-g-P(AMPS)) hydrogel and xanthan gum-graft-2-acrylamido-2-methyl-1-propane sulfonic acid/montmorillonite (XG-g-P(AMPS)/MMT) hydrogel composite were studied. The structure and morphologies of the xanthan-based hydrogels were characterized by Fourier transform infrared spectroscopy (FTIR) and scanning electron microscope (SEM). Adsorbents comprised a porous crosslink structure with side chains that carried carboxyl, hydroxyl and sulfonate. Maximum adsorption was observed in the pH=5.2, initial concentrations of Cu(2+)=321.8 mg/L, Temperature=45 °C, contact time=5 h with 0.2 g/50 mL of the hydrogels. Adsorption process was found to follow Langmuir isotherm model with maximum adsorption capacity of 24.57, 39.06 and 29.49 mg/g for the XG, XG-g-P(AMPS) and XG-g-P(AMPS)/MMT, respectively. Adsorption kinetics data fitted well with pseudo second order model. The negative ΔG° values and the positive ΔS° confirmed that the adsorption was a spontaneous process. The positive ΔH° values suggested that the adsorption was endothermic in nature. PMID:26917382

  11. Novel opioid peptide derived antagonists containing (2S)-2-methyl-3-(2,6-dimethyl-4-carbamoylphenyl)propanoic acid [(2S)-Mdcp].

    PubMed

    Ghosh, Animesh; Luo, Jie; Liu, Chen; Weltrowska, Grazyna; Lemieux, Carole; Chung, Nga N; Lu, Yixin; Schiller, Peter W

    2008-09-25

    A synthesis of the novel tyrosine analogue (2 S)-2-methyl-3-(2,6-dimethyl-4-carbamoylphenyl)propanoic acid [(2 S)-Mdcp] (15) was developed. In (2 S)-Mdcp, the amino and hydroxyl groups of 2',6'-dimethyltyrosine are replaced by a methyl and a carbamoyl group, respectively, and its substitution for Tyr (1) in opioid agonist peptides resulted in compounds showing antagonism at all three opioid receptors. The cyclic peptide (2 S)-Mdcp-c[D-Cys-Gly-Phe(pNO 2)-D-Cys]NH 2 (1) was a potent and selective mu antagonist, whereas (2 S)-Mdcp-c[D-Pen-Gly-Phe(pF)-Pen]-Phe-OH (3) showed subnanomolar delta antagonist activity and extraordinary delta selectivity. PMID:18800771

  12. Novel Opioid Peptide Derived Antagonists Containing (2S)-2-Methyl-3-(2,6-dimethyl-4-carbamoylphenyl)propanoic Acid [(2S)-Mdcp

    PubMed Central

    Ghosh, Animesh; Luo, Jie; Liu, Chen; Weltrowska, Grazyna; Lemieux, Carole; Chung, Nga N.; Lu, Yixin; Schiller, Peter W.

    2009-01-01

    A synthesis of the novel tyrosine analogue (2S)-2-methyl-3-(2,6-dimethyl-4-carbamoylphenyl)propanoic acid [(2S)-Mdcp] (15) was developed. In (2S)-Mdcp the amino- and hydroxyl groups of 2',6'-dimethyltyrosine are replaced by a methyl- and a carbamoyl group, respectively, and its substitution for Tyr1 in opioid agonist peptides resulted in compounds showing antagonism at all three opioid receptors. The cyclic peptide (2S)-Mdcp-c[D-Cys-Gly-Phe(pNO2)-D-Cys]NH2 (1) was a potent and selective μ antagonist, whereas (2S)-Mdcp-c[D-Pen-Gly-Phe(pF)-Pen]-Phe-OH (3) showed subnanomolar δ antagonist activity and extraordinary δ selectivity. PMID:18800771

  13. Transformation of microcystins to 2-methyl-3-methoxy-4-phenylbutyric acid by room temperature ozone oxidation for rapid quantification of total microcystins.

    PubMed

    Zhang, L L; Yu, R P; Wang, L P; Wu, S F; Song, Q J

    2016-04-20

    Microcystins (MCs) are cyanobacterial hepatotoxins capable of accumulation into animal tissues. To determine the total microcystins in water, a novel analytical method, including ozonolysis, methylation of 2-methyl-3-methoxy-4-phenylbutyric acid (MMPB) with methylchloroformate (MCF) and gas chromatography mass spectrometry (GC-MS) detection was developed. The results show that MCs can be oxidized by ozone to produce MMPB at ambient temperature, proving ozonation is an effective, rapid and green method for the transformation of MCs to MMPB without secondary pollution. The oxidation conditions as well as the esterification process were optimized and, subsequently applied to analysis of environmental samples. The method shows wide linear range and high sensitivity with a detection limit of 0.34 μg L(-1). The established method was successfully applied to the analysis of microcystins in water samples. PMID:26975781

  14. SYNTHESIS AND IN VITRO CHARACTERIZATION OF HYDROXYPROPYL METHYLCELLULOSE-GRAFT-POLY (ACRYLIC ACID/2-ACRYLAMIDO-2-METHYL-1-PROPANESULFONIC ACID) POLYMERIC NETWORK FOR CONTROLLED RELEASE OF CAPTOPRIL.

    PubMed

    Furqan Muhammad, Iqbal; Mahmood, Ahmad; Aysha, Rashid

    2016-01-01

    A super-absorbent hydrogel was developed by crosslinking of 2-acrylamido-2-methyl-1-propanesulfonic acid (AMPS) and acrylic acid with hydroxypropyl methylcellulose (HPMC) for controlled release drug delivery of captopril, a well known antihypertensive drug. Acrylic acid and AMPS were polymerized and crosslinked with HPMC by free radical polymerization, a widely used chemical crosslinking method. N,N'-methylenebisacrylamide (MBA) and potassium persulfate (KPS) were added as cross-linker and initiator, respectively. The hydrogel formulation was loaded with captopril (as model drug). The concentration of captopril was monitored at 205 nm using UV spectrophotometer. Equilibrium swelling ratio was determined at pH 2, 4.5 and 7.4 to evaluate the pH responsiveness of the formed hydrogel. The super-absorbent hydrogels were evaluated by FTIR, SEM, XRD, and thermal analysis (DSC and TGA). The formation of new copolymeric network was determined by FTIR, XRD, TGA and DSC analysis. The hydrogel formulations with acrylic acid and AMPS ratio of 4: 1 and lower amounts of crosslinker had shown maximum swelling. Moreover, higher release rate of captopril was observed at pH 7.4 than at pH 2, because of more swelling capacity of copolymer with increasing pH of the aqueous medium. The present research work confirms the development of a stable hydrogel comprising of HPMC with acrylic acid and AMPS. The prepared hydrogels exhibited pH sensitive behav-ior. This superabsorbent composite prepared could be a successful drug carrier for treating hypertension. PMID:27008813

  15. 2-Acrylamido-2-methyl-1-propanesulfonic Acid Grafted Poly(vinylidene fluoride-co-hexafluoropropylene)-Based Acid-/Oxidative-Resistant Cation Exchange for Membrane Electrolysis.

    PubMed

    Pandey, Ravi P; Das, Arindam K; Shahi, Vinod K

    2015-12-30

    For developing acid-/oxidative-resistant aliphatic-polymer-based cation-exchange membrane (CEM), macromolecular modification of poly(vinylidene fluoride-co-hexafluoropropylene) (PVDF-co-HFP) was carried out by controlled chemical grafting of 2-acrylamido-2-methyl-1-propanesulfonic acid (AMPS). To introduce the unsaturation suitable for chemical grafting, dehydrofluorination of commercially available PVDF-co-HFP was achieved under alkaline medium. Sulfonated copolymer (SCP) was prepared by the free radical copolymerization of dehydofluorinated PVDF-co-HFP (DHPVDF-co-HFP) and AMPS in the presence of free radical initiator. Prepared SCP-based CEMs were analyzed for their morphological characteristics, ion-exchange capacity (IEC), water uptake, conductivity, and stabilities (mechanical, chemical, and thermal) in comparison with state-of-art Nafion117 membrane. High bound water content avoids the membrane dehydration, and most optimal (SCP-1.33) membrane exhibited about ∼2.5-fold high bound water content in comparison with that of Nafion117 membrane. Bunsen reaction of iodine-sulfur (I-S) was successfully performed by direct-contact-mode membrane electrolysis in a two-compartment electrolytic cell using different SCP membranes. High current efficiency (83-99%) confirmed absence of any side reaction and 328.05 kJ mol-H2(-1) energy was required for to produce 1 mol of H2 by electrolytic cell with SCP-1.33 membrane. In spite of low conductivity for reported SCP membrane in comparison with that of Nafion117 membrane, SCP-1.33 membrane was assessed as suitable candidate for electrolysis because of its low-cost nature and excellent stabilities in highly acidic environment may be due to partial fluorinated segments in the membrane structure. PMID:26642107

  16. Synthesis and antibacterial activity of thioglycolic amino acid derivatives and dipeptides containing the 2-methyl-3,4-dihydroquinazolin-4-one moiety.

    PubMed

    Atta, F M

    1994-11-01

    3-(2'-Chloroethyl)-2-methyl-3,4-dihydroquinazolin-4-one (I) was reacted with sodio (sodium thioglycolate) in dry dioxane and yielded compound II. By using thionyl chloride, this compound was converted to the corresponding acid chloride (III). The prepared acyl chloride (III) was allowed to interact with different alpha-amino acids such as Gly, L-Ala, L-B-Phe, DL-Asp, L-Glu, L-Thr and L-Val to give new amino acid derivatives (IVa-g). A selected C-terminal derivative of glycine (IVa) was converted into acid chloride (V). The acid chloride formed was reacted with L-Ala, L-B-Phe, DL-Asp, L-Glu, L-Thr and L-Val and yielded the new dipeptides VIa-f. The structures of the synthesized compounds were elucidated by elemental analysis and IR spectra. The prepared peptides were tested for their antimicrobial activities by comparison with tetra-cycline as a reference compound. PMID:7765582

  17. Secondary Organic Aerosol Formation from 2-Methyl-3-Buten-2-ol Photooxidation: Evidence of Acid-Catalyzed Reactive Uptake of Epoxides

    SciTech Connect

    Zhang, Haofei; Zhang, Zhenfa; Cui, Tianqu; Lin, Ying-Hsuan; Bhathela, Neil A.; Ortega, John; Worton, David; Goldstein, Allen H.; Guenther, Alex B.; Jimenez, Jose L.; Gold, Avram; Surratt, Jason D.

    2014-04-08

    Secondary organic aerosol (SOA) formation from 2-methyl-3-buten-2-ol (MBO) photooxidation has recently been observed in both field and laboratory studies. Similar to isoprene, MBO-derived SOA increases with elevated aerosol acidity in the absence of nitric oxide; therefore, an epoxide intermediate, (3,3-dimethyloxiran-2-yl)methanol (MBO epoxide) was synthesized and tentatively proposed here to explain this enhancement. In the present study, the potential of the synthetic MBO epoxide to form SOA via reactive uptake was systematically examined. SOA was observed only in the presence of acidic aerosols. Major SOA constituents, 2,3-dihydroxyisopentanol (DHIP) and MBO-derived organosulfate isomers, were chemically characterized in both laboratory-generated SOA and in ambient fine aerosols collected from the BEACHON-RoMBAS field campaign during summer 2011, where MBO emissions are substantial. Our results support epoxides as potential products of MBO photooxidation leading to formation of atmospheric SOA and suggest that reactive uptake of epoxides may generally explain acid enhancement of SOA observed from other biogenic hydrocarbons.

  18. Effects of a salt of cholestyramine and 2-[4-(p-chlorobenzoyl)phenoxy]2-methyl propionic acid (alpha-1081) on biliary lipid secretion in rats.

    PubMed

    Aldini, R; Barbara, L; Benelli, A; Borzatta, V; Geminiani, S; Mascellani, G; Morselli, A; Roda, A; Roda, E

    1981-11-01

    1 Hypolipidaemic agents may increase biliary cholesterol in man, inducing a supersaturated bile. 2 To evaluate this possible side-effect, we have studied bile lipid secretion over a period of 8 h with intact enterohepatic circulation and 4 h with complete interruption in rats treated for two months with a salt of cholestyramine and 2-[4-(p-chlorobenzoyl)-phenoxy]2-methyl propionic acid (alpha-1081, 1.150 g/kg body wt., daily), cholestyramine (1.125 g/kg body wt. daily), procetofenic acid (25 mg/kg body wt. daily) and saline respectively (six rats for each group). 3 Cholesterol saturation index significantly (P less than 0.005) increased (from 0.21 +/- 0.01 to 0.39 +/- 0.09, mean +/- s.d.), in rats fed with procetofenic acid but it did not in alpha-1081- and cholestyramine-treated animals. 4 Procetofenic acid and, to a lesser extent, cholestyramine increased the bile flow. Procetofenic acid increased cholesterol secretion from 0.45 +/- 0.17 to 0.94 +/- 0.19 mumol kg-1 body wt. h-1 (mean +/- s.d.). 5 Cholestyramine increased both serum cholesterol and bile acid secretion from 0.45 +/- 0.17 to 0.68 +/- 0.10 and 25.8 +/- 9.48 to 39.96 +/- 6.68 mumol kg-1 body wt. h-1 respectively; alpha-1081, on the contrary, had no effect on bile lipid secretion. 6 These data suggest that alpha-1081 may be used as a new hypolipidaemic drug without any risk of increasing cholesterol in bile. PMID:6895340

  19. Effects of a salt of cholestyramine and 2-[4-(p-chlorobenzoyl)phenoxy]2-methyl propionic acid (alpha-1081) on biliary lipid secretion in rats.

    PubMed Central

    Aldini, R.; Barbara, L.; Benelli, A.; Borzatta, V.; Geminiani, S.; Mascellani, G.; Morselli, A.; Roda, A.; Roda, E.

    1981-01-01

    1 Hypolipidaemic agents may increase biliary cholesterol in man, inducing a supersaturated bile. 2 To evaluate this possible side-effect, we have studied bile lipid secretion over a period of 8 h with intact enterohepatic circulation and 4 h with complete interruption in rats treated for two months with a salt of cholestyramine and 2-[4-(p-chlorobenzoyl)-phenoxy]2-methyl propionic acid (alpha-1081, 1.150 g/kg body wt., daily), cholestyramine (1.125 g/kg body wt. daily), procetofenic acid (25 mg/kg body wt. daily) and saline respectively (six rats for each group). 3 Cholesterol saturation index significantly (P less than 0.005) increased (from 0.21 +/- 0.01 to 0.39 +/- 0.09, mean +/- s.d.), in rats fed with procetofenic acid but it did not in alpha-1081- and cholestyramine-treated animals. 4 Procetofenic acid and, to a lesser extent, cholestyramine increased the bile flow. Procetofenic acid increased cholesterol secretion from 0.45 +/- 0.17 to 0.94 +/- 0.19 mumol kg-1 body wt. h-1 (mean +/- s.d.). 5 Cholestyramine increased both serum cholesterol and bile acid secretion from 0.45 +/- 0.17 to 0.68 +/- 0.10 and 25.8 +/- 9.48 to 39.96 +/- 6.68 mumol kg-1 body wt. h-1 respectively; alpha-1081, on the contrary, had no effect on bile lipid secretion. 6 These data suggest that alpha-1081 may be used as a new hypolipidaemic drug without any risk of increasing cholesterol in bile. PMID:6895340

  20. Palladium-catalysed direct C-2 methylation of indoles.

    PubMed

    Tu, Daoquan; Cheng, Xiuzhi; Gao, Yadong; Yang, Panpan; Ding, Yousong; Jiang, Chao

    2016-08-21

    A direct C-2 methylation reaction of indoles bearing a readily removable N-2-pyrimidyl moiety as a site-specific directing group has been developed with a palladium catalyst. This reaction relied on the use of KF to promote efficient methylation. A moderate to good yield was achieved in a range of indole substrates. PMID:27424955

  1. Polyacrylamido-2-methyl-1-propane sulfonic acid-grafted-natural rubber as bio-adsorbent for heavy metal removal from aqueous standard solution and industrial wastewater.

    PubMed

    Phetphaisit, Chor Wayakron; Yuanyang, Siriwan; Chaiyasith, Wipharat Chuachuad

    2016-01-15

    Bio-adsorbent modified natural rubber (modified NR) was prepared, by placing the sulfonic acid functional group on the isoprene chain. This modification was carried out with the aim to prepare material capable to remove heavy metals from aqueous solution. The structures of modified NR materials were characterized by FT-IR and NMR spectroscopies. Thermal gravimetric analysis of modified NR showed that the initial degradation temperature of rubber decreases with increasing amount of polyacrylamido-2-methyl-1-propane sulfonic acid (PAMPS) in the structure. In addition, water uptake of the rubber based materials was studied as a function of time and content of PAMPS. The influence of the amount of PAMPS grafted onto NR, time, pH, concentration of metal ions, temperature, and regeneration were studied in terms of their influence on the adsorption of heavy metals (Pb(2+), Cd(2+) and Cu(2+)). The adsorption isotherms of Pb(2+) and Cd(2+) were fitted to the Freundlich isotherm model, while Cu(2+) was fitted to the Langmuir isotherm. However, the results from these two isotherms resulted in a similar behavior. The adsorption capacity of the modified NR for the various heavy metals was in the following order: Pb(2+)∼Cd(2+)>Cu(2+). The maximum adsorption capacities of Pb(2+), Cd(2+), and Cu(2+) were 272.7, 267.2, and 89.7 mg/g of modified rubber, respectively. Moreover, the modified natural rubber was used for the removal of metal ions in real samples of industrial effluents where the efficiency and regeneration were also investigated. PMID:26348149

  2. Characterization of potential NMDA and cholecystokinin antagonists. II. Lipophilicity studies on 2-methyl-4-oxo-3H-quinazoline-3-alkyl-carboxylic acid derivatives.

    PubMed

    Almási, J; Takács-Novák, K; Kökösi, J; Vámos, J

    1999-03-25

    The lipophilicity of 17 newly synthesized potential NMDA and cholecystokinin antagonist 2-methyl-4-oxo-3H-quinazoline-3-alkyl-carboxylic acid derivatives has been investigated. The apparent partition coefficients of two amphoteric compounds of overlapping protonation (Q1 and Q2) were determined by shake-flask method and converted into true log P values using the protonation microconstants. The difference between their lipophilicity expressed with the true partition coefficients was less, than it could be expected from the 2D structures and was explained with conformational preferences and formation of intramolecular interactions. Out of the other 15 monoprotic quinazolone compounds the lipophilicity of ten molecules (Q8-Q17, experimental set) was determined by TLC method with the help of a calibration set consisting of 12 standard molecules, five quinazolones (Q3-Q7) and seven pyrido[1,2-a]pyrimidines (PP1-PP7). In order to justify the suitability of pyrido-pyrimidines as standards for the chromatographic log P determination of quinazolones, first Q3-Q7 were examined by TLC and HPLC using PP1-PP7 for calibration. Data showed good agreement of results obtained by shake-flask and two different chromatographic methods indicating the similar chromatographic behavior of the two bicyclic systems and the relevance of PP1-PP7 to extend the calibration set of quinazolones. The obtained log P values proved mostly the expected structure-activity relationships. Some findings, however, have revealed specific partition behavior of the compounds providing useful information in the estimation of their pharmacokinetics, and these are discussed in the paper. PMID:10089287

  3. A multiphasic hollow fiber reactor for the whole-cell bioconversion of 2-methyl-1,3-propanediol to (r)-beta-hydroxyisobutyric acid.

    PubMed

    León, R; Prazeres, D M; Fernandes, P; Molinari, F; Cabral, J M

    2001-01-01

    This paper describes the bioconversion of 2-methyl-1,3-propanediol to (R)-beta-hydoxyisobutyric acid (HIBA) by Acetobacter ALEI in a hollow fiber membrane bioreaction system arrangement that allows the integration of three liquid phases: the aqueous bioconversion phase, the organic phase consisting of a solution of trioctyl phosphine oxide (TOPO) in isooctane, and the third phase consisting of a basic stripping solution that allows reextraction of HIBA from the organic phase. A comparison of HIBA mass transfer experiments was carried out in the membrane reactor with two and three phases for different pH and TOPO concentrations. The use of the three-phase arrangement allows the extraction of high quantities of HIBA from the aqueous medium (higher than 85%) independently of the pH, whereas in the two-phase system the percentage of HIBA extracted from the aqueous medium was lower, 42% in the best case, and strongly influenced by the pH. The percentage of the extractive agent TOPO in the organic phase influenced on the mass transfer rate in both bi- and triphasic arrangements. By simply integrating the re-extraction phase in the system it was possible to increase the extraction yield by 2-fold, reduce the amount of TOPO by 4-fold, and operate at the more favorable pH 4. A bioconversion experiment was done in these conditions (pH = 4, TOPO = 5%) to confirm the advantages of including the third stripping solution. Fed-batch operation of the triphasic membrane reactor was maintained for more than 20 h, reaching an HIBA concentration in the stripping solution of 29 g L(-)(1). PMID:11386867

  4. Use of 8-substituted-FAD analogues to investigate the hydroxylation mechanism of the flavoprotein 2-methyl-3-hydroxypyridine-5-carboxylic acid oxygenase.

    PubMed

    Chaiyen, Pimchai; Sucharitakul, Jeerus; Svasti, Jisnuson; Entsch, Barrie; Massey, Vincent; Ballou, David P

    2004-04-01

    2-Methyl-3-hydroxypyridine-5-carboxylic acid (MHPC) oxygenase (MHPCO) is a flavoprotein that catalyzes the oxygenation of MHPC to form alpha-(N-acetylaminomethylene)-succinic acid. Although formally similar to the oxygenation reactions catalyzed by phenol hydroxylases, MHPCO catalyzes the oxygenation of a pyridyl derivative rather than a simple phenol. Therefore, in this study, the mechanism of the reaction was investigated by replacing the natural cofactor FAD with FAD analogues having various substituents (-Cl, -CN, -NH(2), -OCH(3)) at the C8-position of the isoalloxazine. Thermodynamic and catalytic properties of the reconstituted enzyme were investigated and found to be similar to those of the native enzyme, validating that these FAD analogues are reasonable to be used as mechanistic probes. Dissociation constants for the binding of MHPC or the substrate analogue 5-hydroxynicotinate (5HN) to the reconstituted enzymes indicate that the reconstituted enzymes bind well with ligands. Redox potential values of the reconstituted enzymes were measured and found to be more positive than the values of free FAD analogues, which correlated well with the electronic effects of the 8-substituents. Studies of the reductive half-reaction of MHPCO have shown that the rates of flavin reduction by NADH could be described as a parabolic relationship with the redox potential values of the reconstituted enzymes, which is consistent with the Marcus electron transfer theory. Studies of the oxidative half-reaction of MHPCO revealed that the rate of hydroxylation depended upon the different analogues employed. The rate constants for the hydroxylation step correlated with the calculated pK(a) values of the 8-substituted C(4a)-hydroxyflavin intermediates, which are the leaving groups in the oxygen transfer step. It was observed that the rates of hydroxylation were greater when the pK(a) values of C(4a)-hydroxyflavins were lower. Although these results are not as dramatic as those from

  5. Crystal structures of the two salts 2-methyl-1H-imidazol-3-ium nitrate–2-methyl-1H-imidazole (1/1) and 2-methyl-1H-imidazol-3-ium nitrate

    PubMed Central

    Diop, Mouhamadou Birame; Diop, Libasse; Maris, Thierry

    2016-01-01

    The title salts, C4H7N2 +·NO3 −·C4H6N2, (I), and C4H7N2 +·NO3 −, (II), were obtained from solutions containing 2-methyl­imidazole and nitric acid in different concentrations. In the crystal structure of salt (I), one of the –NH H atoms of the imidazole ring shows half-occupancy, hence only every second mol­ecule is in its cationic form. The nitrate anion in this structure lies on a twofold rotation axis. The neutral 2-methyl­imidazole mol­ecule and the 2-methyl-1H-imidazol-3-ium cation inter­act through N—H⋯N hydrogen bonds to form [(C4H6N2)⋯(C4H7N2)+] pairs. These pairs are linked with two nitrate anions on both sides through bifurcated N—H⋯(O,O) hydrogen bonds into chains running parallel to [001]. In the crystal structure of salt (II), the C4H7N2 + cation and the NO3 − anion are both located on a mirror plane, leading to a statistical disorder of the methyl H atoms. The cations and anions again inter­act through bifurcated N—H⋯(O,O) hydrogen bonds, giving rise to the formation of chains consisting of alternating anions and cations parallel to [100]. PMID:27375869

  6. Crystal structures of the two salts 2-methyl-1H-imidazol-3-ium nitrate-2-methyl-1H-imidazole (1/1) and 2-methyl-1H-imidazol-3-ium nitrate.

    PubMed

    Diop, Mouhamadou Birame; Diop, Libasse; Maris, Thierry

    2016-04-01

    The title salts, C4H7N2 (+)·NO3 (-)·C4H6N2, (I), and C4H7N2 (+)·NO3 (-), (II), were obtained from solutions containing 2-methyl-imidazole and nitric acid in different concentrations. In the crystal structure of salt (I), one of the -NH H atoms of the imidazole ring shows half-occupancy, hence only every second mol-ecule is in its cationic form. The nitrate anion in this structure lies on a twofold rotation axis. The neutral 2-methyl-imidazole mol-ecule and the 2-methyl-1H-imidazol-3-ium cation inter-act through N-H⋯N hydrogen bonds to form [(C4H6N2)⋯(C4H7N2)(+)] pairs. These pairs are linked with two nitrate anions on both sides through bifurcated N-H⋯(O,O) hydrogen bonds into chains running parallel to [001]. In the crystal structure of salt (II), the C4H7N2 (+) cation and the NO3 (-) anion are both located on a mirror plane, leading to a statistical disorder of the methyl H atoms. The cations and anions again inter-act through bifurcated N-H⋯(O,O) hydrogen bonds, giving rise to the formation of chains consisting of alternating anions and cations parallel to [100]. PMID:27375869

  7. Production of 2-methyl-1-butanol in engineered Escherichia coli.

    PubMed

    Cann, Anthony F; Liao, James C

    2008-11-01

    Recent progress has been made in the production of higher alcohols by harnessing the power of natural amino acid biosynthetic pathways. Here, we describe the first strain of Escherichia coli developed to produce the higher alcohol and potential new biofuel 2-methyl-1-butanol (2MB). To accomplish this, we explored the biodiversity of enzymes catalyzing key parts of the isoleucine biosynthetic pathway, finding that AHAS II (ilvGM) from Salmonella typhimurium and threonine deaminase (ilvA) from Corynebacterium glutamicum improve 2MB production the most. Overexpression of the native threonine biosynthetic operon (thrABC) on plasmid without the native transcription regulation also improved 2MB production in E. coli. Finally, we knocked out competing pathways upstream of threonine production (DeltametA, Deltatdh) to increase its availability for further improvement of 2MB production. This work led to a strain of E. coli that produces 1.25 g/L 2MB in 24 h, a total alcohol content of 3 g/L, and with yields of up to 0.17 g 2MB/g glucose. PMID:18758769

  8. Fragrance material review on 2-methyl-4-phenyl-2-butanol.

    PubMed

    Scognamiglio, J; Jones, L; Letizia, C S; Api, A M

    2012-09-01

    A toxicologic and dermatologic review of 2-methyl-4-phenyl-2-butanol when used as a fragrance ingredient is presented. 2-methyl-4-phenyl-2-butanol is a member of the fragrance structural group Aryl Alkyl Alcohols and is a tertiary alcohol. The AAAs are a structurally diverse class of fragrance ingredients that includes primary, secondary, and tertiary alkyl alcohols covalently bonded to an aryl (Ar) group, which may be either a substituted or unsubstituted benzene ring. The common structural element for the AAA fragrance ingredients is an alcohol group -C-(R1)(R2)OH and generically the AAA fragrances can be represented as an Ar-C-(R1)(R2)OH or Ar-Alkyl-C-(R1)(R2)OH group. This review contains a detailed summary of all available toxicology and dermatology papers that are related to this individual fragrance ingredient and is not intended as a stand-alone document. Available data for 2-methyl-4-phenyl-2-butanol were evaluated then summarized and includes physical properties, acute toxicity, skin irritation, and skin sensitization data. A safety assessment of the entire Aryl Alkyl Alcohols will be published simultaneously with this document; please refer to Belsito et al. (2012) for an overall assessment of the safe use of this material and all Aryl Alkyl Alcohols in fragrances. assessment of aryl alkyl alcohols when used as fragrance ingredients. PMID:22036982

  9. Fragrance material review on 2-methyl-5-phenylpentanol.

    PubMed

    Scognamiglio, J; Jones, L; Letizia, C S; Api, A M

    2012-09-01

    A toxicologic and dermatologic review of 2-methyl-5-phenylpentanol when used as a fragrance ingredient is presented. 2-Methyl-5-phenylpentanol is a member of the fragrance structural group aryl alkyl alcohols and is a primary alcohol. The AAAs are a structurally diverse class of fragrance ingredients that includes primary, secondary, and tertiary alkyl alcohols covalently bonded to an aryl (Ar) group, which may be either a substituted or unsubstituted benzene ring. The common structural element for the AAA fragrance ingredients is an alcohol group -C-(R1)(R2)OH and generically the AAA fragrances can be represented as an Ar-C-(R1)(R2)OH or Ar-Alkyl-C-(R1)(R2)OH group. This review contains a detailed summary of all available toxicology and dermatology papers that are related to this individual fragrance ingredient and is not intended as a stand-alone document. Available data for 2-methyl-5-phenylpentanol were evaluated then summarized and includes physical properties, acute toxicity, skin irritation, mucous membrane (eye) irritation, skin sensitization, repeated dose, and genotoxicity data. A safety assessment of the entire aryl alkyl alcohols will be published simultaneously with this document; please refer to Belsito et al. (2012) for an overall assessment of the safe use of this material and all other branched chain saturated alcohols in fragrances. PMID:22033092

  10. Fragrance material review on 2-methyl-4-phenylpentanol.

    PubMed

    Scognamiglio, J; Jones, L; Letizia, C S; Api, A M

    2012-09-01

    A toxicologic and dermatologic review of 2-methyl-4-phenylpentanol when used as a fragrance ingredient is presented. 2-Methyl-4-phenylpentanol is a member of the fragrance structural group Aryl Alkyl Alcohols and is a primary alcohol. The AAAs are a structurally diverse class of fragrance ingredients that includes primary, secondary, and tertiary alkyl alcohols covalently bonded to an aryl (Ar) group, which may be either a substituted or unsubstituted benzene ring. The common structural element for the AAA fragrance ingredients is an alcohol group -C-(R1)(R2)OH and generically the AAAs fragrances can be represented as an Ar-C-(R1)(R2)OH or Ar-Alkyl-C-(R1)(R2)OH group. This review contains a detailed summary of all available toxicology and dermatology papers that are related to this individual fragrance ingredient and is not intended as a stand-alone document. Available data for 2-methyl-4-phenylpentanol were evaluated then summarized and includes physical properties, acute toxicity, skin irritation, mucous membrane (eye) irritation, skin sensitization, repeated dose, and genotoxicity data. A safety assessment of the entire Aryl Alkyl Alcohols will be published simultaneously with this document; please refer to Belsito et al. (2012) for an overall assessment of the safe use of this material and all Aryl Alkyl Alcohols in fragrances. PMID:22036976

  11. Dehydration of 2-Methyl-1-Cyclohexanol: New Findings from a Popular Undergraduate Laboratory Experiment

    ERIC Educational Resources Information Center

    Friesen, J. Brent; Schretzman, Robert

    2011-01-01

    The mineral acid-catalyzed dehydration of 2-methyl-1-cyclohexanol has been a popular laboratory exercise in second-year organic chemistry for several decades. The dehydration experiment is often performed by organic chemistry students to illustrate Zaitsev's rule. However, sensitive analytical techniques reveal that the results do not entirely…

  12. Crystal structure of 2-methyl-1H-imidazol-3-ium hydrogen oxalate dihydrate.

    PubMed

    Diop, Mouhamadou Birame; Diop, Libasse; Plasseraud, Laurent; Cattey, Hélène

    2016-08-01

    Single crystals of the title mol-ecular salt, C4H7N2 (+)·HC2O4 (-)·2H2O, were isolated from the reaction of 2-methyl-1H-imidazole and oxalic acid in a 1:1 molar ratio in water. In the crystal, the cations and anions are positioned alternately along an infinite [010] ribbon and linked together through bifurcated N-H⋯(O,O) hydrogen bonds. The water mol-ecules of crystallization link the chains into (10-1) bilayers, with the methyl groups of the cations organized in an isotactic manner. PMID:27536393

  13. Crystal structure of 2-methyl-1H-imidazol-3-ium hydrogen oxalate dihydrate

    PubMed Central

    Diop, Mouhamadou Birame; Diop, Libasse; Plasseraud, Laurent; Cattey, Hélène

    2016-01-01

    Single crystals of the title mol­ecular salt, C4H7N2 +·HC2O4 −·2H2O, were isolated from the reaction of 2-methyl-1H-imidazole and oxalic acid in a 1:1 molar ratio in water. In the crystal, the cations and anions are positioned alternately along an infinite [010] ribbon and linked together through bifurcated N—H⋯(O,O) hydrogen bonds. The water mol­ecules of crystallization link the chains into (10-1) bilayers, with the methyl groups of the cations organized in an isotactic manner. PMID:27536393

  14. [Synthesis of 2-methyl-5-substituted phenoxy-primaquine and antimalarials activity].

    PubMed

    Zhong, B H; Deng, R X; Zhong, J X; Wang, J

    1990-01-01

    In searching for efficient, safe and radically curative agent and causal prophylactics for malaria, seven 2-methyl-5-substituted phenoxy-6-methoxy-8-(1-methyl-4-aminobutylamino)-quinolines (II1-7) were synthesized and their antimalarial activities were compared with the corresponding 4-methyl substituted derivatives of primaquine. The starting material, 2-nitro-4-methoxy-5-bromo-acetanilide (III), was prepared from p-methoxy aniline through acetylation, bromination and nitration. III was then condensed with substituted phenols in the presence of potassium carbonate. The condensed products were subsequently hydrolyzed with dilute alcoholic hydrochloric acid to yield 2-nitro-4-methoxy-5-substituted phenoxy-aniline (V) which underwent Skraup's reaction with 2-butenal to provide the key intermediates 2-methyl-5-substituted phenoxy-6-methoxy-8-nitroquinolines (VI). These 8-nitroquinoline derivatives were reduced to 8-aminoquinoline derivatives (VII). The latter were condensed with 4-bromo-1-phthalimido-pentane and then hydrolyzed with hydrazine hydrate, the final products were obtained as oxalate or succinate. The structure of the target compounds and unknown intermediates were confirmed by elementary and spectral analysis. Primary biological evaluation showed that all compounds II1-7 were much less active than the 4-methyl substituted derivatives and slightly less active than primaquine in both causal prophylactic test against Plasmodium yoelii and suppressive antimalarial test against P. berhei. PMID:2239331

  15. Enantioselective syntheses and sensory properties of 2-methyl-tetrahydrofuran-3-thiol acetates.

    PubMed

    Dai, Yifeng; Shao, Junqiang; Yang, Shaoxiang; Sun, Baoguo; Liu, Yongguo; Ning, Ting; Tian, Hongyu

    2015-01-21

    The enantioselective synthesis of four stereoisomers of 2-methyl-tetrahydrofuran-3-thiol acetate was achieved. The two enantiomers of the important intermediate cis-2-methyl-3-hydroxy-tetrahydrofuran were obtained by Sharpless asymmetric dihydroxylation (AD), whereas the two enantiomers of trans-2-methyl-3-hydroxy-tetrahydrofuran were derived from the corresponding optically active cis-isomers by Mitsunobu reaction. Each stereoisomer of 2-methyl-3-hydroxy-tetrahydrofuran went through mesylation and nucleophilic substitution to afford the corresponding product with specific configuration. (2R,3S)- and (2R,3R)-2-methyl-tetrahydrofuran-3-thiol acetate were obtained in 80% ee, whereas the (2S,3R)- and (2S,3S)-isomers were in 62% ee. The odor properties of the synthesized four stereoisomers were evaluated by gas chromatography-olfactometry (GC-O), which revealed perceptible differences among stereoisomers both in odor features and in intensities. PMID:25560460

  16. Excess molar enthalpies of ternary mixtures for propanone or benzene + aniline + 2-methyl-1-propanol and of binary mixtures for propanone or aniline + 2-methyl-1-propanol at 298.15 K

    SciTech Connect

    Nagata, Isamu; Tamura, Kazuhiro; Miyai, Koichi

    1996-11-01

    Experimental excess molar enthalpies for the ternary mixtures 2-methyl-1-propanol + aniline + propanone and 2-methyl-1-propanol + aniline + benzene and their constituent binary mixtures 2-methyl-1-propanol + aniline and 2-methyl-1-propanol + propanone at the temperature 298.15 K, measured by using an isothermal dilution calorimeter, are reported. The results have been analyzed using a polynomial equation and the UNIQUAC-associated solution model with binary and ternary parameters.

  17. 40 CFR 721.8485 - 2-Propenoic acid, 2-methyl-, (octahydro-4,7-methano-1H- indene-5-diyl)bis(methylene) ester.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ...-, (octahydro-4,7-methano-1H- indene-5-diyl)bis(methylene) ester. 721.8485 Section 721.8485 Protection of...-methyl-, (octahydro-4,7-methano-1H- indene-5-diyl)bis(methylene) ester. (a) Chemical substance and...-, (octahydro-4,7-methano- 1H- indene-5-diyl)bis(methylene) ester (PMN P-99-1075; CAS No. 43048-08-4) is...

  18. 40 CFR 721.8485 - 2-Propenoic acid, 2-methyl-, (octahydro-4,7-methano-1H- indene-5-diyl)bis(methylene) ester.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ...-, (octahydro-4,7-methano-1H- indene-5-diyl)bis(methylene) ester. 721.8485 Section 721.8485 Protection of...-methyl-, (octahydro-4,7-methano-1H- indene-5-diyl)bis(methylene) ester. (a) Chemical substance and...-, (octahydro-4,7-methano- 1H- indene-5-diyl)bis(methylene) ester (PMN P-99-1075; CAS No. 43048-08-4) is...

  19. Environmental analysis of the life cycle emissions of 2-methyl tetrahydrofuran solvent manufactured from renewable resources.

    PubMed

    Slater, C Stewart; Savelski, Mariano J; Hitchcock, David; Cavanagh, Eduardo J

    2016-01-01

    An environmental analysis has been conducted to determine the cradle to gate life cycle emissions to manufacture the green solvent, 2-methyl tetrahydrofuran. The solvent is considered a greener chemical since it can be manufactured from renewable resources with a lower life cycle footprint. Analyses have been performed using different methods to show greenness in both its production and industrial use. This solvent can potentially be substituted for other ether and chlorinated solvents commonly used in organometallic and biphasic reactions steps in pharmaceutical and fine chemical syntheses. The 2-methyl tetrahydrofuran made from renewable agricultural by-products is marketed by Penn A Kem under the name ecoMeTHF™. The starting material, 2-furfuraldehyde (furfural), is produced from corn cob waste by converting the available pentosans by acid hydrolysis. An evaluation of each step in the process was necessary to determine the overall life cycle and specific CO2 emissions for each raw material/intermediate produced. Allocation of credits for CO2 from the incineration of solvents made from renewable feedstocks significantly reduced the overall carbon footprint. Using this approach, the overall life cycle emissions for production of 1 kg of ecoMeTHF™ were determined to be 0.191 kg, including 0.150 kg of CO2. Life cycle emissions generated from raw material manufacture represents the majority of the overall environmental impact. Our evaluation shows that using 2-methyl tetrahydrofuran in an industrial scenario results in a 97% reduction in emissions, when compared to typically used solvents such as tetrahydrofuran, made through a conventional chemical route. PMID:26889729

  20. Solubility of nitrous oxide in aqueous blends of N-methyldiethanolamine and 2-amino-2-methyl-1-propanol

    SciTech Connect

    Davis, R.A.; Pogainis, B.J.

    1995-11-01

    Aqueous solutions of alkanolamines have applications in acid gas treatment for the removal of acid gases such as carbon dioxide and hydrogen sulfide. The solubility of nitrous oxide in aqueous blends of N-methyldiethanolamine and 2-amino-2-methyl-1 propanol was measured over the temperature range 10--60 C. The total composition of the alkanolamines in water ranged from 30 to 50 mass %. The experimental results were interpreted in terms of Henry`s constants.

  1. Phase 2 Methyl Iodide Deep-Bed Adsorption Tests

    SciTech Connect

    Soelberg, Nick; Watson, Tony

    2014-09-01

    Nuclear fission produces fission products (FPs) and activation products, including iodine-129, which could evolve into used fuel reprocessing facility off-gas systems, and could require off-gas control to limit air emissions to levels within acceptable emission limits. Research, demonstrations, and some reprocessing plant experience have indicated that diatomic iodine can be captured with efficiencies high enough to meet regulatory requirements. Research on the capture of organic iodides has also been performed, but to a lesser extent. Several questions remain open regarding the capture of iodine bound in organic compounds. Deep-bed methyl iodide adsorption testing has progressed according to a multi-laboratory methyl iodide adsorption test plan. This report summarizes the second phase of methyl iodide adsorption work performed according to this test plan using the deep-bed iodine adsorption test system at the Idaho National Laboratory (INL), performed during the second half of Fiscal Year (FY) 2014. Test results continue to show that methyl iodide adsorption using AgZ can achieve total iodine decontamination factors (DFs, ratios of uncontrolled and controlled total iodine levels) above 1,000, until breakthrough occurred. However, mass transfer zone depths are deeper for methyl iodide adsorption compared to diatomic iodine (I2) adsorption. Methyl iodide DFs for the Ag Aerogel test adsorption efficiencies were less than 1,000, and the methyl iodide mass transfer zone depth exceeded 8 inches. Additional deep-bed testing and analyses are recommended to (a) expand the data base for methyl iodide adsorption under various conditions specified in the methyl iodide test plan, and (b) provide more data for evaluating organic iodide reactions and reaction byproducts for different potential adsorption conditions.

  2. UNIFAC parameters for maleic anhydride and 2-methyl furan in p-dioxane system

    SciTech Connect

    Daumn, K.J.

    1983-01-01

    The purpose of this work was to develop a method for calculating equilibrium concentrations for reversible liquid phase reactions from a minimum of experimental data. The example reaction studied was the Diels Alder reaction between 2-methyl furan and maleic anhydride. Specifically, interaction parameters of the UNIFAC model for groups in the compounds 2-methyl furan, maleic anhydride and the solvent, p-dioxane, were determined. The activity coefficient of each substance was then predicted by the UNIFAC method. Equilibrium constants at 45/sup 0/C for the Diels Alder reaction between 2-methyl furan and maleic anhydride were then calculated from these activity coefficients and two previously determined sets of equilibrium concentrations at 45/sup 0/C. These two equilibrium constants were within 12% of each other, which demonstrated the validity of the method.

  3. Biodegradation-inspired bioproduction of methylacetoin and 2-methyl-2,3-butanediol

    PubMed Central

    Jiang, Xinglin; Zhang, Haibo; Yang, Jianming; Zheng, Yanning; Feng, Dexin; Liu, Wei; Xu, Xin; Cao, Yujin; Zou, Huibin; Zhang, Rubin; Cheng, Tao; Jiao, Fengjiao; Xian, Mo

    2013-01-01

    Methylacetoin (3-hydroxy-3-methylbutan-2-one) and 2-methyl-2,3-butanediol are currently obtained exclusively via chemical synthesis. Here, we report, to the best of our knowledge, the first alternative route, using engineered Escherichia coli. The biological synthesis of methylacetoin was first accomplished by reversing its biodegradation, which involved modifying the enzyme complex involved, switching the reaction substrate, and coupling the process to an exothermic reaction. 2-Methyl-2,3-butanediol was then obtained by reducing methylacetoin by exploiting the substrate promiscuity of acetoin reductase. A complete biosynthetic pathway from renewable glucose and acetone was then established and optimized via in vivo enzyme screening and host metabolic engineering, which led to titers of 3.4 and 3.2 g l−1 for methylacetoin and 2-methyl-2,3-butanediol, respectively. This work presents a biodegradation-inspired approach to creating new biosynthetic pathways for small molecules with no available natural biosynthetic pathway. PMID:23945710

  4. Pharmacological profile of novel acid pump antagonist 7-(4-fluorobenzyloxy)-2,3-dimethyl-1-{[(1S,2S)-2-methyl cyclopropyl]methyl}-1H-pyrrolo[2,3-d]pyridazine (CS-526).

    PubMed

    Ito, Keiichi; Kinoshita, Kazuya; Tomizawa, Atsuyuki; Inaba, Fumi; Morikawa-Inomata, Yuka; Makino, Mitsuko; Tabata, Keiichi; Shibakawa, Nobuhiko

    2007-10-01

    The pharmacological profiles of the novel acid pump antagonist 7-(4-fluorobenzyloxy)-2,3-dimethyl-1-{[(1S,2S)-2-methylcyclopropyl]methyl}-1H-pyrrolo[2,3-d]pyridazine (CS-526) were investigated in terms of hog gastric H+,K+-ATPase activity, gastric acid secretion, and acute gastroesophageal lesions in comparison with other proton pump inhibitors (PPIs). CS-526 inhibited H+,K+-ATPase activity in a concentration-dependent manner, with an IC50 value of 61 nM. The inhibitory effect of CS-526 on H+,K+-ATPase activity was more potent than that of any of the other PPIs examined. The inhibitory mechanism of CS-526 on H+,K+-ATPase was a competitive antagonism to the K+ binding site of H+,K+-ATPase, and it was also a reversible inhibition. In pylorus-ligated rats, intraduodenal or oral administration of CS-526 inhibited gastric acid secretion in a dose-dependent manner, and the ID50 values were 2.8 or 0.7 mg/kg, respectively. In Heidenhain pouch dogs, intrapouch administration of CS-526 inhibited histamine-stimulated gastric acid secretion in a dose- and retention time-dependent manner. In a reflux esophagitis model, intraduodenal and oral administration of CS-526 prevented esophageal lesions with ID50 values of 5.4 and 1.9 mg/kg, respectively. Lansoprazole prevented esophagitis only by intraduodenal administration (ID50 = 2.2 mg/kg). Furthermore, CS-526 inhibited acute gastric mucosal lesions. These data demonstrate that the novel acid pump antagonist CS-526 has potent antisecretory and antiulcer effects. These findings indicate that CS-526 would have a curative effect on gastroesophageal reflux disease via its potent antisecretory and antiulcer actions. PMID:17630360

  5. 40 CFR 721.9500 - Silane, (1,1-dimethylethoxy) dimethoxy(2-methyl propyl)-.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Silane, (1,1-dimethylethoxy) dimethoxy... New Uses for Specific Chemical Substances § 721.9500 Silane, (1,1-dimethylethoxy) dimethoxy(2-methyl... substance silane, (1,1-dimethylethoxy) dimethoxy (2-methylpropyl)- (PMN P-89-906) is subject to...

  6. 40 CFR 721.9500 - Silane, (1,1-dimethylethoxy) dimethoxy(2-methyl propyl)-.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Silane, (1,1-dimethylethoxy) dimethoxy... New Uses for Specific Chemical Substances § 721.9500 Silane, (1,1-dimethylethoxy) dimethoxy(2-methyl... substance silane, (1,1-dimethylethoxy) dimethoxy (2-methylpropyl)- (PMN P-89-906) is subject to...

  7. 40 CFR 721.9500 - Silane, (1,1-dimethylethoxy) dimethoxy(2-methyl propyl)-.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Silane, (1,1-dimethylethoxy) dimethoxy... New Uses for Specific Chemical Substances § 721.9500 Silane, (1,1-dimethylethoxy) dimethoxy(2-methyl... substance silane, (1,1-dimethylethoxy) dimethoxy (2-methylpropyl)- (PMN P-89-906) is subject to...

  8. 40 CFR 721.9500 - Silane, (1,1-dimethylethoxy) dimethoxy(2-methyl propyl)-.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Silane, (1,1-dimethylethoxy) dimethoxy... New Uses for Specific Chemical Substances § 721.9500 Silane, (1,1-dimethylethoxy) dimethoxy(2-methyl... substance silane, (1,1-dimethylethoxy) dimethoxy (2-methylpropyl)- (PMN P-89-906) is subject to...

  9. 40 CFR 721.9500 - Silane, (1,1-dimethylethoxy) dimethoxy(2-methyl propyl)-.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Silane, (1,1-dimethylethoxy) dimethoxy... New Uses for Specific Chemical Substances § 721.9500 Silane, (1,1-dimethylethoxy) dimethoxy(2-methyl... substance silane, (1,1-dimethylethoxy) dimethoxy (2-methylpropyl)- (PMN P-89-906) is subject to...

  10. 40 CFR 721.10049 - Phenol, 4,4′- cyclohexylidene bis[2-methyl-.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Phenol, 4,4â²- cyclohexylidene bis[2... Specific Chemical Substances § 721.10049 Phenol, 4,4′- cyclohexylidene bis[2-methyl-. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as a...

  11. 40 CFR 721.10049 - Phenol, 4,4′- cyclohexylidene bis[2-methyl-.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Phenol, 4,4â²- cyclohexylidene bis[2... Specific Chemical Substances § 721.10049 Phenol, 4,4′- cyclohexylidene bis[2-methyl-. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as a...

  12. 40 CFR 721.10049 - Phenol, 4,4′- cyclohexylidene bis[2-methyl-.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Phenol, 4,4â²- cyclohexylidene bis[2... Specific Chemical Substances § 721.10049 Phenol, 4,4′- cyclohexylidene bis[2-methyl-. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as a...

  13. 40 CFR 721.10049 - Phenol, 4,4′- cyclohexylidene bis[2-methyl-.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Phenol, 4,4â²- cyclohexylidene bis[2... Specific Chemical Substances § 721.10049 Phenol, 4,4′- cyclohexylidene bis[2-methyl-. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as a...

  14. 40 CFR 721.10049 - Phenol, 4,4′- cyclohexylidene bis[2-methyl-.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Phenol, 4,4â²- cyclohexylidene bis[2... Specific Chemical Substances § 721.10049 Phenol, 4,4′- cyclohexylidene bis[2-methyl-. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as a...

  15. Sulfur-containing flavors: gas phase structures of dihydro-2-methyl-3-thiophenone.

    PubMed

    Mouhib, Halima; Van, Vinh; Stahl, Wolfgang

    2013-08-01

    Dihydro-2-methyl-3-thiophenone was investigated using a combination of quantum chemical calculations and molecular beam Fourier transform microwave spectroscopy. The substance is present in coffee, roasted peanuts, and whiskey. The microwave spectrum was recorded under molecular beam conditions in the frequency range from 9 to 14 GHz. We report on the two main conformers of dihydro-2-methyl-3-thiophenone, for which highly accurate rotational constants and centrifugal distortion constants were obtained. No splittings due to internal rotation of the methyl group could be observed in the microwave spectrum. This is in agreement with the theoretical predictions of the barrier heights, which have been determined to be more than 1000 cm(-1) at the MP2/6-311++G(d,p) level of theory. In addition to the most abundant (32)S-isotopologue of the main conformer, also the (34)S-isotopologue was assigned, which occurs with a natural abundance of about 4%. Using the experimental rotational constants, different quantum chemical calculations were validated for the two observed conformers. To complete the theoretical investigation of dihydro-2-methyl-3-thiophenone, different transition states were optimized to understand the intramolecular conversion between the two conformers at the MP2/6-311++G(d,p) level. The transition states were optimized using the Berny algorithm. PMID:23815419

  16. Synthesis, Radiolabeling and Biological Evaluation of (R)- and (S)-2-Amino-3-[18F]Fluoro-2-Methylpropanoic Acid (FAMP) and (R)- and (S)-3-[18F]Fluoro-2-Methyl-2-N-(Methylamino)propanoic Acid (NMeFAMP) as Potential PET Radioligands for Imaging Brain Tumors

    PubMed Central

    Yu, Weiping; McConathy, Jonathan; Williams, Larry; Camp, Vernon M.; Malveaux, Eugene J.; Zhang, Zhaobin; Olson, Jeffrey J.; Goodman, Mark M.

    2009-01-01

    The non-natural amino acids (R)- and (S)-2-amino-3-fluoro-2-methylpropanoic acid 5 and (R)- and (S)-3-fluoro-2-methyl-2-N-(methylamino)propanoic acid 8 were synthesized in shorter reaction sequences than in the original report starting from enantiomerically pure (S)- and (R)-α-methyl-serine, respectively. The reaction sequence provided the cyclic sulfamidate precursors for radiosynthesis of (R)- and (S)-[18F]5 and (R)- and (S)-[18F]8 in fewer steps than in the original report. (R)- and (S)-[18F]5 and(R)- and (S)-[18F]8 were synthesized by no-carrier-added nucleophilic [18F]fluorination in 52–66% decay-corrected-yields with radiochemical purity over 99%. The cell assays showed that all four compounds were substrates for amino acid transport and enter 9L rat gliosarcoma cells in vitro at least in part by system-A amino acid transport. The biodistribution studies demonstrated that in vivo tumor to normal brain ratios for all compounds were high with ratios of 20:1 to115:1 in rats with intracranial 9L tumors. The (R)- enantiomers of [18F]5 and [18F]8 demonstrated higher tumor uptake in vivo compared to the (S)- enantiomers. PMID:20028004

  17. Microwave spectrum and structure of 2-methyl-1,3-dioxane

    NASA Astrophysics Data System (ADS)

    Shapkin, A. A.; Galeev, R. V.; Gunderova, L. N.; Fayzullin, M. G.; Mamleev, A. H.

    2006-12-01

    The microwave rotational spectra of parent and five isotopic species with 13C and 180 in natural abundance for 2- methyl-1,3-dioxane, C 5H 100 II, have been observed in the 28.0 - 44.0 GHz frequency region. The a - and c - type transitions with 4 <= J <= 10 have been assigned. The rotational constants for all isotopomers were determined. The substituted coordinates of the heavy atoms were calculated from the principal moments of inertia of normal and 13C(2) 12C 4H 10 160 II, 13C(4) 12C 4H 10 160 II, 13C(5) 12C 4H 10 160 II, 13C(7) 12C 4H 10 160, C 5H 10 160 180 isotopomers using Kraitchman's equations. Partial substituted r s structure of 2-methyl-1,3-dioxane molecule has been determined.

  18. (Biphenyl-2-yl)bromidobis(2-methyl-tetra-hydro-furan-κO)magnesium(II).

    PubMed

    Nordschild, Simon; Wohlgemuth, D; Bolte, Michael

    2009-01-01

    In the title Grignard reagent, [MgBr(C(12)H(9))(C(5)H(10)O)(2)], the Mg centre adopts a distorted tetra-hedral MgCO(2)Br arrangement. The dihedral angle between the two aromatic rings of the biphenyl residue is 44.00 (14)°. Each mol-ecule incorporates one R- and one S-configured 2-methyl-tetra-hydro-furan mol-ecule. PMID:21583743

  19. 75 FR 4288 - Oxirane, 2-Methyl-, Polymer with Oxirane, Dimethyl Ether; Tolerance Exemption

    Federal Register 2010, 2011, 2012, 2013, 2014

    2010-01-27

    ...This regulation establishes an exemption from the requirement of a tolerance for residues of oxirane, 2-methyl-,polymer with oxirane, dimethyl ether (CAS Reg. No. 61419-46-3); minimum number average molecular weight (in AMW) 2,800; when used as an inert ingredient in a pesticide chemical formulation under 40 CFR 180.960. BASF Corporation, 100 Campus Dr., Florham Park, NJ 07932 submitted a......

  20. Two-dimensional hydrogen-bonded polymers in the crystal structures of the ammonium salts of phen­oxy­acetic acid, (4-fluoro­phen­oxy)acetic acid and (4-chloro-2-methyl­phen­oxy)acetic acid

    PubMed Central

    Smith, Graham

    2014-01-01

    The structures of the ammonium salts of phen­oxy­acetic acid, NH4 +·C8H6O3 −, (I), (4-fluoro­phen­oxy)acetic acid, NH4 +·C8H5FO3 −, (II), and the herbicidally active (4-chloro-2-methyl­phen­oxy)acetic acid (MCPA), NH4 +·C9H8ClO3 −·0.5H2O, (III) have been determined. All have two-dimensional layered structures based on inter-species ammonium N—H⋯O hydrogen-bonding associations, which give core substructures consisting primarily of conjoined cyclic motifs. The crystals of (I) and (II) are isomorphous with the core comprising R 1 2(5), R 1 2(4) and centrosymmetric R 4 2(8) ring motifs, giving two-dimensional layers lying parallel to (100). In (III), the water mol­ecule of solvation lies on a crystallographic twofold rotation axis and bridges two carboxyl O atoms in an R 4 4(12) hydrogen-bonded motif, creating two R 4 3(10) rings, which together with a conjoined centrosymmetric R 4 2(8) ring incorporating both ammonium cations, generate two-dimensional layers lying parallel to (100). No π–π ring associations are present in any of the structures. PMID:25552984

  1. Crystallization of lysozyme with (R)-, (S)- and (RS)-2-methyl-2, 4-pentanediol

    SciTech Connect

    Stauber, Mark; Jakoncic, Jean; Berger, Jacob; Karp, Jerome M.; Axelbaum, Ariel; Sastow, Dahniel; Buldyrev, Sergey V.; Hrnjez, Bruce J.; Asherie, Neer

    2015-03-01

    Crystallization of lysozyme with (R)-2-methyl-2, 4-pentanediol produces more ordered crystals and a higher resolution protein structure than crystallization with (S)-2-methyl-2, 4-pentanediol. The results suggest that chiral interactions with chiral additives are important in protein crystal formation. Chiral control of crystallization has ample precedent in the small-molecule world, but relatively little is known about the role of chirality in protein crystallization. In this study, lysozyme was crystallized in the presence of the chiral additive 2-methyl-2, 4-pentanediol (MPD) separately using the R and S enantiomers as well as with a racemic RS mixture. Crystals grown with (R)-MPD had the most order and produced the highest resolution protein structures. This result is consistent with the observation that in the crystals grown with (R)-MPD and (RS)-MPD the crystal contacts are made by (R)-MPD, demonstrating that there is preferential interaction between lysozyme and this enantiomer. These findings suggest that chiral interactions are important in protein crystallization.

  2. Dispersed Fluorescence Spectroscopy of Jet-Cooled Isobutoxy, 2-METHYL-1-BUTOXY, and Isopentoxy Radicals

    NASA Astrophysics Data System (ADS)

    Reza, Md Asmaul; Reilly, Neil J.; Alam, Jahangir; Mason, Amy; Liu, Jinjun

    2015-06-01

    It is well known that rate constants of certain reactions of alkoxy radicals, e.g., unimolecular dissociation (decomposition by C-C bond fission) and isomerization via 1,5 H-shift, are highly sensitive to the molecular structure. In the present and the next talks, we report dispersed fluorescence (DF) spectra of various alkoxy radicals obtained under supersonic jet-cooled conditions by pumping different vibronic bands of their tilde B ← tilde X laser induced fluorescence (LIF) excitation spectra. This talk focuses on the DF spectra of 2-methyl-1-propoxy (isobutoxy), 2-methyl-1-butoxy, and 3-methyl-1-butoxy (isopentoxy). In all cases, strong CO-stretch progressions were observed, as well as transitions to other vibrational levels, including low-frequency ones. Quantum chemical calculations were carried out to aid the assignment of the DF spectra. Franck-Condon factors were calculated using the ezSpectrum program. Wu, Q.; Liang, G.; Zu, L.; Fang, W. J. Phys. Chem A 2012, 116, 3156-3162. Lin, J.; Wu, Q.; Liang, G.; Zu, L.; Fang, W. RSC Adv. 2012, 2, 583-589. Liang, G.; Liu , C.; Hao, H.; Zu, L.; Fang, W. J. Phys. Chem. A 2013, 117, 13229- 13235. V. Mozhayskiy and A. I. Krylov, http://iopenshell.usc.edu/

  3. Solubility of carbon dioxide in aqueous solutions of 2-amino-2-methyl-1,3-propanediol

    SciTech Connect

    Baek, J.I.; Yoon, J.H.

    1998-07-01

    The equilibrium solubility of carbon dioxide in aqueous solutions of 2-amino-2-methyl-1,3-propanediol (AMPD) has been measured at (30, 40, and 60) C and the partial pressure of carbon dioxide ranging from (0.5 to 3065) kPa. The concentrations of the aqueous solutions were (10 and 30) mass % AMPD. The tendency of the solubility of carbon dioxide in 30 mass % AMPD aqueous solution at 40 C was found to be similar to that in 30 mass % N-methyldiethanolamine aqueous solution.

  4. The infrared spectra of spiropentane methylenecyclobutane and 2-methyl-1-butene

    NASA Technical Reports Server (NTRS)

    Cleaves, Alden P; Sherrick, Mildred E

    1946-01-01

    The infrared spectra of spiropentane, methylenecyclobutane, and 2-methyl-1-butene were measured in the region from 3 to 14 microns with a rock salt prism spectrometer of medium dispersion. The pure samples were prepared at the NACA Cleveland Laboratory. The vapors of these three C5 hydrocarbons were investigated at room temperature and at pressures in the range from 80 to 300 millimeters of mercury absolute in a 10-centimeter cell. The spectra were compared with each other and with Ramon spectra for the same compounds.

  5. Interconversion of mechanical and dielectrical relaxation measurements for dicyclohexylmethyl-2-methyl succinate.

    PubMed

    Díaz-Calleja, R; Garcia-Bernabé, A; Sanchis, M J; del Castillo, L F

    2005-11-01

    A comparison between results of dielectrical relaxation and dynamic mechanical spectroscopies is carried out for the alpha-relaxation of the ester dicyclohexyl methyl-2-methyl succinate (DCMMS). The results for the dielectric permittivity and the shear modulus measurements are presented according to the empirical Havriliak-Negami (HN) equation. By using the time-temperature principle a master curve in each case was obtained for several temperatures. The comparative analysis presented here is based on the assumption of a relationship between rotational and shear viscosities. The former one is associated to the dielectrical relaxation, whereas the latter is associated to mechanical relaxation. Both viscosities are not necessarily equal in general, and we assume that the difference between them is an important factor to appropriately compare the dielectrical and mechanical results. PMID:16383609

  6. Association between SMN2 methylation and disease severity in Chinese children with spinal muscular atrophy* #

    PubMed Central

    Cao, Yan-yan; Qu, Yu-jin; He, Sheng-xi; Li, Yan; Bai, Jin-li; Jin, Yu-wei; Wang, Hong; Song, Fang

    2016-01-01

    The homozygous loss of the survival motor neuron 1 (SMN1) gene is the primary cause of spinal muscular atrophy (SMA), a neuromuscular degenerative disease. A genetically similar gene, SMN2, which is not functionally equivalent in all SMA patients, modifies the clinical SMA phenotypes. We analyzed the methylation levels of 4 CpG islands (CGIs) in SMN2 in 35 Chinese children with SMA by MassARRAY. We found that three CpG units located in CGI 1 (nucleotides (nt) −871, −735) and CGI 4 (nt +999) are significantly hypomethylated in SMA type III compared with type I or II children after receiving Bonferroni correction. In addition to the differentially methylated CpG unit of nt −871, the methylation level of the nt −290/−288/−285 unit was negatively correlated with the expression of SMN2 full-length transcripts (SMN2-fl). In addition, the methylation level at nt +938 was inversely proportional to the ratio of SMN2-fl and lacking exon 7 transcripts (SMN2-(7, fl/(7), and was not associated with the SMN2 transcript levels. Thus, we can conclude that SMN2 methylation may regulate the SMA disease phenotype by modulating its transcription. PMID:26739529

  7. A 2:1 co-crystal of 2-methyl­benzoic acid and N,N′-bis­(pyridin-4-ylmeth­yl)ethanedi­amide: crystal structure and Hirshfeld surface analysis

    PubMed Central

    Syed, Sabrina; Jotani, Mukesh M.; Halim, Siti Nadiah Abdul; Tiekink, Edward R. T.

    2016-01-01

    The asymmetric unit of the title 2:1 co-crystal, 2C8H8O2·C14H14N4O2, comprises an acid mol­ecule in a general position and half a di­amide mol­ecule, the latter being located about a centre of inversion. In the acid, the carb­oxy­lic acid group is twisted out of the plane of the benzene ring to which it is attached [dihedral angle = 28.51 (8)°] and the carbonyl O atom and methyl group lie approximately to the same side of the mol­ecule [hy­droxy-O—C—C—C(H) torsion angle = −27.92 (17)°]. In the di­amide, the central C4N2O2 core is almost planar (r.m.s. deviation = 0.031 Å), and the pyridyl rings are perpendicular, lying to either side of the central plane [central residue/pyridyl dihedral angle = 88.60 (5)°]. In the mol­ecular packing, three-mol­ecule aggregates are formed via hy­droxy-O—H⋯N(pyrid­yl) hydrogen bonds. These are connected into a supra­molecular layer parallel to (12) via amide-N—H⋯O(carbon­yl) hydrogen bonds, as well as methyl­ene-C—H⋯O(amide) inter­actions. Significant π–π inter­actions occur between benzene/benzene, pyrid­yl/benzene and pyrid­yl/pyridyl rings within and between layers to consolidate the three-dimensional packing. PMID:27006815

  8. A 2:1 co-crystal of 2-methyl-benzoic acid and N,N'-bis-(pyridin-4-ylmeth-yl)ethanedi-amide: crystal structure and Hirshfeld surface analysis.

    PubMed

    Syed, Sabrina; Jotani, Mukesh M; Halim, Siti Nadiah Abdul; Tiekink, Edward R T

    2016-03-01

    The asymmetric unit of the title 2:1 co-crystal, 2C8H8O2·C14H14N4O2, comprises an acid mol-ecule in a general position and half a di-amide mol-ecule, the latter being located about a centre of inversion. In the acid, the carb-oxy-lic acid group is twisted out of the plane of the benzene ring to which it is attached [dihedral angle = 28.51 (8)°] and the carbonyl O atom and methyl group lie approximately to the same side of the mol-ecule [hy-droxy-O-C-C-C(H) torsion angle = -27.92 (17)°]. In the di-amide, the central C4N2O2 core is almost planar (r.m.s. deviation = 0.031 Å), and the pyridyl rings are perpendicular, lying to either side of the central plane [central residue/pyridyl dihedral angle = 88.60 (5)°]. In the mol-ecular packing, three-mol-ecule aggregates are formed via hy-droxy-O-H⋯N(pyrid-yl) hydrogen bonds. These are connected into a supra-molecular layer parallel to (12[Formula: see text]) via amide-N-H⋯O(carbon-yl) hydrogen bonds, as well as methyl-ene-C-H⋯O(amide) inter-actions. Significant π-π inter-actions occur between benzene/benzene, pyrid-yl/benzene and pyrid-yl/pyridyl rings within and between layers to consolidate the three-dimensional packing. PMID:27006815

  9. Novel ring A stereoisomers of 2-methyl-1alpha,25-dihydroxyvitamin D(3) and 2-methyl-20-epi-1alpha,25-dihydroxyvitamin D(3): transactivation of target genes and modulation of differentiation in human promyelocytic leukemia (HL-60) cells.

    PubMed

    Nakagawa, K; Kurobe, M; Ozono, K; Konno, K; Fujishima, T; Takayama, H; Okano, T

    2000-03-15

    We evaluated the biological activity of two sets of ring A stereoisomers of 2-methyl-1alpha,25-dihydroxyvitamin D(3) (2-methyl-1alpha,25(OH)(2)D(3)) and 2-methyl-20-epi-1alpha, 25-dihydroxyvitamin D(3) (2-methyl-20-epi-1alpha,25(OH)(2)D(3)) in terms of the following: transactivation of a rat 25-hydroxyvitamin D(3)-24-hydroxylase gene promoter including two vitamin D response elements (VDREs) and a human osteocalcin gene promoter including a VDRE in transfected human osteosarcoma (MG-63) cells; a vitamin D receptor (VDR)-mediated response using a VDR-GAL4 one-hybrid luciferase reporter system and a retinoid X receptor alpha (RXRalpha)-mediated response using an expressed VDR/RXRalpha-GAL4 modified two-hybrid luciferase reporter system in transfected human epitheloid carcinoma, cervix (HeLa) cells; and modulation of cell surface CD11b antigen expression in human leukemia (HL-60) cells. All the diastereomers of both analogues exhibited unique biological activity profiles depending upon the configurations of the C-1 and C-3 hydroxyl groups, the C-2 methyl group in ring A, and the C-20 methyl group in the side chain. Of the eight possible diastereomers of the 2-methyl analogues, 2alpha-methyl-1alpha,25(OH)(2)D(3) was the most potent and exhibited comparable or even greater biological potency than 1alpha,25(OH)(2)D(3). Of the eight possible diastereomers of the 2-methyl-20-epi analogues, 2alpha-methyl-20-epi-1alpha,25(OH)(2)D(3) was the most potent and exhibited 100- to 200-fold higher transcriptional potencies than 1alpha,25(OH)(2)D(3) and exceptionally high cell regulatory activities. 2beta-methyl-20-epi-1alpha,25(OH)(2)D(3) was nearly as potent as its 2-epimer, 2alpha-methyl-20-epi-1alpha,25(OH)(2)D(3), whereas its 20-epimer, 2beta-methyl-1alpha,25(OH)(2)D(3), was almost completely biologically inactive. In these respects, it can be postulated that the double modification of 2-methyl substitution and 20-epimerization to 1alpha,25(OH)(2)D(3) induces remarkable changes

  10. The variation trends of SFRP2 methylation of tissue, feces, and blood detection in colorectal cancer development.

    PubMed

    Sui, Chengguang; Ma, Jianzhong; Chen, Qun; Yang, Yang

    2016-07-01

    The susceptibility of secreted frizzled-related protein 2 (SFRP2) methylation in colorectal cancer (CRC) has been studied previously. The aim of this study was to determine the risk sizes and variation trends of SFRP2 methylation in CRC development in Chinese populations. Subgroup meta-analysis and the least-squares curve-fitting method were carried out to analyze the risk of SFRP2 methylation in tissue, feces, and blood detection from 2221 samples, including a total of 1103 cases of CRC, 459 cases of adenoma, 257 cases of polyps, and 402 controls. The data showed that odds ratios (95% confidence intervals) between CRC and controls for tissue, feces, and blood detection were 334.01 (104.42-1068.39), 63.76 (20.62-197.63), and 133.75 (18.32-976.32), respectively. There were also significant differences between tissue and feces or blood as well as between feces and blood methylation frequency. These results showed that the risk size in tissue was much greater than that in feces and that in blood. The results pointed out that three curves in tissue, feces, and blood detection described the variation trends of methylation incidence from the control to polyp, to adenoma and to CRC, and that the variation trend of the risk size of SFRP2 methylation was synchronized with the histological evolution process of CRC. The variation trend of the risk size of SFRP2 methylation incidence is consistent with the histological evolution process of CRC. The susceptibility to SFRP2 methylation is an important biomarker in the study of early diagnosis of CRC and high-risk patients. PMID:26258809

  11. Alterations of Cyclooxygenase-2 Methylation Levels Before and After Intervention Trial to Prevent Gastric Cancer in a Chinese Population.

    PubMed

    Zhang, Yang; Zeng, Hong-Mei; Nie, Xiao-Rui; Zhang, Lian; Ma, Jun-Ling; Li, Ji-You; Pan, Kai-Feng; You, Wei-Cheng

    2016-06-01

    To explore the epigenetic mechanisms underlying the effects of anti-Helicobacter pylori (H. pylori) alone and combined with COX-2 inhibitor (celecoxib), we dynamically evaluated the associations between COX-2 methylation alterations and gastric lesion evolution during the process of interventions. In a total of 809 trial participants COX-2 methylation levels were quantitatively detected before and after treatment. The self-comparison at the same stomach site for each subject showed significant methylation alteration differences among intervention groups (P < 0.001). With placebo group as reference, COX-2 methylation levels were decreased in anti-H. pylori [OR, 3.30; 95% confidence interval (CI), 2.16-5.02], celecoxib (OR, 2.04; 95% CI, 1.36-3.07), and anti-H. pylori followed by celecoxib (OR, 2.10; 95% CI, 1.38-3.17) groups. When stratified by baseline histology, the three active arms significantly decreased COX-2 methylation levels in indefinite dysplasia/dysplasia subjects, and ORs were 3.65 (95% CI, 1.96-6.80) for anti-H. pylori, 2.43 (95% CI 1.34-4.39) for celecoxib, and 2.80 (95% CI, 1.52-5.15) for anti-H. pylori followed by celecoxib, respectively. No additive effect on COX-2 methylation was found for anti-H. pylori followed by celecoxib than two treatments alone. Compared with subjects without methylation reduction, higher opportunity for gastric lesion regression was found in subjects with decreased COX-2 methylation levels, especially for indefinite dysplasia/dysplasia subjects (OR, 1.92; 95% CI, 1.03-3.60). These findings suggest that anti-H. pylori or celecoxib treatment alone could decrease COX-2 methylation levels in gastric mucosa. COX-2 methylation alteration was associated with the regression of indefinite dysplasia/dysplasia, which might serve as a potential biomarker for chemoprevention efficacy. Cancer Prev Res; 9(6); 484-90. ©2016 AACR. PMID:27020655

  12. 2-Methyl-3-(2-methyl­phen­yl)-4-oxo-3,4-dihydro­quinazolin-8-yl 4-methyl­benzoate

    PubMed Central

    El-Azab, Adel S.; Abdel-Aziz, Alaa A.-M.; Ng, Seik Weng; Tiekink, Edward R. T.

    2012-01-01

    In the title quinazolin-4-one derivative, C24H20N2O3, both the 4-methyl­benzoate [dihedral angle = 83.90 (9)°] and 2-tolyl [87.88 (9)°] groups are almost orthogonal to the central fused ring system. These aryl groups are oriented towards the quinazolin-4-one-bound methyl group. In the crystal, mol­ecules are connected into a three-dimensional architecture by C—H⋯O, C—H⋯π and π–π [ring centroid-to-centroid separation = 3.6458 (13) Å] inter­actions. PMID:22412615

  13. Mutagenic activity associated with cooling tower waters treated with a biocide containing 5-chloro-2-methyl-4-isothiazolin-3-one

    SciTech Connect

    Woodall, G.M.; Pancorbo, O.C.; Blevins, R.D.; Ferslew, K.E.

    1987-08-01

    With the Ames Salmonella-mammalian microsome test, significant mutagenic activity was detected in cooling tower water shortly (same day) after treatment with a biocide (CL2150) containing 5-chloro-2-methyl-4-isothiazolin-3-one(5-chloro-IT). Dose-related mutagenic responses with TA97 (-S9) and TA100 (-S9) were produced with the acid fraction (extracted at pH <2 with methylene chloride) of this cooling water sample (specific mutagenic activities of 281,000 and 188,000 net revertants/L equiv of water, respectively). This mutagenic activity detected in cooling water sampled in mid-summer did not persist beyond the first day of CL2150 treatment. The mutagenic activity displayed by the cooling waters with TA97 (-S9) exceeded that associated with the extractable 5-chloro-IT concentration (determined by capillary gas chromatography-mass spectrometry). 24 references, 6 figures, 3 tables.

  14. Molecular structure and charge transfer contributions to nonlinear optical property of 2-Methyl-4-nitroaniline: A DFT study

    NASA Astrophysics Data System (ADS)

    Jasmine, G. Femina; Amalanathan, M.; Roy, S. Dawn Dharma

    2016-05-01

    The Charge transfer contributions to the second-order nonlinear optical properties of 2-Methyl-4-nitroaniline have been performed by means of DFT computation. The vibrational contribution studies of 2-Methyl-4-nitroaniline have also been performed using FTIR, FT-Raman analysis. More support on the experimental findings were added from the quantum chemical studies performed with DFT (B3LYP) method using 6-311++G(d,p)basis sets. Natural bond orbital analysis confirms the presence of intramolecular charge transfer and the hydrogen bonding interaction. The HOMO and LUMO analysis reveals the possibility of charge transfer within the molecule. The first order hyperpolarizability (α0) and related properties (β,α0 and Δα) of 2-Methyl-4-nitroaniline were calculated. In addition, molecular electrostatic potential (MEP), charge analysis also were investigated using theoretical calculations.

  15. Crystallization of lysozyme with (R)-, (S)- and (RS)-2-methyl-2,4-pentanediol

    DOE PAGESBeta

    Stauber, Mark; Jakoncic, Jean; Berger, Jacob; Karp, Jerome M.; Axelbaum, Ariel; Sastow, Dahniel; Buldyrev, Sergey V.; Hrnjez, Bruce J.; Asherie, Neer

    2015-03-01

    Chiral control of crystallization has ample precedent in the small-molecule world, but relatively little is known about the role of chirality in protein crystallization. In this study, lysozyme was crystallized in the presence of the chiral additive 2-methyl-2,4-pentanediol (MPD) separately using the R and S enantiomers as well as with a racemic RS mixture. Crystals grown with (R)-MPD had the most order and produced the highest resolution protein structures. This result is consistent with the observation that in the crystals grown with (R)-MPD and (RS)-MPD the crystal contacts are made by (R)-MPD, demonstrating that there is preferential interaction between lysozymemore » and this enantiomer. These findings suggest that chiral interactions are important in protein crystallization.« less

  16. Biogenic 2-methyl-3-buten-2-ol increases regional ozone and HOx sources

    NASA Astrophysics Data System (ADS)

    Steiner, Allison L.; Tonse, Shaheen; Cohen, Ronald C.; Goldstein, Allen H.; Harley, Robert A.

    2007-08-01

    We present the first regional-scale chemistry simulation investigating the effects of biogenic 2-methyl-3-buten-2-ol (MBO) emissions on air quality. In a central California model domain, MBO emissions have a distinctly different regional pattern than isoprene but have similar daily maxima of about 5 mg m-2 hr-1. MBO oxidation causes an increase in ozone, formaldehyde, acetone and consequently hydrogen radical production (PHOx). The addition of MBO increases the daily maximum ozone as much as 3 ppb near source regions (2-5% in rural areas) and as much as 1 ppb in the Central Valley. Formaldehyde concentrations increase by as much as 1 ppb (40%) over the Sierra Nevada Mountains, increasing the production of HOx by 10-20% and accelerating local chemistry. This indicates that inclusion of MBO and other biogenic oxygenated emissions in regional simulations in the western and southeastern United States is essential for accurate representation of ozone and HOx.

  17. Regeneration of 2-amino-2-methyl-1-propanol used for carbon dioxide absorption.

    PubMed

    Zhang, Pei; Shi, Yao; Wei, Jianwen; Zhao, Wei; Ye, Qing

    2008-01-01

    To improve the efficiency of the carbon dioxide cycling process and to reduce the regeneration energy consumption, a sterically hindered amine of 2-amino-2-methyl-1-propranol (AMP) was investigated to determine its regeneration behavior as a CO2 absorbent. The CO2 absorption and amine regeneration characteristics were experimentally examined under various operating conditions. The regeneration efficiency increased from 86.2% to 98.3% during the temperature range of 358 to 403 K. The most suitable regeneration temperature for AMP was 383 K, in this experiment condition, and the regeneration efficiency of absorption/regenerationruns descended from 98.3% to 94.0%. A number of heat-stable salts (HSS) could cause a reduction in CO2 absorption capacity and regeneration efficiency. The results indicated that aqueous AMP was easier to regenerate with less loss of absorption capacity than other amines, such as, monoethanolamine (MEA), diethanolamine (DEA), diethylenetriamine (DETA), and N-methyldiethanolamine (MDEA). PMID:18572520

  18. Crystallization of lysozyme with (R)-, (S)- and (RS)-2-methyl-2,4-pentanediol

    PubMed Central

    Stauber, Mark; Jakoncic, Jean; Berger, Jacob; Karp, Jerome M.; Axelbaum, Ariel; Sastow, Dahniel; Buldyrev, Sergey V.; Hrnjez, Bruce J.; Asherie, Neer

    2015-01-01

    Chiral control of crystallization has ample precedent in the small-molecule world, but relatively little is known about the role of chirality in protein crystallization. In this study, lysozyme was crystallized in the presence of the chiral additive 2-methyl-2,4-pentanediol (MPD) separately using the R and S enantiomers as well as with a racemic RS mixture. Crystals grown with (R)-MPD had the most order and produced the highest resolution protein structures. This result is consistent with the observation that in the crystals grown with (R)-MPD and (RS)-MPD the crystal contacts are made by (R)-MPD, demonstrating that there is preferential interaction between lysozyme and this enantiomer. These findings suggest that chiral interactions are important in protein crystallization. PMID:25760593

  19. The Limits of Template-Directed Synthesis with Nucleoside-5'-Phosphoro(2-Methyl) Imidazolides

    NASA Technical Reports Server (NTRS)

    Hill, Aubrey R., Jr.; Orgel, Leslie E.; Wu, Taifeng

    1993-01-01

    In earlier work we have shown that C-rich templates containing isolated A, T or G residues and short oligo(G) sequences can be copied effectively using nucleoside-5'-phosphoro(2-methyl)imidazolides as substrates. We now show that isolated A or T residues within an oligo(G) sequence are a complete block to copying and that an isolated C residue is copied inefficiently. Replication is possible only if there are two complementary oligonucleotides each of which acts as a template to facilitate the synthesis of the other. We emphasize the severity of the problems that need to be overcome to make possible non-enzymatic replication in homogeneous aqueous solution. We conclude that an efficient catalyst was involved in the origin of polynucleotide replication.

  20. Biochemical properties of a newly synthesized H(+)/K(+) ATPase inhibitor, 1-(2-methyl-4-methoxyphenyl)-4-.

    PubMed

    Cheon, H G; Lim, H; Lee, D H

    2001-01-01

    A new compound, 1-(2-methyl-4-methoxyphenyl)-4-[(3-hydroxypropyl)amino]-6-methyl-2,3-dihydropyrrolo[3,2-c]quinoline (DBM-819), inhibited gastric H(+)/K(+) ATPase in the rabbit (EC 3.6.1.3) with an IC(50) value of 5 microM. However, DBM-819 was a weak inhibitor of kidney Na(+)/K(+) ATPase in the dog, indicating that it has selectivity for the gastric H(+)/K(+) ATPase. The inhibition was reversible and non-competitive with respect to the activating cation K(+). The presence of dithiothreitol did not protect the H(+)/K(+) ATPase from inactivation. The inhibition by DBM-819 was potentiated by acid pretreatment of the compound, suggesting that DBM-819 is converted into a more active intermediate under acidic conditions. The results suggest that DBM-819 is a potent, selective and reversible inhibitor of gastric H(+)/K(+) ATPase, and that the essential cysteine residue may not be involved in the DBM-819-mediated inactivation of gastric H(+)/K(+) ATPase. PMID:11137874

  1. Diacetylene and Polydiacetylene Derivatives of 2-Methyl-4-Nitroaniline for Second-Harmonic Generation

    NASA Technical Reports Server (NTRS)

    Paley, M. S.; Frazier, D. O.; McManus, S. P.; Zutaut, S. E.; Sanghadasa, M.

    1993-01-01

    A novel diacetylene derivative of 2-Methyl-4-NitroAniline (MNA), a well-known material for Second-Harmonic Generation (SHG), is synthesized. This monomer DiAcetylene MethylNitroAniline, (DAMNA) is characterized by means of the Kurtz technique at 1064 nm and is found to have an SHG powder efficiency 62.5 % that of MNA itself. Thin crystalline films of DAMNA are grown onto quartz, Teflon, and Kapton substrates by means of vapor deposition in vacuum. These films are then polymerized in the solid state by exposure to long-wavelength UV radiation to give crystalline polydiacetylene thin films (PDAMNA). The films are next characterized for SHG, using an unpolymerized DAMNA film as a reference. Interestingly, films grown onto Teflon exhibit greater orientation and significantly greater SHG than those grown onto quartz and Kapton. This result is promising in that it demonstrates the potential of PDAMNA as both a crystalline and polymeric material for SHG applications, in which highly oriented thin films are desired. Computational modeling (usingAM1) is also carried out on DAMNA and is compared to the experimental results.

  2. Organosulfates as Tracers for Secondary Organic Aerosol (SOA) Formation from 2-Methyl-3-Buten-2-ol (MBO) in the Atmosphere

    PubMed Central

    2012-01-01

    2-Methyl-3-buten-2-ol (MBO) is an important biogenic volatile organic compound (BVOC) emitted by pine trees and a potential precursor of atmospheric secondary organic aerosol (SOA) in forested regions. In the present study, hydroxyl radical (OH)-initiated oxidation of MBO was examined in smog chambers under varied initial nitric oxide (NO) and aerosol acidity levels. Results indicate measurable SOA from MBO under low-NO conditions. Moreover, increasing aerosol acidity was found to enhance MBO SOA. Chemical characterization of laboratory-generated MBO SOA reveals that an organosulfate species (C5H12O6S, MW 200) formed and was substantially enhanced with elevated aerosol acidity. Ambient fine aerosol (PM2.5) samples collected from the BEARPEX campaign during 2007 and 2009, as well as from the BEACHON-RoMBAS campaign during 2011, were also analyzed. The MBO-derived organosulfate characterized from laboratory-generated aerosol was observed in PM2.5 collected from these campaigns, demonstrating that it is a molecular tracer for MBO-initiated SOA in the atmosphere. Furthermore, mass concentrations of the MBO-derived organosulfate are well correlated with MBO mixing ratio, temperature, and acidity in the field campaigns. Importantly, this compound accounted for an average of 0.25% and as high as 1% of the total organic aerosol mass during BEARPEX 2009. An epoxide intermediate generated under low-NO conditions is tentatively proposed to produce MBO SOA. PMID:22849588

  3. Canopy Level Emissions of 2-methyl-3-buten-2-ol, monoterpenes, and sesquiterpenes from a Pinus taeda Experimental Plantation

    EPA Science Inventory

    Emissions of biogenic volatile organic compounds (BVOC) observed during 2007 from a Pinus taeda experimental plantation in Central North Carolina are compared with model estimates from MEGAN 2.1. Relaxed Eddy Accumulation (REA) estimates of 2-methyl-3-buten-2-ol (MBO) fluxes are ...

  4. Free volume model for the unexpected effect of C2-methylation on the properties of imidazolium ionic liquids.

    PubMed

    Chen, Zheng Jian; Lee, Jong-Min

    2014-03-13

    For 1-alkyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imides and their cationic C2-methylated isomers, that is, [C(n)MIm]NTf2 and [C(n-1)DMIm]NTf2 (n = 3-8), the latter always has much higher viscosities (∼1.66 times at 25 °C) than the former. This finding is unexpected and contrary to the loss of the predominant hydrogen bonding between the cation and anion, caused by the C2-methylation in the imidazolium ionic liquids. In the present study, we propose a free volume model to explain this mysterious phenomenon. For the isomeric pairs, [C(n-1)DMIm]NTf2 was found to possess less unoccupied (free) volume than [C(n)MIm]NTf2 by ∼4.5 mL mol(-1) determined by both Fürth's surface tension and molar volume methods, and the free volume difference can be quantitatively correlated with the C2-methylation effect on viscosity. Generally, the less free volume in [C(n-1)DMIm]NTf2 relative to [C(n)MIm]NTf2 reduces the number of the hole carriers for molecular transport with a resulting increase in viscosity. Besides, the free volume model can also be applied to account for the C2-methylation effect on other properties, such as conductivity, surface tension, density, and refractive index. PMID:24576309

  5. Organosulfates as Tracers for Secondary Organic Aerosol (SOA) Formation from 2-Methyl-3-Buten-2 ol (MBO) in the Atmosphere

    EPA Science Inventory

    2-Methyl-3-buten-2-ol (MBO) is an important biogenic volatile organic compound (BVOC) emitted by pine trees and a potential precursor of atmospheric secondary organic aerosol (SOA) in forested regions. In the present study, hydroxyl radical (OH)-initiated oxidation of MBO was exa...

  6. Statistical thermodynamics of 1-butanol, 2-methyl-1-propanol, and butanal.

    PubMed

    Seal, Prasenjit; Papajak, Ewa; Yu, Tao; Truhlar, Donald G

    2012-01-21

    The purpose of the present investigation is to calculate partition functions and thermodynamic quantities, viz., entropy, enthalpy, heat capacity, and Gibbs free energies, for 1-butanol, 2-methyl-1-propanol, and butanal in the vapor phase. We employed the multi-structural (MS) anharmonicity method and electronic structure calculations including both explicitly correlated coupled cluster theory and density functional theory. The calculations are performed using all structures for each molecule and employing both the local harmonic approximation (MS-LH) and the inclusion of torsional anharmonicity (MS-T). The results obtained from the MS-T calculations are in excellent agreement with experimental data taken from the Thermodynamics Research Center data series and the CRC Handbook of Chemistry and Physics, where available. They are also compared with Benson's empirical group additivity values, where available; in most cases, the present results are more accurate than the group additivity values. In other cases, where experimental data (but not group additivity values) are available, we also obtain good agreement with experiment. This validates the accuracy of the electronic structure calculations when combined with the MS-T method for estimating the thermodynamic properties of systems with multiple torsions, and it increases our confidence in the predictions made with this method for molecules and temperatures where experimental or empirical data are not available. PMID:22280759

  7. Performance of tris(2-methyl-8-quinolinolato)aluminum as fluorescent anionophore.

    PubMed

    Yuchi, Akio; Hiramatsu, Hiroaki; Ohara, Miyuki; Ohata, Nayumi

    2003-08-01

    An X-ray crystallographic study demonstrated that the tris complex of Al3+ with 2-methyl-8-quinolinol (Hmq), [Al(mq)3], had a discrete octahedral geometry in a meridional configuration with respect to mq-; the Al-N bonds were appreciably elongated. In organic solvents, the complex reacted with water to give a lower species of a mu-oxo dimer, [Al2O(mq)4], and a protonated ligand, depending on the concentrations of water and of excess ligand. None of Cl-, Br-, I-, ClO4-, and CH3COO- showed any reactions with [Al(mq)3]. The anions having high affinities to Al3+, such as H2PO4- and F-, replaced all the ligand. The anion having a lower affinity, HSO4-, exclusively formed a mixed-ligand complex of [Al(mq)2HSO4], which had a more intense fluorescence than the others. In contrast, the corresponding 8-quinolinol (Hq) complex, [Alq3], showed no reactions with any anions. PMID:12945673

  8. DFT simulations and vibrational spectra of 2-amino-2-methyl-1,3-propanediol

    NASA Astrophysics Data System (ADS)

    Renuga Devi, T. S.; Sharmi kumar, J.; Ramkumaar, G. R.

    2014-12-01

    The FTIR and FT-Raman spectra of 2-amino-2-methyl-1,3-propanediol were recorded in the regions 4000-400 cm-1 and 4000-50 cm-1 respectively. The structural and spectroscopic data of the molecule in the ground state were calculated using Hartee-Fock and density functional method (B3LYP) with the augmented-correlation consistent-polarized valence double zeta (aug-cc-pVDZ) basis set. The most stable conformer was optimized and the structural and vibrational parameters were determined based on this. The complete assignments were performed on the basis of the Potential Energy Distribution (PED) of the vibrational modes, calculated using Vibrational Energy Distribution Analysis (VEDA) 4 program. With the observed FTIR and FT-Raman data, a complete vibrational assignment and analysis of the fundamental modes of the compound were carried out. Thermodynamic properties and Mulliken charges were calculated using both Hartee-Fock and density functional method using the aug-cc-pVDZ basis set and compared. The calculated HOMO-LUMO energy gap revealed that charge transfer occurs within the molecule. 1H and 13C NMR chemical shifts of the molecule were calculated using Gauge-Independent Atomic Orbital (GIAO) method and were compared with experimental results.

  9. Dispersed Fluorescence Spectroscopy of Jet-Cooled Isobutoxy and 2-Methyl-1-butoxy Radicals.

    PubMed

    Reza, Md Asmaul; Paul, Anam C; Reilly, Neil J; Alam, Jahangir; Liu, Jinjun

    2016-09-01

    We report dispersed fluorescence (DF) spectra of the isobutoxy and 2-methyl-1-butoxy radicals produced by photolysis of corresponding nitrites in supersonic jet expansion. Different vibrational structures have been observed in the DF spectra when different vibronic bands in the laser-induced fluorescence (LIF) spectra of each radical were pumped, which suggests that those vibronic bands be assigned to different conformers. Spectra simulated using calculated vibrational frequencies and Franck-Condon factors well reproduce the experimentally observed ones and support the assignment of the vibronic bands in the LIF spectra to the two lowest-energy conformers of each radical. DF spectra obtained by pumping the B̃ ← X̃ origin bands of the LIF spectra are dominated by CO stretch progressions because of the large difference in CO bond length between the ground (X̃) and the second excited (B̃) electronic states. Furthermore, with non-CO stretch bands pumped, the DF spectra are dominated by progressions of combination bands of the CO stretch and the pumped modes as a result of Duschinsky mixing. Ã-X̃ separation of both conformers of the isobutoxy radical has also been determined in the experiment. PMID:27504673

  10. Synthesis and cytotoxic activity of N-((2-methyl-4(3H)-quinazolinon-6-yl)methyl)dithiocarbamates.

    PubMed

    Cao, Sheng-Li; Wang, Yao; Zhu, Lin; Liao, Ji; Guo, Yan-Wen; Chen, Lin-Lin; Liu, Hong-Qin; Xu, Xingzhi

    2010-09-01

    A series of N-((2-methyl-4(3H)-quinazolinon-6-yl)methyl)dithiocarbamates 5a-w were synthesized and evaluated for their cytotoxic activity against five human cancer cell lines. We found that compound 5k inhibited proliferation of A549, MCF-7, HeLa, HT29 and HCT-116 cells with IC(50) values of 5.44, 7.15, 12.16, 10.35 and 11.44 microM, respectively. Compound 5i was the most potent with an IC(50) value of 3.65 microM against proliferation of MCF-7 cells, while 5n was the most potent with an IC(50) value of 5.09 microM against proliferation of A549 cells. Cell cycle analysis showed that both 5i and 5k arrested A549 cells at S and G2/M phases, suggesting that these compounds act through mechanisms different from 5-fluorouracil, which arrests cells at S phase only. PMID:20538385

  11. SKA2 Methylation is associated with Decreased Prefrontal Cortical Thickness and Greater PTSD Severity among Trauma-Exposed Veterans

    PubMed Central

    Sadeh, Naomi; Spielberg, Jeffrey M.; Logue, Mark W.; Wolf, Erika J.; Smith, Alicia K.; Lusk, Joanna; Hayes, Jasmeet P.; Sperbeck, Emily; Milberg, William P.; McGlinchey, Regina E.; Salat, David H.; Carter, Weleetka C.; Stone, Annjanette; Schichman, Steven A.; Humphries, Donald E.; Miller, Mark W.

    2015-01-01

    Methylation of the SKA2 gene has recently been identified as a promising biomarker of suicide risk. Based on this finding, we examined associations between SKA2 methylation, cortical thickness, and psychiatric phenotypes linked to suicide in trauma-exposed veterans. 200 trauma-exposed white non-Hispanic veterans of the recent conflicts in Iraq and Afghanistan (91% male) underwent clinical assessment and had blood drawn for genotyping and methylation analysis. 145 participants also had neuroimaging data available. Based on previous research, we examined DNA methylation at the CpG locus cg13989295 as well as DNA methylation adjusted for genotype at the methylation-associated SNP (rs7208505) in relationship to whole-brain cortical thickness, posttraumatic stress disorder symptoms (PTSD), and depression symptoms. Whole-brain vertex-wise analyses identified three clusters in prefrontal cortex that were associated with genotype-adjusted SKA2 DNA methylation (methylationadj). Specifically, DNA methylationadj was associated with bilateral reductions of cortical thickness in frontal pole and superior frontal gyrus, and similar effects were found in the right orbitofrontal cortex and right inferior frontal gyrus. PTSD symptom severity was positively correlated with SKA2 DNA methylationadj and negatively correlated with cortical thickness in these regions. Mediation analyses showed a significant indirect effect of PTSD on cortical thickness via SKA2 methylation status. Results suggest that DNA methylationadj of SKA2 in blood indexes stress-related psychiatric phenotypes and neurobiology, pointing to its potential value as a biomarker of stress exposure and susceptibility. PMID:26324104

  12. Experimental and Kinetic Modeling Study of 2-Methyl-2-Butene: Allylic Hydrocarbon Kinetics.

    PubMed

    Westbrook, Charles K; Pitz, William J; Mehl, Marco; Glaude, Pierre-Alexandre; Herbinet, Olivier; Bax, Sarah; Battin-Leclerc, Frederique; Mathieu, Olivier; Petersen, Eric L; Bugler, John; Curran, Henry J

    2015-07-16

    Two experimental studies have been carried out on the oxidation of 2-methyl-2-butene, one measuring ignition delay times behind reflected shock waves in a stainless steel shock tube, and the other measuring fuel, intermediate, and product species mole fractions in a jet-stirred reactor (JSR). The shock tube ignition experiments were carried out at three different pressures, approximately 1.7, 11.2, and 31 atm, and at each pressure, fuel-lean (ϕ = 0.5), stoichiometric (ϕ = 1.0), and fuel-rich (ϕ = 2.0) mixtures were examined, with each fuel/oxygen mixture diluted in 99% Ar, for initial postshock temperatures between 1330 and 1730 K. The JSR experiments were performed at nearly atmospheric pressure (800 Torr), with stoichiometric fuel/oxygen mixtures with 0.01 mole fraction of 2M2B fuel, a residence time in the reactor of 1.5 s, and mole fractions of 36 different chemical species were measured over a temperature range from 600 to 1150 K. These JSR experiments represent the first such study reporting detailed species measurements for an unsaturated, branched hydrocarbon fuel larger than iso-butene. A detailed chemical kinetic reaction mechanism was developed to study the important reaction pathways in these experiments, with particular attention on the role played by allylic C-H bonds and allylic pentenyl radicals. The results show that, at high temperatures, this olefinic fuel reacts rapidly, similar to related alkane fuels, but the pronounced thermal stability of the allylic pentenyl species inhibits low temperature reactivity, so 2M2B does not produce "cool flames" or negative temperature coefficient behavior. The connections between olefin hydrocarbon fuels, resulting allylic fuel radicals, the resulting lack of low-temperature reactivity, and the gasoline engine concept of octane sensitivity are discussed. PMID:25822578

  13. SKA2 methylation is associated with decreased prefrontal cortical thickness and greater PTSD severity among trauma-exposed veterans.

    PubMed

    Sadeh, N; Spielberg, J M; Logue, M W; Wolf, E J; Smith, A K; Lusk, J; Hayes, J P; Sperbeck, E; Milberg, W P; McGlinchey, R E; Salat, D H; Carter, W C; Stone, A; Schichman, S A; Humphries, D E; Miller, M W

    2016-03-01

    Methylation of the SKA2 (spindle and kinetochore-associated complex subunit 2) gene has recently been identified as a promising biomarker of suicide risk. Based on this finding, we examined associations between SKA2 methylation, cortical thickness and psychiatric phenotypes linked to suicide in trauma-exposed veterans. About 200 trauma-exposed white non-Hispanic veterans of the recent conflicts in Iraq and Afghanistan (91% male) underwent clinical assessment and had blood drawn for genotyping and methylation analysis. Of all, 145 participants also had neuroimaging data available. Based on previous research, we examined DNA methylation at the cytosine-guanine locus cg13989295 as well as DNA methylation adjusted for genotype at the methylation-associated single nucleotide polymorphism (rs7208505) in relationship to whole-brain cortical thickness, posttraumatic stress disorder symptoms (PTSD) and depression symptoms. Whole-brain vertex-wise analyses identified three clusters in prefrontal cortex that were associated with genotype-adjusted SKA2 DNA methylation (methylationadj). Specifically, DNA methylationadj was associated with bilateral reductions of cortical thickness in frontal pole and superior frontal gyrus, and similar effects were found in the right orbitofrontal cortex and right inferior frontal gyrus. PTSD symptom severity was positively correlated with SKA2 DNA methylationadj and negatively correlated with cortical thickness in these regions. Mediation analyses showed a significant indirect effect of PTSD on cortical thickness via SKA2 methylation status. Results suggest that DNA methylationadj of SKA2 in blood indexes stress-related psychiatric phenotypes and neurobiology, pointing to its potential value as a biomarker of stress exposure and susceptibility. PMID:26324104

  14. Photodissociation dynamics of 2-nitropropane and 2-methyl-2-nitropropane at 248 and 193 nm.

    PubMed

    Sengupta, Sumana; Indulkar, Yogesh; Kumar, Awadhesh; Dhanya, Suresh; Naik, Prakash Dattatray; Bajaj, Parma Nand

    2008-12-11

    Dynamics of formation of electronically excited NO2 and formation of OH fragment, during photo dissociation of 2-nitropropane (NP) and 2-methyl-2-nitropropane (MNP), were investigated at 193 and 248 nm. The radiative lifetime of the electronically excited NO2 fragment, observed at 193 nm, was measured to be 1.2 ( 0.1 micros and the rate coefficient of quenching of its emission by MNP was measured as (2.7 ( 0.1) x 10(-10) molecule(-1) cm3 s(-1). Formation of the ground electronic state of OH was confirmed in both molecules. State selective laser induced fluorescence technique was used to detect the nascent OH (X 2Pi, v'', J'') fragments in different ro-vibrational states, and to obtain information on energy partitioning. Though MNP and NP differ in the types of the available H atoms, the dynamics of OH formation is found to be the same in both. The relative population in different rotational states does not follow Boltzmann equilibrium distribution in both the molecules at 193 and 248 nm. The translational energies of the OH fragments, calculated from the Doppler width, are 21.2 ( 7.2 and 25.0 ( 2.5 kcal mol-1 for NP at 248 and 193 nm, respectively. The translational energies of the OH fragments, in the case of MNP, are found to be lower, 17.5 ( 4.1 and 22.0 ( 3.2 kcal mol-1,respectively, at 248 nm 193 nm. These results are compared with the earlier reports on photodissociation of nitromethane (NM), nitroethane (NE), and other nitroalkanes. All possible dissociation pathways of these molecules--NM, NE, NP, and MNPs leading to the formation of the OH fragment were investigated computationally, with geometry optimization at the B3LYP/6-311+G(d,p) level and energy calculation at the MP4(SDQ)/6-311+G (d,p) level. The results suggest that in NM, OH is formed after isomerization to CH2N(OH)O, whereas in all other cases OH is formed from HONO, a primary product of molecular elimination of nitroalkanes, formed with sufficient internal energy. PMID:19053556

  15. 2-Methyl-3-(2-methyl­phen­yl)-4-oxo-3,4-dihydro­quinazolin-8-yl benzoate

    PubMed Central

    El-Azab, Adel S.; Abdel-Aziz, Alaa A.-M.; Ng, Seik Weng; Tiekink, Edward R. T.

    2012-01-01

    In the title quinazolin-4-one derivative, C23H18N2O3, both the benzoate [dihedral angle = 79.99 (6)°] and the 2-tolyl [89.02 (7)°] groups are close to orthogonal to the central fused ring system. Both aryl groups are orientated towards the quinazolin-4-one-bound methyl group. In the crystal, mol­ecules are connected into a three-dimensional architecture by C—H⋯O, C—H⋯N and C—H⋯π inter­actions. PMID:22412614

  16. Cloning and analysis of 1-hydroxy-2-methyl-2-(E)-butenyl-4-diphosphate reductase genes HsHDR1 and HsHDR2 in Huperzia serrate

    PubMed Central

    Lv, Haizhou; Zhang, Xin; Liao, Baosheng; Liu, Wanjing; He, Liu; Song, Jingyuan; Sun, Chao; Luo, Hongmei; Chen, Shilin

    2015-01-01

    We cloned and analyzed the two genes of the 1-hydroxy-2-methyl-2-(E)-butenyl-4-diphosphate reductase (HDR) gene family from Huperzia serrate. The two transcripts coding HDR, named HsHDR1 and HsHDR2, were discovered in the transcriptome dataset of H. serrate and were cloned by reverse transcription-polymerase chain reaction (RT-PCR). The physicochemical properties, protein domains, protein secondary structure, and 3D structure of the putative HsHDR1 and HsHDR2 proteins were analyzed. The full-length cDNA of the HsHDR1 gene contained 1431 bp encoding a putative protein with 476 amino acids, whereas the HsHDR2 gene contained 1428 bp encoding a putative protein of 475 amino acids. These two proteins contained the conserved domain of 1-hydroxy-2-methyl-2-(E)-butenyl-4-diphosphate reductase (PF02401), but without the transmembrane region and signal peptide. The most abundant expression of HsHDR1 and HsHDR2 was detected in H. serrate roots, followed by the stems and leaves. Our results provide a foundation for exploring the function of HsHDR1 and HsHDR2 in terpenoid and sterol biosynthesis in Huperziaceae plants. PMID:26713274

  17. 40 CFR 721.10556 - Poly(oxy-1,2-ethanediyl), .alpha.- (2-methyl-2-propen-1-yl) -.omega.-hydroxy-,C12-15-alkyl ethers.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Poly(oxy-1,2-ethanediyl), .alpha.- (2...-ethanediyl), .alpha.- (2-methyl-2-propen-1-yl) -.omega.-hydroxy-,C12-15-alkyl ethers. (a) Chemical substance...-ethanediyl), .alpha.- (2-methyl-2-propen-1-yl) -.omega.-hydroxy-,C12-15-alkyl ethers (PMN P-06-450; CAS...

  18. 40 CFR 721.10557 - Poly(oxy-1,2-ethanediyl), .alpha.- (2-methyl-2-propen-1-yl) -.omega.-hydroxy-,C10-16-alkyl ethers.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Poly(oxy-1,2-ethanediyl), .alpha.- (2...-ethanediyl), .alpha.- (2-methyl-2-propen-1-yl) -.omega.-hydroxy-,C10-16-alkyl ethers. (a) Chemical substance...-ethanediyl), .alpha.- (2-methyl-2-propen-1-yl) -.omega.-hydroxy-,C10-16-alkyl ethers (PMN P-06-451; CAS...

  19. 40 CFR 721.10556 - Poly(oxy-1,2-ethanediyl), .alpha.- (2-methyl-2-propen-1-yl) -.omega.-hydroxy-,C12-15-alkyl ethers.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Poly(oxy-1,2-ethanediyl), .alpha.- (2...-ethanediyl), .alpha.- (2-methyl-2-propen-1-yl) -.omega.-hydroxy-,C12-15-alkyl ethers. (a) Chemical substance...-ethanediyl), .alpha.- (2-methyl-2-propen-1-yl) -.omega.-hydroxy-,C12-15-alkyl ethers (PMN P-06-450; CAS...

  20. 40 CFR 721.10558 - Poly(oxy-1,2-ethanediyl), .alpha.- (2-methyl-2-propen-1-yl) -.omega.-hydroxy-,C12-16-alkyl ethers.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Poly(oxy-1,2-ethanediyl), .alpha.- (2...-ethanediyl), .alpha.- (2-methyl-2-propen-1-yl) -.omega.-hydroxy-,C12-16-alkyl ethers. (a) Chemical substance...-ethanediyl), .alpha.- (2-methyl-2-propen-1-yl) -.omega.-hydroxy-,C12-16-alkyl ethers (PMN P-06-452; CAS...

  1. 40 CFR 721.10557 - Poly(oxy-1,2-ethanediyl), .alpha.- (2-methyl-2-propen-1-yl) -.omega.-hydroxy-,C10-16-alkyl ethers.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Poly(oxy-1,2-ethanediyl), .alpha.- (2...-ethanediyl), .alpha.- (2-methyl-2-propen-1-yl) -.omega.-hydroxy-,C10-16-alkyl ethers. (a) Chemical substance...-ethanediyl), .alpha.- (2-methyl-2-propen-1-yl) -.omega.-hydroxy-,C10-16-alkyl ethers (PMN P-06-451; CAS...

  2. 40 CFR 721.10558 - Poly(oxy-1,2-ethanediyl), .alpha.- (2-methyl-2-propen-1-yl) -.omega.-hydroxy-,C12-16-alkyl ethers.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Poly(oxy-1,2-ethanediyl), .alpha.- (2...-ethanediyl), .alpha.- (2-methyl-2-propen-1-yl) -.omega.-hydroxy-,C12-16-alkyl ethers. (a) Chemical substance...-ethanediyl), .alpha.- (2-methyl-2-propen-1-yl) -.omega.-hydroxy-,C12-16-alkyl ethers (PMN P-06-452; CAS...

  3. Identification of a novel selective peroxisome proliferator-activated receptor alpha agonist, 2-methyl-2-(4-{3-[1-(4-methylbenzyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl]propyl}phenoxy)propanoic acid (LY518674), that produces marked changes in serum lipids and apolipoprotein A-1 expression.

    PubMed

    Singh, Jai Pal; Kauffman, Raymond; Bensch, William; Wang, Guoming; McClelland, Pam; Bean, James; Montrose, Chahrzad; Mantlo, Nathan; Wagle, Asavari

    2005-09-01

    Low high-density lipoprotein-cholesterol (HDL-c) is an important risk factor of coronary artery disease (CAD). Optimum therapy for raising HDL-c is still not available. Identification of novel HDL-raising agents would produce a major impact on CAD. In this study, we have identified a potent (IC50 approximately 24 nM) and selective peroxisome proliferator-activated receptor alpha (PPARalpha) agonist, 2-methyl-2-(4-{3-[1-(4-methylbenzyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl]propyl}phenoxy)propanoic acid (LY518674). In human apolipoprotein A-1 (apoA-1) transgenic mice, LY518674 produced a dose-dependent increase in serum HDL-c, resulting in 208 +/- 15% elevation at optimum dose. A new synthesis of apoA-1 contributed to the increase in HDL-c. LY518674 increased apoA-1 mRNA levels in liver. Moreover, liver slices from animals treated with LY518674 secreted 3- to 6-fold more apoA-1 than control liver slices. In cultured hepatocytes, LY518674 produced 50% higher apoA-1 secretion, which was associated with increase in radiolabeled methionine incorporation in apoA-1. Thus, LY518674 is a potent and selective PPARalpha agonist that produced a much greater increase in serum HDL-c than the known fibrate drugs. The increase in HDL-c was associated with de novo synthesis of apoA-1. PMID:15933217

  4. 2-{[2-Methyl-3-(2-methyl­phen­yl)-4-oxo-3,4-dihydro­quinazolin-8-yl]­oxy}acetonitrile

    PubMed Central

    El-Azab, Adel S.; Abdel-Aziz, Alaa A.-M.; Al-Omar, Mohamed A.; Ng, Seik Weng; Tiekink, Edward R. T.

    2012-01-01

    In the title compound, C18H15N3O2, the fused ring system is almost planar [the dihedral angle between the six-membered rings is 1.81 (6)°]. The 2-tolyl ring is approximately orthogonal to this plane [dihedral angle = 83.03 (7)°] as is the acetonitrile group [C—O—C—C torsion angle = 79.24 (14)°] which is also syn to the methyl substituent of the tolyl group. In the crystal, supra­molecular layers are formed in the bc plane mediated by C—H⋯O, C—H⋯N and C—H⋯π inter­actions. The tolyl group is disordered over two positions in a 0.852 (3):0.148 (3) ratio. PMID:22798783

  5. 8-Benz­yloxy-2-methyl-3-(2-methyl­phenyl)quinazolin-4(3H)-one

    PubMed Central

    El-Azab, Adel S.; Abdel-Aziz, Alaa A.-M.; Ng, Seik Weng; Tiekink, Edward R. T.

    2012-01-01

    In the title methaqua­lone analogue, C23H20N2O2, the planes of the terminal aromatic rings [dihedral angle between them = 64.52 (7)°] approximately face the fused-ring methyl group and both are twisted with respect to the pyrimidine plane (r.m.s. deviation = 0.028 Å), forming dihedral angles of 86.9 (3) (with the 2-tolyl ring) and 65.57 (7)°. The 2-tolyl residue is disordered over two almost coplanar but opposite orientations with the major component having a site-occupancy factor of 0.893 (3). The three-dimensional crystal packing is consolidated by C—H⋯O, C—H⋯π and π–π [2-tol­yl–2-tolyl centroid–centroid distance = 3.8099 (6) Å] inter­actions. PMID:22412719

  6. Biosynthesis of rhodiocyanosides in Lotus japonicus: rhodiocyanoside A is synthesized from (Z)-2-methylbutanaloxime via 2-methyl-2-butenenitrile.

    PubMed

    Saito, Shigeki; Motawia, Mohammed Saddik; Olsen, Carl Erik; Møller, Birger Lindberg; Bak, Søren

    2012-05-01

    Lotus japonicus contains the two cyanogenic glucosides, linamarin and lotaustralin, and the non cyanogenic hydroxynitriles, rhodiocyanoside A and D, with rhodiocyanoside A as the major rhodiocyanoside. Rhodiocyanosides are structurally related to cyanogenic glucosides but are not cyanogenic. In vitro administration of intermediates of the lotaustralin pathway to microsomes prepared from selected L. japonicus accessions identified 2-methyl-2-butenenitrile as an intermediate in the rhodiocyanoside biosynthetic pathway. In vitro inhibitory studies with carbon monoxide and tetcyclacis indicate that the conversion of (Z)-2-methylbutanal oxime to 2-methyl-2-butenenitrile is catalyzed by cytochrome P450(s). Carbon monoxide inhibited cyanogenic glucosides as well as rhodiocyanosides synthesis, but inhibition of the latter pathway was much stronger. These results demonstrate that the cyanogenic glucoside and rhodiocyanosides pathways share CYP79Ds to obtain (Z)-2-methylbutanaloxime from l-isoleucine, whereas the subsequent conversions are catalyzed by different P450s. The aglycon of rhodiocyanoside A forms the cyclic product 3-methyl-2(5H)-furanone. Furanones are known to possess antimicrobial properties indicating that rhodiocyanoside A may have evolved to serve as a phytoanticipin that following β-glucosidase activation and cyclization of the aglycone formed, give rise to a potent defense compound. PMID:22385904

  7. Tris[4-bromo-2-(methyl­imino­meth­yl)phenolato-κ2 N,O]cobalt(III)

    PubMed Central

    Huang, Qiu-Ping; Zhang, Chun-Lian; Zhao, Ru-Xia; Yang, Li; Jiang, Xi-Fu

    2013-01-01

    In the title compound, [Co(C8H7BrNO)3], the CoIII ion is coordinated in a slightly distorted octa­hedral environment by three N atoms and three O atoms from three bidentate 4-bromo-2-(methyl­imino­meth­yl)phenolate ligands. The dihedral angles between the benzene rings are 82.6 (2), 57.1 (2) and 62.9 (2)°. In the crystal, mol­ecules are linked by pairs of weak C—H⋯Br hydrogen bonds, forming inversion dimers. PMID:24454033

  8. Polycyclic aromatic hydrocarbons are associated with insulin receptor substrate 2 methylation in adipose tissues of Korean women.

    PubMed

    Kim, Young Hun; Lee, Yoon Soon; Lee, Duk Hee; Kim, Dong Sun

    2016-10-01

    Polycyclic aromatic hydrocarbons (PAHs) are highly lipid soluble and are an increasing concern for general populations given their various adverse health effects, including obesity-related metabolic dysfunction. DNA methylation can act as a downstream effector for the biological effects of environmental exposures, but whether PAHs influence DNA methylation is unclear. To test for possible adverse effects of PAHs on adipose tissue (AT), we determined the promoter methylation status of 12 genes involved in glucose and lipid metabolism (CS, GLUT4, IR, IRS1, IRS2, LIPIN1, MCAD, PCK1, PCK2, PPARGC1Β, SDHA, and SREBP1) in visceral AT of Korean women by using methylation-specific PCR (MSP). IRS2 methylation alone was significantly associated with concentrations of individual PAH chemicals. When the PAH summary measure was used, the odds ratios of IRS2 hypermethylation across quartile of the PAH summary measure were 1, 1.7, 2.0, and 11.2 (95% confidence interval: 1.5-84.0) after adjusting for age and BMI (P trend=0.02). The strength of association between PAH summary measure and IRS2 hypermethylation was as similar as that of BMI. Collectively, these results suggested that lipophilic PAHs might be contributing factors to the pathogenesis of insulin resistance through methylation-mediated suppression of the IRS2 gene. However, further studies with large sample size are needed to confirm our findings. PMID:27236571

  9. Alumina-supported bimetallics of palladium alloyed with germanium, tin, lead, or antimony from organometallic precursors. II. Gas-phase hydrogenation of 2-methyl-1-buten-3-yne (valylene) and 2-methyl-1,3-butadiene (isoprene)

    SciTech Connect

    Aduriz, H.R.; Bodnariuk, P. ); Coq, B.; Figueras, F. )

    1991-05-01

    A series of PdGe, PdSb, PdSn, and PdPb/{alpha}{minus}Al{sub 2}O{sub 3} catalysts, prepared by the controlled surface reaction (CSR) technique from organometallic precursors have been tested in the gas-phase hydrogenation of 2-methyl-1-buten-3-yne (valylene) and 2-methyl-1,3-butadiene (isoprene). On catalysts reduced at 573 K, the turnover frequencies for valylene (TON{sub v}) and isoprene (TON{sub 1}) hydrogenation were not modified by addition to the 0.09wt% Pd/{alpha}{minus}Al{sub 2}O{sub 3} base catalyst of Ge, Sb, Sn, or Pb, up to0.1 wt% (at 293 K: TON{sub v}= 20 s{sup {minus}1} and TON{sub 1} = 33 s{sup {minus}1}). Pd/{alpha}{minus}Al{sub 2}O{sub 3} reduced at 773 K was severely sintered (d{sub TEM} increased from 2.8nm to 12.4nm) and TON{sub v} and TON{sub 1} at 293 K increased to 190 and 283 s{sup {minus}1}, respectively, as a result of an apparent crystal size effect: the reactants adsorb more strongly on the smaller Pd particles. Upon alloying with Ge, Sb, Sn, or Pb and a subsequent reduction at 773 K, a modest decrease of both TON{sub v} (by a factor of 2) and TON{sub 1} (by a factor of 2{minus}5) was observed. At high conversion, both the selectivity to isoprene (S{sub I}) in valylene hydrogenation, and to olefins (S{sub 0}) in isoprene hydrogenation on Pd/{alpha}{minus}Al{sub 2}O{sub 3} were improved upon alloying with Sb, Sn, or Pb (Ge had no effect). In addition, the isomerization of 2-methyl-1-butene and 3-methyl-1-butene (double bond migration reaction) during isoprene hydrogenation was partially suppressed on PdSn and PdPb/{alpha}{minus}Al{sub 2}O{sub 3}. The improvement in selectivities was interpreted in terms of a change in the relative adsorption strength of the reactants and intermediate products over the new bimetallic sites.

  10. Engineering an isoprenoid pathway in Escherichia coli for production of 2-methyl-3-buten-2-ol: a potential biofuel.

    PubMed

    Gupta, Dinesh; Summers, Michael L; Basu, Chhandak

    2014-06-01

    2-Methyl-3-buten-2-ol (MBO) is a natural volatile 5-carbon alcohol produced by several pine species that have the potential to be used as biofuel. MBO has a high energy content making it superior to ethanol in terms of energy output, and due to its volatility and lower solubility in water, MBO is easier to recover than ethanol. Pine's MBO synthase enzyme utilizes the intermediate dimethylallyl pyrophosphate (DMAPP) produced by the methyl-erythritol-4-phosphate isoprenoid pathway for the production of MBO. In this study, we performed metabolic engineering of Escherichia coli to express an alternate mevalonate dependent pathway for production of DMAPP, along with a codon optimized Pinus sabiniana MBO synthase gene. This heterologous expressed pathway carried out the conversion of an acetyl CoA precursor to DMAPP leading to production of MBO. PMID:24271564

  11. The conformational energies of 2-methyl- and 4-methyl-1,3-dithiane. The breakdown of 1,3- syn diaxial repulsion hypothesis

    NASA Astrophysics Data System (ADS)

    Ribeiro, Douglas S.; Rittner, Roberto

    2003-09-01

    The conformational enthalpies (Δ H) of 2-methyl- (-1.76 kcal mol -1) and 4-methyl-1,3-dithiane (-1.75 kcal mol -1) were obtained by the analysis of 13C chemical shifts as a function of temperature. These energies are in excellent agreement both with calculated values (B3LYP/6-31G(d,p)) and with literature values based on 2,4-dialkyl-1,3-dithiane. The results confirm the similarity between the conformational energies of the methyl group at the 2 and 4 positions of the dithiane ring and that of methylcyclohexane, despite the larger distances between ring 1,3- syn- axial hydrogens and the closest methyl axial hydrogen in the dithiane ring. The possibility of a buttressing effect on the 2,4-dialkyl-1,3-dithianes previously studied and the rationale of 1,3- syn-axial steric interaction are discussed.

  12. N-Butyl-4-butyl­imino-2-methyl­pentan-2-aminium (E)-quercetinate

    PubMed Central

    Grosu, Ioana-Georgeta; Borodi, Gheorghe; Pop, Mihaela Maria

    2012-01-01

    The title salt, C14H31N2 +·C15H9O7 −, was obtained in the reaction of quercetin with n-butyl­amine in a mixture of acetone and hexane. The crystal structure determination shows that the quercetin donates one of its phenol H atoms to the N-butyl-4-butyl­imino-2-methyl­pentan-2-amine mol­ecule. The crystal structure of the salt is stabilized by intramolecular (N—H⋯N for the cation and O—H⋯O for the anion) and intermolecular hydrogen bonding (N—H⋯O between cation–anion pairs and O—H⋯O between anions). Quercetin molecules form dimers connected into a two-dimensional network. The dihedral angle between the quercetin ring systems is 19.61 (8)°. PMID:22904895

  13. Synthesis and characterization of a new photoluminescent material tris (2-methyl-8-hydroxy quinoline) lanthanum La(mq)3

    NASA Astrophysics Data System (ADS)

    Kumar, Rahul; Bhargava, Parag

    2016-05-01

    A new photoluminescence material, tris (2-methyl-8-hydroxy quinoline) lanthanum has been synthesized and characterized by different techniques. The prepared material La(mq)3 was characterized for structural, thermal and photoluminescence analysis. Structural analysis of this material was done by fourier transformed infrared spectroscopy (FTIR) and mass spectroscopy. Thermal analysis of this material was done by thermal gravimetric analysis (TGA) shows the thermal stability up to 400°C. Absorption and emission spectra of the material was measured by UV-visible spectroscopy and photoluminescence spectroscopy. Solution of this material La(mq)3 in ethanol showed absorption peak at 385nm respectively which may be attributed due to (π - π*) transitions. The photoluminescence spectra of La(mq)3 in ethanol solution showed intense peak at 430 nm.

  14. Densities and viscosities of solutions of monoethanolamine + N-Methyldiethanolamine + water and monoethanolamine + 2-amino-2-methyl-1-propanol + water

    SciTech Connect

    Li, M.H.; Lie, Y.C. . Dept. of Chemical Engineering)

    1994-07-01

    The densities and viscosities of aqueous mixtures of monoethanolamine (MEA) with N-methyldiethanolamine (MDEA) and MEA with 2-amino-2-methyl-1-propanol (AMP) have been studied at temperatures from 30 to 80 C. For density measurements, four MEA + MDEA (a total of 20 mass %) + H[sub 2]O mixtures and eight MEA + AMP (20 and 30 mass %) + H[sub 2]O mixtures were studied. For viscosity measurements, ten MEA + MDEA + H[sub 2]O mixtures and eight MEA + AMP + H[sub 2]O mixtures were measured. A Redlich-Kister equation of the excess volume was applied to represent the density of the liquid mixtures. The equation of Grunberg and Nissan of liquid viscosity was used to correlate the viscosity data. Both density and viscosity calculations show satisfactory results.

  15. Energy storage capacity of reversible liquid-phase Diels Alder reaction between maleic anhydride and 2- methyl furan

    SciTech Connect

    Sparks, B.G.; Poling, B.E.

    1983-07-01

    Calorimetry was used to determine the heat of reaction and equilibrium constant at 318 K for the reaction between maleic anhydride (A) and 2-methyl furan (B). The values were-60 kJ/gmol and 614 cm/sup 3//gmol, respectively. The motivation for this work was to find a single phase-reacting system that could be used to store solar energy. Thus, the energy storage capacity was calculated for a mixture of A and B, both initially at 7 kmol/m/sup 3/, in dioxane. The maximum apparent heat capacity of 7.37 J/cm/sup 3/ X K occurred at 334 K. This maximum value is 76% higher than the heat capacity of pure water.

  16. Substituent effects in heterogeneous catalysis. VIII. Reactions of 2-methyl- and 2-ethylcyclohexanone with deuterium catalyzed by platinum metals

    SciTech Connect

    Teratani, S.; Tanaka, K.; Ogawa, H.; Taya, K.

    1981-08-01

    2-Methyl and 2-ethyl derivatives of cyclohexanone were allowed to react with deuterium in t-BuOD using platinum group metals as catalysts. The product alcohols and the remaining ketone were examined by mass spectrometry. Over Ru, Os, and Ir, the simple addition of two deuterium atoms to the carbonyl linkage was predominant, accompanied by little isotopic exchange. Over Pt, however, isotopic exchange was significant and over Rh and Pd quite extensive. The samples obtained over Rh and Pd were further analyzed by NMR spectroscopy to determine the loci of the incorporated deuterium atoms. Deuterium exchange over Pd was almost entirely confined to the C(2) and C(6) positions, while that over Rh was smeared beyond these positions. These results can be accounted for by assuming the intermediacy of ..pi..-absorbed ..pi..-oxaallylic species on Pd and of ..beta..-diadsorbed species on Rh.

  17. Structure and spectroscopic properties of N,S-coordinating 2-methyl­sulfanyl-N-[(1H-pyrrol-2-yl)methyl­idene]aniline methanol monosolvate

    PubMed Central

    Richards, D. Douglas; Ang, M. Trisha C.; McDonald, Robert; Bierenstiel, Matthias

    2015-01-01

    The reaction of pyrrole-2-carboxaldehyde and 2-(methyl­sulfan­yl)aniline in refluxing methanol gave an olive-green residue in which yellow crystals of the title compound, C12H12N2S·CH3OH, were grown from slow evaporation of methanol at 263 K. In the crystal, hydrogen-bonding inter­actions link the aniline mol­ecule and a nearby methanol solvent mol­ecule. These units are linked by a pair of weak C—H⋯Omethanol interactions, forming inversion dimers consisting of two main molecules and two solvent molecules. PMID:26594390

  18. SUV39H2 methylates and stabilizes LSD1 by inhibiting polyubiquitination in human cancer cells

    PubMed Central

    Piao, Lianhua; Suzuki, Takehiro; Dohmae, Naoshi; Nakamura, Yusuke; Hamamoto, Ryuji

    2015-01-01

    LSD1 is a histone lysine demethylase, which is highly expressed in multiple types of human cancer. Although its roles in transcriptional regulation have been well-studied, functional regulation of LSD1 by post-translational modifications still remains unknown. Here, we demonstrate that the histone lysine methyltransferase SUV39H2 trimethylated LSD1 on lysine 322. Knockdown of SUV39H2 resulted in a decrease of LSD1 protein even though the mRNA levels were unchanged. SUV39H2-induced LSD1 methylation suppresses LSD1 polyubiquitination and subsequent degradation. In addition, we also observed indirect effect of SUV39H2 overexpression on LSD1-target genes. Our results reveal the regulatory mechanism of LSD1 protein through its lysine methylation by SUV39H2 in human cancer cells. PMID:26183527

  19. Electron collisions with methyl-substituted ethylenes: Cross section measurements and calculations for 2-methyl-2-butene and 2,3-dimethyl-2-butene

    NASA Astrophysics Data System (ADS)

    Szmytkowski, Czesław; Stefanowska, Sylwia; Zawadzki, Mateusz; Ptasińska-Denga, ElŻbieta; MoŻejko, Paweł

    2015-08-01

    We report electron-scattering cross sections determined for 2-methyl-2-butene [(H3C)HC = C(CH3)2] and 2,3-dimethyl-2-butene [(H3C)2C = C(CH3)2] molecules. Absolute grand-total cross sections (TCSs) were measured for incident electron energies in the 0.5-300 eV range, using a linear electron-transmission technique. The experimental TCS energy dependences for the both targets appear to be very similar with respect to the shape. In each TCS curve, three features are discernible: the resonant-like structure located around 2.6-2.7 eV, the broad distinct enhancement peaking near 8.5 eV, and a weak hump in the vicinity of 24 eV. Theoretical integral elastic (ECS) and ionization (ICS) cross sections were computed up to 3 keV by means of the additivity rule (AR) approximation and the binary-encounter-Bethe method, respectively. Their sums, (ECS+ICS), are in a reasonable agreement with the respective measured TCSs. To examine the effect of methylation of hydrogen sides in the ethylene [H2C = CH2] molecule on the TCS, we compared the TCS energy curves for the sequence of methylated ethylenes: propene [H2C = CH(CH3)], 2-methylpropene [H2C = C(CH3)2], 2-methyl-2-butene [(H3C)HC = C(CH3)2], and 2,3-dimethyl-2-butene [(H3C)2C = C(CH3)2], measured in the same laboratory. Moreover, the isomeric effect is also discussed for the C5H10 and C6H12 compounds.

  20. Ancestral TCDD exposure promotes epigenetic transgenerational inheritance of imprinted gene Igf2: Methylation status and DNMTs.

    PubMed

    Ma, Jing; Chen, Xi; Liu, Yanan; Xie, Qunhui; Sun, Yawen; Chen, Jingshan; Leng, Ling; Yan, Huan; Zhao, Bin; Tang, Naijun

    2015-12-01

    Ancestral TCDD exposure could induce epigenetic transgenerational phenotypes, which may be mediated in part by imprinted gene inheritance. The aim of our study was to evaluate the transgenerational effects of ancestral TCDD exposure on the imprinted gene insulin-like growth factor-2 (Igf2) in rat somatic tissue. TCDD was administered daily by oral gavage to groups of F0 pregnant SD rats at dose levels of 0 (control), 200 or 800 ng/kg bw during gestation day 8-14. Animal transgenerational model of ancestral exposure to TCDD was carefully built, avoiding sibling inbreeding. Hepatic Igf2 expression of the TCDD male progeny was decreased concomitantly with hepatic damage and increased activities of serum hepatic enzymes both in the F1 and F3 generation. Imprinted Control Region (ICR) of Igf2 manifested a hypermethylated pattern, whereas methylation status in the Differentially Methylated Region 2 (DMR2) showed a hypomethylated manner in the F1 generation. These epigenetic alterations in these two regions maintained similar trends in the F3 generation. Meanwhile, the expressions of DNA methyltransferases (DNMT1, DNMT3A and DNMT3B) changed in a non-monotonic manner both in the F1 and F3 generation. This study provides evidence that ancestral TCDD exposure may promote epigenetic transgenerational alterations of imprinted gene Igf2 in adult somatic tissue. PMID:26455773

  1. Bacterial Degradation of tert-Amyl Alcohol Proceeds via Hemiterpene 2-Methyl-3-Buten-2-ol by Employing the Tertiary Alcohol Desaturase Function of the Rieske Nonheme Mononuclear Iron Oxygenase MdpJ

    PubMed Central

    Schuster, Judith; Schäfer, Franziska; Hübler, Nora; Brandt, Anne; Rosell, Mònica; Härtig, Claus; Harms, Hauke; Müller, Roland H.

    2012-01-01

    Tertiary alcohols, such as tert-butyl alcohol (TBA) and tert-amyl alcohol (TAA) and higher homologues, are only slowly degraded microbially. The conversion of TBA seems to proceed via hydroxylation to 2-methylpropan-1,2-diol, which is further oxidized to 2-hydroxyisobutyric acid. By analogy, a branched pathway is expected for the degradation of TAA, as this molecule possesses several potential hydroxylation sites. In Aquincola tertiaricarbonis L108 and Methylibium petroleiphilum PM1, a likely candidate catalyst for hydroxylations is the putative tertiary alcohol monooxygenase MdpJ. However, by comparing metabolite accumulations in wild-type strains of L108 and PM1 and in two mdpJ knockout mutants of strain L108, we could clearly show that MdpJ is not hydroxylating TAA to diols but functions as a desaturase, resulting in the formation of the hemiterpene 2-methyl-3-buten-2-ol. The latter is further processed via the hemiterpenes prenol, prenal, and 3-methylcrotonic acid. Likewise, 3-methyl-3-pentanol is degraded via 3-methyl-1-penten-3-ol. Wild-type strain L108 and mdpJ knockout mutants formed isoamylene and isoprene from TAA and 2-methyl-3-buten-2-ol, respectively. It is likely that this dehydratase activity is catalyzed by a not-yet-characterized enzyme postulated for the isomerization of 2-methyl-3-buten-2-ol and prenol. The vitamin requirements of strain L108 growing on TAA and the occurrence of 3-methylcrotonic acid as a metabolite indicate that TAA and hemiterpene degradation are linked with the catabolic route of the amino acid leucine, including an involvement of the biotin-dependent 3-methylcrotonyl coenzyme A (3-methylcrotonyl-CoA) carboxylase LiuBD. Evolutionary aspects of favored desaturase versus hydroxylation pathways for TAA conversion and the possible role of MdpJ in the degradation of higher tertiary alcohols are discussed. PMID:22194447

  2. 2-Methyl-3-furanthiol and methional are possible off-flavors in stored orange juice: aroma-similarity, NIF/SNIF GC-O, and GC analyses.

    PubMed

    Bezman, Y; Rouseff, R L; Naim, M

    2001-11-01

    The occurrence of methional in fresh orange juice, and possible occurrence of beta-damascenone in heated orange juice, has been previously suggested. Here we report on the occurrence of 2-methyl-3-furanthiol in the headspace, collected by solid-phase micro-extraction, of fresh, pasteurized, and stored orange juice. The contents of 2-methyl-3-furanthiol and methional were quantified, and the relative level of beta-damascenone was estimated, in the headspace of fresh, pasteurized, and stored orange juices using the nasal impact frequency (NIF) and surface of NIF (SNIF) GC-Olfactometry procedure. 2-Methyl-3-furanthiol concentrations were 2 ng/L in fresh and pasteurized Shamuti orange juice, and 270 ng/L in stored juice of the same variety. Methional concentrations were 550, 830, and 11,550 ng/L in fresh, pasteurized, and stored pasteurized juices, respectively. beta-Damascenone content appeared to have increased during pasteurization and storage. Aroma-similarity experiments strongly suggest that 2-methyl-3-furanthiol and methional, at the levels found in stored orange juice (21 days at 35 degrees C), contribute to stored orange juice off-flavor. PMID:11714338

  3. SOA Formation from the Atmospheric Oxidation of 2-Methyl-3-Buten-2-ol and Its Implications for PM2.5

    EPA Science Inventory

    The formation of secondary organic aerosol (SOA) generated by irradiating 2-methyl-3-buten-2-01 (MBO) in the presence and/or absence of NOx H2O2, and/or SO2 was examined. Experiments were conducted. in smog chambers operated either in dyna....

  4. EMISSION OF 2-METHYL-3-BUTEN-2-OL BY PINES: A POTENTIALLY LARGE NATURAL SOURCE OF REACTIVE CARBON TO THE ATMOSPHERE

    EPA Science Inventory

    High rates of emission of 2-methyl-3-buten-2-ol (MBO) were measured from needles of several pine species. Emissions of MBO in the light were 1 to 2 orders of magnitude higher than emissions of monoterpenes and, in contrast to monoterpene emissions from pines, were absent in the d...

  5. Structure–Activity Relationships Comparing N-(6-Methylpyridin-yl)-Substituted Aryl Amides to 2-Methyl-6-(substituted-arylethynyl)pyridines or 2-Methyl-4-(substituted-arylethynyl)thiazoles as Novel Metabotropic Glutamate Receptor Subtype 5 Antagonists†

    PubMed Central

    Kulkarni, Santosh S.; Zou, Mu-Fa; Cao, Jianjing; Deschamps, Jeffrey R.; Rodriguez, Alice L.; Conn, P. Jeffrey; Newman, Amy Hauck

    2010-01-01

    The metabotropic glutamate receptor subtype 5 (mGluR5) has been implicated in anxiety, depression, pain, mental retardation, and addiction. The potent and selective noncompetitive mGluR5 antagonist 2-methyl-6-(phenylethynyl)pyridine (MPEP, 1) has been a critically important tool used to further elucidate the role of mGluR5 in these CNS disorders. In an effort to provide novel and structurally diverse selective mGluR5 antagonists, we previously described a set of analogues with moderate activity wherein the alkyne bond was replaced with an amide group. In the present report, extended series of both amide and alkyne-based ligands were synthesized. MGluR5 binding and functional data were obtained that identified (1) several novel alkynes with comparable affinities to 1 at mGluR5 (e.g., 10 and 20–23), but (2) most structural variations to the amide template were not well tolerated, although a few potent amides were discovered (e.g., 55 and 56). Several of these novel analogues show drug-like physical properties (e.g., cLogP range) 2–5) that support their use for in vivo investigation into the role of mGluR5 in CNS disorders. PMID:19445453

  6. Solubility and diffusivity of N{sub 2}O and CO{sub 2} in (diethanolamine + N-methyldiethanolamine + water) and in (diethanolamine + 2-amino-2-methyl-1-propanol + water)

    SciTech Connect

    Li, M.H.; Lee, W.C.

    1996-05-01

    Acid gases such as CO{sub 2} and H{sub 2}S are frequently removed from natural gas, synthetic natural gas, and other process gas streams by means of absorption into aqueous alkanol-amine solutions. The solubility and diffusivity of N{sub 2}O in (diethanolamine + N-methyldiethanolamine + water) and in (diethanolamine + 2-amino-2-methyl-1-propanol + water) were measured at (30, 35, and 40)C and at atmospheric pressure. Five (diethanolamine + N-methyldiethanolamine + water) and four (diethanolamine + 2-amino-2-methyl-1-propanol + water) systems were studied. The total amine mass percent in all cases was 30. A solubility apparatus was used to measure the solubility of N{sub 2}O in amine solutions. The diffusivity was measured by a wetted wall column absorber. The N{sub 2}O analogy was used to estimate the solubility and diffusivity of CO{sub 2} in (diethanolamine + N-methyldiethanolamine + water) and in (diethanolamine + 2-amino-2-methyl-1-propanol + water).

  7. Solubility and diffusivity of N{sub 2}O and CO{sub 2} in (monoethanolamine + N-methyldiethanolamine + water) and in (monoethanolamine + 2-amino-2-methyl-1-propanol + water)

    SciTech Connect

    Li, M.H.; Lai, M.D.

    1995-03-01

    Solutions of amines are frequently used in gas-treating processes to remove acid gases, such as CO{sub 2} and H{sub 2}S, from gas streams in the natural gas and synthetic ammonia industries and petroleum chemical plants. The solubility and diffusivity of N{sub 2}O in (monoethanolamine + N-methyldiethanolamine + water) and in (monoethanolamine + 2-amino-2-methyl-l-propanol + water) were measured at 30, 35, and 40 C and at atmospheric pressure. Six (monoethanolamine + N-methyldiethanolamine + water) and five (monoethanolamine + 2-amino-2-methyl-l-propanol + water) systems were studied. The total amine mass percent in all cases was 30. The solubilities were measured by a solubility apparatus similar to that of Haimour and Sandall (1984). A wetted wall column absorber was used to obtain the diffusivity of N{sub 2}O in amines. The N{sub 2}O solubilities in amine solutions have been correlated on the basis of the excess Henry constant correlation of Wang et al. (1992). The N{sub 2}O analogy was used to estimate the solubility and diffusivity of CO{sub 2} in (monoethanolamine + N-methyldiethanolamine + water) and in (monoethanolamine + 2-amino-2-methyl-l-propanol + water).

  8. Metabolic pathway involved in 2-methyl-6-ethylaniline degradation by Sphingobium sp. strain MEA3-1 and cloning of the novel flavin-dependent monooxygenase system meaBA.

    PubMed

    Dong, Weiliang; Chen, Qiongzhen; Hou, Ying; Li, Shuhuan; Zhuang, Kai; Huang, Fei; Zhou, Jie; Li, Zhoukun; Wang, Jue; Fu, Lei; Zhang, Zhengguang; Huang, Yan; Wang, Fei; Cui, Zhongli

    2015-12-01

    2-Methyl-6-ethylaniline (MEA) is the main microbial degradation intermediate of the chloroacetanilide herbicides acetochlor and metolachlor. Sphingobium sp. strain MEA3-1 can utilize MEA and various alkyl-substituted aniline and phenol compounds as sole carbon and energy sources for growth. We isolated the mutant strain MEA3-1Mut, which converts MEA only to 2-methyl-6-ethyl-hydroquinone (MEHQ) and 2-methyl-6-ethyl-benzoquinone (MEBQ). MEA may be oxidized by the P450 monooxygenase system to 4-hydroxy-2-methyl-6-ethylaniline (4-OH-MEA), which can be hydrolytically spontaneously deaminated to MEBQ or MEHQ. The MEA microbial metabolic pathway was reconstituted based on the substrate spectra and identification of the intermediate metabolites in both the wild-type and mutant strains. Plasmidome sequencing indicated that both strains harbored 7 plasmids with sizes ranging from 6,108 bp to 287,745 bp. Among the 7 plasmids, 6 were identical, and pMEA02' in strain MEA3-1Mut lost a 37,000-bp fragment compared to pMEA02 in strain MEA3-1. Two-dimensional electrophoresis (2-DE) and protein mass fingerprinting (PMF) showed that MEA3-1Mut lost the two-component flavin-dependent monooxygenase (TC-FDM) MeaBA, which was encoded by a gene in the lost fragment of pMEA02. MeaA shared 22% to 25% amino acid sequence identity with oxygenase components of some TC-FDMs, whereas MeaB showed no sequence identity with the reductase components of those TC-FDMs. Complementation with meaBA in MEA3-1Mut and heterologous expression in Pseudomonas putida strain KT2440 resulted in the production of an active MEHQ monooxygenase. PMID:26386060

  9. Metabolic Pathway Involved in 2-Methyl-6-Ethylaniline Degradation by Sphingobium sp. Strain MEA3-1 and Cloning of the Novel Flavin-Dependent Monooxygenase System meaBA

    PubMed Central

    Dong, Weiliang; Chen, Qiongzhen; Hou, Ying; Li, Shuhuan; Zhuang, Kai; Huang, Fei; Zhou, Jie; Li, Zhoukun; Wang, Jue; Fu, Lei; Zhang, Zhengguang; Huang, Yan; Wang, Fei

    2015-01-01

    2-Methyl-6-ethylaniline (MEA) is the main microbial degradation intermediate of the chloroacetanilide herbicides acetochlor and metolachlor. Sphingobium sp. strain MEA3-1 can utilize MEA and various alkyl-substituted aniline and phenol compounds as sole carbon and energy sources for growth. We isolated the mutant strain MEA3-1Mut, which converts MEA only to 2-methyl-6-ethyl-hydroquinone (MEHQ) and 2-methyl-6-ethyl-benzoquinone (MEBQ). MEA may be oxidized by the P450 monooxygenase system to 4-hydroxy-2-methyl-6-ethylaniline (4-OH-MEA), which can be hydrolytically spontaneously deaminated to MEBQ or MEHQ. The MEA microbial metabolic pathway was reconstituted based on the substrate spectra and identification of the intermediate metabolites in both the wild-type and mutant strains. Plasmidome sequencing indicated that both strains harbored 7 plasmids with sizes ranging from 6,108 bp to 287,745 bp. Among the 7 plasmids, 6 were identical, and pMEA02′ in strain MEA3-1Mut lost a 37,000-bp fragment compared to pMEA02 in strain MEA3-1. Two-dimensional electrophoresis (2-DE) and protein mass fingerprinting (PMF) showed that MEA3-1Mut lost the two-component flavin-dependent monooxygenase (TC-FDM) MeaBA, which was encoded by a gene in the lost fragment of pMEA02. MeaA shared 22% to 25% amino acid sequence identity with oxygenase components of some TC-FDMs, whereas MeaB showed no sequence identity with the reductase components of those TC-FDMs. Complementation with meaBA in MEA3-1Mut and heterologous expression in Pseudomonas putida strain KT2440 resulted in the production of an active MEHQ monooxygenase. PMID:26386060

  10. 3-Ethyl-2-methyl-5-methyl-ene-6,7-di-hydroindol-4(5H)-one.

    PubMed

    Sonar, Vijayakumar N; Parkin, Sean; Crooks, Peter A

    2007-01-01

    The title compound, C(12)H(15)NO, a degradation product of molindone hydro-chloride, was prepared by the reaction of molindone with methyl iodide and subsequent reaction of the resulting quaternary ammonium salt with 2N aqueous sodium hydroxide. The newly formed double bond is exocyclic in nature and the carbonyl group is conjugated with the π-electrons of the pyrrole ring. The six-membered ring is in the half-chair conformation. The H atom attached to the N atom is involved in an inter-molecular hydrogen bond with the O atom of a screw-related mol-ecule, thus forming a continuous chain. PMID:21200723

  11. Treatment of taste and odor causing compounds 2-methyl isoborneol and geosmin in drinking water: a critical review.

    PubMed

    Srinivasan, Rangesh; Sorial, George A

    2011-01-01

    Problems due to the taste and odor in drinking water are common in treatment facilities around the world. Taste and odor are perceived by the public as the primary indicators of the safely and acceptability of drinking water and are mainly caused by the presence of two semi-volatile compounds--2-methyl isoborneol (MIB) and geosmin. A review of these two taste and odor causing compounds in drinking water is presented. The sources for the formation of these compounds in water are discussed along with the health and regulatory implications. The recent developments in the analysis of MIB/geosmin in water which have allowed for rapid measurements in the nanogram per liter concentrations are also discussed. This review focuses on the relevant treatment alternatives, that are described in detail with emphasis on their respective advantages and problems associated with their implementation in a full-scale facility. Conventional treatment processes in water treatment plants, such as coagulation, sedimentation and chlorination have been found to be ineffective for removal of MIB/geosmin. Studies have shown powdered activated carbon, ozonation and biofiltration to be effective in treatment of these two compounds. Although some of these technologies are more effective and show more promise than the others, much work remains to be done to optimize these technologies so that they can be retrofitted or installed with minimal impact on the overall operation and effectiveness of the treatment system. PMID:21476334

  12. 2-Methyl-3-buten-2-ol (MBO) synthase expression in Nostoc punctiforme leads to over production of phytols

    PubMed Central

    Gupta, Dinesh; Ip, Tina; Summers, Michael L; Basu, Chhandak

    2015-01-01

    Phytol is a diterpene alcohol of medicinal importance and it also has potential to be used as biofuel. We found over production of phytol in Nostoc punctiforme by expressing a 2-Methyl-3-buten-2-ol (MBO) synthase gene. MBO synthase catalyzes the conversion of dimethylallyl pyrophosphate (DMAPP) into MBO, a volatile hemiterpene alcohol, in Pinus sabiniana. The result of enhanced phytol production in N. punctiforme, instead of MBO, could be explained by one of the 2 models: either the presence of a native prenyltransferase enzyme with a broad substrate specificity, or appropriation of a MBO synthase metabolic intermediate by a native geranyl diphosphate (GDP) synthase. In this work, an expression vector with an indigenous petE promoter for gene expression in the cyanobacterium N. punctiforme was constructed and MBO synthase gene expression was successfully shown using reverse transcriptase (RT)-PCR and SDS-PAGE. Gas chromatography – mass spectrophotometry (GC-MS) was performed to confirm phytol production from the transgenic N. punctiforme strains. We conclude that the expression of MBO synthase in N. punctiforme leads to overproduction of an economically important compound, phytol. This study provides insights about metabolic channeling of isoprenoids in cyanobacteria and also illustrates the challenges of bioengineering non-native hosts to produce economically important compounds. PMID:25424521

  13. Fungal Symbionts of the Spruce Bark Beetle Synthesize the Beetle Aggregation Pheromone 2-Methyl-3-buten-2-ol.

    PubMed

    Zhao, Tao; Axelsson, Karolin; Krokene, Paal; Borg-Karlson, Anna-Karin

    2015-09-01

    Tree-killing bark beetles depend on aggregation pheromones to mass-attack their host trees and overwhelm their resistance. The beetles are always associated with phytopathogenic ophiostomatoid fungi that probably assist in breaking down tree resistance, but little is known about if or how much these fungal symbionts contribute to the beetles' aggregation behavior. In this study, we determined the ability of four major fungal symbionts of the spruce bark beetle Ips typographus to produce beetle aggregation pheromones. The fungi were incubated on Norway spruce Picea abies bark, malt agar, or malt agar amended with 0.5% (13)C glucose. Volatiles present in the headspace of each fungus were analyzed for 7 days after incubation using a SPME autosampler coupled to a GC/MS. Two Grosmannia species (G. penicillata and G. europhioides) produced large amounts of 2-methyl-3-buten-2-ol (MB), the major component in the beetles' aggregation pheromone blend, when growing on spruce bark or malt agar. Grosmannia europhioides also incorporated (13)C glucose into MB, demonstrating that the fungi can synthesize MB de novo using glucose as a carbon source. This is the first clear evidence that fungal symbionts of bark beetles can produce components in the aggregation pheromone blend of their beetle vectors. This provides new insight into the possible ecological roles of fungal symbionts in bark beetle systems and may deepen our understanding of species interactions and coevolution in these important biological systems. PMID:26302987

  14. LETTER TO THE EDITOR: Characteristics of the terahertz radiation from single crystals of N-substituted 2-methyl-4-nitroaniline

    NASA Astrophysics Data System (ADS)

    Hashimoto, Hideki; Takahashi, Hironori; Yamada, Takashi; Kuroyanagi, Kazuyoshi; Kobayashi, Takayoshi

    2001-06-01

    Terahertz (THz) radiation was generated via optical rectification from organic single crystals, i.e. N-substituted (N-benzyl, N-diphenylmethyl, and N-2-naphthylmethyl) derivatives of 2-methyl-4-nitroaniline (MNA), and it was detected by means of the electro-optic sampling method. The intensity and the spectrum of the THz radiation were compared with those of ZnTe and DAST (N, N-dimethylamino-N'-methylstilbazolium p-toluenesulphonate) crystals. The integrated intensity of the THz radiation from the N-benzyl-MNA crystal was two thirds of that for the ZnTe crystal, the best-known practical THz emitter, and was as intense as that for the DAST crystal, the best organic THz emitter ever studied. The spectrum of the ZnTe crystal extended to 3 THz, while that of the N-benzyl MNA and DAST crystals dropped off around 2.5 THz. The THz radiation intensities from all of the organic crystals were compared quantitatively, on the basis of the consideration of molecular arrangements in the crystals. It was suggested that the absorption due to low-frequency phonon modes affected both the intensity and the spectral band shape of the THz radiation.

  15. 2-Methyl-3-buten-2-ol (MBO) synthase expression in Nostoc punctiforme leads to over production of phytols.

    PubMed

    Gupta, Dinesh; Ip, Tina; Summers, Michael L; Basu, Chhandak

    2015-01-01

    Phytol is a diterpene alcohol of medicinal importance and it also has potential to be used as biofuel. We found over production of phytol in Nostoc punctiforme by expressing a 2-Methyl-3-buten-2-ol (MBO) synthase gene. MBO synthase catalyzes the conversion of dimethylallyl pyrophosphate (DMAPP) into MBO, a volatile hemiterpene alcohol, in Pinus sabiniana. The result of enhanced phytol production in N. punctiforme, instead of MBO, could be explained by one of the 2 models: either the presence of a native prenyltransferase enzyme with a broad substrate specificity, or appropriation of a MBO synthase metabolic intermediate by a native geranyl diphosphate (GDP) synthase. In this work, an expression vector with an indigenous petE promoter for gene expression in the cyanobacterium N. punctiforme was constructed and MBO synthase gene expression was successfully shown using reverse transcriptase (RT)-PCR and SDS-PAGE. Gas chromatography--mass spectrophotometry (GC-MS) was performed to confirm phytol production from the transgenic N. punctiforme strains. We conclude that the expression of MBO synthase in N. punctiforme leads to overproduction of an economically important compound, phytol. This study provides insights about metabolic channeling of isoprenoids in cyanobacteria and also illustrates the challenges of bioengineering non-native hosts to produce economically important compounds. PMID:25424521

  16. Continuous hydrogenation of ethyl levulinate to γ-valerolactone and 2-methyl tetrahydrofuran over alumina doped Cu/SiO2 catalyst: the potential of commercialization

    PubMed Central

    Zheng, Junlin; Zhu, Junhua; Xu, Xuan; Wang, Wanmin; Li, Jiwen; Zhao, Yan; Tang, Kangjian; Song, Qi; Qi, Xiaolan; Kong, Dejin; Tang, Yi

    2016-01-01

    Hydrogenation of levulinic acid (LA) and its esters to produce γ-valerolactone (GVL) and 2-methyl tetrahydrofuran (2-MTHF) is a key step for the utilization of cellulose derived LA. Aiming to develop a commercially feasible base metal catalyst for the production of GVL from LA, with satisfactory activity, selectivity, and stability, Al2O3 doped Cu/SiO2 and Cu/SiO2 catalysts were fabricated by co-precipitation routes in parallel. The diverse physio-chemical properties of these two catalysts were characterized by XRD, TEM, dissociative N2O chemisorptions, and Py-IR methods. The catalytic properties of these two catalysts were systematically assessed in the continuous hydrogenation of ethyl levulinate (EL) in a fixed-bed reactor. The effect of acidic property of the SiO2 substrate on the catalytic properties was investigated. To justify the potential of its commercialization, significant attention was paid on the initial activity, proper operation window, by-products control, selectivity, and stability of the catalyst. The effect of reaction conditions, such as temperature and pressure, on the performance of the catalyst was also thoroughly studied. The development of alumina doped Cu/SiO2 catalyst strengthened the value-chain from cellulose to industrially important chemicals via LA and GVL. PMID:27377401

  17. Continuous hydrogenation of ethyl levulinate to γ-valerolactone and 2-methyl tetrahydrofuran over alumina doped Cu/SiO2 catalyst: the potential of commercialization

    NASA Astrophysics Data System (ADS)

    Zheng, Junlin; Zhu, Junhua; Xu, Xuan; Wang, Wanmin; Li, Jiwen; Zhao, Yan; Tang, Kangjian; Song, Qi; Qi, Xiaolan; Kong, Dejin; Tang, Yi

    2016-07-01

    Hydrogenation of levulinic acid (LA) and its esters to produce γ-valerolactone (GVL) and 2-methyl tetrahydrofuran (2-MTHF) is a key step for the utilization of cellulose derived LA. Aiming to develop a commercially feasible base metal catalyst for the production of GVL from LA, with satisfactory activity, selectivity, and stability, Al2O3 doped Cu/SiO2 and Cu/SiO2 catalysts were fabricated by co-precipitation routes in parallel. The diverse physio-chemical properties of these two catalysts were characterized by XRD, TEM, dissociative N2O chemisorptions, and Py-IR methods. The catalytic properties of these two catalysts were systematically assessed in the continuous hydrogenation of ethyl levulinate (EL) in a fixed-bed reactor. The effect of acidic property of the SiO2 substrate on the catalytic properties was investigated. To justify the potential of its commercialization, significant attention was paid on the initial activity, proper operation window, by-products control, selectivity, and stability of the catalyst. The effect of reaction conditions, such as temperature and pressure, on the performance of the catalyst was also thoroughly studied. The development of alumina doped Cu/SiO2 catalyst strengthened the value-chain from cellulose to industrially important chemicals via LA and GVL.

  18. Poly[(μ2-2-hydr­oxy-2-methyl­propionato-κ3 O 1,O 2:O 1′)(μ2-2-hydr­oxy-2-methyl­propionato-κ2 O 1:κO 1′)dioxido­uranium(VI)

    PubMed Central

    Yoshimura, Takashi; Kikunaga, Hidetoshi; Shinohara, Atsushi

    2009-01-01

    In the title compound, [UO2(C4H7O3)2]n, the dioxouranium(VI) units are linked by 2-hydr­oxy-2-methyl­propionate ligands into a honeycomb structure. The U atom is seven-coordinate in a penta­gonal-bipyramidal geometry. The uncoordinated hydr­oxy groups of the 2-hydr­oxy-2-methyl­propionate ions inter­act with the O atom of the uranyl and with the coordinated hydr­oxy group of an adjacent 2-hydr­oxy-2-methyl­propionate ion through O—H⋯O hydrogen bonds. PMID:21582314

  19. Atomic resolution experimental phase information reveals extensive disorder and bound 2-methyl-2,4-pentanediol in Ca(2+)-calmodulin.

    PubMed

    Lin, Jiusheng; van den Bedem, Henry; Brunger, Axel T; Wilson, Mark A

    2016-01-01

    Calmodulin (CaM) is the primary calcium signaling protein in eukaryotes and has been extensively studied using various biophysical techniques. Prior crystal structures have noted the presence of ambiguous electron density in both hydrophobic binding pockets of Ca(2+)-CaM, but no assignment of these features has been made. In addition, Ca(2+)-CaM samples many conformational substates in the crystal and accurately modeling the full range of this functionally important disorder is challenging. In order to characterize these features in a minimally biased manner, a 1.0 Å resolution single-wavelength anomalous diffraction data set was measured for selenomethionine-substituted Ca(2+)-CaM. Density-modified electron-density maps enabled the accurate assignment of Ca(2+)-CaM main-chain and side-chain disorder. These experimental maps also substantiate complex disorder models that were automatically built using low-contour features of model-phased electron density. Furthermore, experimental electron-density maps reveal that 2-methyl-2,4-pentanediol (MPD) is present in the C-terminal domain, mediates a lattice contact between N-terminal domains and may occupy the N-terminal binding pocket. The majority of the crystal structures of target-free Ca(2+)-CaM have been derived from crystals grown using MPD as a precipitant, and thus MPD is likely to be bound in functionally critical regions of Ca(2+)-CaM in most of these structures. The adventitious binding of MPD helps to explain differences between the Ca(2+)-CaM crystal and solution structures and is likely to favor more open conformations of the EF-hands in the crystal. PMID:26894537

  20. Canopy level emissions of 2-methyl-3-buten-2-ol, monoterpenes, and sesquiterpenes from an experimental Pinus taeda plantation.

    PubMed

    Geron, Christopher D; Daly, Ryan W; Arnts, Robert R; Guenther, Alex B; Mowry, Fred L

    2016-09-15

    Emissions of Biogenic Volatile Organic Compounds (BVOCs) observed during 2007 from an experimental Pinus taeda plantation in Central North Carolina are compared with model estimates from the Model of Emissions of Gases and Aerosols from Nature (MEGAN) version 2.1. Relaxed eddy accumulation (REA) estimates of 2-methyl-3-buten-2-ol (MBO) fluxes are a factor of 3-4 higher than MEGAN estimates. MEGAN monoterpene emission estimates were a factor of approximately two higher than REA flux measurements. MEGAN β-caryophyllene emission estimates were within 60% of growing season REA flux estimates but were several times higher than REA fluxes during cooler, dormant season periods. The sum of other sesquiterpene emissions estimated by MEGAN was several times higher than REA estimates throughout the year. Model components are examined to understand these discrepancies. Measured summertime leaf area index (LAI) (and therefore foliar biomass) is a factor of two higher than assumed in MEGAN for the P. taeda default. Increasing the canopy mean MBO emission factor from 0.35 to 1.0mgm(-2)h(-1) also reduces MEGAN vs. REA flux differences. This increase is within current MBO emission factor uncertainties. The algorithm within MEGAN which adjusts isoprene emission estimates as a function of the temperature and light of the previous 24h seems also to improve the seasonal MEGAN MBO correlation with REA fluxes. Including the effects of the previous 240h, however, seems to degrade temporal model correlation with fluxes. Monoterpene and sesquiterpene composition data from the REA are compared with MEGAN2.1 estimates and also branch enclosure and needle extract data collected at this site. To our knowledge, the flux data presented here are the first reported for MBO and sesquiterpenes from a P. taeda ecosystem. PMID:27232720

  1. N-(2-methyl-indol-1H-5-yl)-1-naphthalenesulfonamide: A novel reversible antimitotic agent inhibiting cancer cell motility.

    PubMed

    Aceves-Luquero, Clara; Galiana-Roselló, Cristina; Ramis, Guillem; Villalonga-Planells, Ruth; García-España, Enrique; Fernández de Mattos, Silvia; Peláez, Rafael; Llinares, José M; González-Rosende, M Eugenia; Villalonga, Priam

    2016-09-01

    A series of compounds containing the sulfonamide scaffold were synthesized and screened for their in vitro anticancer activity against a representative panel of human cancer cell lines, leading to the identification of N-(2-methyl-1H-indol-5-yl)-1-naphthalenesulfonamide (8e) as a compound showing a remarkable activity across the panel, with IC50 values in the nanomolar-to-low micromolar range. Cell cycle distribution analysis revealed that 8e promoted a severe G2/M arrest, which was followed by cellular senescence as indicated by the detection of senescence-associated β-galactosidase (SA-β-gal) in 8e-treated cells. Prolonged 8e treatment also led to the onset of apoptosis, in correlation with the detection of increased Caspase 3/7 activities. Despite increasing γ-H2A.X levels, a well-established readout for DNA double-strand breaks, in vitro DNA binding studies with 8e did not support interaction with DNA. In agreement with this, 8e failed to activate the cellular DNA damage checkpoint. Importantly, tubulin staining showed that 8e promoted a severe disorganization of microtubules and mitotic spindle formation was not detected in 8e-treated cells. Accordingly, 8e inhibited tubulin polymerization in vitro in a dose-dependent manner and was also able to robustly inhibit cancer cell motility. Docking analysis revealed a compatible interaction with the colchicine-binding site of tubulin. Remarkably, these cellular effects were reversible since disruption of treatment resulted in the reorganization of microtubules, cell cycle re-entry and loss of senescent markers. Collectively, our data suggest that this compound may be a promising new anticancer agent capable of both reducing cancer cell growth and motility. PMID:27349984

  2. A high temperature and atmospheric pressure experimental and detailed chemical kinetic modelling study of 2-methyl furan oxidation

    PubMed Central

    Somers, Kieran P.; Simmie, John M.; Gillespie, Fiona; Burke, Ultan; Connolly, Jessica; Metcalfe, Wayne K.; Battin-Leclerc, Frédérique; Dirrenberger, Patricia; Herbinet, Olivier; Glaude, Pierre-Alexandre; Curran, Henry J.

    2013-01-01

    An experimental ignition delay time study for the promising biofuel 2-methyl furan (2MF) was performed at equivalence ratios of 0.5, 1.0 and 2.0 for mixtures of 1% fuel in argon in the temperature range 1200–1800 K at atmospheric pressure. Laminar burning velocities were determined using the heat-flux method for mixtures of 2MF in air at equivalence ratios of 0.55–1.65, initial temperatures of 298–398 K and atmospheric pressure. A detailed chemical kinetic mechanism consisting of 2059 reactions and 391 species has been constructed to describe the oxidation of 2MF and is used to simulate experiment. Accurate reproduction of the experimental data has been obtained over all conditions with the developed mechanism. Rate of production and sensitivity analyses have been carried out to identify important consumption pathways of the fuel and key kinetic parameters under these conditions. The reactions of hydrogen atom with the fuel are highlighted as important under all experimental conditions studied, with abstraction by the hydrogen atom promoting reactivity and hydrogen atom addition to the furan ring inhibiting reactivity. This work, to the authors knowledge, is the first to combine theoretical and experimental work to describe the oxidation of any of the alkylated furans. The mechanism developed herein to describe 2MF combustion should also function as a sub-mechanism to describe the oxidation of 2,5-dimethyl furan whilst also providing key insights into the oxidation of this similar biofuel candidate. PMID:23814505

  3. Photooxidation of 2-methyl-3-Buten-2-ol (MBO) as a potential source of secondary organic aerosol.

    PubMed

    Chan, Arthur W H; Galloway, Melissa M; Kwan, Alan J; Chhabra, Puneet S; Keutsch, Frank N; Wennberg, Paul O; Flagan, Richard C; Seinfeld, John H

    2009-07-01

    2-Methyl-3-buten-2-ol (MBO) is an important biogenic hydrocarbon emitted in large quantities by pine forests. Atmospheric photooxidation of MBO is known to lead to oxygenated compounds, such as glycolaldehyde, which is the precursor to glyoxal. Recent studies have shown that the reactive uptake of glyoxal onto aqueous particles can lead to formation of secondary organic aerosol (SOA). In this work, MBO photooxidation under high- and low-NO(x) conditions was performed in dual laboratory chambers to quantify the yield of glyoxal and investigate the potential for SOA formation. The yields of glycolaldehyde and 2-hydroxy-2-methylpropanal (HMPR), fragmentation products of MBO photooxidation, were observed to be lower at lower NO(x) concentrations. Overall, the glyoxal yield from MBO photooxidation was 25% under high-NO(x) and 4% under low-NO(x) conditions. In the presence of wet ammonium sulfate seed and under high-NO(x) conditions, glyoxal uptake and SOA formation were not observed conclusively, due to relatively low (< 30 ppb) glyoxal concentrations. Slight aerosol formation was observed under low-NO(x) and dry conditions, with aerosol mass yields on the order of 0.1%. The small amount of SOA was not related to glyoxal uptake, but is likely a result of reactions similar to those that generate isoprene SOA under low-NO(x) conditions. The difference in aerosol yields between MBO and isoprene photooxidation under low-NO(x) conditions is consistent with the difference in vapor pressures between triols (from MBO) and tetrols (from isoprene). Despite its structural similarity to isoprene, photooxidation of MBO is not expected to make a significant contribution to SOA formation. PMID:19673246

  4. 1-(2‧-Aminophenyl)- and 1-(2‧-hydroxyphenyl)-2-methyl-4-nitroimidazole: Crystallizing with two molecules in the asymmetric unit

    NASA Astrophysics Data System (ADS)

    Kubicki, Maciej; Wagner, Paweł

    2008-03-01

    Two similar 4-nitroimidazole derivatives, 1-(2'-aminophenyl)-2-methyl-4-nitroimidazole, C 10H 9N 3O 3, and 1-(2'-hydroxyphenyl)-2-methyl-4-nitroimidazole, C 10H 10N 4O 2, crystallize with two molecules in the asymmetric unit ( Z' = 2). Packing conflicts may result from tendency towards closing hydrogen-bonded rings (dimer for amino-, and tetramer for hydroxy-derivative) and molecular stacking. These conflicts are solved in different ways in both compounds, due to the different nature of 2'-substituents, but in both cases the crystal structure involves multiple molecules in the asymmetry unit. The geometrical features of symmetry-independent molecules are similar. The nitro group is almost coplanar with the imidazole plane in amino derivative while it is significantly twisted in hydroxy-one.

  5. The value of SHOX2 methylation test in peripheral blood samples used for the differential diagnosis of lung cancer and other lung disorders.

    PubMed

    Konecny, M; Markus, J; Waczulikova, I; Dolesova, L; Kozlova, R; Repiska, V; Novosadova, H; Majer, I

    2016-01-01

    Methylation of the cytosine residues within the CpG dinucleotides plays an important role in the fundamental cellular processes, human diseases and even cancer. The DNA methylation represents a very stable sign and therefore may be used as a valuable marker for cancer screening. Epigenetic cancer biomarkers are independent of classical morphology and thus show extensive potential to overcome the limitations of cytology. Several epigenetic cancer markers have been reported to be detectable in body fluids such as bronchial aspirate, sputum, plasma and serum.Short stature homeobox gene 2 (SHOX2) encodes a homeo-domain transcription factor, which has been identified as a close homologue of the SHOX gene and both genes are involved in skeletogenesis and heart development. Methylation of SHOX2 gene has been shown to be present at high prevalence in carcinomas of lung, however may also be used to identify other tumour entities.In the presented study, we have compared suitability of two types of material associated with lung cancer for the detection of SHOX2 methylation. We have confirmed that methylation of SHOX2 gene represents reliable marker of lung malignancies. The parallel tests in the blood plasma revealed that it may represent a good alternative material for testing of the SHOX2 methylation, making the test available to patients who are unable to undergo bronchoscopy. PMID:26774146

  6. Assignments of the vibrational spectra of 2,5-dimethyl-2,4-hexadiene, 4-methyl-1,3-pentadiene and (E)-2-methyl-1,3-pentadiene. Effect of the terminal and lateral methyl groups1

    NASA Astrophysics Data System (ADS)

    Aly, M. M. Abo; Baron, M. H.; Coulange, M. J.; Favrot, J.

    The complete assignment of the vibrational spectra of 2,5-dimethyl-2,4-hexadiene, 4-methyl-1,3-pentadiene and ( E)-2-methyl-1,3-pentadiene was obtained from a comparative analysis of their i.r. and Raman spectra (solid, liquid and gas) in the range 3200-50 cm -1. It is shown that particular vibrational motions strongly interact to give rise to very characteristic modes depending on the site of methyl substitution. The comparison of our results with those of analogous shorter and larger polyenes and polyenals allows us to discuss the various local coupled motions characteristic of unsubstituted (CHCH CH)CH and methyl substituted (CHC(CH 3)CH), ((CH 3) 2CCH) or (CH 3CHCH) fragments in polyenic chains.

  7. 2-Methyl-6-(phenylethynyl) pyridine (MPEP) reverses maze learning and PSD-95 deficits in Fmr1 knock-out mice

    PubMed Central

    Gandhi, Réno M.; Kogan, Cary S.; Messier, Claude

    2014-01-01

    Fragile X Syndrome (FXS) is caused by the lack of expression of the fragile X mental retardation protein (FMRP), which results in intellectual disability and other debilitating symptoms including impairment of visual-spatial functioning. FXS is the only single-gene disorder that is highly co-morbid with autism spectrum disorder and can therefore provide insight into its pathophysiology. Lack of FMRP results in altered group I metabotropic glutamate receptor (mGluR) signaling, which is a target for putative treatments. The Hebb-Williams (H-W) mazes are a set of increasingly complex spatial navigation problems that depend on intact hippocampal and thus mGluR-5 functioning. In the present investigation, we examined whether an antagonist of mGluR-5 would reverse previously described behavioral deficits in fragile X mental retardation 1 knock-out (Fmr1 KO) mice. Mice were trained on a subset of the H-W mazes and then treated with either 20 mg/kg of an mGluR-5 antagonist, 2-Methyl-6-(phenylethynyl) pyridine (MPEP; n = 11) or an equivalent dose of saline (n = 11) prior to running test mazes. Latency and errors were dependent variables recorded during the test phase. Immediately after completing each test, marble-burying behavior was assessed, which confirmed that the drug treatment was pharmacologically active during maze learning. Although latency was not statistically different between the groups, MPEP treated Fmr1 KO mice made significantly fewer errors on mazes deemed more difficult suggesting a reversal of the behavioral deficit. MPEP treated mice were also less perseverative and impulsive when navigating mazes. Furthermore, MPEP treatment reversed post-synaptic density-95 (PSD-95) protein deficits in Fmr1 KO treated mice, whereas levels of a control protein (β-tubulin) remained unchanged. These data further validate MPEP as a potentially beneficial treatment for FXS. Our findings also suggest that adapted H-W mazes may be a useful tool to document alterations in

  8. Murine T cell activation is regulated by surfen (bis-2-methyl-4-amino-quinolyl-6-carbamide)

    SciTech Connect

    Warford, Jordan; Doucette, Carolyn D.; Hoskin, David W.; Easton, Alexander S.

    2014-01-10

    Highlights: •Surfen is the first inhibitor of glycosaminoglycan function to be studied in murine T cells. •Surfen reduces T cell proliferation stimulated in vitro and in vivo. •Surfen reduces CD25 expression in T cells activated in vivo but not in vitro. •Surfen increases T cell proliferation when T cell receptor activation is bypassed. •Surfen’s effects are blocked by co-administration of heparin sulfate. -- Abstract: Surfen (bis-2-methyl-4-amino-quinolyl-6-carbamide) binds to glycosaminoglycans (GAGs) and has been shown to influence their function, and the function of proteoglycans (complexes of GAGs linked to a core protein). T cells synthesize, secrete and express GAGs and proteoglycans which are involved in several aspects of T cell function. However, there are as yet no studies on the effect of GAG-binding agents such as surfen on T cell function. In this study, surfen was found to influence murine T cell activation. Doses between 2.5 and 20 μM produced a graduated reduction in the proliferation of T cells activated with anti-CD3/CD28 antibody-coated T cell expander beads. Surfen (20 mg/kg) was also administered to mice treated with anti-CD3 antibody to activate T cells in vivo. Lymphocytes from surfen-treated mice also showed reduced proliferation and lymph node cell counts were reduced. Surfen reduced labeling with a cell viability marker (7-ADD) but to a much lower extent than its effect on proliferation. Surfen also reduced CD25 (the α-subunit of the interleukin (IL)-2 receptor) expression with no effect on CD69 expression in T cells treated in vivo but not in vitro. When receptor activation was bypassed by treating T cells in vitro with phorbyl myristate acetate (10 ng/ml) and ionomycin (100 ng/ml), surfen treatment either increased proliferation (10 μM) or had no effect (2.5, 5 and 20 μM). In vitro treatment of T cells with surfen had no effect on IL-2 or interferon-γ synthesis and did not alter proliferation of the IL-2 dependent cell

  9. Crystal structure of 1-(5-amino-2H-tetra­zol-2-yl)-2-methyl­propan-2-ol

    PubMed Central

    Park, Hyun Sik; Ryu, Ji Yeon; Lee, Junseong

    2015-01-01

    The title compound, C5H11N5O, crystallized with two independent mol­ecules in the asymmetric unit. The two mol­ecules differ in the orientation of the 2-methyl­propan-2-ol unit, with the hy­droxy H atoms pointing in opposite directions. In the crystal, mol­ecules are linked via O—H⋯O and N—H⋯O hydrogen bonds, forming ribbons propagating along [10-1]. The ribbons are linked via N—H⋯N hydrogen bonds, forming a three-dimensional structure. PMID:26870496

  10. Volumetric Properties of the Mixture Propenenitrile C3H3N + C3H6O2 Methyl ethanoate (VMSD1511, LB4267_V)

    NASA Astrophysics Data System (ADS)

    Cibulka, I.; Fontaine, J.-C.; Sosnkowska-Kehiaian, K.; Kehiaian, H. V.

    This document is part of Subvolume C 'Binary Liquid Systems of Nonelectrolytes III' of Volume 26 'Heats of Mixing, Vapor-Liquid Equilibrium, and Volumetric Properties of Mixtures and Solutions' of Landolt-Börnstein Group IV 'Physical Chemistry'. It contains the Chapter 'Volumetric Properties of the Mixture Propenenitrile C3H3N + C3H6O2 Methyl ethanoate (VMSD1511, LB4267_V)' providing data from direct measurement of low-pressure thermodynamic speed of sound at variable mole fraction and constant temperature, in the single-phase region(s).

  11. Volumetric Properties of the Mixture Propenenitrile C3H3N + C3H6O2 Methyl ethanoate (VMSD1111, LB4251_V)

    NASA Astrophysics Data System (ADS)

    Cibulka, I.; Fontaine, J.-C.; Sosnkowska-Kehiaian, K.; Kehiaian, H. V.

    This document is part of Subvolume C 'Binary Liquid Systems of Nonelectrolytes III' of Volume 26 'Heats of Mixing, Vapor-Liquid Equilibrium, and Volumetric Properties of Mixtures and Solutions' of Landolt-Börnstein Group IV 'Physical Chemistry'. It contains the Chapter 'Volumetric Properties of the Mixture Propenenitrile C3H3N + C3H6O2 Methyl ethanoate (VMSD1111, LB4251_V)' providing data from direct low-pressure measurement of mass density at variable mole fraction and constant temperature, in the single-phase region(s).

  12. Volumetric Properties of the Mixture Propenenitrile C3H3N + C3H6O2 Methyl ethanoate (VMSD1212, LB4261_V)

    NASA Astrophysics Data System (ADS)

    Cibulka, I.; Fontaine, J.-C.; Sosnkowska-Kehiaian, K.; Kehiaian, H. V.

    This document is part of Subvolume C 'Binary Liquid Systems of Nonelectrolytes III' of Volume 26 'Heats of Mixing, Vapor-Liquid Equilibrium, and Volumetric Properties of Mixtures and Solutions' of Landolt-Börnstein Group IV 'Physical Chemistry'. It contains the Chapter 'Volumetric Properties of the Mixture Propenenitrile C3H3N + C3H6O2 Methyl ethanoate (VMSD1212, LB4261_V)' providing data by calculation of molar excess volume from low-pressure density measurements at variable mole fraction and constant temperature.

  13. Volumetric Properties of the Mixture Propenenitrile C3H3N + C3H6O2 Methyl ethanoate (VMSD1412, LB4273_V)

    NASA Astrophysics Data System (ADS)

    Cibulka, I.; Fontaine, J.-C.; Sosnkowska-Kehiaian, K.; Kehiaian, H. V.

    This document is part of Subvolume C 'Binary Liquid Systems of Nonelectrolytes III' of Volume 26 'Heats of Mixing, Vapor-Liquid Equilibrium, and Volumetric Properties of Mixtures and Solutions' of Landolt-Börnstein Group IV 'Physical Chemistry'. It contains the Chapter 'Volumetric Properties of the Mixture Propenenitrile C3H3N + C3H6O2 Methyl ethanoate (VMSD1412, LB4273_V)' providing data by calculation of isentropic compressibility from low-pressure density and thermodynamic speed of sound data at variable mole fraction and constant temperature, in the single-phase region(s).

  14. 2-Methyl­pyridinium 5-(2,4-dinitro­phen­yl)-1,3-dimethyl­barbiturate

    PubMed Central

    Sridevi, Gunaseelan; Kalaivani, Doraisamyraja

    2012-01-01

    In the title mol­ecular salt [systematic name: 2-methyl­pyridinium 5-(2,4-dinitro­phen­yl)-1,3-dimethyl-2,6-dioxo-1,2,3,6-tetra­hydro­pyrimidin-4-olate], C6H8N+·C12H9N4O7 −, the cation and anion are linked a through strong N—H⋯O hydrogen bond. In the crystal, C—H⋯O inter­actions link the ions, generating a chain along [010]. PMID:22589914

  15. Mechanism and regioselectivity of the reversible Diels-Alder cycloaddition of 2-methyl-1,3 butadiene with C48B6N6 heterofullerene: a DFT approach.

    PubMed

    Zahedi, Ehsan

    2014-09-01

    A theoretical study of the mechanism and regioslectivity of Diels-Alder [4+2] cycloaddition reactions between 2-methyl-1,3 butadiene and hetero bonds of the most stable isomer of C48B6N6 heterofullerene have been studied at the B3LYP/6-31G(*) level. Three heterobond pathways BC, BN and NC including two regioisomers for each one are considered by different approaches. All studied reactions have normal electron demand nature and corresponding regioisomers are produced via asynchronous processes. Predicted regioselectivities using electronic and energetic results are in complete agreement with each other and show that BC heterobond pathway is more active than others and regioisomer 16 is the major. The local reactivity difference values (Rk) show that all reaction sites at C48B6N6 present ambiphilic activation while reaction sites at 2-methyl-1,3 butadiene show nucleophilic activation. Therefore, it is predictable that C48B6N6 should present electrophilic nature. Plotting of ΔRk and Δs values of six studied channels toward corresponding activation Gibbs free energies showed that the regioisomeric channel with lower ΔRk and Δs values is faster and vice versa. PMID:25203975

  16. Fixation of chiral smectic liquid crystal (S)-(+)-4-(2-methyl-1-butyloyloxy)phenyl 4-[1-(propenoyloxy) butiloxy] benzoate using UV curing techniques

    NASA Astrophysics Data System (ADS)

    Afrizal, Hikam, Muhammad; Soegiyono, Bambang; Riswoko, Asep; Nurdelima, Umeir

    2014-03-01

    Chiral Smectic Liquid Crystal (S)-(+)-4-(2-methyl-1-butyloyloxy)phenyl 4-[1-(propenoyloxy) butiloxy] benzoate has been synthesized using method of steglich esterification at room temperature. The mesomorphic behavior of chiral smectic at 55°C that showed schlieren texture in POM analysis. Fixation of structure chiral smectic liquid crystal by means of photopolymerization of monomer (S)-(+)-4-(2-methyl-1-butyloyloxy)phenyl 4-[1-(propenoyloxy) butiloxy] benzoate under UV irradiation which called UV curing techniques. The curing process using UV 3 lamps 100 volt at 60°C for an hour. The product of photopolymerization could be seen by analysis of FTIR spectra both monomer and polymer. FTIR spectra of monomer, two peaks for ester carbonyl and C-C double bond groups appeared at 1729.09 cm-1and 3123.46 cm-1. After UV curing process, peak for the carbonyl group at 1729.09 cm-1 decreased and a new peak at 1160.21 cm-1 appeared due to the carbonyl group attached to a C-C bond group and then peak at 3123.46 cm-1 for C-C double bond group was disappeared.

  17. Conformational polymorphs of isobutyl-6-amino-5-cyano-2-methyl-4-phenyl-4H-pyran-3-carboxylate: spectroscopic, structural and DFT approach.

    PubMed

    Prasad, A Aditya; Kumar, C Udhaya; Prakasam, B Arul; Meenakshisundaram, S P

    2016-06-01

    The crystal structure of a new crystalline phase, polymorph (II) of isobutyl-6-amino-5-cyano-2-methyl-4-phenyl-4H-pyran-3-carboxylate, was accurately determined by single-crystal X-ray diffraction analysis providing a clean identification of polymorphic forms. Comparison with a known phase, referred to as polymorph (I), reveals the type of supramolecular assembly. Inter- and intramolecular hydrogen-bonding interactions exhibit various supramolecular architectures in crystal packing and these variations confirm well the polymorphism in isobutyl-6-amino-5-cyano-2-methyl-4-phenyl-4H-pyran-3-carboxylate (IAPC) crystal structure. Crystal cohesion is achieved by N-H...N, N-H...O and C-H...H-C interactions, responsible for the formation and strengthening of the supramolecular assembly. The objective of this investigation is to study crystalline forms which can offer enhanced physicochemical properties, and also to recognize the molecular orientations between such forms. The conformational polymorphs of IAPC were compared spectroscopically by FT-IR and FT-Raman. The bulk phases were studied by X-ray powder diffraction patterns. External morphology was investigated using scanning electron microscopic images. The molecular interactions were quantified using Hirshfeld surface and fingerprint analysis. Density functional theory (DFT) computations were used to optimize the structure. The optimized structure is further subjected to an analysis of Mulliken population, natural population and electrostatic potential. PMID:27240761

  18. Effects of 5-chloro-2-methyl-4-isothiazolin-3-one and other candidate biodiesel biocides on rat alveolar macrophages and NR8383 cells.

    PubMed

    Poon, R; Rigden, M; Edmonds, N; Charman, N; Lamy, S

    2011-11-01

    Biocides are added to biodiesels to inhibit and remove microbial growth. The effects of 5-chloro-2-methyl-4-isothiazolin-3-one (CMIT), a candidate biodiesel biocide, were studied using freshly isolated rat alveolar macrophages (AM) and NR8383 cell line. CMIT markedly inhibited phagocytic oxidative burst as measured by zymosan-induced chemiluminescence, and cellular cytokine secretion as measured by zymosan-induced TNF-α secretion. The 50% inhibition concentration (LC(50)) for CMIT was 0.002-0.004 mM for both cellular functions. AM exposed to CMIT for as little as 2 min showed markedly inhibited functions that persisted for at least 5 h. Sodium metabisulfite was able to partially neutralize the inhibitory activity of CMIT. Cysteine and glutathione, when present at a molar ratio of 2-1 or higher against CMIT, were effective neutralizers, while serine, histidine, alanine, and albumin were without effect. When the AM testing system was used to compare the toxicity of CMIT against three other candidate biodiesel biocides, methylene dithiocyanate (MDC) was found to be of comparable toxicity to CMIT, 2-methyl-4-isothiazolin-3-one (MIT) was much less toxic, and dimethyl acetylenedicarboxylate (DMAD) was non-toxic. Because AM is among the first cell-type exposed to inhaled biodiesel aerosols, the result suggested that CMIT present in biodiesel may produce respiratory effects, and further investigations including animal studies are warranted. PMID:21445588

  19. Fixation of chiral smectic liquid crystal (S)-(+)-4-(2-methyl-1-butyloyloxy)phenyl 4-[1-(propenoyloxy) butiloxy] benzoate using UV curing techniques

    SciTech Connect

    Afrizal, Nurdelima,; Umeir; Hikam, Muhammad; Soegiyono, Bambang; Riswoko, Asep

    2014-03-24

    Chiral Smectic Liquid Crystal (S)-(+)-4-(2-methyl-1-butyloyloxy)phenyl 4-[1-(propenoyloxy) butiloxy] benzoate has been synthesized using method of steglich esterification at room temperature. The mesomorphic behavior of chiral smectic at 55°C that showed schlieren texture in POM analysis. Fixation of structure chiral smectic liquid crystal by means of photopolymerization of monomer (S)-(+)-4-(2-methyl-1-butyloyloxy)phenyl 4-[1-(propenoyloxy) butiloxy] benzoate under UV irradiation which called UV curing techniques. The curing process using UV 3 lamps 100 volt at 60°C for an hour. The product of photopolymerization could be seen by analysis of FTIR spectra both monomer and polymer. FTIR spectra of monomer, two peaks for ester carbonyl and C-C double bond groups appeared at 1729.09 cm-1and 3123.46 cm{sup −1}. After UV curing process, peak for the carbonyl group at 1729.09 cm{sup −1} decreased and a new peak at 1160.21 cm{sup −1} appeared due to the carbonyl group attached to a C-C bond group and then peak at 3123.46 cm{sup −1} for C-C double bond group was disappeared.

  20. 40 CFR 721.2078 - 1-Piperidinecarboxylic acid, 2-[(dichloro-hydroxy-carbomonocycle)hydrazono]-, methyl ester...

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... generically identified as 1-piperidinecarboxylic acid, 2- -, methyl ester (PMN P-96-756) is subject to....125 (a), (b), (c), (d), (f), (g), (h), and (i) are applicable to manufacturers, importers, and... AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES...

  1. 40 CFR 721.2078 - 1-Piperidinecarboxylic acid, 2-[(dichloro-hydroxy-carbomonocycle)hydrazono]-, methyl ester...

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... generically identified as 1-piperidinecarboxylic acid, 2- -, methyl ester (PMN P-96-756) is subject to....125 (a), (b), (c), (d), (f), (g), (h), and (i) are applicable to manufacturers, importers, and... AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES...

  2. Isopropyl methyl phosphonic acid (IMPA)

    Integrated Risk Information System (IRIS)

    Isopropyl methyl phosphonic acid ( IMPA ) ; CASRN 1832 - 54 - 8 Human health assessment information on a chemical substance is included in the IRIS database only after a comprehensive review of toxicity data , as outlined in the IRIS assessment development process . Sections I ( Health Hazard Assess

  3. Spectrophotometric, Fourier transform infrared spectroscopic and theoretical studies of the charge-transfer complexes between methyldopa [(S)-2 amino-3-(3,4-dihydroxyphenyl)-2-methyl propanoic acid] and the acceptors (chloranilic acid, o-chloranil and dichlorodicyanobenzoquinone) in acetonitrile and their thermodynamic properties

    NASA Astrophysics Data System (ADS)

    Sharma, K.; Sharma, S. P.; Lahiri, S. C.

    Methyldopa is a much used antihypertensive drug. It is the subject matter of study mostly for the determination and estimation of methyldopa in pharmaceutical properties. These considerations led us to study the charge-transfer interactions between methyldopa, a centrally acting antihypertensive agent of limited use with the known acceptors like o-chloranil (o-ClN), chloranilic acid (ClA) and dichlorodicyanobenzoquinone (DDQ). Methyldopa (MDP) formed beautifully colored complexes (having absorption maxima at 581 nm and 368 nm; 519 nm; 583.5 nm, 547 nm and 346 nm, respectively) with the acceptors mentioned before. The physico-chemical properties of the complexes were studied using UV-visible spectrophotometry and FTIR measurements. The composition, the accurate association constants and thermodynamics of the complexes were determined spectrophotometrically. Attempts were made to interpret the thermodynamics of complexes in terms of IDV, EAV and hνCT. Solid CT complexes between MDP + o-ClN, MDP + ClA and MDP + DDQ were prepared and FTIR spectra of the complexes were studied. The energies hνCT of the charge-transfer complexes and vertical ionization potential IDV of methyldopa were compared with the theoretical values of hνCT obtained from HOMO and LUMO of the donors and acceptors calculated using Density Function Theory utilizing different basis sets. The agreement between the results can be regarded to be reasonable. Oscillator strengths and dipole strengths of the complexes were determined theoretically and experimentally and the limitations of the calculations were outlined.

  4. Spectrophotometric, Fourier transform infrared spectroscopic and theoretical studies of the charge-transfer complexes between methyldopa [(S)-2 amino-3-(3,4-dihydroxyphenyl)-2-methyl propanoic acid] and the acceptors (chloranilic acid, o-chloranil and dichlorodicyanobenzoquinone) in acetonitrile and their thermodynamic properties.

    PubMed

    Sharma, K; Sharma, S P; Lahiri, S C

    2012-06-15

    Methyldopa is a much used antihypertensive drug. It is the subject matter of study mostly for the determination and estimation of methyldopa in pharmaceutical properties. These considerations led us to study the charge-transfer interactions between methyldopa, a centrally acting antihypertensive agent of limited use with the known acceptors like o-chloranil (o-ClN), chloranilic acid (ClA) and dichlorodicyanobenzoquinone (DDQ). Methyldopa (MDP) formed beautifully colored complexes (having absorption maxima at 581 nm and 368 nm; 519 nm; 583.5 nm, 547 nm and 346 nm, respectively) with the acceptors mentioned before. The physico-chemical properties of the complexes were studied using UV-visible spectrophotometry and FTIR measurements. The composition, the accurate association constants and thermodynamics of the complexes were determined spectrophotometrically. Attempts were made to interpret the thermodynamics of complexes in terms of I(D)(V), E(A)(V) and hν(CT). Solid CT complexes between MDP+o-ClN, MDP+ClA and MDP+DDQ were prepared and FTIR spectra of the complexes were studied. The energies hν(CT) of the charge-transfer complexes and vertical ionization potential I(D)(V) of methyldopa were compared with the theoretical values of hν(CT) obtained from HOMO and LUMO of the donors and acceptors calculated using Density Function Theory utilizing different basis sets. The agreement between the results can be regarded to be reasonable. Oscillator strengths and dipole strengths of the complexes were determined theoretically and experimentally and the limitations of the calculations were outlined. PMID:22446770

  5. 2-Chloro-4-[[(1R,2R)-2-hydroxy-2-methyl-cyclopentyl]amino]-3-methyl-benzonitrile: A Transdermal Selective Androgen Receptor Modulator (SARM) for Muscle Atrophy.

    PubMed

    Saeed, Ashraf; Vaught, Grant M; Gavardinas, Kostas; Matthews, Donald; Green, Jonathan E; Losada, Pablo Garcia; Bullock, Heather A; Calvert, Nathan A; Patel, Nita J; Sweetana, Stephanie A; Krishnan, Venkatesh; Henck, Judith W; Luz, John G; Wang, Yong; Jadhav, Prabhakar

    2016-01-28

    A transdermal SARM has a potential to have therapeutic benefit through anabolic activity in muscle while sparing undesired effects of benign prostate hyperplasia (BPH) and liver-mediated decrease in HDL-C. 2-Chloro-4-[(2-hydroxy-2-methyl-cyclopentyl)amino]-3-methyl-benzonitrile 6 showed the desired muscle and prostate effects in a preclinical ORX rat model. Compound 6 had minimal effect on HDL-C levels in cynomolgus monkeys and showed human cadaver skin permeability, thus making it an effective tool for proof-of-concept studies in a clinical setting. PMID:26683992

  6. Crystal structure of (+)-methyl (E)-3-[(2S,4S,5R)-2-amino-5-hy-droxy-meth-yl-2-tri-chloro-methyl-1,3-dioxolan-4-yl]-2-methyl-prop-2-enoate.

    PubMed

    Oishi, Takeshi; Yasushima, Daichi; Yuasa, Kihiro; Sato, Takaaki; Chida, Noritaka

    2016-03-01

    In the title compound, C10H14Cl3NO5, the five-membered dioxolane ring adopts an envelope conformation. The C atom at the flap, which is bonded to the hy-droxy-methyl substituent, deviates from the mean plane of other ring atoms by 0.357 (5) Å. There are two intra-molecular hydrogen bonds (O-H⋯N and N-H⋯O) between the hy-droxy and amino groups, so that O- and N-bound H atoms involved in these hydrogen bonds are each disordered with equal occupancies of 0.50. The methyl 2-methyl-prop-2-enoate substituent also shows a disordered structure over two sets of sites with refined occupancies of 0.482 (5) and 0.518 (5). In the crystal, mol-ecules are connected into a dimer by an O-H⋯O hydrogen bond. The dimers are further linked by N-H⋯O, C-H⋯N and C-H⋯O inter-actions, extending a sheet structure parallel to ([Formula: see text]01). PMID:27006804

  7. The Oncogenic Polycomb Histone Methyltransferase EZH2 Methylates Lysine 120 on Histone H2B and Competes Ubiquitination12

    PubMed Central

    Kogure, Masaharu; Takawa, Masashi; Saloura, Vassiliki; Sone, Kenbun; Piao, Lianhua; Ueda, Koji; Ibrahim, Reem; Tsunoda, Tatsuhiko; Sugiyama, Masanori; Atomi, Yutaka; Nakamura, Yusuke; Hamamoto, Ryuji

    2013-01-01

    The histone methyltransferase enhancer of zeste 2 (EZH2) is known to be a polycomb protein homologous to Drosophila enhancer of zeste and catalyzes the addition of methyl groups to histone H3 at lysine 27 (H3K27). We previously reported that EZH2 was overexpressed in various types of cancer and plays a crucial role in the cell cycle regulation of cancer cells. In the present study, we demonstrated that EZH2 has the function to monomethylate lysine 120 on histone H2B (H2BK120). EZH2-dependent H2BK120 methylation in cancer cells was confirmed with an H2BK120 methylation-specific antibody. Overexpression of EZH2 significantly attenuated the ubiquitination of H2BK120, a key posttranslational modification of histones for transcriptional regulation. Concordantly, knockdown of EZH2 increased the ubiquitination level of H2BK120, suggesting that the methylation of H2BK120 by EZH2 may competitively inhibit the ubiquitination of H2BK120. Subsequent chromatin immunoprecipitation-Seq and microarray analyses identified downstream candidate genes regulated by EZH2 through the methylation of H2BK120. This is the first report to describe a novel substrate of EZH2, H2BK120, unveiling a new aspect of EZH2 functions in human carcinogenesis. PMID:24339737

  8. Crystal structure of bis­(2-methyl-1H-imidazol-3-ium) μ-oxalato-bis­[n-butyl­tri­chlorido­stannate(IV)

    PubMed Central

    Diop, Mouhamadou Birame; Diop, Libasse; Oliver, Allen G.

    2016-01-01

    The SnIV atom in the centrosymmetric anion of the title salt, (C4H7N2)2[Sn2(C4H9)2(C2O4)Cl6], is coordinated in a distorted octa­hedral mode by two O atoms of a bridging oxalate moiety, three Cl atoms and a C atom of an n-butyl group. The latter is disordered over two sets of sites in a 0.66:0.33 occupancy ratio. N—H⋯O and N—H⋯Cl hydrogen bonds involving the 2-methyl­imidazolium cation and neighbouring anions result in the formation of chains extending parallel to [001]. PMID:27308059

  9. Properties of 4-dicyanomethylene-2-methyl-6-(p-dimethyl-aminostyryl)-4H-pyran-doped Alq layers as optically pumped lasers

    NASA Astrophysics Data System (ADS)

    Jakabovič, J.; Lengyel, O.; Kováč, J.; Wong, T. C.; Lee, C. S.; Lee, S. T.

    2003-08-01

    The optical properties of tris-(8-hydroxyquinoline) aluminum (Alq) doped with 4-dicyanomethylene-2-methyl-6-(p-dimethyl-aminostyryl)-4H-pyran (DCM) in solutions and in solid films were studied by measuring the steady-state excitation and spontaneous emission spectra. The emission peak in the solid films shifted from 628 to 659 nm as the doping concentration of DCM changed from 0.9% to 11%. The optically pumped waveguide lasers were fabricated by coevaporation of Alq films with 1.3 wt % DCM onto gallium arsenide (GaAs) substrates using silicon dioxide (SiO2) and magnesium fluoride (MgF2) as cladding layers. Both types of waveguide laser structures showed optical confinement and simulated emission at a threshold pumping energy near 1.4 μJ. The result suggests a thin MgF2 may be used as a confinement layer that has the advantage of preparation by low-temperature evaporation.

  10. Crystal structure of bis-(2-methyl-1H-imidazol-3-ium) μ-oxalato-bis-[n-butyl-tri-chlorido-stannate(IV)].

    PubMed

    Diop, Mouhamadou Birame; Diop, Libasse; Oliver, Allen G

    2016-06-01

    The Sn(IV) atom in the centrosymmetric anion of the title salt, (C4H7N2)2[Sn2(C4H9)2(C2O4)Cl6], is coordinated in a distorted octa-hedral mode by two O atoms of a bridging oxalate moiety, three Cl atoms and a C atom of an n-butyl group. The latter is disordered over two sets of sites in a 0.66:0.33 occupancy ratio. N-H⋯O and N-H⋯Cl hydrogen bonds involving the 2-methyl-imidazolium cation and neighbouring anions result in the formation of chains extending parallel to [001]. PMID:27308059

  11. Conformations of solid 2-methyl-4-( p-X-phenylazo)imidazoles by 13C CP MAS NMR spectroscopy and PM3 semi-empirical calculations

    NASA Astrophysics Data System (ADS)

    Maciejewska, Dorota

    1999-03-01

    Solid 2-methyl-4-( p-X-phenylazo)imidazoles form hydrogen bonded chains with N-H⋯N bonds and C-H⋯O or C-H⋯N interaction. Depending on the nature and orientation of the substituents X it was possible to identify one tautomer if XH ( 2), Br ( 3), NO 2 ( 4) and the two, a- and b-tautomers in the crystal unit if XOCH 3 ( 1). The 13C CP MAS NMR spectra of ( 4) indicate the presence of phenyl ring dynamics. A preferred structure present in the solid state is that with different lengths of C1'-N and C4-N bonds and with higher dipole moment.

  12. Crystallization of lysozyme with (R)-, (S)- and (RS)-2-methyl-2,4-pentanediol

    SciTech Connect

    Stauber, Mark; Jakoncic, Jean; Berger, Jacob; Karp, Jerome M.; Axelbaum, Ariel; Sastow, Dahniel; Buldyrev, Sergey V.; Hrnjez, Bruce J.; Asherie, Neer

    2015-03-01

    Chiral control of crystallization has ample precedent in the small-molecule world, but relatively little is known about the role of chirality in protein crystallization. In this study, lysozyme was crystallized in the presence of the chiral additive 2-methyl-2,4-pentanediol (MPD) separately using the R and S enantiomers as well as with a racemic RS mixture. Crystals grown with (R)-MPD had the most order and produced the highest resolution protein structures. This result is consistent with the observation that in the crystals grown with (R)-MPD and (RS)-MPD the crystal contacts are made by (R)-MPD, demonstrating that there is preferential interaction between lysozyme and this enantiomer. These findings suggest that chiral interactions are important in protein crystallization.

  13. A novel 3-acetoxy-2-methyl-N-(4-methoxyphenyl)benzamide: Molecular structural describe, antioxidant activity with use X-ray diffractions and DFT calculations

    NASA Astrophysics Data System (ADS)

    Demir, Sibel; Cakmak, Sukriye; Dege, Necmi; Kutuk, Halil; Odabasoglu, Mustafa; Kepekci, R. Aysun

    2015-11-01

    In this work, the structure of a novel 3-acetoxy-2-methyl-N-(4-methoxyphenyl) benzamide, was analyzed both experimentally and theoretically using three methods, X-ray single crystal diffraction technique, IR spectroscopy, and quantum chemical computation. The X-ray diffraction analysis indicates that 3-acetoxy-2-methyl-N-(4-methoxyphenyl) benzamide molecula crystallizes in a triclinic system (space group P-1) and the calculated lattice constants are, a = 5.1205 ± 0.0004 Å, b = 9.8598 ± 0.0008 Å, c = 15.3398 ± 0.0013 Å, α = 80.79(7)°, β = 83.142(6)°, γ= 85.411(6)°, and Z = 2. In addition, the molecular geometry and vibrational frequencies of the title compound in ground state have been calculated using density functional theory (DFT) at B3LYP level 6-31G+(d,p) basis set. The geometrical parameters of the title compound obtained from XRD studies are good in agreement with the calculated values. The electronic properties, such as HOMO and LUMO energies and thermodynamic properties were calculated with DFT (using B3LYP/6-31G+(d,p) basis set) approach. To estimate the chemical reactivity of the molecule, the molecular electrostatic potential (MEP) surface map of the title molecule and PES scan were investigated with theoretical calculations at the B3LYP/6-31+G(d,p) and B3LYP/3-21G levels, respectively. Antioxidant properties are determined using DPPH free radical scavenging test.

  14. Temperature-dependence of the influence of the position-2-methyl group on the structure-directing effect of piperazine in the synthesis of open-framework aluminophosphates

    PubMed Central

    Huang, Pai; Xu, Jun; Qi, Guodong; Deng, Feng; Xu, Ruren; Yan, Wenfu

    2016-01-01

    The temperature-dependence of the influence of the position-2-methyl group on the structure-directing effect of piperazine in the synthesis of open-framework aluminophosphates was investigated. By heating the initial mixture with the composition of Al2O3:1.5 P2O5:R:125 H2O at 160 °C, where R is the structure-directing agent of 2-methylpiperazine or piperazine, layered aluminophosphates APMeP150 (R = 2-methylpiperazine) and AP2pip (R = piperazine) were obtained. When the same initial reaction mixture was heated at 190 °C, layered aluminophosphates APMeP200 (R = 2-methylpiperazine) and AP2pip (R = piperazine) were crystallized. APMeP200 and AP2pip have the same inorganic sheet topology. We investigated the crystallization processes of the four open-framework aluminophosphates and found that increasing the heating temperature slowed the crystallization of the initial mixtures. The non-bonding interactions between the inorganic layers of the four open-framework aluminophosphates and the experimental or theoretically generated structure-directing agents were calculated. The possible starting points of the crystallization of the four open-framework aluminophosphates were analysed and compared. The temperature-dependence of the influence of the position-2-methyl group on the structure-directing effect of piperazine revealed that the structure-directing effect, the most important factor in the synthesis of zeolites and related open-framework materials, is determined by multiple factors. The structural parameters of the same compound can be affected by the synthesis conditions. PMID:26912387

  15. Kinetic studies on the acid hydrolysis of the methyl ketoside of unsubstituted and O-acetylated N-acetylneuraminic acid

    PubMed Central

    Neuberger, A.; Ratcliffe, Wendy A.

    1973-01-01

    The hydrolysis of the model compound 2-O-methyl-4,7,8,9-tetra-O-acetyl-N-acetyl-α-d-neuraminic acid and neuraminidase (Vibrio cholerae) closely resembled that of the O-acetylated sialic acid residues of rabbit Tamm–Horsfall glycoprotein. This confirmed that O-acetylation was responsible for the unusually slow rate of acid hydrolysis of O-acetylated sialic acid residues observed in rabbit Tamm–Horsfall glycoprotein and their resistance to hydrolysis by neuraminidase. The first-order rate constant of hydrolysis of 2-methyl-N-acetyl-α-d-neuraminic acid by 0.05m-H2SO4 was 56-fold greater than that of 2-O-methyl-4,7,8,9-tetra-O-acetyl-N-acetyl -α-d-neuraminic acid. Kinetic studies have shown that in the pH range 1.00–3.30, the observed rate of hydrolysis of 2-methyl-N-acetyl-α-d-neuraminic acid can be attributed to acid-catalysed hydrolysis of the negatively charged CO2− form of the methyl ketoside. PMID:4748825

  16. 5-Chloro-2-methyl­sulfonyl-1,2,4-triazolo[1,5-a]quinazoline

    PubMed Central

    Al-Salahi, Rashad; Al-Omar, Mohamed; Marzouk, Mohamed; Ng, Seik Weng

    2012-01-01

    The triazoloquinazole fused-ring system of the title compound, C10H7ClN4O2S, is essentially planar (r.m.s. deviation = 0.009 Å). In the methyl­sulfonyl substituent, the two S—O bonds are of equal length [1.402 (2) Å]. In the crystal, adjacent mol­ecules inter­act weakly through Cl⋯N contacts [ca 3.197 (2) Å]. PMID:22719581

  17. Impact of Stepwise NH2-Methylation of Triapine on the Physicochemical Properties, Anticancer Activity, and Resistance Circumvention

    PubMed Central

    2016-01-01

    One of the most promising classes of iron chelators are α-N-heterocyclic thiosemicarbazones with Triapine as the most prominent representative. In several clinical trials Triapine showed anticancer activity against hematological diseases, however, studies on solid tumors failed due to widely unknown reasons. Some years ago, it was recognized that “terminal dimethylation” of thiosemicarbazones can lead to a more than 100-fold increased activity, probably due to interactions with cellular copper depots. To better understand the structural requirements for the switch to nanomolar cytotoxicity, we systematically synthesized all eight possible N-methylated derivatives of Triapine and investigated their potential against Triapine-sensitive as well as -resistant cell lines. While only the “completely” methylated compound exerted nanomolar activity, the data revealed that all compounds with at least one N-dimethylation were not affected by acquired Triapine resistance. In addition, these compounds were highly synergistic with copper treatment accompanied by induction of reactive oxygen species and massive necrotic cell death. PMID:27336684

  18. Impact of Stepwise NH2-Methylation of Triapine on the Physicochemical Properties, Anticancer Activity, and Resistance Circumvention.

    PubMed

    Kowol, Christian R; Miklos, Walter; Pfaff, Sarah; Hager, Sonja; Kallus, Sebastian; Pelivan, Karla; Kubanik, Mario; Enyedy, Éva A; Berger, Walter; Heffeter, Petra; Keppler, Bernhard K

    2016-07-28

    One of the most promising classes of iron chelators are α-N-heterocyclic thiosemicarbazones with Triapine as the most prominent representative. In several clinical trials Triapine showed anticancer activity against hematological diseases, however, studies on solid tumors failed due to widely unknown reasons. Some years ago, it was recognized that "terminal dimethylation" of thiosemicarbazones can lead to a more than 100-fold increased activity, probably due to interactions with cellular copper depots. To better understand the structural requirements for the switch to nanomolar cytotoxicity, we systematically synthesized all eight possible N-methylated derivatives of Triapine and investigated their potential against Triapine-sensitive as well as -resistant cell lines. While only the "completely" methylated compound exerted nanomolar activity, the data revealed that all compounds with at least one N-dimethylation were not affected by acquired Triapine resistance. In addition, these compounds were highly synergistic with copper treatment accompanied by induction of reactive oxygen species and massive necrotic cell death. PMID:27336684

  19. Crystal structure of 1,1'-bis-(2-meth-oxy-carbonyl-2-methyl-prop-yl)ferrocene.

    PubMed

    Guo, Yan-Feng; Wang, Jian-Jun; Xu, Wei-Juan; Sun, Dong-Hao; Gao, Qiang

    2015-12-01

    The Fe atom in the title ferrocene derivative, [Fe(C11H15O2)2], is situated on an inversion centre. As a result of the point-group symmetry -1 of the mol-ecule, the ferrocene moiety adopts a staggered conformation. The average Fe-C(Cp) bond length (Cp is cyclo-penta-dien-yl) is 2.045 (4) Å, in agreement with that of other disubstituted ferrocenes. The Fe-C bond length involving the substituted C atom is slightly longer [2.0521 (17) Å] than the remaining Fe-C bond lengths caused by the inductive effect of the methyl-ene group on the Cp ring. Apart from van der Waals forces, no significant inter-molecular inter-actions are observed in the crystal packing. PMID:26870430

  20. Stability constants and molar absorptivities for complexes of copper(II) with N-methyldiethanolamine, 1,4-bis(2-hydroxypropyl)-2-methylpiperazine, and 2-amino-2-methyl-1-propanol.

    PubMed

    Siefker, J R; Aroc, R V

    1986-09-01

    The stability constants and molar absorptivities of complexes of Cu(2+) with N-methyldiethanolamine, 1,4-bis(2-hydroxypropyl)-2-methylpiperazine, and 2-amino-2-methyl-1-propanol have been determined from spectrophotometric data for very dilute aqueous solutions. PMID:18964197

  1. Substituent and ring effects on enthalpies of formation: 2-methyl- and 2-ethylbenzimidazoles versus benzene- and imidazole-derivatives

    NASA Astrophysics Data System (ADS)

    Jiménez, Pilar; Roux, María Victoria; Dávalos, Juan Z.; Temprado, Manuel; Ribeiro da Silva, Manuel A. V.; Ribeiro da Silva, Maria Das Dores M. C.; Amaral, Luísa M. P. F.; Cabildo, Pilar; Claramunt, Rosa M.; Mó, Otilia; Yáñez, Manuel; Elguero, José

    The enthalpies of combustion, heat capacities, enthalpies of sublimation and enthalpies of formation of 2-methylbenzimidazole (2MeBIM) and 2-ethylbenzimidazole (2EtBIM) are reported and the results compared with those of benzimidazole itself (BIM). Theoretical estimates of the enthalpies of formation were obtained through the use of atom equivalent schemes. The necessary energies were obtained in single-point calculations at the B3LYP/6-311+G(d,p) on B3LYP/6-31G* optimized geometries. The comparison of experimental and calculated values of benzenes, imidazoles and benzimidazoles bearing H (unsubstituted), methyl and ethyl groups shows remarkable homogeneity. The energetic group contribution transferability is not followed, but either using it or adding an empirical interaction term, it is possible to generate an enormous collection of reasonably accurate data for different substituted heterocycles (pyrazole-derivatives, pyridine-derivatives, etc.) from the large amount of values available for substituted benzenes and those of the parent (pyrazole, pyridine) heterocycles.

  2. The Silencing of CCND2 by Promoter Aberrant Methylation in Renal Cell Cancer and Analysis of the Correlation between CCND2 Methylation Status and Clinical Features.

    PubMed

    Wang, Lu; Cui, Yun; Zhang, Lian; Sheng, Jindong; Yang, Yang; Kuang, Guanyu; Fan, Yu; Zhang, Qian; Jin, Jie

    2016-01-01

    Cyclin D2 (CCND2) is a member of the D-type cyclins, which plays a pivotal role in cell cycle regulation, differentiation and malignant transformation. However, its expression status and relative regulation mechanism remains unclear in renal cell cancer (RCC). In our study, the mRNA expression level of CCND2 is down-regulated in 22/23 paired RCC tissues (p<0.05). In addition, its protein expression level is also decreased in 43/43 RCC tumor tissues compared with its corresponding non-malignant tissues (p<0.001). We further detected that CCND2 was down-regulated or silenced in 6/7 RCC cell lines, but expressed in "normal" human proximal tubular (HK-2) cell line. Subsequently, MSP and BGS results showed that the methylation status in CCND2 promoter region is closely associated with its expression level in RCC cell lines. Treatment with 5-Aza with or without TSA restored CCND2 expression in several methylated RCC cell lines. Among the 102 RCC tumors, methylation of CCND2 was detected in 29/102 (28%) cases. Only 2/23 (8.7%) adjacent non-malignant tissues showed methylation. We then analyzed the correlation of clinical features and its promoter methylation. Collectively, our data suggested that loss of CCND2 expression is closely associated with the promoter aberrant methylation. PMID:27583477

  3. Polydopamine-assisted partial hydrolyzed poly(2-methyl-2-oxazolinze) as coating for determination of melamine in milk by capillary electrophoresis.

    PubMed

    Zhang, Yalin; Chen, Lijuan; Zhang, Chong; Liu, Songtao; Zhu, Haikun; Wang, Yanmei

    2016-04-01

    Nitrogen-rich melamine (66% by mass) had been found to be illegally adulterated to milk products and animal feed in order to increase the apparent protein content, and ingestion of melamine may lead to the formation of kidney stones. Hence, the development of reliable analytical methods for the monitoring of melamine in milk products is necessary. The common methods for melamine analysis in milk products are performed via GC-MS or HPLC, however, these procedures require a large of organic solvent and several pretreatment steps. In this study, a new and facile approach was developed to modify a fused-silica capillary inner surface based on poly(dopamine) (PDA) and partial hydrolyzed poly(2-methyl-2-oxazoline) (PMOXA-EI) mixed coating, which was used to determine the melamine in milk powder quantitatively by capillary electrophoresis with ultraviolet (CE-UV) detection with simple analytes pretreatment. Firstly, the influences of the molecular mass of poly(2-methyl-2-oxazoline) (PMOXA), the hydrolysis degree of PMOXA, and the concentration ratio of DA to PMOXA-EI on the separation properties of a mixture of four basic proteins (cytochrome c, lysozyme, ribonuclease A, and α-chymotrypsinogen A) were studied in detail. As a consequence, fast and efficient separation of four proteins was obtained using PDA/PMOXA1k-EI0.4 coating (once coating). Then, a modified facile coating workflow was carried out to acquire a novel twice coating (i.e. PDA/PMOXA1k-EI0.4+PMOXA1k-EI0.4 coated capillary) for highly sensitive and stable analysis of melamine. Under the optimal conditions, the linear response of melamine concentration ranged from 6.25 to 100 µg/mL with high correlation coefficient of 0.9910, and the limit of detection (LOD) for melamine was 0.097 µg/mL. The minimum amount of melamine determined in milk powder with our proposed method was 4 mg/kg. The recoveries and relative standard deviations (RSDs) were 92.13-102.47%, 92.22-100.30%, 2.07-4.98%, and 2

  4. Inhibitory effect of 2-methyl-naphtho[1,2,3-de]quinolin-8-one on melanosome transport and skin pigmentation

    PubMed Central

    Park, Jong il; Lee, Ha Yeon; Lee, Ji Eun; Myung, Cheol hwan; Hwang, Jae Sung

    2016-01-01

    Melanosomes are lysosome-related organelles with specialized capabilities of melanin synthesis and movement mediated by the Rab27a-Melanophilin-MyosinVa protein complex. In this study, we found that 2-methyl-naphtho[1,2,3-de]quinolin-8-one (MNQO) induced melanosome aggregation around the nucleus in melan-a melanocytes and in melan-a melanocytes/SP-1 keratinocyte co-cultures without inducing toxicity or changing the melanin content. Western blot and real-time PCR analyses showed that MNQO decreased expression of the Rab27a, Melanophilin and MyosinVa proteins and mRNAs, respectively, in melan-a melanocytes. In a reconstituted human epidermis model, treatment with 0.001% MNQO reduced skin pigmentation. Also, MNQO reduced skin pigmentation in brown guinea pigs induced by UVB irradiation. These results indicated that regulation of melanosome transport may serve as a good target for new skin depigmenting agents and MNQO itself could be a candidate. PMID:27381646

  5. A study of the molecular structure and vibrational spectra of 1,3-dichloro-2-propanol and 1,1,1-trichloro-2-methyl-2-propanol (chlorobutanol).

    PubMed

    Badawi, Hassan M

    2012-02-15

    The conformational stability of 1,3-dichloro-2-propanol and 1,1,1-trichloro-2-methyl-2-propanol (chlorobutanol) was investigated by the DFT-B3LYP/6-311+G**, MP2/6-311+G** and MP4(SDQ)/6-311+G** levels of theory. From the calculations chlorobutanol was predicted to exist in a non-planar gauche structure. The planar cis and trans structures of chlorobutanol were calculated to be about 3kcal/mol higher in energy than the gauche structure. From the calculations 1,3-dichloro-2-propanol was predicted to exist in a Ggg1 and Ggg conformational mixture at ambient temperature. In the low energy structures of both alcohols the non-bonded Cl⋯H(O) distance was calculated to be of about 2.6-2.7Å. The observation of a broad and very intense band at about 3400cm(-1) in the infrared spectra of the two alcohols supports the presence of strong intermolecular Cl⋯H(O) dipolar interactions in their condensed phases. The analysis of the Raman spectra of 1,3-dichloro-2-propanol suggests the presence of a second high energy Ggg structure of the dichloride at room temperature. The vibrational frequencies of 1,3-dichloro-2-propanol and chlorobutanol in their low energy structures were computed at the B3LYP level and tentative vibrational assignments were made for their normal modes on the basis of combined calculated and experimental data. PMID:22154261

  6. A study of the molecular structure and vibrational spectra of 1,3-dichloro-2-propanol and 1,1,1-trichloro-2-methyl-2-propanol (chlorobutanol)

    NASA Astrophysics Data System (ADS)

    Badawi, Hassan M.

    2012-02-01

    The conformational stability of 1,3-dichloro-2-propanol and 1,1,1-trichloro-2-methyl-2-propanol (chlorobutanol) was investigated by the DFT-B3LYP/6-311+G**, MP2/6-311+G** and MP4(SDQ)/6-311+G** levels of theory. From the calculations chlorobutanol was predicted to exist in a non-planar gauche structure. The planar cis and trans structures of chlorobutanol were calculated to be about 3 kcal/mol higher in energy than the gauche structure. From the calculations 1,3-dichloro-2-propanol was predicted to exist in a Ggg1 and Ggg conformational mixture at ambient temperature. In the low energy structures of both alcohols the non-bonded Cl⋯H(O) distance was calculated to be of about 2.6-2.7 Å. The observation of a broad and very intense band at about 3400 cm -1 in the infrared spectra of the two alcohols supports the presence of strong intermolecular Cl⋯H(O) dipolar interactions in their condensed phases. The analysis of the Raman spectra of 1,3-dichloro-2-propanol suggests the presence of a second high energy Ggg structure of the dichloride at room temperature. The vibrational frequencies of 1,3-dichloro-2-propanol and chlorobutanol in their low energy structures were computed at the B3LYP level and tentative vibrational assignments were made for their normal modes on the basis of combined calculated and experimental data.

  7. Purification of a vitamin K epoxide reductase that catalyzes conversion of vitamin K 2,3-epoxide to 3-hydroxy-2-methyl-3-phytyl-2,3-dihydronaphthoquinone.

    PubMed Central

    Mukharji, I; Silverman, R B

    1985-01-01

    An enzyme from bovine liver microsomes that catalyzes the reduction of vitamin K 2,3-epoxide to 2- and 3-hydroxy-2-methyl-3-phytyl-2,3-dihydronaphthoquinone was purified 1152-fold to apparent homogeneity. Microsomes were solubilized with 3-[3-cholamidopropyl)dimethylammonio]-1-propanesulfonate (CHAPS), and the enzyme was purified by chromatography on PBE-94 ion exchanger, hydroxylapatite, and DEAE-cellulose, and then gel filtration on Sephacryl S-200. The homogeneity of the final preparation was established by polyacrylamide slab gel electrophoresis in the presence of sodium dodecyl sulfate. The molecular weight of the native enzyme is 25,000 and that of denatured enzyme is 12,400, which suggests that the enzyme is a dimer with identical subunits. No chromophoric cofactors are associated with the enzyme. Dithiothreitol and CHAPS are essential for activity, but high concentrations of glycerol reduces the activity. The enzyme is not inhibited by warfarin, a potent inhibitor of the vitamin K epoxide reductase, which catalyzes the conversion of vitamin K 2,3-epoxide to vitamin K. Evidence is presented indicating that the purified enzyme is not simply a fragment of the warfarin-sensitive vitamin K epoxide reductase. Images PMID:3857611

  8. Growth of amorphous zinc tin oxide films using plasma-enhanced atomic layer deposition from bis(1-dimethylamino-2-methyl-2propoxy)tin, diethylzinc, and oxygen plasma

    NASA Astrophysics Data System (ADS)

    Han, Jeong Hwan; Lee, Byoung Kook; Jung, Eun Ae; Kim, Hyo-Suk; Kim, Seong Jun; Kim, Chang Gyoun; Chung, Taek-Mo; An, Ki-Seok

    2015-12-01

    Amorphous ZnSnOx (ZTO) films were prepared using plasma-enhanced atomic layer deposition (PEALD) in a temperature range of 100-200 °C. Metal-organic precursors of Sn(dmamp)2 (dmamp = bis(1-dimethylamino-2-methyl-2-propoxide) and diethylzinc were employed as sources of Sn and Zn, respectively, in combination with O2 plasma as a reactant. Sn levels in the ZTO films were controlled by varying the SnO2/ZnO cycle ratio from 0 to 8. According to the growth behaviour of the ZTO film by alternating SnO2 and ZnO PEALD cycles, it was observed that ZnO growth on Sn-rich ZTO film is retarded, whereas SnO2 growth is enhanced on Zn-rich ZTO film. The chemical states of the ZTO films were confirmed by X-ray photoelectron spectroscopy (XPS); the chemical compositions of the ZTO films were characterised by XPS depth profiling. Grazing-angle X-ray diffraction revealed that the PEALD ZTO films possess an amorphous structure, irrespective of Sn levels from 20 to 59 at.%. ZTO films with intermediate Sn at.% exhibited smooth surface morphology compared to binary ZnO and SnO2 films. Additionally, the step coverage of a ZTO film deposited on hole pattern with an aspect ratio of 8 and opening diameter of 110 nm was about 93%, suggesting the realisation of self-limited growth.

  9. Comparative assessment of the stability of nonfouling poly(2-methyl-2-oxazoline) and poly(ethylene glycol) surface films: an in vitro cell culture study.

    PubMed

    Chen, Yin; Pidhatika, Bidhari; von Erlach, Thomas; Konradi, Rupert; Textor, Marcus; Hall, Heike; Lühmann, Tessa

    2014-09-01

    Poly(ethylene glycol) (PEG) has been the most frequently reported and commercially used polymer for surface coatings to convey nonfouling properties. PEGylated surfaces are known to exhibit limited chemical stability, particularly due to oxidative degradation, which limits long-term applications. In view of excellent anti-adhesive properties in the brush conformation and resistance to oxidative degradation, poly(2-methyl-2-oxazoline) (PMOXA) has been proposed recently as an alternative to PEG. In this study, the authors systematically compare the (bio)chemical stability of PEG- and PMOXA-based polymer brush monolayer thin films when exposed to cultures of human umbilical vein endothelial cells (HUVECs) and human foreskin fibroblasts (HFFs). To this end, the authors used cell-adhesive protein micropatterns in a background of the nonfouling PEG and PMOXA brushes, respectively, and monitored the outgrowth of HUVECs and HFFs for up to 21 days and 1.5 months. Our results demonstrate that cellular micropatterns spaced by PMOXA brushes are significantly more stable under serum containing cell culture conditions in terms of confinement of cells to the adhesive patterns, when compared to corresponding micropatterns generated by PEG brushes. Moreover, homogeneous PEG and PMOXA-based brush monolayers on Nb2O5 surfaces were investigated after immersion in endothelial cell medium using ellipsometry and x-ray photoelectron spectroscopy. PMID:25280844

  10. Growth, optical, luminescence, thermal and mechanical behavior of an organic single crystal: 3-Acetyl-2-methyl-4-phenylquinolin-1-ium chloride.

    PubMed

    Nirosha, M; Kalainathan, S; Sarveswari, S; Vijayakumar, V

    2014-04-01

    A single crystal of 3-acetyl-2-methyl-4-phenylquinolin-1-ium chloride has grown by slow evaporation solution growth technique using ethanol as solvent. The structural, thermal, optical and mechanical property has studied for the grown crystal. Single crystal XRD revealed that the crystal belongs to monoclinic system with space group P21/c. The presences of Functional groups in the crystallized material have confirmed using the FTIR vibrational spectrum. The optical absorbance spectrum recorded from 190 to 1100nm shows the cut-off wavelength occurs at 371nm. The material shows its transparency in the entire region of the visible spectrum. The photoluminescence spectrum shows the ultraviolet and blue emission in the crystal. Thermogravimetric and differential thermal analysis reveal the thermal stability of the grown crystal. Etching study shows the grown mechanism and surface features of the crystal. Vickers microhardness studies have carried out on the (01-1) plane to understand the mechanical properties of the grown crystal. The hardness of the title compound increases on increasing the load. The Meyer's index number (n), and the stiffness constants for different loads has calculated and reported. PMID:24389003

  11. Inhibitory effect of 2-methyl-naphtho[1,2,3-de]quinolin-8-one on melanosome transport and skin pigmentation.

    PubMed

    Park, Jong Il; Lee, Ha Yeon; Lee, Ji Eun; Myung, Cheol Hwan; Hwang, Jae Sung

    2016-01-01

    Melanosomes are lysosome-related organelles with specialized capabilities of melanin synthesis and movement mediated by the Rab27a-Melanophilin-MyosinVa protein complex. In this study, we found that 2-methyl-naphtho[1,2,3-de]quinolin-8-one (MNQO) induced melanosome aggregation around the nucleus in melan-a melanocytes and in melan-a melanocytes/SP-1 keratinocyte co-cultures without inducing toxicity or changing the melanin content. Western blot and real-time PCR analyses showed that MNQO decreased expression of the Rab27a, Melanophilin and MyosinVa proteins and mRNAs, respectively, in melan-a melanocytes. In a reconstituted human epidermis model, treatment with 0.001% MNQO reduced skin pigmentation. Also, MNQO reduced skin pigmentation in brown guinea pigs induced by UVB irradiation. These results indicated that regulation of melanosome transport may serve as a good target for new skin depigmenting agents and MNQO itself could be a candidate. PMID:27381646

  12. The metabotropic glutamate receptor subtype 5 antagonist fenobam is analgesic and has improved in vivo selectivity compared with the prototypical antagonist 2-methyl-6-(phenylethynyl)-pyridine.

    PubMed

    Montana, Michael C; Cavallone, Laura F; Stubbert, Kristi K; Stefanescu, Andrei D; Kharasch, Evan D; Gereau, Robert W

    2009-09-01

    Metabotropic glutamate receptor subtype 5 (mGlu5) has been demonstrated to play a role in the modulation of numerous nociceptive modalities. When administered via peripheral, intrathecal, or systemic routes, mGlu5 antagonists have analgesic properties in a variety of preclinical pain models. Despite a wealth of data supporting the use of mGlu5 antagonists to treat pain, studies have been limited to preclinical animal models due to a lack of mGlu5 antagonists that are approved for use in humans. It has been demonstrated previously that fenobam [N-(3-chlorophenyl)-N'-(4,5-dihydro-1-methyl-4-oxo-1H-imidazole-2-yl)urea], an anxiolytic shown to be safe and effective in human trials, is a selective and potent noncompetitive antagonist of mGlu5 (J Pharmacol Exp Ther 315:711-721, 2005). Here, we report a series of studies aimed at testing whether fenobam, similar to the prototypical mGlu5 antagonist 2-methyl-6-(phenylethynyl)-pyridine (MPEP), has analgesic properties in mice. We show that fenobam reduces formalin-induced pain behaviors and relieves established inflammation-induced thermal hypersensitivity in mice. Similar results were seen with MPEP. Administration of fenobam resulted in an increase in locomotor activity in the open-field task but did not impair performance on the accelerating Rotarod. Analysis of brain and plasma fenobam levels indicated that fenobam is rapidly concentrated in brain after intraperitoneal administration in mice but is essentially cleared from circulation within 1 h after injection. Fenobam had no analgesic effect in mGlu5 knockout mice, whereas the prototypical antagonist MPEP retained significant analgesic efficacy in mGlu5 knockouts. These results demonstrate that fenobam is analgesic in mice and has an improved in vivo selectivity for mGlu5 over MPEP. PMID:19515968

  13. A comparative study on vibrational, conformational and electronic structure of 1,2-dimethyl-5-nitroimidazole and 2-methyl-5-nitroimidazole

    NASA Astrophysics Data System (ADS)

    Arjunan, V.; Ravindran, P.; Santhanam, R.; Raj, Arushma; Mohan, S.

    2012-11-01

    The FTIR and FT-Raman spectra of 1,2-dimethyl-5-nitroimidazole and 2-methyl-5-nitroimidazole have been recorded in the regions 4000-400 and 4000-100 cm-1, respectively. The conformational analyses were performed and the energies of the different possible conformers were determined. The geometry of different conformers of the compounds were optimised with B3LYP and B3PW91 methods using 6-311++G∗∗ and aug-cc-pVTZ basis sets to characterise all stationary points as minima. The optimised structural parameters of the most stable conformer were used in the vibrational frequency calculations. The Raman activities were also determined with B3LYP method using 6-311++G∗∗ basis sets. The force constants obtained from the B3LYP/6-311++G∗∗ method have been utilised in the normal coordinate analysis. The temperature dependence of the thermodynamic properties heat capacity at constant pressure (Cp), entropy (S) and enthalpy change (ΔH0→T) for both the compounds were also determined by B3LYP/6-311++G∗∗ method. The total electron density and MESP surfaces of the molecules were constructed by NBO analysis using B3LYP/6-311++G∗∗ method to display electrostatic potential (electron + nuclei) distribution, molecular shape, size, and dipole moments of the molecule. The electronic properties HOMO and LUMO energies were measured. The influences of nitro and methyl groups on the skeletal modes have been investigated.

  14. Cloning, molecular characterization and functional analysis of 1-hydroxy-2-methyl-2-(E)-butenyl-4-diphosphate reductase (HDR) gene for diterpenoid tanshinone biosynthesis in Salvia miltiorrhiza Bge. f. alba.

    PubMed

    Hao, Gangping; Shi, Renjiu; Tao, Ru; Fang, Qian; Jiang, Xingyu; Ji, Haiwei; Feng, Lei; Huang, Luqi

    2013-09-01

    The enzyme 1-hydroxy-2-methyl-2-(E)-butenyl-4-diphosphate reductase (HDR) is a terminal-acting enzyme in the plastid MEP pathway, which produce isoprenoid precursors. The full-length cDNA of HDR, designated SmHDR1 (Genbank Accession No. JX516088), was isolated for the first time from Salvia miltiorrhiza Bge. f. alba. SmHDR1 contains a 1389-bp open reading frame encoding 463 amino acids. The deduced SmHDR1 protein, which shows high identity to HDRs of other plant species, is predicted to possess a chloroplast transit peptide at the N-terminus and four conserved cysteine residues. Transcription pattern analysis revealed that SmHDR1 has high levels of transcription in leaves and low levels of transcription in roots and stems. The expression of SmHDR1 was induced by 0.1 mM methyl-jasmonate (MeJA) and salicylic acid (SA), but not by 0.1 mM abscisic acid (ABA), in the hairy roots of S. miltiorrhiza Bge. f. alba. Complementation of SmHDR1 in the Escherichia coli HDR mutant MG1655 ara < > ispH demonstrated the function of this enzyme. A functional color assay in E. coli showed that SmHDR1 accelerates the biosynthesis of β-carotene, indicating that SmHDR1 encodes a functional protein. Overexpression of SmHDR1 enhanced the production of tanshinones in cultured hairy roots of S. miltiorrhiza Bge. f. alba. These results indicate that SmHDR1 is a novel and important enzyme involved in the biosynthesis of diterpenoid tanshinones in S. miltiorrhiza Bge. f. alba. PMID:23770591

  15. Kinetics of the gas-phase reaction between ozone and three unsaturated oxygenated compounds: Ethyl 3,3-dimethyl acrylate, 2-methyl-2-pentenal and 6-methyl-5-hepten-2-one at atmospheric pressure

    NASA Astrophysics Data System (ADS)

    Gaona Colmán, Elizabeth; Blanco, María B.; Barnes, Ian; Teruel, Mariano A.

    2015-05-01

    Rate coefficients for the gas-phase reactions of O3 molecules with three unsaturated oxygenated compounds have been determined using the relative kinetic technique in an environmental chamber with FTIR detection of the reactants at (298 ± 2) K in 760 Torr total pressure of synthetic air. The following rate coefficients (in units of 10-17 cm3 molecule-1 s-1) were determined: ethyl 3,3-dimethyl acrylate (0.82 ± 0.19), 2-methyl-2-pentenal (0.71 ± 0.16) and 6-methyl-5-hepten-2-one (26 ± 7). The different reactivity of the unsaturated oxygenated compounds toward O3 is discussed in terms of their chemical structure. In addition, a correlation between the reactivity of structurally different unsaturated compounds (alkenes and unsaturated oxygenated VOCs, such as ethers, esters, aldehydes, ketones and alcohols) toward O3 molecules and the HOMO (Highest Occupied Molecular Orbital) of the compounds is presented. Using the kinetic parameters determined in this work, residence times of these unsaturated compounds in the atmosphere with respect to reaction with O3 have been calculated. In urban and rural areas the main sink of 6-methyl-5-hepten-2-one is reaction with O3 molecules with a residence time in the order of few minutes.

  16. Plumbagin (5-hydroxy-2-methyl-1,4-naphthoquinone), isolated from Plumbago zeylanica, inhibits ultraviolet radiation-induced development of squamous cell carcinomas

    PubMed Central

    Sand, Jordan M.; Hafeez, Bilal Bin; Jamal, Mohammad Sarwar; Witkowsky, Olya; Siebers, Emily M.; Fischer, Joseph; Verma, Ajit K.

    2012-01-01

    Plumbagin (PL) (5-hydroxy-2-methyl-1,4-napthoquinone), a medicinal plant-derived naphthoquinone, was isolated from the roots of the Plumbago zeylanica L. (also known as Chitrak). The roots of P. zeylanica L. have been used in Indian medicine for >2500 years as an anti-atherogenic, cardiotonic, hepatoprotective and neuroprotective agent. We present here that topical application of non-toxic doses (100–500 nmol) of PL to skin elicits dose-dependent inhibition of ultraviolet radiation (UVR)-induced development of squamous cell carcinomas (SCC). In this experiment, FVB/N mice were exposed to UVR (2 kJ/m2) three times weekly from a bank of six Kodacel-filtered FS40 sunlamps (∼60% UVB and 40% UVA). Carcinoma incidence in mice treated with vehicle, 100, 200 or 500 nmol PL, at 44 weeks post-UVR, were 86, 80 (P = 0.67), 53 (P = 0.12) and 7% (P = 0.0075), respectively. Both vehicle and PL-treated mice gained weight and did not exhibit any signs of toxicity during the entire period of the experiment. Molecular mechanisms associated with inhibition of UVR-induced development of SCC involved induction of apoptosis and inhibition of cell proliferation. Specific findings are that PL treatment (i) inhibited UVR-induced DNA binding of activating protein-1, nuclear factor-kappaB, Stat3 transcription factors and Stat3-regulated molecules (cdc25A and Survivin); (ii) inhibited protein levels of pERK1/2, PI3K85, pAKTSer473, Bcl2, BclxL, proliferating cell nuclear antigen and cell cycle inhibitory proteins p27 and p21 and (iii) increased UVR-induced Fas-associated death domain expression, poly (ADP-ribose) polymerase protein cleavage and Bax/Bcl2 ratio. Taken together, our findings suggest that PL may be a novel agent for the prevention of skin cancer. PMID:22072620

  17. ABT-089 [2-methyl-3-(2-(S)-pyrrolidinylmethoxy)pyridine dihydrochloride]: II. A novel cholinergic channel modulator with effects on cognitive performance in rats and monkeys.

    PubMed

    Decker, M W; Bannon, A W; Curzon, P; Gunther, K L; Brioni, J D; Holladay, M W; Lin, N H; Li, Y; Daanen, J F; Buccafusco, J J; Prendergast, M A; Jackson, W J; Arneric, S P

    1997-10-01

    ABT-089 [2-methyl-3-(2-(S)-pyrrolidinylmethoxy)pyridine dihydrochloride], a novel ligand at neuronal nicotinic acetylcholine receptors with reduced adverse effects and improved oral bioavailability relative to (-)-nicotine, was tested in a variety of cognitive tests in rats and monkeys. Administered acutely, ABT-089 only marginally improved the spatial discrimination water maze performance of septal-lesioned rats. However, more robust improvement (45% error reduction on the last training day) was observed when ABT-089 was administered continuously via subcutaneous osmotic pumps (minimum effective dose: 1.3 micromol/kg/day). Continuous infusion of (-)-nicotine produced comparable improvement in the spatial discrimination water maze performance of septal-lesioned rats, but a 40-fold higher dose of (-)-nicotine was required (62 micromol/kg/day). Continuous infusion of ABT-089 to aged rats enhanced spatial learning in a standard Morris water maze, as indexed by spatial bias exhibited during a probe trial conducted after 4 days of training, but not when they were subsequently trained in a two-platform spatial discrimination water maze. The compound induced a small impairment in young rats on the standard water maze, but not on the two-platform task. A probe trial conducted after additional training in the standard water maze revealed no age or drug effects. ABT-089 did not affect performance of either the aged or young rats during inhibitory (passive) avoidance training. Also, continuous infusion of ABT-089 did not affect responses to acoustic startle or prepulse inhibition of acoustic startle in young, aged or septal-lesioned rats and did not affect locomotor activity in either sham-lesioned or septal-lesioned rats. In monkeys, acute administration of ABT-089 modestly improved the delayed matching-to-sample performance of mature, adult monkeys and more robustly improved performance in aged monkeys. Improved performance in the aged monkeys was restricted to the longest

  18. Atomic resolution experimental phase information reveals extensive disorder and bound 2-methyl-2,4-pentanediol in Ca 2+ -calmodulin

    SciTech Connect

    Lin, Jiusheng; van den Bedem, Henry; Brunger, Axel T.; Wilson, Mark A.

    2016-01-01

    Calmodulin (CaM) is the primary calcium signaling protein in eukaryotes and has been extensively studied using various biophysical techniques. Prior crystal structures have noted the presence of ambiguous electron density in both hydrophobic binding pockets of Ca2+-CaM, but no assignment of these features has been made. In addition, Ca2+-CaM samples many conformational substates in the crystal and accurately modeling the full range of this functionally important disorder is challenging. In order to characterize these features in a minimally biased manner, a 1.0 Å resolution single-wavelength anomalous diffraction data set was measured for selenomethionine-substituted Ca2+-CaM. Density-modified electron-density maps enabled the accurate assignment of Ca2+-CaM main-chain and side-chain disorder. These experimental maps also substantiate complex disorder models that were automatically built using low-contour features of model-phased electron density. Furthermore, experimental electron-density maps reveal that 2-methyl-2,4-pentanediol (MPD) is present in the C-terminal domain, mediates a lattice contact between N-terminal domains and may occupy the N-terminal binding pocket. The majority of the crystal structures of target-free Ca2+-CaM have been derived from crystals grown using MPD as a precipitant, and thus MPD is likely to be bound in functionally critical regions of Ca2+-CaM in most of these structures. The adventitious binding of MPD helps to explain differences between the Ca2+-CaM crystal and solution structures and is likely to favor more open conformations of the EF-hands in the crystal.

  19. Design and construction of new potentiometric sensors for determination of Al3+ ion based on (Z)-2-(2-methyl benzylidene)-1-(2,4-dinitrophenyl) hydrazine.

    PubMed

    Mizani, F; Salmanzadeh Ardabili, S; Ganjaliab, M R; Faridbod, F; Payehghadr, M; Azmoodeh, M

    2015-04-01

    (Z)-2-(2-methyl benzylidene)-1-(2,4-dinitrophenyl) hydrazine (L) was used as an active component of PVC membrane electrode (PME), coated graphite electrode (CGE) and coated silver wire electrode (CWE) for sensing Al(3+) ion. The electrodes exhibited linear Nernstian responses to Al(3+) ion in the concentration range of 1.0×10(-6) to 1.0×10(-1)M (for PME, LOD=8.8×10(-7)M), 5.5×10(-7) to 2.0×10(-1)M (for CWE, LOD=3.3×10(-7)M) and 1.5×10(-7) to 1.0×10(-1)M (for CGE, LOD=9.2×10(-8)M). The best performances were observed with the membranes having the composition of L:PVC:NPOE:NaTPB in the ratio of 5:35:57:3 (w/w; mg). The electrodes have a response time of 6s and an applicable pH range of 3.5-9.1. The sensors have a lifetime of about 15weeks and exhibited excellent selectivity over a number of mono-, bi-, and tri-valent cations including alkali, alkaline earth metal, heavy and transition metal ions. Analytical utility of the proposed sensor has been further tested by using it as an indicator electrode in the potentiometric titration of Al(3+) with EDTA. The electrode was also successfully applied for the determination of Al(3+) ion in real and pharmaceutical samples. PMID:25687018

  20. In vitro activities of 3-hydroxy-1,5,6-trimethoxy-2-methyl-9,10-anthraquinone against non-small cell lung carcinoma.

    PubMed

    Feng, Shi-Xiu; Guan, Qiunong; Chen, Tao; Du, Caigan

    2012-07-01

    Medicinal herbs are the preferred candidates for drug discovery against human diseases including cancer. The roots of Prismatomeris connata have been used in traditional herbal medicine to treat many health problems, particularly pneumoconiosis. This study was to test the anti-tumor activity of 3-hydroxy-1,5,6-trimethoxy-2-methyl-9,10-anthraquinone (PCON6), a major anthraquinone derivative from C. connata, against lung cancer. Cell viability in cultures was assessed by MTT assay. Cell death or apoptosis was determined with annexin-V and 7-aminoactinomycin D staining. Cell cycle was analyzed by both propidium iodide DNA staining and BrdU incorporation assay. Here we showed that in a panel of fifteen different tumor cells lines, a group of four non-small cell lung carcinoma (NSCLC) cell lines exhibited a relatively higher sensitivity to PCON6 growth inhibition than the rest of most non-lung cancer cell lines (p = 0.0461). Further studies demonstrated that the suppression of NSCLC H520 cell growth by PCON6 was associated with its induction of apoptosis at 20 μM (p = 0.0008), and of cell accumulation at S phase cell cycle (p < 0.05) that was further supported by a decrease in cdc2 protein expression. This preliminary study suggests that natural compound PCON6 has relatively selective cytotoxicity against NSCLC growth and represent a concept of developing a novel drug therapy specific for NSCLC based on the roots of C. connata or PCON6. PMID:22864748

  1. Leaf-Level Controls Over Emissions of Methanol and 2-Methyl-3-buten-2-ol, Oxygenated VOC With Different Production Mechanisms and Solubilities.

    NASA Astrophysics Data System (ADS)

    Harley, P. C.; Greenberg, J. P.; Guenther, A. B.

    2002-12-01

    Oxygenated VOC fluxes were investigated in leaves of deciduous trees and grasses, and needles of conifers, using a temperature-controlled leaf cuvette and a proton transfer reaction mass spectrometer. Two alcohols, 2-methyl-3-buten-2-ol (MBO) and methanol, emitted by these plants, illustrate two contrasting patterns of oxygenated VOC emissions. MBO is restricted to a small section of the genus Pinus, and is maximal in mature needles. Methanol production appears to be ubiquitous among higher plants, associated with demethylation of pectin during cell wall maturation, and emissions are therefore maximal during rapid leaf growth, decreasing in mature leaves. Although emissions of both compounds respond to variation in leaf temperature and incident light, the nature of the control is quite different. Production and emission of MBO are tightly coupled, and leaf pools are small. Light and temperature affect emissions directly through their effect on production which ceases rapidly in the dark. Effects of light and temperature on production of methanol are unknown, although emissions, and presumably production, continue through the night at reduced rates. Effects of light and temperature on methanol emission are indirect, through their effects on stomatal conductance and evapotranspiration. Data will be presented to justify a conceptual model in which methanol released in the demethylation of pectin partitions into the gas and liquid phase according to Henry's Law. Gas phase methanol is then emitted through the stomata. However, methanol emissions correlate more strongly with rates of evapotranspiration than with stomatal conductance, suggesting that much of the methanol is released from the dissolved pool along with the transpiration stream. At night, when stomatal conductance is low, and assuming constant production, gas phase concentrations increase, and the size of the aqueous pool increases in response. This aqueous pool then empties rapidly upon stomatal opening

  2. Synthesis, characterization, and tyrosinase biomimetic catalytic activity of copper(II) complexes with schiff base ligands derived from α-diketones with 2-methyl-3-amino-(3 H)-quinazolin-4-one

    NASA Astrophysics Data System (ADS)

    Ramadan, Abd El-Motaleb M.; Ibrahim, Mohamed M.; Shaban, Shaban Y.

    2011-12-01

    A template condensation of α-diketones (biacetyl, benzile and 2,3-pentanedione) with 2-methyl-3-amino-(3 H)-quinazolin-4-one (AMQ) in the presence of CuX 2 (X = Cl -, Br -, NO3- or ClO4-) resulted in the formation of tetradentate Schiff base copper(II) complexes of the type [CuLX]X and [CuL]X 2. Structural characterization of the complex species was achieved by several physicochemical methods, namely elemental analysis, electronic spectra, IR, ESR, molar conductivity, thermal analysis (TAG & DTG), and magnetic moment measurements. The stereochemistry, the nature of the metal chelates, and the catalytic reactivity are markedly dependent upon the type of counter anions and the ligand substituent within the carbonyl moiety. A square planar monomeric structure is proposed for the perchlorate, nitrate, and bromide complexes, in which the counter anions are loosely bonded to copper(II) ion. For the chloride complexes, the molar conductivities and the spectral data indicated that they have square-pyramidal environments around copper(II) center. The reported copper(II) complexes exhibit promising tyrosinase catalytic activity towards the hydroxylation of phenol followed by the aerobic oxidation of the resulting catechol. A linear correlation almost exists between the catalytic reactivity and the Lewis-acidity of the central copper(II) ion created by the donating properties of the parent ligand. The steric considerations could be accounted to clarify the difference in the catalytic activity of these functional models.

  3. Crystal structure of bis­(2-methyl-1H-imidazole-κN 3)(meso-tetra-p-tol­ylporphyrinato-κ4 N)iron(III) perchlorate tetra­hydro­furan sesquisolvate

    PubMed Central

    Sun, Wenyan; Li, Jianfeng

    2016-01-01

    In the title compound, [Fe(C48H36N4)(C4H6N2)2]ClO4·1.5C4H8O, the iron(III) metal is coordinated in a distorted octa­hedral geometry by four pyrrole N atoms of the porphyrin ligand in the equatorial plane and two N atoms of 2-methyl­imidazole ligands in the axial sites. The complex has a highly ruffled porphyrin core with mean absolute core-atom displacements C a, C b, C m and C av of 0.25 (5), 0.17 (12), 0.432 (16) and 0.25 (13) Å, respectively. One of the four phenyl groups of the porphyrin is disordered over two sets of sites with refined occupancy ratio of 0.718 (7):0.282 (7). The mean Fe—Np (Np is a porphyrin N atom) bond length [1.975 (9) Å] indicates the low-spin state of the iron atom. The two 2-methyl­imidazole ligands are nearly perpendicular and form a dihedral angle of 86.93 (10)°. The dihedral angles between the 2-methyl­imidazole ligands and the closest Fe—Np vector are 38.04 (9) and 35.00 (7)°. In the crystal, the complex cations inter­act with the perchlorate anions through N—H⋯O hydrogen bonds, forming chains running parallel to [110]. PMID:27536394

  4. Crystal structure of bis-(2-methyl-1H-imidazole-κN (3))(meso-tetra-p-tol-ylporphyrinato-κ(4) N)iron(III) perchlorate tetra-hydro-furan sesquisolvate.

    PubMed

    Sun, Wenyan; Li, Jianfeng

    2016-08-01

    In the title compound, [Fe(C48H36N4)(C4H6N2)2]ClO4·1.5C4H8O, the iron(III) metal is coordinated in a distorted octa-hedral geometry by four pyrrole N atoms of the porphyrin ligand in the equatorial plane and two N atoms of 2-methyl-imidazole ligands in the axial sites. The complex has a highly ruffled porphyrin core with mean absolute core-atom displacements C a, C b, C m and C av of 0.25 (5), 0.17 (12), 0.432 (16) and 0.25 (13) Å, respectively. One of the four phenyl groups of the porphyrin is disordered over two sets of sites with refined occupancy ratio of 0.718 (7):0.282 (7). The mean Fe-Np (Np is a porphyrin N atom) bond length [1.975 (9) Å] indicates the low-spin state of the iron atom. The two 2-methyl-imidazole ligands are nearly perpendicular and form a dihedral angle of 86.93 (10)°. The dihedral angles between the 2-methyl-imidazole ligands and the closest Fe-Np vector are 38.04 (9) and 35.00 (7)°. In the crystal, the complex cations inter-act with the perchlorate anions through N-H⋯O hydrogen bonds, forming chains running parallel to [110]. PMID:27536394

  5. 5-Meth­oxy-2,2-dimethyl-6-[(2E)-2-methyl­but-2-eno­yl]-10-phenyl-2H,8H-pyrano[2,3-f]chromen-8-one (calophyllolide)

    PubMed Central

    Kalyanaraman, L.; Mohan Kumar, R.; Vishweshwar, Peddy; Pichai, R.; Narasimhan, S.

    2010-01-01

    The title compound, C26H24O5, was isolated from calophyllum inophyllum seeds. In the mol­ecule, the phenyl and 2-methyl­but-2-enoyl groups are almost orthogonal to the chromene fragment [C—C—C—C torsion angles = 81.4 (3) and −90.1 (2)°, respectively]. In the crystal packing, centrosymmetrically related mol­ecules are linked by C—H⋯O contacts into dimers, which are connected via further C—H⋯O inter­actions into a double chain along [010]. PMID:21579166

  6. 5-Meth-oxy-2,2-dimethyl-6-[(2E)-2-methyl-but-2-eno-yl]-10-phenyl-2H,8H-pyrano[2,3-f]chromen-8-one (calophyllolide).

    PubMed

    Kalyanaraman, L; Mohan Kumar, R; Vishweshwar, Peddy; Pichai, R; Narasimhan, S

    2010-01-01

    The title compound, C(26)H(24)O(5), was isolated from calophyllum inophyllum seeds. In the mol-ecule, the phenyl and 2-methyl-but-2-enoyl groups are almost orthogonal to the chromene fragment [C-C-C-C torsion angles = 81.4 (3) and -90.1 (2)°, respectively]. In the crystal packing, centrosymmetrically related mol-ecules are linked by C-H⋯O contacts into dimers, which are connected via further C-H⋯O inter-actions into a double chain along [010]. PMID:21579166

  7. Surface tension of binary mixtures of water + N-methyldiethanolamine and ternary mixtures of this amine and water with monoethanolamine, diethanolamine, and 2-amino-2-methyl-1-propanol from 25 to 50 C

    SciTech Connect

    Alvarez, E.; Rendo, R.; Sanjurjo, B.; Sanchez-Vilas, M.; Navaza, J.M.

    1998-11-01

    The surface tension of aqueous solutions of N-methyldiethanolamine and diethanolamine + N-methyldiethanolamine, monoethanolamine + N-methyldiethanolamine and 2-amino-2-methyl-1-propanol + N-methyldiethanolamine was measured at temperatures from 25 C to 50 C. For binary mixtures the concentration range was 0--50 mass % N-methyldiethanolamine, and for the tertiary mixtures the concentration range for each amine was 0--50 mass %. The experimental values were correlated with temperature and mole fraction. The maximum deviation in both cases was always less than 0.5%.

  8. Solubility of carbon dioxide in aqueous solutions of 2-amino-2-methyl-1-propanol and N-methyldiethanolamine and their mixtures in the temperature range of 313 to 353 K and pressures up to 2.7 MPa

    SciTech Connect

    Silkenbaeumer, D.; Lichtenthaler, R.N.; Rumpf, B.

    1998-08-01

    The solubility of carbon dioxide in aqueous solutions containing 2-amino-2-methyl-1-propanol (AMP) was measured in the temperature range from 313 to 353 K at total pressures up to 2.7 MPa using an analytical method. A model taking into account chemical reactions in the liquid phase as well as physical interactions is used to correlate the new data. To test the predictive capability of the model, the solubility of carbon dioxide in an aqueous solution containing AMP and N-methyldiethanolamine (MDEA) was measured at 313 K. Experimental results are reported and compared to literature data and calculations.

  9. (E)-4-(5-Hydr­oxy-2-methyl­benzyl­idene­amino)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one

    PubMed Central

    Zheng, Yun-Fa; Yang, Ming-Hua

    2008-01-01

    The title compound, C19H19N3O2, is a Schiff base compound derived from 4-amino­anti­pyrine and 5-hydr­oxy-2-methyl­benzaldehyde. The mol­ecule adopts a trans configuration about the central C=N bond. There is an intra­molecular O—H⋯N hydrogen bond. Futhermore, weak C—H⋯O hydrogen bonds lead to the formation of a chain developing parallel to the b axis. PMID:21201212

  10. Lipid encapsulated docosahexaenoic acid methyl ester

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Encapsulation of structurally sensitive compounds within a solid lipid matrix provides a barrier to prooxidant compounds and effectively limits the extent of oxidative degradation. Encapsulated docosahexaenoic acid (DHA) methyl ester was examined as a model compound for functional foods and feeds. S...

  11. 40 CFR 721.8660 - Propionic acid methyl ester (generic).

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Propionic acid methyl ester (generic... Substances § 721.8660 Propionic acid methyl ester (generic). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as a propionic acid methyl...

  12. 40 CFR 721.8660 - Propionic acid methyl ester (generic).

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Propionic acid methyl ester (generic... Substances § 721.8660 Propionic acid methyl ester (generic). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as a propionic acid methyl...

  13. Simultaneous Determination of Salicylic Acid, Jasmonic Acid, Methyl Salicylate, and Methyl Jasmonate from Ulmus pumila Leaves by GC-MS

    PubMed Central

    Huang, Zhi-hong; Wang, Zhi-li; Shi, Bao-lin; Wei, Dong; Chen, Jian-xin; Wang, Su-li; Gao, Bao-jia

    2015-01-01

    Salicylic acid, jasmonic acid, methyl salicylate, and methyl jasmonate are important phytohormones and defensive signaling compounds, so it is of great importance to determine their levels rapidly and accurately. The study uses Ulmus pumila leaves infected by Tetraneura akinire Sasaki at different stages as materials; after extraction with 80% methanol and ethyl acetate and purification with primary secondary amine (PSA) and graphitized carbon blacks (GCB), the contents of signal compounds salicylic acid, jasmonic acid, methyl salicylate, and methyl jasmonate were determined by GC-MS. The results showed that the level of salicylic acid, jasmonic acid, methyl salicylate, and methyl jasmonate increased remarkably in U. pumila once infected by T. akinire Sasaki, but the maximums of these four compounds occurred at different times. Salicylic acid level reached the highest at the early stage, and jasmonic acid level went to the maximum in the middle stage; by contrast, change of content of methyl salicylate and methyl jasmonate was the quite opposite. PMID:26457083

  14. Simultaneous Determination of Salicylic Acid, Jasmonic Acid, Methyl Salicylate, and Methyl Jasmonate from Ulmus pumila Leaves by GC-MS.

    PubMed

    Huang, Zhi-Hong; Wang, Zhi-Li; Shi, Bao-Lin; Wei, Dong; Chen, Jian-Xin; Wang, Su-Li; Gao, Bao-Jia

    2015-01-01

    Salicylic acid, jasmonic acid, methyl salicylate, and methyl jasmonate are important phytohormones and defensive signaling compounds, so it is of great importance to determine their levels rapidly and accurately. The study uses Ulmus pumila leaves infected by Tetraneura akinire Sasaki at different stages as materials; after extraction with 80% methanol and ethyl acetate and purification with primary secondary amine (PSA) and graphitized carbon blacks (GCB), the contents of signal compounds salicylic acid, jasmonic acid, methyl salicylate, and methyl jasmonate were determined by GC-MS. The results showed that the level of salicylic acid, jasmonic acid, methyl salicylate, and methyl jasmonate increased remarkably in U. pumila once infected by T. akinire Sasaki, but the maximums of these four compounds occurred at different times. Salicylic acid level reached the highest at the early stage, and jasmonic acid level went to the maximum in the middle stage; by contrast, change of content of methyl salicylate and methyl jasmonate was the quite opposite. PMID:26457083

  15. Neural tube defects, folic acid and methylation.

    PubMed

    Imbard, Apolline; Benoist, Jean-François; Blom, Henk J

    2013-09-01

    Neural tube defects (NTDs) are common complex congenital malformations resulting from failure of the neural tube closure during embryogenesis. It is established that folic acid supplementation decreases the prevalence of NTDs, which has led to national public health policies regarding folic acid. To date, animal studies have not provided sufficient information to establish the metabolic and/or genomic mechanism(s) underlying human folic acid responsiveness in NTDs. However, several lines of evidence suggest that not only folates but also choline, B12 and methylation metabolisms are involved in NTDs. Decreased B12 vitamin and increased total choline or homocysteine in maternal blood have been shown to be associated with increased NTDs risk. Several polymorphisms of genes involved in these pathways have also been implicated in risk of development of NTDs. This raises the question whether supplementation with B12 vitamin, betaine or other methylation donors in addition to folic acid periconceptional supplementation will further reduce NTD risk. The objective of this article is to review the role of methylation metabolism in the onset of neural tube defects. PMID:24048206

  16. 76 FR 41135 - 2-Propenoic acid, 2-methyl-, phenylmethyl ester, polymer with 2-propenoic acid and sodium 2...

    Federal Register 2010, 2011, 2012, 2013, 2014

    2011-07-13

    ... Findings In the Federal Register of April 20, 2011 (76 FR 22069) (FRL-8869- 7), EPA issued a notice... Regulatory Planning and Review (58 FR 51735, October 4, 1993). Because this final rule has been exempted from... Actions Concerning Regulations That Significantly Affect Energy Supply, Distribution, or Use (66 FR...

  17. Novel GluN2B selective NMDA receptor antagonists: relative configuration of 7-meth-oxy-2-methyl-2,3,4,5-tetra-hydro-1H-3-benzazepin-1-ols.

    PubMed

    Tewes, Bastian; Frehland, Bastian; Fröhlich, Roland; Wünsch, Bernhard

    2016-05-01

    The title compounds, C22H29NO2 (3) and C22H29NO2 (4) [systematic names: (1S*,2R*)-7-meth-oxy-2-methyl-3-(4-phenyl-but-yl)-2,3,4,5-tetra-hydro-1H-3-benzazepin-1-ol and (1R*,2R*)-7-meth-oxy-2-methyl-3-(4-phenyl-but-yl)-2,3,4,5-tetra-hydro-1H-3-benzazepin-1-ol, are diastereomers with the relative configuration of the adjacent hydroxyl and methyl groups at the seven-membered azepine ring being trans in (3) and cis in (4). In the crystals the orientation of these groups is -anti-periplanar (3) and +syn-clinal (4). In both cases, the crystals studied proved to be of a racemic mixture, with relative configurations (R*,S*)-3 and (R*,R*)-4. In both compounds, the seven-membered azepine ring has a chair-like conformation, and the 4-phenyl-butyl side chain adopts a extended conformation in (R*,S*)-3, but a twisted conformation in (R*,R*)-4. In the crystal of (S*,R*)-3, mol-ecules are linked via C-H⋯O hydrogen bonds, forming slabs parallel to the ac plane. In the crystal of (R*,R*)-4, mol-ecules are linked via O-H⋯N hydrogen bonds, forming chains propagating along the c-axis direction. The chains are linked by C-H⋯O hydrogen bonds, forming slabs parallel to the ac plane. PMID:27308019

  18. Novel GluN2B selective NMDA receptor antagonists: relative configuration of 7-meth­oxy-2-methyl-2,3,4,5-tetra­hydro-1H-3-benzazepin-1-ols

    PubMed Central

    Tewes, Bastian; Frehland, Bastian; Fröhlich, Roland; Wünsch, Bernhard

    2016-01-01

    The title compounds, C22H29NO2 (3) and C22H29NO2 (4) [systematic names: (1S*,2R*)-7-meth­oxy-2-methyl-3-(4-phenyl­but­yl)-2,3,4,5-tetra­hydro-1H-3-benzazepin-1-ol and (1R*,2R*)-7-meth­oxy-2-methyl-3-(4-phenyl­but­yl)-2,3,4,5-tetra­hydro-1H-3-benzazepin-1-ol, are diastereomers with the relative configuration of the adjacent hydroxyl and methyl groups at the seven-membered azepine ring being trans in (3) and cis in (4). In the crystals the orientation of these groups is −anti-periplanar (3) and +syn-clinal (4). In both cases, the crystals studied proved to be of a racemic mixture, with relative configurations (R*,S*)-3 and (R*,R*)-4. In both compounds, the seven-membered azepine ring has a chair-like conformation, and the 4-phenyl­butyl side chain adopts a extended conformation in (R*,S*)-3, but a twisted conformation in (R*,R*)-4. In the crystal of (S*,R*)-3, mol­ecules are linked via C—H⋯O hydrogen bonds, forming slabs parallel to the ac plane. In the crystal of (R*,R*)-4, mol­ecules are linked via O—H⋯N hydrogen bonds, forming chains propagating along the c-axis direction. The chains are linked by C—H⋯O hydrogen bonds, forming slabs parallel to the ac plane. PMID:27308019

  19. N-[Eth­yl(2-hy­droxy­eth­yl)carbamo­thio­yl]-2-methyl­benzamide

    PubMed Central

    Yamin, Bohari M.; Hizam, Sara Maira M.; Yusoff, Siti Fairus M.; Hasbullah, Siti Aishah

    2014-01-01

    The title compound, C13H18N2O2S, adopts a cis conformation between the methyl­benzoyl and thiono groups across their thio­urea C—N bond. However, the methyl­benzoyl group and N2CS thio­urea moiety are twisted by 15.03 (3)°. In the molecule there is an N—H⋯O hydrogen bond. In the crystal, mol­ecules are linked by O—H⋯O inter­actions, generating chains extending along the c-axis direction. PMID:24860396

  20. Novel light-conversion hybrids of SBA-16 functionalized with rare earth (Eu3+, Nd3+, Yb3+) complexes of modified 2-methyl-9-hydroxyphenalenone and 1,10-phenanthroline

    NASA Astrophysics Data System (ADS)

    Gu, Yan-Jing; Yan, Bing; Qiao, Xiao-Fei

    2013-03-01

    Novel rare earth complex-functionalized mesoporous SBA-16-type hybrid materials are synthesized by the co-condensation of modified 2-methyl-9-hydroxyphenalenone (MHPOSi), from modified 3-(triethoxysilyl)-propyl isocyanate (TEPIC), and tetraethoxysilane (TEOS) in the presence of Pluronic F127 as a template. These inorganic-organic mesoporous hybrids are characterized by FT-IR spectra, small-angle X-ray diffraction (SAXRD), N2 adsorption-desorption measurements, thermal analysis and spectroscopy. Their photophysical properties, which show novel light conversion properties, are discussed in detail. The Eu3+ hybrid system shows ultraviolet excitation and visible emission, and the Nd+ and Yb3+ hybrids exhibit visible excitation and NIR emission.

  1. 2-Methyl-4-oxo-N-(4-oxo-2-phenyl substituted-1,3-thiazolidin-3-yl)-3,4-dihydroquinazoline-5-carboxamides--a new range of fluorescent whiteners: synthesis and photophysical characterization.

    PubMed

    Patil, Vikas S; Padalkar, Vikas S; Sekar, Nagaiyan

    2014-07-01

    Fluorescent quinazolinones were synthesized form ethyl 2-methyl-4-oxo-3,4-dihydroquinazoline -5-carboxylate intermediate. The photophysical properties of the compounds were evaluated in DMF solvent. The experimental absorption and emission of the compounds were compared with the vertical excitation and emission obtained Density Functional Theory (DFT) and Time Dependent Density Functional Theory (TD-DFT) computation. Application of the fluorescent compounds as a fluorescent brightening agent was tested on polyester fiber. Changes in the electronic transition, energy levels, and orbital diagrams of quinazolin-4(3H)-one analogues were investigated using the DFT computations and were correlated with the experimental spectral data. The experimental absorption and emission wavelengths are in good agreement with those predicted using the DFT and TD-DFT. PMID:24849738

  2. The Role of Placental 11-Beta Hydroxysteroid Dehydrogenase Type 1 and Type 2 Methylation on Gene Expression and Infant Birth Weight.

    PubMed

    Green, Benjamin B; Armstrong, David A; Lesseur, Corina; Paquette, Alison G; Guerin, Dylan J; Kwan, Lauren E; Marsit, Carmen J

    2015-06-01

    Maternal stress has been linked to infant birth weight outcomes, which itself may be associated with health later in life. The placenta acts as a master regulator for the fetal environment, mediating intrauterine exposures to stress through the activity of genes regulating glucocorticoids, including the 11beta-hydroxysteroid dehydrogenase (HSD11B) type 1 and 2 genes, and so we hypothesized that variation in these genes will be associated with infant birth weight. We investigated DNA methylation levels at six sites across the two genes, as well as mRNA expression for each, and the relationship to infant birth weight. Logistic regressions correcting for potential confounding factors revealed a significant association between methylation at a single CpG site within HSD11B1 and being born large for gestational age. In addition, our analysis identified correlations between methylation and gene expression, including sex-specific transcriptional regulation of HSD11B2. Our work is one of the first comprehensive views of DNA methylation and expression in the placenta for both HSD11B types 1 and 2, linking epigenetic alterations with the regulation of fetal stress and birth weight outcomes. PMID:25788665

  3. Promoter Methylation of the Retinoic Acid Receptor Beta2 (RARβ2) Is Associated with Increased Risk of Breast Cancer: A PRISMA Compliant Meta-Analysis

    PubMed Central

    Shen, Xian-Feng; Wei, Xue-Mei; Yu, Guo-Zheng; Zeng, Xian-Tao

    2015-01-01

    Background Epigenetic studies demonstrate that an association may exist between methylation of the retinoic acid receptor beta2 (RARβ2) gene promoter and breast cancer onset risk, tumor stage, and histological grade, however the results of these studies are not consistent. Hence, we performed this meta-analysis to ascertain a more comprehensive and accurate association. Materials and Methods Relevant studies were retrieved from the PubMed, Embase and Chinese National Knowledge Infrastructure databases up to February 28, 2015. After two independent reviewers screened the studies and extracted the necessary data, meta-analysis was performed using Review Manager 5.2 software. Results Nineteen eligible articles, including 20 studies, were included in our analysis. Compared to non-cancerous controls, the frequency of RARβ2 methylation was 7.27 times higher in patients with breast cancer (odds ratio (OR) = 7.27, 95% confidence interval (CI) = 3.01–17.52). Compared to late-stage RARβ2 methylated patients, the pooled OR of early-stage ones was 0.81 (OR = 0.81, 95% CI = 0.55–1.17). The OR of low-grade RARβ2 methylated patients was 0.96 (OR = 0.96, 95% CI = 0.74–1.25) compared to high-grade RARβ2 methylated patients. Conclusion RARβ2 methylation is significantly increased in breast cancer samples when compared to non-cancerous controls. RARβ2 could serve as a potential epigenetic marker for breast cancer detection and management. PMID:26451736

  4. SULF2 Methylation is Prognostic for Lung Cancer Survival and Increases Sensitivity to Topoisomerase-I inhibitors via Induction of ISG15

    PubMed Central

    Tessema, Mathewos; Yingling, Christin M.; Thomas, Cynthia L.; Klinge, Donna M.; Bernauer, Amanda M.; Liu, Yushi; Dacic, Sanja; Siegfried, Jill M.; Dahlberg, Suzanne E.; Schiller, Joan H.; Belinsky, Steven A.

    2011-01-01

    The heparan sulfate 6-O-endosulfatase (SULF2) promotes growth and metastasis of solid tumors. We recently identified that cytosine methylation of the SULF2 promoter is associated with better survival of resected lung adenocarcinoma patients and now also demonstrate a marginal improvement in survival of advanced non-small cell lung cancer (NSCLC) patients receiving standard chemotherapy (HR = 0.63, p = 0.07). Subsequent studies focused on investigating the effect of methylation on SULF2 expression and its genome-wide impact. The genes and pathways modulated by epigenetic inactivation of SULF2 and the effects on sensitivity to chemotherapy were characterized in vitro and in vivo. Silencing SULF2 through siRNA or methylation primarily increased expression of interferon-inducible genes including ISG15, a marker for increased sensitivity to topoisomerase-1 inhibitors such as camptothecin. NSCLC cell lines with methylated SULF2 (SULF2M) express 60-fold higher ISG15 compared to SULF2 unmethylated (SULF2U) NSCLC cell lines and normal human bronchial epithelial cells. In vitro, SULF2M and high ISG15 (ISG15H) expressing NSCLC cell lines were 134-fold more sensitive to camptothecin than SULF2U and low ISG15 (ISG15L) expressing cell lines. Topotecan, a soluble analogue of camptothecin and FDA approved anti-cancer drug, dramatically arrested the growth of SULF2M-ISG15H, but not SULF2U-ISG15L lung tumors in nude mice (p < 0.002). Similarly, high ISG15 expression that is comparable to the topotecan sensitive NSCLC cell lines was found in tumors from 25% of NSCLC patients compared to normal lung indicating a potential to identify and target the most sensitive NSCLC subpopulation for personalized topotecan therapy. PMID:22158045

  5. Production of methyl-vinyl ketone from levulinic acid

    DOEpatents

    Dumesic, James A.; West; Ryan M.

    2011-06-14

    A method for converting levulinic acid to methyl vinyl ketone is described. The method includes the steps of reacting an aqueous solution of levulinic acid, over an acid catalyst, at a temperature of from room temperature to about 1100 K. Methyl vinyl ketone is thereby formed.

  6. Pyrrolidone - a new solvent for the methylation of humic acid

    USGS Publications Warehouse

    Wershaw, R. L.; Pinckney, D.J.; Booker, S.E.

    1975-01-01

    In the past, humic acid has been methylated by suspending it in a solution of diazomethane in diethyl ether, and degrading the partly methylated humic acid to release those parts of the molecule that were methylated. Only small fragments of the molecule have been identified by this technique. In the procedure described here the humic acid is dissolved in 2-pyrrolidone and methylated by the addition of diazomethane in diethyl ether and ethanol to the solution. Because the humic acid is completely dissolved in the reaction medium, disaggregation of the humic acid particles takes place and much more complete methylation is obtained. The methylated products may be fractionated by countercurrent distribution and analyzed by mass spectrometry.

  7. Identification of 2,5-dimethyl-4-hydroxy-3(2H)-furanone (DMHF) and 4-hydroxy-2(or 5)-ethyl-5(or 2)-methyl-3(2H)-furanone (HEMF) with DNA breaking activity in soy sauce.

    PubMed

    Li, X; Hiramoto, K; Yoshida, M; Kato, T; Kikugawa, K

    1998-04-01

    Components with DNA breaking activity in soy sauce were investigated. It was found that there were water soluble high molecular weight DNA breaking components in soy sauce. Two DNA breaking components in the ethyl acetate extract of soy sauce were identified as fragrant components, 2,5-dimethyl-4-hydroxy-3(2H)-furanone (DMHF) and 4-hydroxy-2(or 5)-ethyl-5(or 2)-methyl-3(2H)-furanone (HEMF), in addition to the previously characterized DNA breaking fragrant component 4-hydroxy-5-methyl-3(2H)-furanone (HMF) (Hiramoto et al., 1996b). Characterization of DNA breaking activity of HEMF was performed, and the mechanisms for the breaking were considered. HEMF cleaved the single strands of supercoiled pBR 322 DNA at pH 7.4 dose dependently and time dependently. DNA breaking was inhibited by superoxide dismutase, catalase, hydroxyl radical scavengers, spin trapping agents and metal chelators, and enhanced by Fe(III) ion. Electron spin resonance-spin trapping technique revealed the generation of hydroxyl radical. Hence, active oxygen species derived from interaction of HEMF with metal ions and oxygen participated in the cleavage. HEMF exhibited mutagenicity to Salmonella typhimurium TA100 without metabolic activation and induced micronucleated mouse peripheral reticulocytes. PMID:9651047

  8. Crystal structure of (+)-methyl (E)-3-[(2S,4S,5R)-2-amino-5-hy­droxy­meth­yl-2-tri­chloro­methyl-1,3-dioxolan-4-yl]-2-methyl­prop-2-enoate

    PubMed Central

    Oishi, Takeshi; Yasushima, Daichi; Yuasa, Kihiro; Sato, Takaaki; Chida, Noritaka

    2016-01-01

    In the title compound, C10H14Cl3NO5, the five-membered dioxolane ring adopts an envelope conformation. The C atom at the flap, which is bonded to the hy­droxy­methyl substituent, deviates from the mean plane of other ring atoms by 0.357 (5) Å. There are two intra­molecular hydrogen bonds (O—H⋯N and N—H⋯O) between the hy­droxy and amino groups, so that O- and N-bound H atoms involved in these hydrogen bonds are each disordered with equal occupancies of 0.50. The methyl 2-methyl­prop-2-enoate substituent also shows a disordered structure over two sets of sites with refined occupancies of 0.482 (5) and 0.518 (5). In the crystal, mol­ecules are connected into a dimer by an O—H⋯O hydrogen bond. The dimers are further linked by N—H⋯O, C—H⋯N and C—H⋯O inter­actions, extending a sheet structure parallel to (01). PMID:27006804

  9. Crystal structure and conformational analysis of 2-hy­droxy-3-(2-methyl­prop-1-en-1-yl)naphthalene-1,4-dione

    PubMed Central

    Alcantara Emiliano, Sannyele; Welma Duarte Silva, Sheyla; Alves Pereira, Mariano; R.dos Santos Malta, Valeria; Luciano Balliano, Tatiane

    2016-01-01

    In the structure of the title compound, C14H12O3, the substituent side chain, in which the H atoms of both methyl groups are disordered over six equivalent sites, lies outside of the plane of the naphthalene­dione ring. The ring-to-chain C—C—C—C torsion angles are 50.7 (3), −176.6 (2) and 4.9 (4)°. An intra­molecular meth­yl–hy­droxy C—H⋯O hydrogen bond is present. In the crystal, mol­ecules are primarily connected by inter­molecular O—H⋯O hydrogen bonds, forming a centrosymmetric cyclic dimer motif [graph set R 2 2(10)]. Also present is a weak inter­molecular C—H⋯O hydrogen bond linking the dimers and a weak π–π ring inter­action [ring centroid separation = 3.7862 (13) Å], giving layers parallel to (10-3). PMID:26958384

  10. Crystal structure and conformational analysis of 2-hy-droxy-3-(2-methyl-prop-1-en-1-yl)naphthalene-1,4-dione.

    PubMed

    Alcantara Emiliano, Sannyele; Welma Duarte Silva, Sheyla; Alves Pereira, Mariano; R Dos Santos Malta, Valeria; Luciano Balliano, Tatiane

    2016-02-01

    In the structure of the title compound, C14H12O3, the substituent side chain, in which the H atoms of both methyl groups are disordered over six equivalent sites, lies outside of the plane of the naphthalene-dione ring. The ring-to-chain C-C-C-C torsion angles are 50.7 (3), -176.6 (2) and 4.9 (4)°. An intra-molecular meth-yl-hy-droxy C-H⋯O hydrogen bond is present. In the crystal, mol-ecules are primarily connected by inter-molecular O-H⋯O hydrogen bonds, forming a centrosymmetric cyclic dimer motif [graph set R 2 (2)(10)]. Also present is a weak inter-molecular C-H⋯O hydrogen bond linking the dimers and a weak π-π ring inter-action [ring centroid separation = 3.7862 (13) Å], giving layers parallel to (10-3). PMID:26958384

  11. Crystal structure of 5-(5-chloro-2-hydroxy­benzo­yl)-2-(2-methyl-1H-indol-3-yl)nicotino­nitrile

    PubMed Central

    Vimala, G.; Poomathi, N.; AaminaNaaz, Y.; Perumal, P. T.; SubbiahPandi, A.

    2015-01-01

    In the title compound, C22H14ClN3O2, the indole unit is essentially coplanar, with a maximum deviation of 0.035 Å for the C atom bearing the methyl group. The central pyridine ring is inclined to the indole ring system by 43.7 (1)°. The dihedral angle between the phenyl ring and the indole ring system is 15.7 (2)°, while that between the phenyl ring and the central pyridine ring is 46.3 (1)°. The mol­ecular structure is stabilized by an intra­molecular O—H⋯O hydrogen bonding, forming an S(6) ring motif. In the crystal, mol­ecules are linked via pairs of N—H⋯N hydrogen bonds, forming inversion dimers with an R 2 2(16) ring motif. The crystal structure also features C—H⋯π and π–π inter­actions [centroid–centroid separation = 3.688 (1) Å]. PMID:26594546

  12. 3-(2-Chloro­ethyl)-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one

    PubMed Central

    Jasinski, Jerry P.; Butcher, Ray J.; Hakim Al-Arique, Q. N. M.; Yathirajan, H. S.; Narayana, B.

    2009-01-01

    In the title mol­ecule, C11H11ClN2O, the pyrido[1,2-a]pyrimidine ring system is planar (maximum deviation = 0.0148 Å) and the methyl C and carbonyl O atoms are nearly coplanar to it. The chloro­ethyl side chain is in a synclinal conformation, nearly orthogonal to the pyrimidine ring, with a dihedral angle between the chloro­ethyl side chain and the pyrimidine ring of 88.5 (1)°. Weak inter­molecular C—H⋯N and C—H⋯Cl hydrogen bonds along with π–π inter­actions between the pyrimidine and pyridine rings [centroid–centroid distance is 3.538 (2) Å] form a three-dimensional network. The crystal is a racemic twin with a 0.68 (12):0.32 (12) domain ratio. MOPAC AM1 and density functional theory (DFT) theoretical calculations at the B3-LYP/6–311+G(d,p) level support these observations. PMID:21583662

  13. 40 CFR 721.8500 - 2-Propenoic acid, 2-methyl-, 7-oxabicyclo [4.1.0]hept-3-ylmethyl ester.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... § 721.63 (a)(1), (a)(3), (a)(4), (a)(5)(viii), (a)(5)(xv), (a)(6)(i), (a)(6)(ii), (a)(6)(iv), (b) (concentration set at 0.1 percent), and (c). (ii) Hazard communication program. Requirements as specified in... hept-3-ylmethyl ester. (a) Chemical substance and significant new uses subject to reporting. (1)...

  14. 40 CFR 721.8500 - 2-Propenoic acid, 2-methyl-, 7-oxabicyclo [4.1.0]hept-3-ylmethyl ester.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... § 721.63 (a)(1), (a)(3), (a)(4), (a)(5)(viii), (a)(5)(xv), (a)(6)(i), (a)(6)(ii), (a)(6)(iv), (b) (concentration set at 0.1 percent), and (c). (ii) Hazard communication program. Requirements as specified in... hept-3-ylmethyl ester. (a) Chemical substance and significant new uses subject to reporting. (1)...

  15. Toxicokinetics, including saturable protein binding, of 4-chloro-2-methyl phenoxyacetic acid (MCPA) in patients with acute poisoning.

    PubMed

    Roberts, Darren M; Dawson, Andrew H; Senarathna, Lalith; Mohamed, Fahim; Cheng, Ron; Eaglesham, Geoffrey; Buckley, Nick A

    2011-03-25

    Human data on protein binding and dose-dependent changes in toxicokinetics for MCPA are very limited. 128 blood samples were obtained in 49 patients with acute MCPA poisoning and total and unbound concentrations of MCPA were determined. The Scatchard plot was biphasic suggesting protein binding to two sites. The free MCPA concentration increased when the total concentration exceeded 239mg/L (95% confidence interval 198-274mg/L). Nonlinear regression using a two-site binding hyperbola model estimated saturation of the high affinity binding site at 115mg/L (95%CI 0-304). Further analyses using global fitting of serial data and adjusting for the concentration of albumin predicted similar concentrations for saturable binding (184mg/L and 167mg/L, respectively) without narrowing the 95%CI. In 25 patients, the plasma concentration-time curves for both bound and unbound MCPA were approximately log-linear which may suggest first order elimination, although sampling was infrequent so zero order elimination cannot be excluded. Using a cut-off concentration of 200mg/L, the half-life of MCPA at higher concentrations was 25.5h (95%CI 15.0-83.0h; n=16 patients) compared to 16.8h (95%CI 13.6-22.2h; n=10 patients) at lower concentrations. MCPA is subject to saturable protein binding but the influence on half-life appears marginal. PMID:21256202

  16. 77 FR 20314 - 2-Propenoic Acid, 2-Methyl-, 2-Ethylhexyl Ester, Telomer With 1-Dodecanethiol, Ethenylbenzene and...

    Federal Register 2010, 2011, 2012, 2013, 2014

    2012-04-04

    ... Register of Friday, December 30, 2011 (76 FR 82238) (FRL-9331-1), EPA issued a notice pursuant to section... these rules from review under Executive Order 12866, entitled Regulatory Planning and Review (58 FR... That Significantly Affect Energy Supply, Distribution, or Use (66 FR 28355, May 22, 2001) or...

  17. 75 FR 4292 - 2-Propenoic acid, 2-ethylhexyl ester, polymer with ethenylbenzene and 2-methylpropyl 2-methyl-2...

    Federal Register 2010, 2011, 2012, 2013, 2014

    2010-01-27

    ... Findings In the Federal Register of October 7, 2009 (74 FR 51597) (FRL-8792- 7), EPA issued a notice... Planning and Review (58 FR 51735, October 4, 1993). Because this final rule has been exempted from review... Concerning Regulations That Significantly Affect Energy Supply, Distribution, or Use (66 FR 28355, May...

  18. An alternative mechanism for guanidinoacetic acid to affect methylation cycle.

    PubMed

    Ostojic, Sergej M

    2014-12-01

    Guanidinoacetic acid (also known as glycocyamine; GAA) is an endogenous substance which occurs in humans and plays a central role in the biosynthesis of creatine. The formation of creatine from GAA consumes methyl groups, and increases production of homocysteine. GAA may have the potential to stimulate insulin secretion. Insulin reduces plasma homocysteine and raises methyl group supply. It is possible that the ability of GAA to trigger the insulin secretion modulates methyl group metabolism, and comparatively counterbalance for the direct effect of GAA on increased methylation demand. Possible insulinotropic effect of GAA may contribute to total in vivo methylation demand during biotransformation. PMID:25468046

  19. Screening of High-Level 4-Hydroxy-2 (or 5)-Ethyl-5 (or 2)-Methyl-3(2H)-Furanone-Producing Strains from a Collection of Gene Deletion Mutants of Saccharomyces cerevisiae

    PubMed Central

    Watanabe, Jun; Akao, Takeshi; Watanabe, Daisuke; Mogi, Yoshinobu; Shimoi, Hitoshi

    2014-01-01

    4-Hydroxy-2 (or 5)-ethyl-5 (or 2)-methyl-3(2H)-furanone (HEMF) is an important flavor compound that contributes to the sensory properties of many natural products, particularly soy sauce and soybean paste. The compound exhibits a caramel-like aroma and several important physiological activities, such as strong antioxidant activity. HEMF is produced by yeast species in soy sauce manufacturing; however, the enzymes involved in HEMF production remain unknown, hindering efforts to breed yeasts with high-level HEMF production. In this study, we identified high-level HEMF-producing mutants among a Saccharomyces cerevisiae gene deletion mutant collection. Fourteen deletion mutants were screened as high-level HEMF-producing mutants, and the ADH1 gene deletion mutant (adh1Δ) exhibited the maximum HEMF production capacity. Further investigations of the adh1Δ mutant implied that acetaldehyde accumulation contributes to HEMF production, agreeing with previous findings. Therefore, acetaldehyde might be a precursor for HEMF. The ADH1 gene deletion mutant of Zygosaccharomyces rouxii, which is the dominant strain of yeast found during soy sauce fermentation, also produces HEMF effectively, suggesting that acetaldehyde accumulation might be a benchmark for breeding industrial yeasts with excellent HEMF production abilities. PMID:25362059

  20. Screening of high-level 4-hydroxy-2 (or 5)-ethyl-5 (or 2)-methyl-3(2H)-furanone-producing strains from a collection of gene deletion mutants of Saccharomyces cerevisiae.

    PubMed

    Uehara, Kenji; Watanabe, Jun; Akao, Takeshi; Watanabe, Daisuke; Mogi, Yoshinobu; Shimoi, Hitoshi

    2015-01-01

    4-Hydroxy-2 (or 5)-ethyl-5 (or 2)-methyl-3(2H)-furanone (HEMF) is an important flavor compound that contributes to the sensory properties of many natural products, particularly soy sauce and soybean paste. The compound exhibits a caramel-like aroma and several important physiological activities, such as strong antioxidant activity. HEMF is produced by yeast species in soy sauce manufacturing; however, the enzymes involved in HEMF production remain unknown, hindering efforts to breed yeasts with high-level HEMF production. In this study, we identified high-level HEMF-producing mutants among a Saccharomyces cerevisiae gene deletion mutant collection. Fourteen deletion mutants were screened as high-level HEMF-producing mutants, and the ADH1 gene deletion mutant (adh1Δ) exhibited the maximum HEMF production capacity. Further investigations of the adh1Δ mutant implied that acetaldehyde accumulation contributes to HEMF production, agreeing with previous findings. Therefore, acetaldehyde might be a precursor for HEMF. The ADH1 gene deletion mutant of Zygosaccharomyces rouxii, which is the dominant strain of yeast found during soy sauce fermentation, also produces HEMF effectively, suggesting that acetaldehyde accumulation might be a benchmark for breeding industrial yeasts with excellent HEMF production abilities. PMID:25362059

  1. Structural, vibrational and DFT studies on 2-chloro-1H-isoindole-1,3(2H)-dione and 2-methyl-1H-isoindole-1,3(2H)-dione.

    PubMed

    Arjunan, V; Saravanan, I; Ravindran, P; Mohan, S

    2009-10-15

    The Fourier transform infrared (FTIR) and FT-Raman spectra of 2-chloro-1H-isoindole-1,3(2H)-dione and 2-methyl-1H-isoindole-1,3(2H)-dione have been measured in the range of 4000-400 and 4000-100 cm(-1), respectively. Complete vibrational assignment and analysis of the fundamental modes of the compounds were performed using the observed FTIR and FT-Raman data. The geometry was optimised without any symmetry constraints using the DFT/B3LYP method with 6-31G(d,p) and 6-311++G(d,p) basis sets. The vibrational frequencies determined experimentally are compared with those obtained theoretically from DFT gradient calculations employing the B3LYP/6-31G(d,p) and B3LYP/6-311++G(d,p) methods for the optimised geometry of the compounds. The structural parameters and normal modes of vibration obtained from DFT method are in good agreement with the experimental data. The force fields obtained from DFT method were utilised and the potential energy distributions of all the fundamental vibrations of the compounds were calculated. PMID:19660980

  2. Structural, vibrational and DFT studies on 2-chloro-1H-isoindole-1,3(2H)-dione and 2-methyl-1H-isoindole-1,3(2H)-dione

    NASA Astrophysics Data System (ADS)

    Arjunan, V.; Saravanan, I.; Ravindran, P.; Mohan, S.

    2009-10-01

    The Fourier transform infrared (FTIR) and FT-Raman spectra of 2-chloro-1H-isoindole-1,3(2H)-dione and 2-methyl-1H-isoindole-1,3(2H)-dione have been measured in the range of 4000-400 and 4000-100 cm -1, respectively. Complete vibrational assignment and analysis of the fundamental modes of the compounds were performed using the observed FTIR and FT-Raman data. The geometry was optimised without any symmetry constraints using the DFT/B3LYP method with 6-31G(d,p) and 6-311++G(d,p) basis sets. The vibrational frequencies determined experimentally are compared with those obtained theoretically from DFT gradient calculations employing the B3LYP/6-31G(d,p) and B3LYP/6-311++G(d,p) methods for the optimised geometry of the compounds. The structural parameters and normal modes of vibration obtained from DFT method are in good agreement with the experimental data. The force fields obtained from DFT method were utilised and the potential energy distributions of all the fundamental vibrations of the compounds were calculated.

  3. Identification and characterization of a novel cross-link lesion in d(CpC) upon 365-nm irradiation in the presence of 2-methyl-1,4-naphthoquinone

    PubMed Central

    Liu, Zhenjiu; Gao, Yuan; Wang, Yinsheng

    2003-01-01

    We report the isolation and characterization for the first time of a cross-link lesion between two adjacent cytosines from the 2-methyl-1,4-naphthoquinone (menadione)-sensitized 365-nm irradiation of d(CpC). Electrospray ionization mass spectrometry (ESI-MS), tandem MS and 1H NMR results indicate that the cross-link occurs between the C5 carbon atom of one cytosine and the N4 nitrogen atom of the other cytosine. Furthermore, we synthesized d(CpC) with a 15N being incorporated on the amino group of either of the two cytosines. We then irradiated the two 15N-labeled dinucleoside monophosphates, isolated the cross-link products and characterized them by MS and multi-stage tandem MS. The latter results established unambiguously that the N4 nitrogen atom of the 3′-nucleobase is involved in the covalent bond formation between the two cytosines. This, in combination with two-dimensional nuclear Overhauser effect spectroscopy (NOESY) results, demonstrates that the cross-link arises from the formation of a covalent bond between the C5 carbon atom of the 5′ cytosine and the N4 nitrogen atom of the 3′ cytosine. We also show that the solution pH has a significant effect on the formation of the cross-link lesion, which supports that the deprotonation at the exocyclic amino group of cytosine cation radical is essential for the formation of the cross-link lesion. PMID:12954778

  4. Quantification of Bacterial Fatty Acids by Extraction and Methylation

    PubMed Central

    Politz, Mark; Lennen, Rebecca; Pfleger, Brian

    2016-01-01

    This protocol describes two similar methods for the extraction and methylation of fatty acids from bacterial cultures. The acid derivatization protocol (Lennen et al., 2013; Bligh and Dyer, 1959) results in the extraction and methylation of all fatty acids, both free and bound, from a bacterial culture, while the base derivatization protocol (Lennen and Pfleger, 2013) captures only bound (phospholipid, acyl-thioester) species. After extraction into hexane, the lipids may be analyzed by gas chromatography.

  5. Dissociation of the effects of MTEP [3-[(2-methyl-1,3-thiazol-4-yl)ethynyl]piperidine] on conditioned reinstatement and reinforcement: comparison between cocaine and a conventional reinforcer.

    PubMed

    Martin-Fardon, R; Baptista, M A S; Dayas, C V; Weiss, F

    2009-06-01

    To advance understanding of the potential of metabotropic glutamate receptor (mGluR) 5 as treatment targets for cocaine addiction, the effects of MTEP [3-[(2-methyl-1,3-thiazol-4-yl) ethynyl]piperidine] (a selective mGluR5 antagonist) on conditioned reinstatement of cocaine seeking were examined. To test whether modification of conditioned reinstatement by MTEP is selective for drug-directed behavior or reflects general actions on motivated behavior, effects of MTEP on reinstatement induced by a stimulus conditioned to palatable conventional reward, sweetened condensed milk (SCM), were also evaluated. Previous data suggest that mGluR manipulations preferentially interfere with conditioned reinstatement compared with cocaine self-administration. Therefore, the effects of MTEP on cocaine self-administration were compared with MTEP's effects on SCM-reinforced behavior using the same cocaine doses and SCM concentrations employed for establishing conditioned reinstatement. Male Wistar rats were trained to associate a discriminative stimulus (S(D)) with response-contingent availability of cocaine or SCM and subjected to reinstatement tests after extinction of cocaine or SCM-reinforced behavior. MTEP (0.3-10 mg/kg i.p.) dose-dependently attenuated the response-reinstating effects of both the cocaine S(D) and SCM S(D). MTEP also decreased cocaine self-administration without a clear graded dose-response profile and did not modify SCM-reinforced responding. The findings implicate mGluR5-regulated glutamate transmission in appetitive behavior controlled by reward-related stimuli but without selectivity for cocaine seeking. However, the data suggest a differential role for mGluR5 in the acute reinforcing effects of cocaine versus conventional reward. These observations identify mGluR5 as potential treatment targets for cocaine relapse prevention, although the profile of action of mGluR5 antagonists remains to be more closely examined for potential anhedonic effects. PMID

  6. A series of dinuclear Dy(iii) complexes bridged by 2-methyl-8-hydroxylquinoline: replacement on the periphery coordinated β-diketonate terminal leads to different single-molecule magnetic properties.

    PubMed

    Zhang, Wan-Ying; Tian, Yong-Mei; Li, Hong-Feng; Chen, Peng; Sun, Wen-Bin; Zhang, Yi-Quan; Yan, Peng-Fei

    2016-03-01

    A series of HMq-bridged dinuclear dysprosium complexes, namely, [Dy(acac)2(CH3OH)]2(μ-HMq)2 (1), [Dy(DBM)2]2(μ-HMq)2(n-C6H14) (2), [Dy(hmac)2]2(μ-HMq)2 (3) and [Dy(hfac)3]2(μ-HMq)2 (4) (HMq = 2-methyl-8-hydroxyquinoline, acac = acetylacetone, DBM = dibenzoylmethane, hmac = hexamethylacetylacetonate and hfac = hexafluoroacetylacetonate), were structurally and magnetically characterized. X-ray crystallographic analyses of the structures reveal that HMq serves as the effective bridge to link two Dy(III) centers by means of the phenoxyl oxygen and nitrogen atoms and the periphery β-diketonate ligands complete the coordination sphere by bidentate oxygen atoms. The different substituents on the β-diketonate terminal lead to different coordination models mostly due to the steric hindrance of these substituents, and the electron-withdrawing or donating effects likely influence the strength of the ligand fields and the Dy(III) ion anisotropy. Measurements of alternating-current (ac) susceptibility on complexes 1-4 reveal that complexes 3 and 4 display significant zero-field single-molecule magnetic (SMM) behavior with barrier energy Ueff/kB = 14.8 K, τ0 = 1.8 × 10(-5) s and Ueff/kB = 9.2 K, τ0 = 1.7 × 10(-5) s, respectively, whereas 1 and 2 exhibit field-induced SMM behavior, and these differences are attributed to the alteration on the periphery β-diketonate ligands. Their distinct slow magnetic relaxation behaviors were related to their different individual Dy(III) ion magnetic anisotropy and intramolecular coupling, which were confirmed by ab initio calculations. PMID:26905041

  7. Synthesis, characterization of (3E)-1-(6-chloro-2-methyl-4-phenyl quinolin-3-Yl)-3-aryl prop-2-en-1-ones through IR, NMR, single crystal X-ray diffraction and insights into their electronic structure using DFT calculations

    NASA Astrophysics Data System (ADS)

    Sarveswari, S.; Srikanth, A.; Arul Murugan, N.; Vijayakumar, V.; Jasinski, Jerry P.; Beauchesne, Hanna C.; Jarvis, Ethan E.

    2015-02-01

    3E-1-(6-Chloro-2-methyl-4-phenylquinolin-3-yl)-3-arylprop-2-en-1-ones were synthesized and characterized by FTIR, 1H NMR, 13C NMR, HSQC, DEPT-135. In addition the compound 3E-1-(6-chloro-2-methyl-4-phenylquinolin-3-yl)-3-(2,5-dimethoxyphenyl)prop-2-en-1-one was subjected to the single crystal X-ray diffraction studies. Density functional theory calculations were carried out for this chalcone and its derivatives to investigate into their electronic structure, chemical reactivity, linear and non-linear optical properties. The structure predicted from DFT for chalcone is in good agreement with the structure from XRD measurement.

  8. Ternary Copper(II) Complexes With Indomethacin, a Potent Non-Steroidal Antiinflammatory Drug. Crystal Structure of Bis (Dimethylformamide)-Tetrakis[1-(4-Chlorobenzoyl)-5-Methoxy-2-Methyl-1-H-Indole-3-Acetato]Dicopper(II). Antiinflammatory Properties and Prevention of Gastrointestinal Side Effects by Nanocapsules

    PubMed Central

    Guessous, Fadila; Daran, Jean-Claude; Viossat, Bernard; Morgant, Georges; Labouze, Xavier; Leroy, Anne Laure; Roch-Arveiller, Monique

    1998-01-01

    Two ternary copper(ll) complexes of indomethacin [1-(4-chlorobenzoyl)-5-methoxy-2- methyl-1-H-indole-3-acetic acid] called hereafter lndo, were prepared and characterized by single crystal X-ray diffraction. The first complex Cu2(Indo)4(DMF)2 I crystallizes in space group P-1 (a = 10.829(2), b = 13.379(2), c = 16.491(3) Å; α = 105.58(2), β = 101.06(2), γ = 106.96(2)°; V= 2104.6(6) Å3, Z= 1). The title molecule is a centrosymmetric binuclear complex, with Cu atoms bridged by the carboxylate moieties of four indomethacinate ligands. The four nearest O atoms around each Cu atom form a square planar arrangement with the square pyramidal coordination completed by the O atom of N,N′-dimethylformamide. Daily administration for seven days of 1 mg/kg of indomethacin, I and I encapsulated into liposomes induces a weak inflammation of rat gastrointestinal tract. I was less inflammatory than indomethacin but the better protection was brought by encapsulation of the compound. This might be of interest in sustained therapies of chronic inflammatory diseases. PMID:18475870

  9. Effects of the amino-carbonyl reaction of ribose and glycine on the formation of the 2(or 5)-ethyl-5(or 2)-methyl-4-hydroxy-3(2H)-furanone aroma component specific to miso by halo-tolerant yeast.

    PubMed

    Sugawara, Etsuko; Ohata, Motoko; Kanazawa, Toshinari; Kubota, Kikue; Sakurai, Yonekichi

    2007-07-01

    The formation of HEMF[2(or 5)-ethyl-5(or 2)-methyl-4-hydroxy-3(2H)-furanone], the aroma component specific to miso and soy sauce, was promoted by cultivating the halo-tolerant yeast, Zygosaccharomyces rouxii, in a medium including the amino-carbonyl reaction products based on ribose and glycine. The glucose concentration in the medium influenced the HEMF formation by Z. rouxii. PMID:17617718

  10. Genetic and epigenetic transgenerational implications related to omega-3 fatty acids. Part I: maternal FADS2 genotype and DNA methylation correlate with polyunsaturated fatty acid status in toddlers: an exploratory analysis.

    PubMed

    Lupu, Daniel S; Cheatham, Carol L; Corbin, Karen D; Niculescu, Mihai D

    2015-11-01

    Polyunsaturated fatty acid metabolism in toddlers is regulated by a complex network of interacting factors. The contribution of maternal genetic and epigenetic makeup to this milieu is not well understood. In a cohort of mothers and toddlers 16 months of age (n = 65 mother-child pairs), we investigated the association between maternal genetic and epigenetic fatty acid desaturase 2 (FADS2) profiles and toddlers' n-6 and n-3 fatty acid metabolism. FADS2 rs174575 variation and DNA methylation status were interrogated in mothers and toddlers, as well as food intake and plasma fatty acid concentrations in toddlers. A multivariate fit model indicated that maternal rs174575 genotype, combined with DNA methylation, can predict α-linolenic acid plasma concentration in all toddlers and arachidonic acid concentrations in boys. Arachidonic acid intake was predictive for its plasma concentration in girls, whereas intake of 3 major n-3 species (eicosapentaenoic, docosapentaenoic, and docosahexaenoic acids) were predictive for their plasma concentrations in boys. FADS2 genotype and DNA methylation in toddlers were not related to plasma concentrations or food intakes, except for CpG8 methylation. Maternal FADS2 methylation was a predictor for the boys' α-linolenic acid intakes. This exploratory study suggests that maternal FADS2 genetic and epigenetic status could be related to toddlers' polyunsaturated fatty acid metabolism. PMID:26439440

  11. Differential effects of a short-term high-fat diet in an animal model of depression in rats treated with the 5-HT3 receptor antagonist, ondansetron, the 5-HT3 receptor agonist, 2-methyl-5-HT, and the SSRI, fluoxetine.

    PubMed

    Sumaya, Isabel C; Bailey, Dee; Catlett, Susan L

    2016-05-01

    Investigation into the effects of a high-fat diet on depression in the context of 5-HT3 receptor function is important given 5-HT3 antagonism may represent a novel candidate for drug discovery. To more fully understand the relationship between the 5-HT3 receptor system, depression, and high-fat intake, our main interest was to study the short-term effects of a high-fat diet on the 5-HT3 receptor antagonist, ondansetron, and the 5-HT3 receptor agonist, 2-methyl-5-HT, as well as the SSRI, fluoxetine, in an animal model of depression. Male Sprague Dawley rats were fed either a standard diet (11% fat) or a high-fat diet (32.5% fat) for seven days then treated with either fluoxetine (10mg/kg, ip), ondansetron (1mg/kg, ip), 2-methyl-5-HT (3mg/kg, ip), fluoxetine+ondansetron or, 2-methyl-5-HT+ondansetron prior to the Forced Swim Test. In the standard diet group, treatment with the 5HT3 receptor agonist, 2-methyl-5-HT, served to significantly decrease time of immobility as compared to controls thus showing anti-depressive-like effects. Treatment with the 5-HT3 receptor antagonist, ondansetron, served to enhance the anti-depressive like effects of the SSRI, fluoxetine, as treatment with both the SSRI and 5-HT3 receptor antagonist dramatically decreased immobility. Importantly, in the high-fat diet groups, a week of high-fat intake served to: 1) counteract the anti-depressive-like effect of the SSRI, fluoxetine, 2) reverse the anti-depressive-like effect of the 5HT3 receptor agonist, 2-methyl-5-HT and 3) provide protection against the depressive-like effects induced by the Forced Swim Test as rats fed a high-fat diet displayed the lowest amounts of immobility. In the aggregate, these data suggest that both SSRIs and the 5HT3 receptor system are affected by short-term high-fat intake and that a short-term high-fat diet protects against depressive-like effects in an animal model of depression. PMID:26979154

  12. Anticancer potential of pyrrole (1, 2, a) pyrazine 1, 4, dione, hexahydro 3-(2-methyl propyl) (PPDHMP) extracted from a new marine bacterium, Staphylococcus sp. strain MB30.

    PubMed

    Lalitha, P; Veena, V; Vidhyapriya, P; Lakshmi, Pragna; Krishna, R; Sakthivel, N

    2016-05-01

    Marine bacterium, strain MB30 isolated from the deep sea sediment of Bay of Bengal, India, exhibited antimicrobial activity against human pathogenic bacteria. Based on the 16S rRNA sequence homology and subsequent phylogenetic tree analysis, the strain MB30 was identified as Staphylococcus sp. The bioactive metabolite produced by the strain MB30 was purified through silica gel column chromatography and preparative HPLC. Purified metabolite was further characterized by FT-IR, LC-MS and NMR analyses. On the basis of spectroscopic data, the metabolite was identified as pyrrole (1, 2, a) pyrazine 1, 4, dione, hexahydro 3-(2-methyl propyl) (PPDHMP). The PPDHMP exhibited in vitro anticancer potential against lung (A549) and cervical (HeLa) cancer cells in a dose-dependent manner with the IC50 concentration of 19.94 ± 1.23 and 16.73 ± 1.78 μg ml(-1) respectively. The acridine orange (AO)/ethidium bromide (EB) and 4,6-diamidino-2-phenylindole dihydrochloride (DAPI) staining of the IC50 concentration of PPDHMP-treated cancer cells exhibited an array of morphological changes such as nuclear condensation, cell shrinkage and formation of apoptotic bodies. The PPDHMP-treated cancer cells induced the progressive accumulation of fragmented DNA in a time-dependent manner. Based on the flow cytometric analysis, it has become evident that the compound was also effective in arresting the cell cycle at G1 phase. Further, the Western blotting analysis confirmed the down-regulation of cyclin-D1, cyclin dependent kinase (CDK-2), anti-apoptotic Bcl-2 family proteins (Bcl-2 and Bcl-xL), activation of caspase-9 and 3 with the cleavage of PARP. The PPDHMP-treated cancer cells also showed the inhibition of migration and invasive capacity of cancer cells. In the present investigation, for the first time, we have reported the extraction, purification and characterization of an anticancer metabolite, PPDHMP from a new marine bacterium, Staphylococcus sp. strain MB30. PMID:26852140

  13. First total syntheses of (Z)-15-methyl-10-hexadecenoic acid and the (Z)-13-methyl-8-tetradecenoic acid

    PubMed Central

    Carballeira, Néstor M.; Montano, Nashbly; Padilla, Luis F.

    2006-01-01

    The first total syntheses for the (Z)-15-methyl-10-hexadecenoic acid and the (Z)-13-methyl-8-tetradecenoic acid were accomplished in seven steps and in 31–32% overall yields. The (trimethylsilyl)acetylene was the key reagent in both syntheses. It is proposed that the best synthetic strategy towards monounsaturated iso methyl-branched fatty acids with double bonds close to the ω end of the acyl chain is first acetylide coupling of (trimethylsilyl)acetylene to a long-chain bifunctional bromoalkane followed by a second acetylide coupling to a short-chain iso bromoalkane, since higher yields are thus obtained. Spectral data is also presented for the first time for these two unusual fatty acids with potential as biomarkers and as topoisomerase I inhibitors. PMID:17125759

  14. Associations between Serum Perfluoroalkyl Acids and LINE-1 DNA Methylation

    PubMed Central

    Watkins, Deborah J.; Wellenius, Gregory A.; Butler, Rondi A.; Bartell, Scott M.; Fletcher, Tony; Kelsey, Karl T.

    2014-01-01

    Perfluoroalkyl acids (PFAAs) are persistent, synthetic compounds that are used in a number of consumer products. Perfluorooctanoic acid (PFOA) and perfluorooctane sulfonate (PFOS) have been associated with cardiovascular risk factors, and changes in gene expression and DNA methylation in animals and cellular systems. However, whether PFAA exposure is associated with LINE-1 DNA methylation, a potential marker of cardiovascular risk, in humans remains unknown. We sought to evaluate the cross-sectional associations between serum PFAAs and LINE-1 DNA methylation in a population highly exposed to PFOA. We measured serum PFAAs twice four to five years apart in 685 adult participants (47% male, mean age ± SD=42 ± 11 years). We measured percent LINE-1 DNA methylation in peripheral blood leukocytes at the second time point (follow-up), and estimated absolute differences in LINE-1 methylation associated with an interquartile (IQR) shift in mean PFAA serum levels. IQR increases in mean serum PFOA, PFOS, perfluorononanoic acid (PFNA), and perfluorohexane sulfonate (PFHxS) were associated with differences of −0.04 (p=0.16), 0.20 (p=0.001), 0.06 (p=0.19), and 0.02 (p=0.57), respectively, in % LINE-1 methylation at follow-up after adjustment for potential confounders. We observed a monotonic increase in LINE-1 DNA methylation across tertiles of PFOS and PFNA (ptrend=0.02 for both associations), but not across tertiles of PFOA or PFHxS (ptrend=0.71 and 0.44, respectively). In summary, serum PFOS was associated with LINE-1 methylation, while serum PFOA, PFHxS, and PFNA were not. Additional research is needed to more precisely determine whether these compounds are epigenetically active. PMID:24263140

  15. Novel fatty acid methyl esters from the actinomycete Micromonospora aurantiaca

    PubMed Central

    Bruns, Hilke; Riclea, Ramona

    2011-01-01

    Summary The volatiles released by Micromonospora aurantiaca were collected by means of a closed-loop stripping apparatus (CLSA) and analysed by GC–MS. The headspace extracts contained more than 90 compounds from different classes. Fatty acid methyl esters (FAMEs) comprised the major compound class including saturated unbranched, monomethyl and dimethyl branched FAMEs in diverse structural variants: Unbranched, α-branched, γ-branched, (ω−1)-branched, (ω−2)-branched, α- and (ω−1)-branched, γ- and (ω−1)-branched, γ- and (ω−2)-branched, and γ- and (ω−3)-branched FAMEs. FAMEs of the last three types have not been described from natural sources before. The structures for all FAMEs have been suggested based on their mass spectra and on a retention index increment system and verified by the synthesis of key reference compounds. In addition, the structures of two FAMEs, methyl 4,8-dimethyldodecanoate and the ethyl-branched compound methyl 8-ethyl-4-methyldodecanoate were deduced from their mass spectra. Feeding experiments with isotopically labelled [2H10]leucine, [2H10]isoleucine, [2H8]valine, [2H5]sodium propionate, and [methyl-2H3]methionine demonstrated that the responsible fatty acid synthase (FAS) can use different branched and unbranched starter units and is able to incorporate methylmalonyl-CoA elongation units for internal methyl branches in various chain positions, while the methyl ester function is derived from S-adenosyl methionine (SAM). PMID:22238549

  16. Effects of high-melting methyl esters on crystallization properties of fatty acid methyl ester mixtures

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Biodiesel is a renewable alternative diesel fuel made from vegetable oils and animal fats. The most common form of biodiesel in the United States are fatty acid methyl esters (FAME) from soybean, canola, and used cooking oils, waste greases, and tallow. Cold flow properties of biodiesel depend on th...

  17. Direct acid methylation for extraction of fatty acid content from microalgae cells.

    PubMed

    Frigo-Vaz, Benjamin D; Wang, Ping

    2014-08-01

    Direct acid methylation was examined as a means for both analysis of fatty acid content in microalgal cells and biodiesel production without pretreatment. Microalgal cells of Chlamydomonas reinhardtii and Dunaliella tertiolecta were prepared and examined. It appeared that direct acid methylation extracted higher fatty acid content than the solvent-based Soxhlet extraction process. It also revealed that the latter was prone to extract a significant amount of nonlipid hydrophobic impurities, including hydrophobic proteins and phytol-type compounds, while direct methylation produces essentially pure ester product. This work demonstrates that direct acid methylation provides superior fatty acid extraction, promising an efficient process for either quantification of lipid content or production of biodiesel. PMID:24838798

  18. 40 CFR 721.1576 - 1,3-Benzenedicarboxylic acid, bis[[4-[(ethenyloxy)methyl] cyclohexyl] methyl] ester.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... cyclohexyl] methyl] ester. 721.1576 Section 721.1576 Protection of Environment ENVIRONMENTAL PROTECTION...] methyl] ester. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as 1,3-benzenedicarboxylic acid, bis cyclohexyl] methyl] ester (PMN P-98-1162; CAS...

  19. 40 CFR 721.1576 - 1,3-Benzenedicarboxylic acid, bis[[4-[(ethenyloxy)methyl] cyclohexyl] methyl] ester.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... cyclohexyl] methyl] ester. 721.1576 Section 721.1576 Protection of Environment ENVIRONMENTAL PROTECTION...] methyl] ester. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as 1,3-benzenedicarboxylic acid, bis cyclohexyl] methyl] ester (PMN P-98-1162; CAS...

  20. 40 CFR 721.1578 - 1,4-Benzenedicarboxylic acid, bis[[4-[(ethenyloxy)methyl] cyclohexyl] methyl] ester.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... cyclohexyl] methyl] ester. 721.1578 Section 721.1578 Protection of Environment ENVIRONMENTAL PROTECTION...] methyl] ester. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as 1,4-benzenedicarboxylic acid, bis cyclohexyl] methyl] ester (PMN P-98-1164; CAS...

  1. 40 CFR 721.1578 - 1,4-Benzenedicarboxylic acid, bis[[4-[(ethenyloxy)methyl] cyclohexyl] methyl] ester.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... cyclohexyl] methyl] ester. 721.1578 Section 721.1578 Protection of Environment ENVIRONMENTAL PROTECTION...] methyl] ester. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as 1,4-benzenedicarboxylic acid, bis cyclohexyl] methyl] ester (PMN P-98-1164; CAS...

  2. Aerobic Copper-Catalyzed O-Methylation with Methylboronic Acid.

    PubMed

    Jacobson, Clare E; Martinez-Muñoz, Noelia; Gorin, David J

    2015-07-17

    The oxidative coupling of alkylboronic acids with oxygen nucleophiles offers a strategy for replacing toxic, electrophilic alkylating reagents. Although the Chan-Lam reaction has been widely applied in the arylation of heteroatom nucleophiles, O-alkylation with boronic acids is rare. We report a Cu-catalyzed nondecarboxylative methylation of carboxylic acids with methylboronic acid that proceeds in air with no additional oxidant. An isotope-labeling study supports an oxidative cross-coupling mechanism, in analogy to that proposed for Chan-Lam arylation. PMID:26111825

  3. Folic acid and the methylation of homocysteine by Bacillus subtilis

    PubMed Central

    Salem, A. R.; Pattison, J. R.; Foster, M. A.

    1972-01-01

    1. Cell-free extracts of Bacillus subtilis synthesize methionine from serine and homocysteine without added folate. The endogenous folate may be replaced by tetrahydropteroyltriglutamate or an extract of heated Escherichia coli for the overall C1 transfer, but tetrahydropteroylmonoglutamate is relatively inactive. 2. Extracts of B. subtilis contain serine transhydroxymethylase and 5,10-methylenetetrahydrofolate reductase, which are non-specific with respect to the glutamate content of the folate substrates. Methyl transfer to homocysteine requires a polyglutamate folate as methyl donor. These properties are not affected by growth of the organism with added vitamin B12. 3. The synthesis of methionine from 5-methyltetrahydropteroyltriglutamate and homocysteine has the characteristics of the cobalamin-independent reaction of E. coli. No evidence for a cobalamin-dependent transmethylation was obtained. 4. S-Adenosylmethionine was not a significant precursor of the methyl group of methionine with cell-free extracts, neither was S-adenosylmethionine generated by methylation of S-adenosylhomocysteine by 5-methyltetrahydrofolate. 5. A procedure for the isolation and analysis of folic acid derivatives from natural sources is described. 6. The folates isolated from lysozyme extracts of B. subtilis are sensitive to folic acid conjugase. One has been identified as 5-formyltetrahydropteroyltriglutamate; the other is possibly a diglutamate folate. 7. A sequence is proposed for methionine biosynthesis in B. subtilis in which methyl groups are generated from serine and transferred to homocysteine by means of a cobalamin-independent pathway mediated by conjugated folate coenzymes. PMID:4627401

  4. Allosteric inhibition of glycogen phosphorylase a by the potential antidiabetic drug 3-isopropyl 4-(2-chlorophenyl)-1,4-dihydro-1-ethyl-2-methyl-pyridine-3,5,6-tricarbo xylate.

    PubMed Central

    Oikonomakos, N. G.; Tsitsanou, K. E.; Zographos, S. E.; Skamnaki, V. T.; Goldmann, S.; Bischoff, H.

    1999-01-01

    The effect of the potential antidiabetic drug (-)(S)-3-isopropyl 4-(2-chlorophenyl)-1,4-dihydro-1-ethyl-2-methyl-pyridine-3,5,6-tricarbox ylate (W1807) on the catalytic and structural properties of glycogen phosphorylase a has been studied. Glycogen phosphorylase (GP) is an allosteric enzyme whose activity is primarily controlled by reversible phosphorylation of Ser14 of the dephosphorylated enzyme (GPb, less active, predominantly T-state) to form the phosphorylated enzyme (GPa, more active, predominantly R-state). Upon conversion of GPb to GPa, the N-terminal tail (residues 5-22), which carries the Ser14(P), changes its conformation into a distorted 3(10) helix and its contacts from intrasubunit to intersubunit. This alteration causes a series of tertiary and quaternary conformational changes that lead to activation of the enzyme through opening access to the catalytic site. As part of a screening process to identify compounds that might contribute to the regulation of glycogen metabolism in the noninsulin dependent diabetes diseased state, W1807 has been found as the most potent inhibitor of GPb (Ki = 1.6 nM) that binds at the allosteric site of T-state GPb and produces further conformational changes, characteristic of a T'-like state. Kinetics show W1807 is a potent competitive inhibitor of GPa (-AMP) (Ki = 10.8 nM) and of GPa (+1 mM AMP) (Ki = 19.4 microM) with respect to glucose 1-phosphate and acts in synergism with glucose. To elucidate the structural features that contribute to the binding, the structures of GPa in the T-state conformation in complex with glucose and in complex with both glucose and W1807 have been determined at 100 K to 2.0 A and 2.1 A resolution, and refined to crystallographic R-values of 0.179 (R(free) = 0.230) and 0.189 (R(free) = 0.263), respectively. W1807 binds tightly at the allosteric site and induces substantial conformational changes both in the vicinity of the allosteric site and the subunit interface. A disordering of the N

  5. Allosteric inhibition of glycogen phosphorylase a by the potential antidiabetic drug 3-isopropyl 4-(2-chlorophenyl)-1,4-dihydro-1-ethyl-2-methyl-pyridine-3,5,6-tricarbo xylate.

    PubMed

    Oikonomakos, N G; Tsitsanou, K E; Zographos, S E; Skamnaki, V T; Goldmann, S; Bischoff, H

    1999-10-01

    The effect of the potential antidiabetic drug (-)(S)-3-isopropyl 4-(2-chlorophenyl)-1,4-dihydro-1-ethyl-2-methyl-pyridine-3,5,6-tricarbox ylate (W1807) on the catalytic and structural properties of glycogen phosphorylase a has been studied. Glycogen phosphorylase (GP) is an allosteric enzyme whose activity is primarily controlled by reversible phosphorylation of Ser14 of the dephosphorylated enzyme (GPb, less active, predominantly T-state) to form the phosphorylated enzyme (GPa, more active, predominantly R-state). Upon conversion of GPb to GPa, the N-terminal tail (residues 5-22), which carries the Ser14(P), changes its conformation into a distorted 3(10) helix and its contacts from intrasubunit to intersubunit. This alteration causes a series of tertiary and quaternary conformational changes that lead to activation of the enzyme through opening access to the catalytic site. As part of a screening process to identify compounds that might contribute to the regulation of glycogen metabolism in the noninsulin dependent diabetes diseased state, W1807 has been found as the most potent inhibitor of GPb (Ki = 1.6 nM) that binds at the allosteric site of T-state GPb and produces further conformational changes, characteristic of a T'-like state. Kinetics show W1807 is a potent competitive inhibitor of GPa (-AMP) (Ki = 10.8 nM) and of GPa (+1 mM AMP) (Ki = 19.4 microM) with respect to glucose 1-phosphate and acts in synergism with glucose. To elucidate the structural features that contribute to the binding, the structures of GPa in the T-state conformation in complex with glucose and in complex with both glucose and W1807 have been determined at 100 K to 2.0 A and 2.1 A resolution, and refined to crystallographic R-values of 0.179 (R(free) = 0.230) and 0.189 (R(free) = 0.263), respectively. W1807 binds tightly at the allosteric site and induces substantial conformational changes both in the vicinity of the allosteric site and the subunit interface. A disordering of the N

  6. 75 FR 770 - Acrylic acid-benzyl methacrylate-1-propanesulfonic acid, 2-methyl-2-[(1-oxo-2-propenyl)amino...

    Federal Register 2010, 2011, 2012, 2013, 2014

    2010-01-06

    ... Findings In the Federal Register of October 7, 2009 (74 FR 51600) (FRL-8792- 7), EPA issued a notice..., entitled Regulatory Planning and Review (58 FR 51735, October 4, 1993). Because this final rule has been... FR 28355, May 22, 2001) or Executive Order 13045, entitled Protection of Children from...

  7. Deoxyribonucleic acid methylation and chromatin organization in Tetrahymena thermophila.

    PubMed Central

    Pratt, K; Hattman, S

    1981-01-01

    Deoxyribonucleic acid (DNA) of the transcriptionally active macronucleus of Tetrahymena thermophila is methylated at the N6 position of adenine to produce methyladenine (MeAde); approximately 1 in every 125 adenine residues (0.8 mol%) is methylated. Transcriptionally inert micronuclear DNA is not methylated (< or = 0.01 mol% MeAde; M. A. Gorovsky, S. Hattman, and G. L. Pleger, J. Cell Biol. 56:697-701, 1973). There is no detectable cytosine methylation in macronuclei in Tetrahymena DNA (< or = 0.01 mol% 5-methylcytosine). MeAde-containing DNA sequences in macronuclei are preferentially digested by both staphylococcal nuclease and pancreatic deoxyribonuclease I. In contrast, there is no preferential release of MeAde during digestion of purified DNA. These results indicate that MeAde residues are predominantly located in "linker DNA" and perhaps have a function in transcription. Pulse-chase studies showed that labeled MeAde remains preferentially in linker DNA during subsequent rounds of DNA replication; i.e., there is little, if any, movement of nucleosomes during chromatin replication. This implies that nucleosomes may be phased with respect to DNA sequence. PMID:9279374

  8. Combined Experimental and Theoretical Study on the Formation of the Elusive 2-Methyl-1-silacycloprop-2-enylidene Molecule under Single Collision Conditions via Reactions of the Silylidyne Radical (SiH; X(2)Π) with Allene (H2CCCH2; X(1)A1) and D4-Allene (D2CCCD2; X(1)A1).

    PubMed

    Yang, Tao; Dangi, Beni B; Maksyutenko, Pavlo; Kaiser, Ralf I; Bertels, Luke W; Head-Gordon, Martin

    2015-12-17

    The crossed molecular beam reactions of the ground-state silylidyne radical (SiH; X(2)Π) with allene (H2CCCH2; X(1)A1) and D4-allene (D2CCCD2; X(1)A1) were carried out at collision energies of 30 kJ mol(-1). Electronic structure calculations propose that the reaction of silylidyne with allene has no entrance barrier and is initiated by silylidyne addition to the π electron density of allene either to one carbon atom (C1/C2) or to both carbon atoms simultaneously via indirect (complex forming) reaction dynamics. The initially formed addition complexes isomerize via two distinct reaction pathways, both leading eventually to a cyclic SiC3H5 intermediate. The latter decomposes through a loose exit transition state via an atomic hydrogen loss perpendicularly to the plane of the decomposing complex (sideways scattering) in an overall exoergic reaction (experimentally: -19 ± 13 kJ mol(-1); computationally: -5 ± 3 kJ mol(-1)). This hydrogen loss yields the hitherto elusive 2-methyl-1-silacycloprop-2-enylidene molecule (c-SiC3H4), which can be derived from the closed-shell cyclopropenylidene molecule (c-C3H2) by replacing a hydrogen atom with a methyl group and the carbene carbon atom by the isovalent silicon atom. The synthesis of the 2-methyl-1-silacycloprop-2-enylidene molecule in the bimolecular gas-phase reaction of silylidyne with allene enriches our understanding toward the formation of organosilicon species in the gas phase of the interstellar medium in particular via exoergic reactions of no entrance barrier. This facile route to 2-methyl-1-silacycloprop-2-enylidene via a silylidyne radical reaction with allene opens up a versatile approach to form hitherto poorly characterized silicon-bearing species in extraterrestrial environments; this reaction class might represent the missing link, leading from silicon-bearing radicals via organosilicon chemistry eventually to silicon-carbon-rich interstellar grains even in cold molecular clouds where temperatures are as

  9. New radioiodinated methyl-branched fatty acids for cardiac studies

    SciTech Connect

    Knapp, F.F. Jr.; Ambrose, K.R.; Goodman, M.M.

    1985-01-01

    The effects of 3-methyl-substitution on the heart retention and metabolism of 3-R,S-methyl-(BMIPP) and 3,3-dimethyl-(DMIPP) analogues of 15-(p-iodophenyl)-pentadecanoic acid (IPP) have been studied in rats. Methyl-substitution considerably increased the myocardial half-time values in fasted rats: IPP, 5 to 10 min; BMIPP, 30 to 45 min; DMIPP, 6 to 7 h. Because of the observed differences in the relative myocardial uptake and retention of these agents, an evaluation of the subcellular distribution profiles and the distribution of radioactivity within various lipid pools extracted from cell components was performed. Studies with DMIPP in fasted rats have shown high levels of the free fatty acid and only slow conversion to triglycerides. These data are in contrast to the rapid clearance of the straight chain IPP analogue and rapid incorporation into triglycerides. These data suggest that the prolonged myocardial retention observed with DMIPP in vivo may result from inhibition of US -oxidation. Subcellular distribution studies have shown predominate association of DMIPP and BMIPP with the mitochondrial and microsomal fractions, while IPP was primarily found in the cytoplasm. Because of the unique ''trapping'' properties and the high heart:blood ratios, ( STI)DMIPP should be useful for evaluation of aberrations in regional myocardial uptake. 7 refs., 9 figs., 1 tab.

  10. Synthesis of Branched Methyl Hydroxy Stearates Including an Ester from Bio-Based Levulinic Acid

    Technology Transfer Automated Retrieval System (TEKTRAN)

    We report the synthesis of 5 useful branched methyl alpha-hydroxy oleate esters from commercially available methyl oleate and common organic acids. Of special interest is the synthesis utilizing the natural byproduct, levulinic acid. The other common organic acids used herein were propionic acid, ...

  11. Lewis acid catalysed methylation of N-(9H-fluoren-9-yl)methanesulfonyl (Fms) protected lipophilic α-amino acid methyl esters.

    PubMed

    Leggio, Antonella; Alò, Danila; Belsito, Emilia Lucia; Di Gioia, Maria Luisa; Romio, Emanuela; Siciliano, Carlo; Liguori, Angelo

    2015-08-01

    This work reports an efficient Lewis acid catalysed N-methylation procedure of lipophilic α-amino acid methyl esters in solution phase. The developed methodology involves the use of the reagent system AlCl3/diazomethane as methylating agent and α-amino acid methyl esters protected on the amino function with the (9H-fluoren-9-yl)methanesulfonyl (Fms) group. The removal of Fms protecting group is achieved under the same conditions to those used for Fmoc removal. Thus the Fms group can be interchangeable with the Fmoc group in the synthesis of N-methylated peptides using standard Fmoc-based strategies. Finally, the absence of racemization during the methylation reaction and the removal of Fms group were demonstrated by synthesising a pair of diastereomeric dipeptides. PMID:25921656

  12. Complexes of polyadenylic acid and the methyl esters of amino acids

    NASA Technical Reports Server (NTRS)

    Khaled, M. A.; Mulins, D. W., Jr.; Swindle, M.; Lacey, J. C., Jr.

    1983-01-01

    A study of amino acid methyl esters binding to polyadenylic acid supports the theory that the genetic code originated through weak but selective affinities between amino acids and nucleotides. NMR, insoluble complex analysis, and ultraviolet spectroscopy are used to illustrate a correlation between the hydrophybicities of A amino acids and their binding constants, which, beginning with the largest, are in the order of Phe (having nominally a hydrophobic AAA anticodon), Ile, Leu, Val and Gly (having a hydrophilic anticodon with no A). In general, the binding constants are twice the values by Reuben and Polk (1980) for monomeric AMP, which suggests that polymer amino acids are interacting with only one base. No real differences are found betwen poly A binding for free Phe, Phe methyl ester or Phe amide, except that the amide value is slightly lower.

  13. Discovery of 5-[[4-[(2,3-Dimethyl-2H-indazol-6-yl)methylamino]-2-pyrimidinyl]amino]-2-methyl-benzenesulfonamide (Pazopanib), a Novel and Potent Vascular Endothelial Growth Factor Receptor Inhibitor

    SciTech Connect

    Harris, Philip A.; Boloor, Amogh; Cheung, Mui; Kumar, Rakesh; Crosby, Renae M.; Davis-Ward, Ronda G.; Epperly, Andrea H.; Hinkle, Kevin W.; Hunter, III, Robert N.; Johnson, Jennifer H.; Knick, Victoria B.; Laudeman, Christopher P.; Luttrell, Deirdre K.; Mook, Robert A.; Nolte, Robert T.; Rudolph, Sharon K.; Szewczyk, Jerzy R.; Truesdale, Anne T.; Veal, James M.; Wang, Liping; Stafford, Jeffrey A.

    2009-05-18

    Inhibition of the vascular endothelial growth factor (VEGF) signaling pathway has emerged as one of the most promising new approaches for cancer therapy. We describe herein the key steps starting from an initial screening hit leading to the discovery of pazopanib, N{sup 4}-(2,3-dimethyl-2H-indazol-6-yl)-N{sup 4}-methyl-N{sup 2}-(4-methyl-3-sulfonamidophenyl)-2,4-pyrimidinediamine, a potent pan-VEGF receptor (VEGFR) inhibitor under clinical development for renal-cell cancer and other solid tumors.

  14. Electron driven processes in chlorodifluoroacetic acid methyl ester

    NASA Astrophysics Data System (ADS)

    Kopyra, Janina

    2014-07-01

    Dissociative electron attachment to gas phase 2-chloro-2,2-difluoroacetic acid methyl ester (CClF2COOCH3) is studied by means of a crossed beams apparatus. Effective cleavage of the C-Cl bond is observed within a broad resonance in the energy range 0-1 eV and visible via the appearance of the light fragment Cl-. In chlorodifluoroacetic acid cleavage of the C-Cl bond was observed not only via the Cl- anion formation but predominantly via expulsion of the neutral chlorine atom leading to the formation of the (M-Cl)- anion. Similar to the previously studied esters CF3COOCH3 and CF3COOC2H5[I. Martin, J. Langer, E. Illenberger, Z. Phys. Chem. 222, 1185 (2008)], we observe reaction due to the cleavage of the ester bond resulting in the formation of the closed shell (M-CH3)- anion.

  15. 40 CFR 721.10424 - Benzoic acid, 4-(1,1-dimethylethyl)-, methyl.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Benzoic acid, 4-(1,1-dimethylethyl... Specific Chemical Substances § 721.10424 Benzoic acid, 4-(1,1-dimethylethyl)-, methyl. (a) Chemical... acid, 4-(1,1-dimethylethyl)-, methyl (PMN P-12-33, CAS No. 26537-19-9) is subject to reporting...

  16. 40 CFR 721.10424 - Benzoic acid, 4-(1,1-dimethylethyl)-, methyl.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Benzoic acid, 4-(1,1-dimethylethyl... Specific Chemical Substances § 721.10424 Benzoic acid, 4-(1,1-dimethylethyl)-, methyl. (a) Chemical... acid, 4-(1,1-dimethylethyl)-, methyl (PMN P-12-33, CAS No. 26537-19-9) is subject to reporting...

  17. 40 CFR 721.10424 - Benzoic acid, 4-(1,1-dimethylethyl)-, methyl.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Benzoic acid, 4-(1,1-dimethylethyl... Specific Chemical Substances § 721.10424 Benzoic acid, 4-(1,1-dimethylethyl)-, methyl. (a) Chemical... acid, 4-(1,1-dimethylethyl)-, methyl (PMN P-12-33, CAS No. 26537-19-9) is subject to reporting...

  18. Crystal structure of ethyl (1RS,6SR)-4-(2-methyl-1H-imidazol-4-yl)-2-oxo-6-(2,3,5-tri­chloro­phen­yl)cyclo­hex-3-ene-1-carboxyl­ate

    PubMed Central

    Mohan, Billava J.; Sarojini, Balladka K.; Yathirajan, Hemmige S.; Rathore, Ravindranath; Glidewell, Christopher

    2016-01-01

    The title compound, C19H17Cl3N2O3, has been prepared in a cyclo­condensation reaction between 2,3,5-tri­chloro­benzaldehye and 4-acetyl-2-methyl-1H-imidazole. The cyclo­hexenone ring adopts an envelope conformation with the C atom substituted by the tri­chloro­phenyl ring as the flap. The mutually trans ester and aryl substituents both occupy equatorial sites. In the crystal, a combination of N—H⋯O and C—H⋯N hydrogen bonds links the mol­ecules into ribbons of edge-fused centrosymmetric rings, which enclose R 2 2(14) and R 4 4(16) alternate ring motifs, propagating along the b-axis direction. PMID:26870579

  19. Trichlorido{2-[2-(η5-cyclo­penta­dien­yl)-2-methyl­prop­yl]-1-trimethyl­silyl-1H-imidazole-κN 3}titanium(IV) tetra­hydro­furan hemisolvate

    PubMed Central

    Ge, Fang; Nie, Wanli; Borzov, Maxim V.; Churakov, Andrei V.

    2010-01-01

    The title compound, [Ti(C15H23N2Si)Cl3]·0.5C4H8O, has been prepared from {2-[2-(η5-cyclo­penta­dien­yl)-2-methyl­prop­yl]-1H-imidazolyl-κN 1}bis­(N,N-diethyl­amido-κN)titanium(IV), (C12H14N2)Ti(NEt2)2, by reaction with excess of Me3SiCl in tetra­hydro­furan (THF) at 353 K. The crystal structure contains THF as adduct solvent, disordered around a center of inversion. The presence of THF and the adduct ratio has been independently supported by 1H NMR spectroscopy. The coordination polyhedron of the Ti atom is distorted square-pyramidal, assuming the cyclo­penta­dienyl (Cp) ring occupies one coordination site. The Ti, Si and CH2 group C atoms only deviate slightly from the imidazole ring plane [by 0.021 (4), 0.133 (4) and 0.094 (4) Å, respectively]. Comparison of the principal geometric parameters with those of the few known structurally characterized analogues reveal small differences in bond lengths and angles at the Ti atom. The title complex is only stable in THF-d 8 in the presence of excess Me3SiCl, otherwise it exists in an equilibrium with equimolar amounts of dichlorido{2-[2-(η5-cyclo­penta­dien­yl)-2-methyl­prop­yl]-1H-imidazolyl-κN 3}titanium(IV) and chloro­trimethyl­silane. PMID:21579034

  20. An Arabidopsis thaliana methyltransferase Capable of Methylating Farnesoic Acid

    SciTech Connect

    Yang,Y.; Yuan, J.; Ross, J.; Noel, J.; Pichersky, E.

    2006-01-01

    We previously reported the identification of a new family of plant methyltransferases (MTs), named the SABATH family, that use S-adenosyl-l-methionine (SAM) to methylate a carboxyl moiety or a nitrogen-containing functional group on a diverse array of plant compounds. The Arabidopsis genome alone contains 24 distinct SABATH genes. To identify the catalytic specificities of members of this protein family in Arabidopsis, we screened recombinantly expressed and purified enzymes with a large number of potential substrates. Here, we report that the Arabidopsis thaliana gene At3g44860 encodes a protein with high catalytic specificity towards farnesoic acid (FA). Under steady-state conditions, this farnesoic acid carboxyl methyltransferase (FAMT) exhibits K{sub M} values of 41 and 71 {mu}M for FA and SAM, respectively. A three-dimensional model of FAMT constructed based upon similarity to the experimentally determined structure of Clarkia breweri salicylic acid methyltransferase (SAMT) suggests a reasonable model for FA recognition in the FAMT active site. In plants, the mRNA levels of At3g44860 increase in response to the exogenous addition of several compounds previously shown to induce plant defense responses at the transcriptional level. Although methyl farnesoate (MeFA) has not yet been detected in Arabidopsis, the presence of a FA-specific carboxyl methyltransferase in Arabidopsis capable of producing MeFA, an insect juvenile hormone made by some plants as a presumed defense against insect herbivory, suggests that MeFA or chemically similar compounds are likely to serve as new specialized metabolites in Arabidopsis.

  1. Pseudo catalytic transformation of volatile fatty acids into fatty acid methyl esters.

    PubMed

    Jung, Jong-Min; Cho, Jinwoo; Kim, Ki-Hyun; Kwon, Eilhann E

    2016-03-01

    Instead of anaerobic digestion of biodegradable wastes for producing methane, this work introduced the transformation of acidogenesis products (VFAs) into fatty acid methyl esters (FAMEs) to validate the feasible production of short-chained fatty alcohols via hydrogenation of FAMEs. In particular, among VFAs, this work mainly described the mechanistic explanations for transforming butyric acid into butyric acid methyl ester as a case study. Unlike the conventional esterification process (conversion efficiency of ∼94%), the newly introduced esterification under the presence of porous materials via the thermo-chemical process reached up to ∼99.5%. Furthermore, the newly introduced esterification via the thermo-chemical pathway in this work showed extremely high tolerance of impurities: the conversion efficiency under the presence of impurities reached up to ∼99±0.3%; thus, the inhibition behaviors attributed from the impurities used for the experimental work were negligible. PMID:26720136

  2. Effect of methyl jasmonate application to grapevine leaves on grape amino acid content.

    PubMed

    Garde-Cerdán, Teresa; Portu, Javier; López, Rosa; Santamaría, Pilar

    2016-07-15

    Over the last few years, considerable attention has been paid to the application of elicitors to vineyard. However, research about the effect of elicitors on grape amino acid content is scarce. Therefore, the aim of this study was to evaluate the influence of foliar application of methyl jasmonate on must amino acid content. Results revealed that total amino acid content was not modified by the application of methyl jasmonate. However, the individual content of certain amino acids was increased as consequence of methyl jasmonate foliar application, i.e., histidine, serine, tryptophan, phenylalanine, tyrosine, asparagine, methionine, and lysine. Among them, phenylalanine content was considerably increased; this amino acid is precursor of phenolic and aromatic compounds. In conclusion, foliar application of methyl jasmonate improved must nitrogen composition. This finding suggests that methyl jasmonate treatment might be conducive to obtain wines of higher quality since must amino acid composition could affect the wine volatile composition and the fermentation kinetics. PMID:26948648

  3. Green chromatography determination of fatty acid methyl esters in biodiesel.

    PubMed

    Mayo, Carlos Molina; Alayón, Andrea Brito; García Rodríguez, María Teresa; Jiménez Abizanda, Ana Isabel; Moreno, Francisco Jiménez

    2015-01-01

    This work proposes a green, simple and rapid chromatographic methodology for separation and determination of a group of 13 fatty acids methyl esters (FAMEs) by using a capillary gas chromatography with a flame ionization detector. The method was successfully applied for the determination of FAMEs in biodiesel samples from commercial and waste cooking oils, synthesized by homogeneous catalysis. Detection and quantification limits were in the μg L(-1) level. Direct injection of sample solution was compared with solid-phase extraction and solid-phase microextraction procedures, giving similar results. The lower analysis time represent considerable improvement compared with other papers. The described methodology is especially suitable for process control applications. The samples analysed showed total contents of FAMEs higher than 96.5%, which verifies the European regulations. PMID:25666201

  4. Fatty acid methyl ester profiles of bat wing surface lipids.

    PubMed

    Pannkuk, Evan L; Fuller, Nathan W; Moore, Patrick R; Gilmore, David F; Savary, Brett J; Risch, Thomas S

    2014-11-01

    Sebocytes are specialized epithelial cells that rupture to secrete sebaceous lipids (sebum) across the mammalian integument. Sebum protects the integument from UV radiation, and maintains host microbial communities among other functions. Native glandular sebum is composed primarily of triacylglycerides (TAG) and wax esters (WE). Upon secretion (mature sebum), these lipids combine with minor cellular membrane components comprising total surface lipids. TAG and WE are further cleaved to smaller molecules through oxidation or host enzymatic digestion, resulting in a complex mixture of glycerolipids (e.g., TAG), sterols, unesterified fatty acids (FFA), WE, cholesteryl esters, and squalene comprising surface lipid. We are interested if fatty acid methyl ester (FAME) profiling of bat surface lipid could predict species specificity to the cutaneous fungal disease, white nose syndrome (WNS). We collected sebaceous secretions from 13 bat spp. using Sebutape(®) and converted them to FAME with an acid catalyzed transesterification. We found that Sebutape(®) adhesive patches removed ~6× more total lipid than Sebutape(®) indicator strips. Juvenile eastern red bats (Lasiurus borealis) had significantly higher 18:1 than adults, but 14:0, 16:1, and 20:0 were higher in adults. FAME profiles among several bat species were similar. We concluded that bat surface lipid FAME profiling does not provide a robust model predicting species susceptibility to WNS. However, these results provide baseline data that can be used for lipid roles in future ecological studies, such as life history, diet, or migration. PMID:25227993

  5. DFT STUDY OF THE ISOMERIZATION OF HEXYL SPECIES INVOLVED IN THE ACID-CATALYZED CONVERSION OF 2-METHYL-PENTENE-2. (R825370C056)

    EPA Science Inventory

    The perspectives, information and conclusions conveyed in research project abstracts, progress reports, final reports, journal abstracts and journal publications convey the viewpoints of the principal investigator and may not represent the views and policies of ORD and EPA. Concl...

  6. Crystal structure of 2-{[1-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-yl­oxy]carbon­yl}benzoic acid

    PubMed Central

    Shahid, Hafiz Abdullah; Jahangir, Sajid; Shah, Syed Adnan Ali; Zaki, Hamizah Mohd; Naz, Humera

    2014-01-01

    In the title compound, C15H15N3O6, the dihedral angle between the planes of the benzene and imidazole rings is 34.93 (10)°. An intra­molecular C—H⋯O hydrogen bond is observed. In the crystal, O—H⋯N hydrogen bonds link the mol­ecules into chains parallel to the c axis. PMID:25553019

  7. 40 CFR 721.2075 - Carbamodithioic acid, methyl-, compound with methanamine (1:1).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ...-, compound with methanamine (1:1). 721.2075 Section 721.2075 Protection of Environment ENVIRONMENTAL... Significant New Uses for Specific Chemical Substances § 721.2075 Carbamodithioic acid, methyl-, compound with... substance identified generically as carbamodithioic acid, methyl-, compound with methanamine (1:1)...

  8. 40 CFR 721.2075 - Carbamodithioic acid, methyl-, compound with methanamine (1:1).

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ...-, compound with methanamine (1:1). 721.2075 Section 721.2075 Protection of Environment ENVIRONMENTAL... Significant New Uses for Specific Chemical Substances § 721.2075 Carbamodithioic acid, methyl-, compound with... substance identified generically as carbamodithioic acid, methyl-, compound with methanamine (1:1)...

  9. 40 CFR 721.2075 - Carbamodithioic acid, methyl-, compound with methanamine (1:1).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ...-, compound with methanamine (1:1). 721.2075 Section 721.2075 Protection of Environment ENVIRONMENTAL... Significant New Uses for Specific Chemical Substances § 721.2075 Carbamodithioic acid, methyl-, compound with... substance identified generically as carbamodithioic acid, methyl-, compound with methanamine (1:1)...

  10. 40 CFR 721.2075 - Carbamodithioic acid, methyl-, compound with methanamine (1:1).

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ...-, compound with methanamine (1:1). 721.2075 Section 721.2075 Protection of Environment ENVIRONMENTAL... Significant New Uses for Specific Chemical Substances § 721.2075 Carbamodithioic acid, methyl-, compound with... substance identified generically as carbamodithioic acid, methyl-, compound with methanamine (1:1)...

  11. 40 CFR 721.2075 - Carbamodithioic acid, methyl-, compound with methanamine (1:1).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ...-, compound with methanamine (1:1). 721.2075 Section 721.2075 Protection of Environment ENVIRONMENTAL... Significant New Uses for Specific Chemical Substances § 721.2075 Carbamodithioic acid, methyl-, compound with... substance identified generically as carbamodithioic acid, methyl-, compound with methanamine (1:1)...

  12. A Combined Experimental and Theoretical Study on the Formation of the 2-Methyl-1-silacycloprop-2-enylidene Molecule via the Crossed Beam Reactions of the Silylidyne Radical (SiH; X(2)Π) with Methylacetylene (CH3CCH; X(1)A1) and D4-Methylacetylene (CD3CCD; X(1)A1).

    PubMed

    Yang, Tao; Dangi, Beni B; Kaiser, Ralf I; Bertels, Luke W; Head-Gordon, Martin

    2016-07-14

    The bimolecular gas-phase reactions of the ground-state silylidyne radical (SiH; X(2)Π) with methylacetylene (CH3CCH; X(1)A1) and D4-methylacetylene (CD3CCD; X(1)A1) were explored at collision energies of 30 kJ mol(-1) under single-collision conditions exploiting the crossed molecular beam technique and complemented by electronic structure calculations. These studies reveal that the reactions follow indirect scattering dynamics, have no entrance barriers, and are initiated by the addition of the silylidyne radical to the carbon-carbon triple bond of the methylacetylene molecule either to one carbon atom (C1; [i1]/[i2]) or to both carbon atoms concurrently (C1-C2; [i3]). The collision complexes [i1]/[i2] eventually isomerize via ring-closure to the c-SiC3H5 doublet radical intermediate [i3], which is identified as the decomposing reaction intermediate. The hydrogen atom is emitted almost perpendicularly to the rotational plane of the fragmenting complex resulting in a sideways scattering dynamics with the reaction being overall exoergic by -12 ± 11 kJ mol(-1) (experimental) and -1 ± 3 kJ mol(-1) (computational) to form the cyclic 2-methyl-1-silacycloprop-2-enylidene molecule (c-SiC3H4; p1). In line with computational data, experiments of silylidyne with D4-methylacetylene (CD3CCD; X(1)A1) depict that the hydrogen is emitted solely from the silylidyne moiety but not from methylacetylene. The dynamics are compared to those of the related D1-silylidyne (SiD; X(2)Π)-acetylene (HCCH; X(1)Σg(+)) reaction studied previously in our group, and from there, we discovered that the methyl group acts primarily as a spectator in the title reaction. The formation of 2-methyl-1-silacycloprop-2-enylidene under single-collision conditions via a bimolecular gas-phase reaction augments our knowledge of the hitherto poorly understood silylidyne (SiH; X(2)Π) radical reactions with small hydrocarbon molecules leading to the synthesis of organosilicon molecules in cold molecular

  13. 3-(2-Chloro-3-hy­droxy-4-meth­oxy­phen­yl)-1-(4,5-dimeth­oxy-2-methyl­phen­yl)prop-2-en-1-one

    PubMed Central

    Patel, U. H.; Gandhi, S. A.; Barot, V. M.; Patel, M. C.

    2012-01-01

    The title compound, C19H19ClO5, is a chloro derivative of a biologically significant chalcone family. The mean plane of the two substituted benzene rings are twisted by 55.33 (8)° with respect to each other. An intra­molecular C—H⋯Cl hydrogen bond generates an S(5) graph-set motif. In the crystal, a bifurcated O—H⋯(O,O) hydrogen bond leads to an R 1 2(5) graph-set motif and to the formation of zigzag chains propagating along the c-axis direction. A weak π–π inter­action involving the methyl­phenyl rings [centroid–centroid distance = 3.8185 (10) Å] and C—H⋯π inter­actions also occur. PMID:23125715

  14. 2-[(4-Chloro­benz­yl)sulfan­yl]-4-(2-methyl­prop­yl)-6-(phenyl­sulfan­yl)pyrimidine-5-carbonitrile

    PubMed Central

    El-Emam, Ali A.; Al-Deeb, Omar A.; Al-Turkistani, Abdulghafoor A.; Ng, Seik Weng; Tiekink, Edward R. T.

    2012-01-01

    In the title compound, C22H20ClN3S2, the S-bound benzene rings are inclined [dihedral angles = 78.13 (10) and 36.70 (9)°] with respect to the pyrimidine ring. The methyl­propyl group occupies a position normal to the pyrimidine ring [N—C—C—C torsion angle = 92.3 (2)°]. In the crystal, supra­molecular layers are formed in the bc plane, being consolidated by C—H⋯π and π—π inter­actions, the latter between the pyrimidine and S-bound benzene rings [inter-centroid distance = 3.7683 (12) Å]. PMID:22807879

  15. Studies of the acidic components of the Colorado Green River formation oil shale-Mass spectrometric identification of the methyl esters of extractable acids.

    NASA Technical Reports Server (NTRS)

    Haug, P.; Schnoes, H. K.; Burlingame, A. L.

    1971-01-01

    Study of solvent extractable acidic constituents of oil shale from the Colorado Green River Formation. Identification of individual components is based on gas chromatographic and mass spectrometric data obtained for their respective methyl esters. Normal acids, isoprenoidal acids, alpha, omega-dicarboxylic acids, mono-alpha-methyl dicarboxylic acids and methyl ketoacids were identified. In addition, the presence of monocyclic, benzoic, phenylalkanoic and naphthyl-carboxylic acids, as well as cycloaromatic acids, is demonstrated by partial identification.

  16. Crystal structure of 1-[(2S*,4R*)-6-fluoro-2-methyl-1,2,3,4-tetra­hydro­quinolin-4-yl]pyrrolidin-2-one

    PubMed Central

    Pradeep, P. S.; Naveen, S.; Kumara, M. N.; Mahadevan, K. M.; Lokanath, N. K.

    2014-01-01

    In the title compound, C14H17FN2O, the 1,2,3,4-tetra­hydro­pyridine ring of the quinoline moiety adopts a half-chair conformation, while the pyrrolidine ring has an envelope conformation with the central methyl­ene C atom as the flap. The pyrrolidine ring lies in the equatorial plane and its mean plane is normal to the mean plane of the quinoline ring system, with a dihedral angle value of 88.37 (9)°. The bridging N—C bond distance [1.349 (3) Å] is substanti­ally shorter than the sum of the covalent radii (d cov: C—N = 1.47 Å and C=N = 1.27 Å), which indicates partial double-bond character for this bond, resulting in a certain degree of charge delocalization. In the crystal, mol­ecules are linked by N—H⋯O and C—H⋯O hydrogen bonds, forming sheets lying parallel to (10-1). These two-dimensional networks are linked via C—H⋯F hydrogen bonds and C—H⋯π inter­actions, forming a three-dimensional structure. PMID:25309166

  17. PLASMID DNA DAMAGE CAUSED BY METHYLATED ARSENICALS, ASCORBIC ACID AND HUMAN LIVER FERRITIN

    EPA Science Inventory

    PLASMID DNA DAMAGE CAOUSED BY METHYLATED ARSENICALS, ASCORBIC ACID AND HUMAN LIVER FERRITIN

    ABSTRACT

    Both dimethylarsinic acid (DMA(V)) and dimethylarsinous acid (DMA(III)) release iron from human liver ferritin (HLF) with or without the presence of ascorbic acid. ...

  18. A relationship between vitamin B sub 12 , folic acid, ascorbic acid, and mercury uptake and methylation

    SciTech Connect

    Zorn, N.E.; Smith, J.T. )

    1990-01-01

    Ingestion of megadoses of certain vitamins appears to influence the in vivo methylation of mercuric chloride in guinea pigs. The addition of megadoses of vitamin B{sub 12} fed either singularly or in combination with folic acid resulted in increased methylmercury concentrations in the liver. Moreover, percent methylmercury levels were significantly increased with B{sub 12} treatment in the liver (B{sub 12} only and B{sub 12}/folic acid) and brain (B{sub 12}/vitamin C). Incorporation of high levels of folic acid into the dietary regime also increased the methylmercury concentration particularly in the liver and hair tissues. The addition of vitamin C in the diet, particularly in combination with B{sub 12} (brain) or folic acid (muscle) resulted in increased methylmercury levels in these tissues and percent methylmercury values with B{sub 12} in the muscle and brain tissue.

  19. Functional analysis of a tomato salicylic acid methyl transferase and its role in synthesis of the flavor volatile methyl salicylate

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Methyl salicylate (MeSA) is a volatile plant secondary metabolite that is an important contributor to taste and scent of many fruits and flowers. It is synthesized from salicylic acid (SA), a phytohormone that contributes to plant pathogen defense. MeSA is synthesized by members of a family of O-met...

  20. A new sesquiterpene lactone glycoside and a new quinic acid methyl ester from Patrinia villosa.

    PubMed

    Yang, Yong-Fen; Ma, Hong-Mei; Chen, Gang; Wang, Hai-Feng; Xiang, Zheng; Feng, Qing-Mei; Hua, Hui-Ming; Pei, Yue-Hu

    2016-10-01

    A new sesquiterpene lactone glycoside (1) and a new quinic acid methyl ester (2) were isolated from Patrinia villosa, together with another two known compounds chlorogenic acid n-butyl ester (3), 3, 4-di-O-caffeoylquinic acid methyl ester (4). Their structures were established using 1D/2D-NMR spectroscopy, mass spectrometry, and comparing with spectroscopic data reported in the literature. PMID:27156969

  1. Methyl esters from vegetable oils with hydroxy fatty acids: Comparison of lesquerella and castor methyl esters

    Technology Transfer Automated Retrieval System (TEKTRAN)

    The search for alternative feedstocks for biodiesel as partial replacement for petrodiesel has recently extended to castor oil. In this work, the castor oil methyl esters were prepared and their properties determined in comparison to the methyl esters of lesquerella oil, which in turn is seen as alt...

  2. [Neuroepigenetics: Desoxyribonucleic acid methylation in Alzheimer's disease and other dementias].

    PubMed

    Mendioroz Iriarte, Maite; Pulido Fontes, Laura; Méndez-López, Iván

    2015-05-21

    DNA methylation is an epigenetic mechanism that controls gene expression. In Alzheimer's disease (AD), global DNA hypomethylation of neurons has been described in the human cerebral cortex. Moreover, several variants in the methylation pattern of candidate genes have been identified in brain tissue when comparing AD patients and controls. Specifically, DNA methylation changes have been observed in PSEN1 and APOE, both genes previously being involved in the pathophysiology of AD. In other degenerative dementias, methylation variants have also been described in key genes, such as hypomethylation of the SNCA gene in Parkinson's disease and dementia with Lewy bodies or hypermethylation of the GRN gene promoter in frontotemporal dementia. The finding of aberrant DNA methylation patterns shared by brain tissue and peripheral blood opens the door to use those variants as epigenetic biomarkers in the diagnosis of neurodegenerative diseases. PMID:24907105

  3. Chemically modified fatty acid methyl esters: their potential for use as lubrication fluids and surfactants

    Technology Transfer Automated Retrieval System (TEKTRAN)

    A review of recent developments in the synthesis and characterization of lubrication fluids and surfactants from methyl oleate. The synthesis of materials made using an epoxidation route is the focus. This versatile method of chemical modification of fatty acid methyl esters improves their oxidati...

  4. Comparison crystal structure conformations of two structurally related biphenyl analogues: 4,4′-bis­[3-(pyrrolidin-1-yl)prop-1-yn-1-yl]-1,1′-biphenyl and 4,4′-bis­{3-[(S)-2-methyl­pyrrolidin-1-yl]prop-1-yn-1-yl}-1,1′-biphen­yl

    PubMed Central

    Wan, Anqi; Penthala, Narsimha Reddy; Fifer, E. Kim; Parkin, Sean; Crooks, Peter A.

    2015-01-01

    The title compounds, C26H28N2, (I), and C28H32N2, (II), were designed based on the structure of the potent α9α10 nicotinic acetyl­choline receptor antagonist ZZ161C {1,1′-[[1,1′-biphen­yl]-4,4′-diylbis(prop-2-yne-3,1-di­yl)]bis­(3,4-di­methyl­pyridin-1-ium) bromide}. In order to improve the druglikeness properties of ZZ161C for potential oral administration, the title compounds (I) and (II) were prepared by coupling 4,4′-bis­(3-bromo­prop-1-yn-1-yl)-1,1′-biphenyl with pyrrol­idine, (I), and (S)-2-methyl­pyrrolidine, (II), respectively, in aceto­nitrile at room temperature. The asymmetric unit of (I) contains two half mol­ecules that each sit on sites of crystallographic inversion. As a result, the biphenyl ring systems in compound (I) are coplanar. The biphenyl ring system in compound (II), however, has a dihedral angle of 28.76 (11)°. In (I), the two independent mol­ecules differ in the orientation of the pyrrolidine ring (the nitro­gen lone pair points towards the biphenyl rings in one mol­ecule, but away from the rings in the other). The torsion angles about the ethynyl groups between the planes of the phenyl rings and the pyrrolidine ring N atoms are 84.15 (10) and −152.89 (10)°. In compound (II), the corresponding torsion angles are 122.0 (3) and 167.0 (3)°, with the nitro­gen lone pairs at both ends of the mol­ecule directed away from the central biphenyl rings. PMID:26594393

  5. Design and biological properties of iodine-123 labeled. beta. -methyl-branched fatty acids

    SciTech Connect

    Knapp, F.F. Jr.; Goodman, M.M.

    1984-01-01

    The synthetic strategy, synthesis, preclinical evaluation and potential clinical applications of 3-methyl-branched radioiodinated iodophenyl- and iodovinyl-substituted fatty acids are reviewed for use as myocardial imaging agents. 50 references, 6 figures. (ACR)

  6. AVOIDING PITFALLS IN THE DETERMINATION OF HALOCARBOXYLIC ACIDS: THE PHOTOCHEMISTRY OF METHYLATION

    EPA Science Inventory

    Haloethanoic (haloacetic) acids are formed during chlorination of drinking water and are regulated by the Environmental Protection Agency (EPA). These compounds are normally quantified by gas chromatography with electron capture detection (GC-ECD) ad the methyl esters. EPA Meth...

  7. Spectroscopic and quantum chemical analysis of Isonicotinic acid methyl ester

    NASA Astrophysics Data System (ADS)

    Shoba, D.; Periandy, S.; Govindarajan, M.; Gayathri, P.

    2015-02-01

    In this present study, an organic compound Isonicotinic acid methyl ester (INAME) was structurally characterized by FTIR, FT-Raman, and NMR and UV spectroscopy. The optimized geometrical parameters and energies of all different and possible conformers of INAME are obtained from Density Functional Theory (DFT) by B3LYP/6-311++G(d,p) method. There are three conformers (SI, SII-1, and SII-2) for this molecule (ground state). The most stable conformer of INAME is SI conformer. The molecular geometry and vibrational frequencies of INAME in the ground state have been calculated by using HF and density functional method (B3LYP) 6-311++G (d,p) basis set. Detailed vibrational spectral analysis has been carried out and assignments of the observed fundamental bands have been proposed on the basis of peak positions and relative intensities. The computed vibrational frequencies were compared with the experimental frequencies, which yield good agreement between observed and calculated frequencies. A study on the electronic properties, such as HOMO and LUMO energies were performed by time independent DFT approach. Besides, molecular electrostatic potential (MEP) and thermodynamic properties were performed. The electric dipole moment (μ) and first hyper polarizability (β) values of the investigated molecule were computed using ab initio quantum mechanical calculations. The calculated results show that the INAME molecule may have microscopic nonlinear optical (NLO) behavior with non zero values. The 1H and 13C nuclear magnetic resonance (NMR) chemical shifts of the molecule were calculated by gauge independent atomic orbital (GIAO) method.

  8. Preparation of fatty acid methyl esters from Osage orange (Maclura pomifera) oil and evaluation as biodiesel

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Fatty acid methyl esters were prepared in high yield by transesterification of Osage orange (Maclura pomifera) oil. Extracted using supercritical CO2, the crude oil was initially treated with mineral acid and methanol to lower its content of free fatty acids, thus rendering it amenable to homogeneou...

  9. 40 CFR 721.1728 - Benzoic acid, 2-(3-phenylbutylidene)amino-, methyl ester.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... New Uses for Specific Chemical Substances § 721.1728 Benzoic acid, 2-(3-phenylbutylidene)amino... substance identified as benzoic acid, 2-(3-phenylbutylidene)amino-, methyl ester (PMN P-85-1211) is subject... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Benzoic acid,...

  10. 40 CFR 721.1728 - Benzoic acid, 2-(3-phenylbutylidene)amino-, methyl ester.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... New Uses for Specific Chemical Substances § 721.1728 Benzoic acid, 2-(3-phenylbutylidene)amino... substance identified as benzoic acid, 2-(3-phenylbutylidene)amino-, methyl ester (PMN P-85-1211) is subject... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Benzoic acid,...

  11. 40 CFR 721.1728 - Benzoic acid, 2-(3-phenylbutylidene)amino-, methyl ester.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... New Uses for Specific Chemical Substances § 721.1728 Benzoic acid, 2-(3-phenylbutylidene)amino... substance identified as benzoic acid, 2-(3-phenylbutylidene)amino-, methyl ester (PMN P-85-1211) is subject... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Benzoic acid,...

  12. 40 CFR 721.1728 - Benzoic acid, 2-(3-phenylbutylidene)amino-, methyl ester.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... New Uses for Specific Chemical Substances § 721.1728 Benzoic acid, 2-(3-phenylbutylidene)amino... substance identified as benzoic acid, 2-(3-phenylbutylidene)amino-, methyl ester (PMN P-85-1211) is subject... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Benzoic acid,...

  13. 40 CFR 721.1728 - Benzoic acid, 2-(3-phenylbutylidene)amino-, methyl ester.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... New Uses for Specific Chemical Substances § 721.1728 Benzoic acid, 2-(3-phenylbutylidene)amino... substance identified as benzoic acid, 2-(3-phenylbutylidene)amino-, methyl ester (PMN P-85-1211) is subject... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Benzoic acid,...

  14. Functional analysis of a tomato salicylic acid methyl transferase and its role in synthesis of the flavor volatile methyl salicylate.

    PubMed

    Tieman, Denise; Zeigler, Michelle; Schmelz, Eric; Taylor, Mark G; Rushing, Sarah; Jones, Jeffrey B; Klee, Harry J

    2010-04-01

    Methyl salicylate (MeSA) is a volatile plant secondary metabolite that is an important contributor to taste and scent of many fruits and flowers. It is synthesized from salicylic acid (SA), a phytohormone that contributes to plant pathogen defense. MeSA is synthesized by members of a family of O-methyltransferases. In order to elaborate the mechanism of MeSA synthesis in tomato, we screened a set of O-methyltransferases for activity against multiple substrates. An enzyme that specifically catalyzes methylation of SA, SlSAMT, as well as enzymes that act upon jasmonic acid and indole-3-acetic acid were identified. Analyses of transgenic over- and under-producing lines validated the function of SlSAMT in vivo. The SlSAMT gene was mapped to a position near the bottom of chromosome 9. Analysis of MeSA emissions from an introgression population derived from a cross with Solanum pennellii revealed a quantitative trait locus (QTL) linked to higher fruit methyl salicylate emissions. The higher MeSA emissions associate with significantly higher SpSAMT expression, consistent with SAMT gene expression being rate limiting for ripening-associated MeSA emissions. Transgenic plants that constitutively over-produce MeSA exhibited only slightly delayed symptom development following infection with the disease-causing bacterial pathogen, Xanthomonas campestris pv. vesicatoria (Xcv). Unexpectedly, pathogen-challenged leaves accumulated significantly higher levels of SA as well as glycosylated forms of SA and MeSA, indicating a disruption in control of the SA-related metabolite pool. Taken together, the results indicate that SlSAMT is critical for methyl salicylate synthesis and methyl salicylate, in turn, likely has an important role in controlling SA synthesis. PMID:20070566

  15. 40 CFR 721.1645 - Benzenesulfonic acid, 4-methyl-, reaction products with oxirane mono[(C10-16-alkyloxy)methyl...

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ...-, reaction products with oxirane mono derivatives and 2,2,4(or 2,4,4)-trimethyl-1,6-hexanediamine. 721.1645... Substances § 721.1645 Benzenesulfonic acid, 4-methyl-, reaction products with oxirane mono derivatives and 2... to reporting. (1) The chemical substance benzenesulfonic acid, 4-methyl-, reaction products...

  16. 40 CFR 721.1645 - Benzenesulfonic acid, 4-methyl-, reaction products with oxirane mono[(C10-16-alkyloxy)methyl...

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ...-, reaction products with oxirane mono derivatives and 2,2,4(or 2,4,4)-trimethyl-1,6-hexanediamine. 721.1645... Substances § 721.1645 Benzenesulfonic acid, 4-methyl-, reaction products with oxirane mono derivatives and 2... to reporting. (1) The chemical substance benzenesulfonic acid, 4-methyl-, reaction products...

  17. 40 CFR 721.1645 - Benzenesulfonic acid, 4-methyl-, reaction products with oxirane mono[(C10-16-alkyloxy)methyl...

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ...-, reaction products with oxirane mono derivatives and 2,2,4(or 2,4,4)-trimethyl-1,6-hexanediamine. 721.1645... Substances § 721.1645 Benzenesulfonic acid, 4-methyl-, reaction products with oxirane mono derivatives and 2... to reporting. (1) The chemical substance benzenesulfonic acid, 4-methyl-, reaction products...

  18. Associations between whole peripheral blood fatty acids and DNA methylation in humans

    PubMed Central

    de la Rocha, Carmen; Pérez-Mojica, J. Eduardo; León, Silvia Zenteno-De; Cervantes-Paz, Braulio; Tristán-Flores, Fabiola E.; Rodríguez-Ríos, Dalia; Molina-Torres, Jorge; Ramírez-Chávez, Enrique; Alvarado-Caudillo, Yolanda; Carmona, F. Javier; Esteller, Manel; Hernández-Rivas, Rosaura; Wrobel, Katarzyna; Wrobel, Kazimierz; Zaina, Silvio; Lund, Gertrud

    2016-01-01

    Fatty acids (FA) modify DNA methylation in vitro, but limited information is available on whether corresponding associations exist in vivo and reflect any short-term effect of the diet. Associations between global DNA methylation and FAs were sought in blood from lactating infants (LI; n = 49) and adult males (AMM; n = 12) equally distributed across the three conventional BMI classes. AMM provided multiple samples at 2-hour intervals during 8 hours after either a single Western diet-representative meal (post-prandial samples) or no meal (fasting samples). Lipid/glucose profile, HDAC4 promoter and PDK4 5’UTR methylation were determined in AMM. Multiple regression analysis revealed that global (in LI) and both global and PDK4-specific DNA methylation (in AMM) were positively associated with eicosapentaenoic and arachidonic acid. HDAC4 methylation was inversely associated with arachidonic acid post-prandially in AMM. Global DNA methylation did not show any defined within-day pattern that would suggest a short-term response to the diet. Nonetheless, global DNA methylation was higher in normal weight subjects both post-prandially and in fasting and coincided with higher polyunsaturated relative to monounsaturated and saturated FAs. We show for the first time strong associations of DNA methylation with specific FAs in two human cohorts of distinct age, diet and postnatal development stage. PMID:27181711

  19. Associations between whole peripheral blood fatty acids and DNA methylation in humans.

    PubMed

    de la Rocha, Carmen; Pérez-Mojica, J Eduardo; León, Silvia Zenteno-De; Cervantes-Paz, Braulio; Tristán-Flores, Fabiola E; Rodríguez-Ríos, Dalia; Molina-Torres, Jorge; Ramírez-Chávez, Enrique; Alvarado-Caudillo, Yolanda; Carmona, F Javier; Esteller, Manel; Hernández-Rivas, Rosaura; Wrobel, Katarzyna; Wrobel, Kazimierz; Zaina, Silvio; Lund, Gertrud

    2016-01-01

    Fatty acids (FA) modify DNA methylation in vitro, but limited information is available on whether corresponding associations exist in vivo and reflect any short-term effect of the diet. Associations between global DNA methylation and FAs were sought in blood from lactating infants (LI; n = 49) and adult males (AMM; n = 12) equally distributed across the three conventional BMI classes. AMM provided multiple samples at 2-hour intervals during 8 hours after either a single Western diet-representative meal (post-prandial samples) or no meal (fasting samples). Lipid/glucose profile, HDAC4 promoter and PDK4 5'UTR methylation were determined in AMM. Multiple regression analysis revealed that global (in LI) and both global and PDK4-specific DNA methylation (in AMM) were positively associated with eicosapentaenoic and arachidonic acid. HDAC4 methylation was inversely associated with arachidonic acid post-prandially in AMM. Global DNA methylation did not show any defined within-day pattern that would suggest a short-term response to the diet. Nonetheless, global DNA methylation was higher in normal weight subjects both post-prandially and in fasting and coincided with higher polyunsaturated relative to monounsaturated and saturated FAs. We show for the first time strong associations of DNA methylation with specific FAs in two human cohorts of distinct age, diet and postnatal development stage. PMID:27181711

  20. 40 CFR 721.4097 - 7-Oxabicyclo[4.1.0]heptane-3-carboxylic acid, methyl ester.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ..., methyl ester. 721.4097 Section 721.4097 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.4097 7-Oxabicyclo heptane-3-carboxylic acid, methyl ester. (a) Chemical...-oxabicyclo heptane-3-carboxylic acid, methyl ester (PMN P-98-101) is subject to reporting under this...

  1. 40 CFR 721.4097 - 7-Oxabicyclo[4.1.0]heptane-3-carboxylic acid, methyl ester.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ..., methyl ester. 721.4097 Section 721.4097 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.4097 7-Oxabicyclo heptane-3-carboxylic acid, methyl ester. (a) Chemical...-oxabicyclo heptane-3-carboxylic acid, methyl ester (PMN P-98-101) is subject to reporting under this...

  2. Proton affinity of methyl nitrate - Less than proton affinity of nitric acid

    NASA Technical Reports Server (NTRS)

    Lee, Timothy J.; Rice, Julia E.

    1992-01-01

    Several state-of-the-art ab initio quantum mechanical methods were used to investigate the equilibrium structure, dipole moments, harmonic vibrational frequencies, and IR intensities of methyl nitrate, methanol, and several structures of protonated methyl nitrate, using the same theoretical methods as in an earlier study (Lee and Rice, 1992) of nitric acid. The ab initio results for methyl nitrate and methanol were found to be in good agreement with available experimental data. The proton affinity (PA) of methyl nitrate was calculated to be 176.9 +/-5 kcal/mol, in excellent agreement with the experimental value 176 kcal/mol obtained by Attina et al. (1987) and less than the PA value of nitric acid. An explanation of the discrepancy of the present results with those of an earlier study on protonated nitric acid is proposed.

  3. N-tert-Butyl-2-methyl­propanamide

    PubMed Central

    Kluge, Kelly A.; Fridyland, Diana; MacBeth, Cora E.; Hardcastle, Kenneth I.

    2011-01-01

    The title compound, C8H17NO, crystallizes with two independent mol­ecules in the asymmetric unit. In the crystal, inter­molecular N—H⋯O hydrogen bonding is observed between neighboring mol­ecules, forming continuous mol­ecular chains along the c-axis direction. PMID:22091159

  4. N-tert-Butyl-2-methyl-propanamide.

    PubMed

    Kluge, Kelly A; Fridyland, Diana; Macbeth, Cora E; Hardcastle, Kenneth I

    2011-08-01

    The title compound, C(8)H(17)NO, crystallizes with two independent mol-ecules in the asymmetric unit. In the crystal, inter-molecular N-H⋯O hydrogen bonding is observed between neighboring mol-ecules, forming continuous mol-ecular chains along the c-axis direction. PMID:22091159

  5. Phenolic analogues of diastereoisomeric 2-methyl reversed esters of pethidine.

    PubMed

    Casy, A F; Dewar, G H; Pascoe, R A

    1989-03-01

    The preparation and stereochemical characterization of alpha- and beta-isomers of 1,2-dimethyl-4-m-hydroxyphenyl-4-propionyloxypiperidine are described. Both the alpha (axial 4-aryl/chair) and beta (equatorial 4-aryl/chair) isomers were of low potency or inactive in mice antinociceptive tests. Shortcomings of the alpha-isomer as a model for the 4-arylpiperidine moiety of morphine are discussed. PMID:2568454

  6. Turnover of the methyl moiety of 5-methyltetrahydropteroylglutamic acid in the cobalamin-inactivated rat.

    PubMed

    Lumb, M; Chanarin, I; Perry, J; Deacon, R

    1985-11-01

    The metabolism of the methyl group of 5-methyltetrahydrofolate was studied in rats in which cobalamin had been inactivated by exposure to nitrous oxide and in air-breathing control animals. Methylfolate labeled with [14C] in the methyl group and with [3H] in the pteridine-PABA portion was injected and the disappearance of [14C]H3- relative to [3H]folate was measured in liver. The half-time of the methyl group in the livers of control rats was two hours. There was no turnover of the methyl group for the first 72 hours after cobalamin inactivation. After 72 hours, there was a slow turnover of the methyl group, with a half-time of 43 hours. In control rats, it is assumed that the methyl group was metabolized by transfer to homocysteine to form methionine. In cobalamin-inactivated rats, it was shown that methylfolate was used as the substrate for forming folate polyglutamate, and analogues with 3, 4, and 5 glutamic acid residues were present. It is likely that oxidation of the methyl group by methylene tetrahydrofolate reductase occurs from folate polyglutamate containing six and seven glutamic acid residues, (Brody et al, Biochemistry 21: 276, 1982), since we were unable to demonstrate labeled methyl in longer chain analogues. PMID:4052631

  7. Biosorption of methyl blue onto tartaric acid modified wheat bran from aqueous solution

    PubMed Central

    2012-01-01

    Tartaric acid modified wheat bran was utilized as adsorbent to remove methyl blue, a basic dye from aqueous solution. Batch experiments were carried out to study the effect of various experimental parameters such as initial solution pH, contact time, initial dye concentration and adsorbent dosage, on dye adsorption. The results showed that the modification of wheat bran by tartaric acid significantly improved its adsorption capacity, and made this material a suitable adsorbent to remove methyl blue. The adsorption capacity of modified wheat bran was about 1.6 times higher than that of unmodified one. The amount of methyl blue adsorbed was found to vary with initial solution pH, adsorbent dosage, contact time and initial methyl blue concentration. Kinetics study showed that the overall adsorption rate of methyl blue was illustrated by pseudo-second-order kinetic model. The applicability of the Langmuir and Freundlich models for the data was tested. Both models adequately described the experimental data of the biosorption of methyl blue. The maximum adsorption capacity for methyl blue calculated from Langmuir model was 25.18 mg/g. The study has shown the effectiveness of modified wheat bran in the removal of methyl blue, and that it can be considered as an attractive alternative to the more expensive technologies used in wastewater treatment. PMID:23369295

  8. Biosorption of methyl blue onto tartaric acid modified wheat bran from aqueous solution.

    PubMed

    Yao, Shuhua; Lai, Hong; Shi, Zhongliang

    2012-01-01

    Tartaric acid modified wheat bran was utilized as adsorbent to remove methyl blue, a basic dye from aqueous solution. Batch experiments were carried out to study the effect of various experimental parameters such as initial solution pH, contact time, initial dye concentration and adsorbent dosage, on dye adsorption. The results showed that the modification of wheat bran by tartaric acid significantly improved its adsorption capacity, and made this material a suitable adsorbent to remove methyl blue. The adsorption capacity of modified wheat bran was about 1.6 times higher than that of unmodified one. The amount of methyl blue adsorbed was found to vary with initial solution pH, adsorbent dosage, contact time and initial methyl blue concentration. Kinetics study showed that the overall adsorption rate of methyl blue was illustrated by pseudo-second-order kinetic model. The applicability of the Langmuir and Freundlich models for the data was tested. Both models adequately described the experimental data of the biosorption of methyl blue. The maximum adsorption capacity for methyl blue calculated from Langmuir model was 25.18 mg/g. The study has shown the effectiveness of modified wheat bran in the removal of methyl blue, and that it can be considered as an attractive alternative to the more expensive technologies used in wastewater treatment. PMID:23369295

  9. Methyl-branched poly(hydroxyalkanoate) biosynthesis from 13- methyltetradecanoic acid and mixed isostearic acid isomer substrates

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Pseudomonas resinovorans, a known medium-chain-length (mcl-) poly(hydroxyalkanoate) (PHA) producer, was grown on 13-methyltetradecanoic acid (13-MTDA) and a mixture of isostearic acid (IA) isomers to produce methyl-branched mcl-PHA polymers. Shake flask experiments revealed polymer productivities (...

  10. Pharmacokinetics and pharmacodynamics of DPC 333 ((2R)-2-((3R)-3-amino-3{4-[2-methyl-4-quinolinyl) methoxy] phenyl}-2-oxopyrrolidinyl)-N-hydroxy-4-methylpentanamide)), a potent and selective inhibitor of tumor necrosis factor alpha-converting enzyme in rodents, dogs, chimpanzees, and humans.

    PubMed

    Qian, Mingxin; Bai, Stephen A; Brogdon, Bernice; Wu, Jing-Tao; Liu, Rui-Qin; Covington, Maryanne B; Vaddi, Kris; Newton, Robert C; Fossler, Michael J; Garner, C Edwin; Deng, Yuzhong; Maduskuie, Thomas; Trzaskos, James; Duan, James J-W; Decicco, Carl P; Christ, David D

    2007-10-01

    DPC 333 ((2R)-2-((3R)-3-amino-3{4-[2-methyl-4-quinolinyl) methoxy] phenyl}-2-oxopyrrolidinyl)-N-hydroxy-4-methylpentanamide)) is a potent and selective inhibitor of tumor necrosis factor (TNF)-alpha-converting enzyme (TACE). It significantly inhibits lipopolysaccharide-induced soluble TNF-alpha production in blood from rodents, chimpanzee, and human, with IC(50) values ranging from 17 to 100 nM. In rodent models of endotoxemia, DPC 333 inhibited the production of TNF-alpha in a dose-dependent manner, with an oral ED(50) ranging from 1.1 to 6.1 mg/kg. Oral dosing of DPC 333 at 5.5 mg/kg daily for 2 weeks in a rat collagen antibody-induced arthritis model suppressed the maximal response by approximately 50%. DPC 333 was distributed widely to tissues including the synovium, the site of action for antiarthritic drugs. Pharmacokinetic and pharmacodynamic studies in chimpanzee revealed a systemic clearance of 0.4 l/h/kg, a V(ss) of 0.6 l/kg, an oral bioavailability of 17%, and an ex vivo IC(50) for the suppression of TNF-alpha production of 55 nM (n = 1). In a phase I clinical trial with male volunteers after single escalating doses of oral DPC 333, the terminal half-life was between 3 and 6 h and the ex vivo IC(50) for suppressing TNF-alpha production was 113 nM. Measurement of the suppression of TNF-alpha production ex vivo may serve as a good biomarker in evaluating the therapeutic efficacy of TACE inhibitors. Overall, the pharmacological profiles of DPC 333 support the notion that suppression of TNF-alpha with TACE inhibitors like DPC 333 may provide a novel approach in the treatment of various inflammatory diseases including rheumatoid arthritis, via control of excessive TNF-alpha production. PMID:17656469

  11. Conversion of methyl oleate to branched-chain hydroxy fatty acid derivatives

    Technology Transfer Automated Retrieval System (TEKTRAN)

    As part of a project to develop new and expanded uses of oilseed products and by-products (such as biodiesel, fuel additives, and lubricants), studies were conducted on the synthetic conversion of oleic acid (in ester form) to branched-chain fatty acid ester derivatives. In these studies, methyl ol...

  12. Selective microbial degradation of saturated methyl branched chain fatty acid isomers

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Three strains of Pseudomonas bacteria were screened for their capabilities of degrading chemically synthesized saturated branched-chain fatty acids (sbc-FAs). Mixtures of sbc-FAs with the methyl-branch located at various locales along the fatty acid were used as a carbon feedstock in shake-flask cu...

  13. Coriander Seed Oil Methyl Esters as Biodiesel Fuel: Unique Fatty Acid Composition and Excellent Oxidative Stability

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Coriander (Coriandrum sativum L.) seed oil methyl esters were prepared and evaluated as an alternative biodiesel fuel and contained an unusual fatty acid (FA) hitherto unreported as the principle component in biodiesel fuels: petroselinic (6Z-octadecenoic; 68.5 wt %) acid. Most of the remaining FA...

  14. Low-temperature phase behavior of fatty acid methyl esters by differential scanning calorimetry (DSC)

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Fatty acid methyl ester (FAME) mixtures have many uses including biodiesel, lubricants, metal-working fluids, surfactants, polymers, coatings, green solvents and phase-change materials. The physical properties of a FAME mixture depends on the fatty acid concentration (FAC) profile. Some products hav...

  15. The vibrational spectra and structure of 4-methyl oxaloacetate (carbomethoxypyruvic acid)

    NASA Astrophysics Data System (ADS)

    Schiering, David W.; Katon, J. E.

    1986-04-01

    The vibrational spectra of solid 4-methyl oxalocetate have been recorded. Infrared spectra were collected at ambient and liquid nitrogen temperatures; Raman spectra were collected at ambient temperature only. A tentative vibrational assignment of the solid is proposed based on a dimer structure composed of two enolic monomer units hydrogen bonded through the carboxylic acid group. 4-Methyl oxaloacetate was found to undergo keto—enol tautomerization in solution, and the solvent dependency of this equilibrium was demonstrated.

  16. The Acid Catalyzed Nitration of Methanol: Formation of Methyl Nitrate via Aerosol Chemistry

    NASA Technical Reports Server (NTRS)

    Riffel, Brent G.; Michelsen, Rebecca R.; Iraci, Laura T.

    2004-01-01

    The liquid phase acid catalyzed reaction of methanol with nitric acid to yield methyl nitrate under atmospheric conditions has been investigated using gas phase infrared spectroscopy. This nitration reaction is expected to occur in acidic aerosol particles found in the upper troposphere/lower stratosphere as highly soluble methanol and nitric acid diffuse into these aerosols. Gaseous methyl nitrate is released upon formation, suggesting that some fraction of NO(x) may he liberated from nitric acid (methyl nitrate is later photolyzed to NO(x)) before it is removed from the atmosphere by wet deposition. Thus, this reaction may have important implications for the NO(x) budget. Reactions have been initiated in 45-62 wt% H2SO4 solutions at 10.0 C. Methyl nitrate production rates increased exponentially with acidity within the acidity regime studied. Preliminary calculations suggest that the nitronium ion (NO2(+) is the active nitrating agent under these conditions. The reaction order in methanol appears to depend on the water/methanol ratio and varies from first to zeroth order under conditions investigated. The nitration is first order in nitronium at all acidities investigated. A second order rate constant, kappa(sub 2), has been calculated to be 1 x 10(exp 8)/ M s when the reaction is first order in methanol. Calculations suggest the nitration is first order in methanol under tropospheric conditions. The infinitesimal percentage of nitric acid in the nitronium ion form in this acidity regime probably makes this reaction insignificant for the upper troposphere; however, this nitration may become significant in the mid stratosphere where colder temperatures increase nitric acid solubility and higher sulfuric acid content shifts nitric acid speciation toward the nitronium ion.

  17. Effect of methyl-branched fatty acids on the structure of lipid bilayers.

    PubMed

    Poger, David; Caron, Bertrand; Mark, Alan E

    2014-12-01

    Methyl-branched fatty acids are widespread in prokaryotic membranes. Although anteiso and iso branching (that is on the antepenultimate and penultimate carbons) and the presence of multiple methyl branches in the phytanoyl chain are known to modify the thermotropic behavior and enhance the fluidity of lipid bilayers, little is known about the effect of methyl branching on the structure of lipid bilayers. In this study, molecular dynamics simulations are used to examine systematically the impact of one or more methyl branches at different positions along the sn-1 palmitoyl chain on the structural properties of a 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC) lipid bilayer. It is found that methyl branching reduces lipid condensation, decreases the bilayer thickness, and lowers chain ordering. Branching also results in the formation of kinks at the branching point, thereby enhancing the fluidity of lipid bilayers. Furthermore, this effect varies in a methyl-position-dependent fashion. In the case of polymethylated chains, the simulations suggest that if the gap between the methyl groups is sufficient (two or three carbons), the effects of the methyl branches are additive and equivalent to the combined effect of the corresponding monomethyl-branched lipids. PMID:25380125

  18. GENOTOXICITY OF ACRYLIC ACID, METHYL ACRYLATE, ETHYL ACRYLATE, METHYL METHACRYLATE, AND ETHYL METHACRYLATE IN L5178Y MOUSE LYMPHOMA CELLS (JOURNAL VERSION)

    EPA Science Inventory

    A series of monomeric acrylate/methacrylate esters (methyl acrylate, ethyl acrylate, methyl methacrylate, and ethyl methacrylate) as well as acrylic acid were examined for genotoxic activity in L5178Y mouse lymphoma cells without exogenous activation. All five compounds induced c...

  19. Hippuric acid and methyl hippuric acid in rat hair: possible monitoring of xylene and toluene exposure.

    PubMed

    Saito, Takeshi; Kusakabe, Takahiko; Takeichi, Sanae

    2003-04-23

    Thinner is mainly composed of toluene and xylenes, and we studied the incorporation of the main metabolites of toluene and xylenes, hippuric acid (HA) and o-, m-, and p-methyl hippuric acids (o-, m-, p-MHA), in dark agouti rats' hair. Rat black hair was shaved before any exposure with an electric shaver designed for animals. Studies were performed in vivo with exposures of 30 min per day at three different concentrations (100, 300, and 1000 ppm) of toluene and o-, m-, and p-xylene for a total of 10 times over 2 weeks. Newly grown hair was tweezed out from the root with tweezers at seventh of the last exposure. Hair samples were then washed, extracted, derivatized, and analyzed by gas chromatography-mass spectrometry (GC-MS). HA and o-, m-, and p-MHA were not detected (ND) in the unexposed rat hair. After exposure, the metabolite concentration in the hair changed depending on the exposure concentration. Mean concentrations ranged from ND to 7.6 ng/mg, from ND to 13.8 ng/mg, from ND to 10.1 ng/mg, and from ND to 9.2 ng/ml hair for HA, o-, m-, and p-MHA, respectively. These results indicate that the metabolites concentrations in hair are effective indices of thinner exposure. PMID:12742703

  20. An enhanced procedure for measuring organic acids and methyl esters in PM2.5

    NASA Astrophysics Data System (ADS)

    Liu, F.; Duan, F.; He, K.; Ma, Y.; Rahn, K. A.; Zhang, Q.

    2015-03-01

    We have developed an enhanced analytical procedure to measure organic acids and methyl esters in fine aerosol with much greater specificity and sensitivity than previously available. This capability is important because of these species and their low concentrations, even in highly polluted atmospheres like Beijing, China. The procedure first separates the acids and esters from the other organic compounds with anion-exchange solid- phase extraction (SPE), then, quantifies them by gas chromatography coupled with mass spectrometry. This allows us to accurately quantify the C4-C11 dicarboxylic and the C8-C30 monocarboxylic acids. Then the acids are separated from the esters on an aminopropyl SPE cartridge, whose weak retention isolates and enriches the acids from esters prevents the fatty acids and dimethyl phthalate from being overestimated. The resulting correlations between the aliphatic acids and fatty acid methyl esters (FAMEs) suggest that FAMEs had sources similar to those of the carboxylic acids, or were formed by esterifying carboxylic acids, or that aliphatic acids were formed by hydrolyzing FAMEs. In all, 17 aromatic acids were identified and quantified using this procedure coupled with gas chromatography-tandem mass spectrometry, including the five polycyclic aromatic hydrocarbon (PAH) acids 2-naphthoic, biphenyl-4-carboxylic, 9-oxo-9H-fluorene-1-carboxylic, biphenyl-4,4´-dicarboxylic, and phenanthrene-1-carboxylic acid, plus 1,8-naphthalic anhydride. Correlations between the PAH-acids and the dicarboxylic and aromatic acids indicated that the first three acids and 1,8-naphthalic anhydride were mainly secondary, the last two mainly primary.

  1. 21 CFR 172.225 - Methyl and ethyl esters of fatty acids produced from edible fats and oils.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... from edible fats and oils. 172.225 Section 172.225 Food and Drugs FOOD AND DRUG ADMINISTRATION... Methyl and ethyl esters of fatty acids produced from edible fats and oils. Methyl esters and ethyl esters of fatty acids produced from edible fats and oils may be safely used in food, subject to...

  2. 21 CFR 172.225 - Methyl and ethyl esters of fatty acids produced from edible fats and oils.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... from edible fats and oils. 172.225 Section 172.225 Food and Drugs FOOD AND DRUG ADMINISTRATION... Methyl and ethyl esters of fatty acids produced from edible fats and oils. Methyl esters and ethyl esters of fatty acids produced from edible fats and oils may be safely used in food, subject to...

  3. 21 CFR 172.225 - Methyl and ethyl esters of fatty acids produced from edible fats and oils.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... from edible fats and oils. 172.225 Section 172.225 Food and Drugs FOOD AND DRUG ADMINISTRATION... Methyl and ethyl esters of fatty acids produced from edible fats and oils. Methyl esters and ethyl esters of fatty acids produced from edible fats and oils may be safely used in food, subject to...

  4. 21 CFR 172.225 - Methyl and ethyl esters of fatty acids produced from edible fats and oils.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... from edible fats and oils. 172.225 Section 172.225 Food and Drugs FOOD AND DRUG ADMINISTRATION... Methyl and ethyl esters of fatty acids produced from edible fats and oils. Methyl esters and ethyl esters of fatty acids produced from edible fats and oils may be safely used in food, subject to...

  5. Beyond fatty acid methyl esters: Expanding the renewable carbon profile with alkenones from Isochrysis sp.

    Technology Transfer Automated Retrieval System (TEKTRAN)

    In addition to characteristic fatty acid methyl esters (FAMEs), biodiesel produced from Isochrysis sp. contains a significant amount (14% dry weight) of predominantly C37 and C38 longchain alkenones. These compounds are members of a class of lipids known collectively as polyunsaturated long-chain al...

  6. Chemically Modified Fatty Acid Methyl Esters: Potential as Lubricant and Surfactant

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Renewable raw materials are going to play a noteworthy role in the development of sustainable green chemistry because of their eco-friendly and non-toxic nature. A novel process was developed for the production of biodegradable lubricant base stocks from epoxidized fatty acid methyl esters and comm...

  7. 21 CFR 573.640 - Methyl esters of higher fatty acids.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... 21 Food and Drugs 6 2014-04-01 2014-04-01 false Methyl esters of higher fatty acids. 573.640 Section 573.640 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) ANIMAL DRUGS, FEEDS, AND RELATED PRODUCTS FOOD ADDITIVES PERMITTED IN FEED AND DRINKING WATER OF ANIMALS Food Additive Listing §...

  8. 21 CFR 573.640 - Methyl esters of higher fatty acids.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... 21 Food and Drugs 6 2012-04-01 2012-04-01 false Methyl esters of higher fatty acids. 573.640 Section 573.640 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) ANIMAL DRUGS, FEEDS, AND RELATED PRODUCTS FOOD ADDITIVES PERMITTED IN FEED AND DRINKING WATER OF ANIMALS Food Additive Listing §...

  9. 21 CFR 573.640 - Methyl esters of higher fatty acids.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... 21 Food and Drugs 6 2011-04-01 2011-04-01 false Methyl esters of higher fatty acids. 573.640 Section 573.640 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) ANIMAL DRUGS, FEEDS, AND RELATED PRODUCTS FOOD ADDITIVES PERMITTED IN FEED AND DRINKING WATER OF ANIMALS Food Additive Listing §...

  10. 21 CFR 573.640 - Methyl esters of higher fatty acids.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... 21 Food and Drugs 6 2013-04-01 2013-04-01 false Methyl esters of higher fatty acids. 573.640 Section 573.640 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) ANIMAL DRUGS, FEEDS, AND RELATED PRODUCTS FOOD ADDITIVES PERMITTED IN FEED AND DRINKING WATER OF ANIMALS Food Additive Listing §...

  11. 21 CFR 573.640 - Methyl esters of higher fatty acids.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... 21 Food and Drugs 6 2010-04-01 2010-04-01 false Methyl esters of higher fatty acids. 573.640 Section 573.640 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) ANIMAL DRUGS, FEEDS, AND RELATED PRODUCTS FOOD ADDITIVES PERMITTED IN FEED AND DRINKING WATER OF ANIMALS Food Additive Listing §...

  12. Catalytic synthesis of fatty acid methyl esters from extremely low quality greases

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Biodiesel (BD) is a renewable fuel for compression ignition engines that is composed of the simple alkyl esters, usually methyl-, of fatty acids (FAME). It is typically produced via base-catalyzed transesterification between refined vegetable oil or animal fat (e.g., soybean oil, tallow) and an alc...

  13. PLASMID DNA DAMAGE CAUSED BY METHYLATED ARSENICALS, ASCORBIC ACID AND HUMAN LIVER FERRITIN

    EPA Science Inventory

    Plasmid DNA damage caused by methylated arsenicals, ascorbic acid and human liver ferritin.

    Arsenic causes cancer in human skin, urinary bladder, lung, liver and kidney and is a significant world-wide public health problem. Although the metabolism of inorganic arsenic is ...

  14. Prediction of preweaning ADG in beef calves from milk fatty acid methyl esters

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Research has shown milk yield (MWT) has an important influence on calf preweaning ADG (PRWADG), but MWT accounts for only a moderate amount of variation in PRWADG. The objective of this study was to determine if milk fatty acid methyl esters (FAME), alone and in combination with MWT, could improve a...

  15. Cold flow properties of fatty acid methyl esters: Additives versus diluents

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Biodiesel is typically composed of fatty acid methyl esters (FAME) converted from agricultural lipids. Common feedstocks include soybean oil, canola oil, rapeseed oil, sunflower oil, and palm oil. Recent debate on the conversion of edible oils into non-food products has created opportunities to deve...

  16. Esterification and transesterification of greases to fatty acid methyl esters with highly active diphanylammonium salts

    Technology Transfer Automated Retrieval System (TEKTRAN)

    We have conducted an investigation designed to identify alternate catalysts for the production of fatty acid methyl esters (FAME) to be used as biodiesel. Diphenylammonium sulfate (DPAS) and diphenylammonium chloride (DPA-HCl) salts were found to be highly active homogeneous catalysts for the simu...

  17. Esterification and Transesterification of greases to fatty acid methyl esters with highly active diphenylamine salts

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Diphenylamine sulfate (DPAS) and diphenylamine hydrochloride (DPACl) salts were found to be highly active catalysts for esterification and transesterification of inexpensive greases to fatty acid methyl esters (FAME). In the presence of catalytic amounts of DPAS or DPACl and excess methanol, the fr...

  18. 40 CFR 721.10448 - Acetic acid, hydroxy- methoxy-, methyl ester, reaction products with substituted alkylamine...

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... ester, reaction products with substituted alkylamine (generic). 721.10448 Section 721.10448 Protection... NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.10448 Acetic acid, hydroxy- methoxy-, methyl ester, reaction products with substituted alkylamine (generic)....

  19. 76 FR 69659 - Methacrylic Acid-Methyl Methacrylate-Polyethylene Glycol Monomethyl Ether Methacrylate Graft...

    Federal Register 2010, 2011, 2012, 2013, 2014

    2011-11-09

    ...This regulation establishes an exemption from the requirement of a tolerance for residues of methacrylic acid-methyl methacrylate- polyethylene glycol monomethyl ether methacrylate graft copolymer when used as an inert ingredient in a pesticide chemical formulation. Akzo Noel Surface Chemistry LLC submitted a petition to EPA under the Federal Food, Drug, and Cosmetic Act (FFDCA), requesting an......

  20. An enhanced procedure for measuring organic acids and methyl esters in PM2.5

    NASA Astrophysics Data System (ADS)

    Liu, F.; Duan, F. K.; He, K. B.; Ma, Y. L.; Rahn, K. A.; Zhang, Q.

    2015-11-01

    A solid-phase extraction (SPE) pretreatment procedure allowing organic acids to be separated from methyl esters in fine aerosol has been developed. The procedure first separates the organic acids from fatty acid methyl esters (FAMEs) and other nonacid organic compounds by aminopropyl-based SPE cartridge and then quantifies them by gas chromatography/mass spectrometry. The procedure prevents the fatty acids and dimethyl phthalate from being overestimated, and so allows us to accurately quantify the C4-C11 dicarboxylic acids (DCAs) and the C8-C30 monocarboxylic acids (MCAs). Results for the extraction of DCAs, MCAs, and AMAs in eluate and FAMEs in effluate by SAX and NH2 SPE cartridges exhibited that the NH2 SPE cartridge gave higher extraction efficiency than the SAX cartridge. The recoveries of analytes ranged from 67.5 to 111.3 %, and the RSD ranged from 0.7 to 10.9 %. The resulting correlations between the aliphatic acids and FAMEs suggest that the FAMEs had sources similar to those of the carboxylic acids, or were formed by esterifying carboxylic acids, or that aliphatic acids were formed by hydrolyzing FAMEs. Through extraction and cleanup using this procedure, 17 aromatic acids in eluate were identified and quantified by gas chromatography/tandem mass spectrometry, including five polycyclic aromatic hydrocarbon (PAH): acids 2-naphthoic, biphenyl-4-carboxylic, 9-oxo-9H-fluorene-1-carboxylic, biphenyl-4,4´-dicarboxylic, and phenanthrene-1-carboxylic acid, plus 1,8-naphthalic anhydride. Correlations between the PAH acids and the dicarboxylic and aromatic acids suggested that the first three acids and 1,8-naphthalic anhydride were secondary atmospheric photochemistry products and the last two mainly primary.

  1. Experimental and Computational Study on the Molecular Energetics of 2-Pyrrolecarboxylic Acid and 1-Methyl-2-pyrrolecarboxylic Acid

    NASA Astrophysics Data System (ADS)

    Santos, Ana Filipa L. O. M.; Silva, Manuel A. V. Ribeiro Da

    2009-08-01

    This paper reports a combined thermochemical experimental and computational study of 2-pyrrolecarboxylic acid and 1-methyl-2-pyrrolecarboxylic acid. Static bomb combustion calorimetry and Knudsen mass-loss effusion technique were used to determine the standard (p° = 0.1 MPa) molar enthalpies of combustion, ΔcHm°, and sublimation, ΔcrgHm°, respectively, from which the standard (p° = 0.1 MPa) molar enthalpies of formation, in the gaseous phase, at T = 298.15 K, were derived. The values obtained were -(286.3 ± 1.7) and -(291.6 ± 1.7) kJ·mol for 2-pyrrolecarboxylic acid and 1-methyl-2-pyrrolecarboxylic acid, respectively. For comparison purposes, the gas-phase enthalpies of formation of these two compounds were estimated by G3(MP2)//B3LYP and MP2 approaches, using a set of gas-phase working reactions; the results are in excellent agreement with experimental data. G3(MP2)//B3LYP computations were also extended to the calculation of N-H bond dissociation enthalpies, gas-phase acidities and basicities, proton and electron affinities and adiabatic ionization enthalpies. Moreover, the results are also discussed in terms of the energetic effects of the addition of a carboxylic and of a methyl groups to the pyrrole ring and compared with structurally similar compounds.

  2. A novel methyltransferase from the intracellular pathogen Plasmodiophora brassicae methylates salicylic acid.

    PubMed

    Ludwig-Müller, Jutta; Jülke, Sabine; Geiß, Kathleen; Richter, Franziska; Mithöfer, Axel; Šola, Ivana; Rusak, Gordana; Keenan, Sandi; Bulman, Simon

    2015-05-01

    The obligate biotrophic pathogen Plasmodiophora brassicae causes clubroot disease in Arabidopsis thaliana, which is characterized by large root galls. Salicylic acid (SA) production is a defence response in plants, and its methyl ester is involved in systemic signalling. Plasmodiophora brassicae seems to suppress plant defence reactions, but information on how this is achieved is scarce. Here, we profile the changes in SA metabolism during Arabidopsis clubroot disease. The accumulation of SA and the emission of methylated SA (methyl salicylate, MeSA) were observed in P. brassicae-infected Arabidopsis 28 days after inoculation. There is evidence that MeSA is transported from infected roots to the upper plant. Analysis of the mutant Atbsmt1, deficient in the methylation of SA, indicated that the Arabidopsis SA methyltransferase was not responsible for alterations in clubroot symptoms. We found that P. brassicae possesses a methyltransferase (PbBSMT) with homology to plant methyltransferases. The PbBSMT gene is maximally transcribed when SA production is highest. By heterologous expression and enzymatic analyses, we showed that PbBSMT can methylate SA, benzoic and anthranilic acids. PMID:25135243

  3. Nitrogen Derivatives of Soybean Oil and Fatty Acid Methyl Esters

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Vegetable oil based products are eco-friendly and non-toxic in nature, which is increasing their utilization in lot of applications. The presence of double bonds in some of the fatty acids, are attractive sites for functionalization. In this study we have used these sites for functionalization usi...

  4. Tailoring acidity of HZSM-5 nanoparticles for methyl bromide dehydrobromination by Al and Mg incorporation.

    PubMed

    Liu, Zhen; Zhang, Zhongdong; Xing, Wei; Komarneni, Sridhar; Yan, Zifeng; Gao, Xionghou; Zhou, Xiaoping

    2014-01-01

    Three kinds of HZSM-5 nanoparticles with different acidity were tailored by impregnating MgO or varying Si/Al ratios. Both the textural and acidic properties of the as-prepared nanoparticles were characterized by nitrogen adsorption-desorption measurements, X-ray diffraction (XRD), scanning electron microscopy (SEM), ammonia temperature-programmed desorption (NH3-TPD) and Fourier transform infrared spectroscopy (FTIR or Py-FTIR). It was found that the intensity of Lewis acid sites with weak strength was enhanced by impregnating MgO or reducing Al concentration, and such an enhancement could be explained by the formation of Mg(OH)(+) or charge unbalance of the MgO framework on the surface of HZSM-5 support. The effect of HZSM-5 nanoparticles' acidity on methyl bromide dehydrobromination as catalyst was evaluated. As the results, MgHZ-360 catalyst with the highest concentration of Lewis acid sites showed excellent stability, which maintained methyl bromide conversion of up 97% in a period of 400 h on stream. Coke characterization by BET measurements and TGA/DTA and GC/MS analysis revealed that polymethylated naphthalenes species were formed outside the channels of the catalyst with higher acid intensity and higher Brønsted acid concentration during the initial period of reaction, while graphitic carbon formed in the channels of catalyst with lower acid intensity and higher Lewis acid concentration during the stable stage. PMID:25328502

  5. Tailoring acidity of HZSM-5 nanoparticles for methyl bromide dehydrobromination by Al and Mg incorporation

    PubMed Central

    2014-01-01

    Three kinds of HZSM-5 nanoparticles with different acidity were tailored by impregnating MgO or varying Si/Al ratios. Both the textural and acidic properties of the as-prepared nanoparticles were characterized by nitrogen adsorption-desorption measurements, X-ray diffraction (XRD), scanning electron microscopy (SEM), ammonia temperature-programmed desorption (NH3-TPD) and Fourier transform infrared spectroscopy (FTIR or Py-FTIR). It was found that the intensity of Lewis acid sites with weak strength was enhanced by impregnating MgO or reducing Al concentration, and such an enhancement could be explained by the formation of Mg(OH)+ or charge unbalance of the MgO framework on the surface of HZSM-5 support. The effect of HZSM-5 nanoparticles' acidity on methyl bromide dehydrobromination as catalyst was evaluated. As the results, MgHZ-360 catalyst with the highest concentration of Lewis acid sites showed excellent stability, which maintained methyl bromide conversion of up 97% in a period of 400 h on stream. Coke characterization by BET measurements and TGA/DTA and GC/MS analysis revealed that polymethylated naphthalenes species were formed outside the channels of the catalyst with higher acid intensity and higher Brønsted acid concentration during the initial period of reaction, while graphitic carbon formed in the channels of catalyst with lower acid intensity and higher Lewis acid concentration during the stable stage. PMID:25328502

  6. Thermochemistry of C-O, (CO)-O, and (CO)-C bond breaking in fatty acid methyl esters

    SciTech Connect

    Osmont, Antoine; Yahyaoui, Mohammed; Catoire, Laurent; Goekalp, Iskender; Swihart, Mark T.

    2008-10-15

    Density functional theory quantum chemical calculations corrected with empirical atomic increments have been used to examine C-O, (CO)-O, and (CO)-C bond scission enthalpies in gas-phase fatty acid methyl esters (FAMEs) present in biodiesel derived from rapeseed oil methyl ester and soybean oil methyl ester. Mechanistic information, currently not available elsewhere for these large species, is obtained based on thermochemical considerations and compared to thermochemical considerations reported for methyl butanoate, a small methyl ester sometimes used as a model for FAMEs. These results are compared to previously reported C-C and C-H bond scissions in these FAMEs, derived using this same protocol. (author)

  7. Efficient production of the Nylon 12 monomer ω-aminododecanoic acid methyl ester from renewable dodecanoic acid methyl ester with engineered Escherichia coli.

    PubMed

    Ladkau, Nadine; Assmann, Miriam; Schrewe, Manfred; Julsing, Mattijs K; Schmid, Andreas; Bühler, Bruno

    2016-07-01

    The expansion of microbial substrate and product scopes will be an important brick promoting future bioeconomy. In this study, an orthogonal pathway running in parallel to native metabolism and converting renewable dodecanoic acid methyl ester (DAME) via terminal alcohol and aldehyde to 12-aminododecanoic acid methyl ester (ADAME), a building block for the high-performance polymer Nylon 12, was engineered in Escherichia coli and optimized regarding substrate uptake, substrate requirements, host strain choice, flux, and product yield. Efficient DAME uptake was achieved by means of the hydrophobic outer membrane porin AlkL increasing maximum oxygenation and transamination activities 8.3 and 7.6-fold, respectively. An optimized coupling to the pyruvate node via a heterologous alanine dehydrogenase enabled efficient intracellular L-alanine supply, a prerequisite for self-sufficient whole-cell transaminase catalysis. Finally, the introduction of a respiratory chain-linked alcohol dehydrogenase enabled an increase in pathway flux, the minimization of undesired overoxidation to the respective carboxylic acid, and thus the efficient formation of ADAME as main product. The completely synthetic orthogonal pathway presented in this study sets the stage for Nylon 12 production from renewables. Its effective operation achieved via fine tuning the connectivity to native cell functionalities emphasizes the potential of this concept to expand microbial substrate and product scopes. PMID:26969251

  8. Pulsed field capillary electrophoresis of multikilobase length nucleic acids in dilute methyl cellulose solutions.

    PubMed

    Kim, Y; Morris, M D

    1994-10-01

    Pulsed field capillary gel electrophoresis in dilute methyl cellulose solutions is used to separate nucleic acid fragments in the size range 75-23,000 base pairs. Field inversion is shown to increase resolution for fragments longer than about 500 base pairs. Methyl cellulose solutions as dilute as 0.01% can be used. Intermolecular hydrogen bonding is suggested as the cause of apparent cellulose fiber entanglement at concentrations below the calculated entanglement limit. The 1-kb DNA ladder and the lambda DNA/HindIII restriction fragment mixtures are each baseline resolved in a 28-cm capillary in less than 9 min at 180 V/cm (dc component). PMID:7978303

  9. Gas chromatography-vacuum ultraviolet spectroscopy for analysis of fatty acid methyl esters.

    PubMed

    Fan, Hui; Smuts, Jonathan; Bai, Ling; Walsh, Phillip; Armstrong, Daniel W; Schug, Kevin A

    2016-03-01

    A new vacuum ultraviolet (VUV) detector for gas chromatography was recently developed and applied to fatty acid methyl ester (FAME) analysis. VUV detection features full spectral acquisition in a wavelength range of 115-240nm, where virtually all chemical species absorb. VUV absorption spectra of 37 FAMEs, including saturated, monounsaturated, and polyunsaturated types were recorded. Unsaturated FAMEs show significantly different gas phase absorption profiles than saturated ones, and these classes can be easily distinguished with the VUV detector. Another advantage includes differentiating cis/trans-isomeric FAMEs (e.g. oleic acid methyl ester and linoleic acid methyl ester isomers) and the ability to use VUV data analysis software for deconvolution of co-eluting signals. As a universal detector, VUV also provides high specificity, sensitivity, and a fast data acquisition rate, making it a powerful tool for fatty acid screening when combined with gas chromatography. The fatty acid profile of several food oil samples (olive, canola, vegetable, corn, sunflower and peanut oils) were analyzed in this study to demonstrate applicability to real world samples. PMID:26471553

  10. Determination of the specific radioactivity of fatty acids separated as their methyl esters by gas-liquid chromatography.

    PubMed

    Bishop, C; Glascock, R F; Newell, E M; Welch, V A

    1971-11-01

    Free or combined (3)H-labeled fatty acids are converted to their methyl-(14)C esters or, if labeled with (14)C, to their methyl-(3)H esters. For a given specific radioactivity of the methyl group, the nuclide ratio in the esters separated by GLC is a direct measure of the specific radioactivity of the fatty acids, and quantitative collection is unnecessary. Methods of methylation with minimum quantities of labeled methanol, and of deriving nuclide ratios from channel ratios in a scintillation spectrometer, are given. PMID:5124543

  11. Preparation of sphingolipid fatty acid methyl esters for determination by gas-liquid chromatography.

    PubMed

    MacGee, J; Williams, M G

    1981-01-30

    Sphingolipid fatty acids are first converted to a mixture of free acids and their n-butyl esters by heating the specimen at 85 degree C in aqueous butanolic hydrogen chloride; the butyl esters are then saponified with methanolic potassium hydroxide. After acidification and extraction into hexane, the fatty acids are extracted into a very small volume of aqueous trimethyl(m-trifluorotolyl)ammonium hydroxide (TMTFTH), injection of an aliquot of the TMTFTH extract into the gas chromatograph yields the fatty acid methyl esters by pyrolytic methylation of the quaternary ammonium salts of the fatty acids. The preparation of a specimen ready for the gas--liquid chromatographic (GLC) analysis with quantitative recovery of the sphingolipid fatty acids can be accomplished in less than 2 h. By comparison, none of a number of well-accepted techniques for the release of sphingomyelin fatty acids by hydrolysis or methanolysis released the fatty acids quantitatively in less than 3 h, and all required additional manipulations before GLC analysis. PMID:7217267

  12. Syntheses and antifolate activity of 5-methyl-5-deaza analogues of aminopterin, methotrexate, folic acid, and N10-methylfolic acid.

    PubMed

    Piper, J R; McCaleb, G S; Montgomery, J A; Kisliuk, R L; Gaumont, Y; Sirotnak, F M

    1986-06-01

    Evidence indicating that modifications at the 5- and 10-positions of classical folic acid antimetabolites lead to compounds with favorable differential membrane transport in tumor vs. normal proliferative tissue prompted an investigation of 5-alkyl-5-deaza analogues. 2-Amino-4-methyl-3,5-pyridinedicarbonitrile, prepared by hydrogenolysis of its known 6-chloro precursor, was treated with guanidine to give 2,4-diamino-5-methylpyrido[2,3-d]pyrimidine-6-carbonitrile which was converted via the corresponding aldehyde and hydroxymethyl compound to 6-(bromomethyl)-2,4-diamino-5-methylpyrido[2,3-d]pyrimidine. Reductive condensation of the nitrile 8 with diethyl N-(4-amino-benzoyl)-L-glutamate followed by ester hydrolysis gave 5-methyl-5-deazaaminopterin. Treatment of 12 with formaldehyde and Na(CN)BH3 afforded 5-methyl-5-deazamethotrexate, which was also prepared from 15 and dimethyl N-[(4-methylamino)benzoyl]-L-glutamate followed by ester hydrolysis. 5-Methyl-10-ethyl-5-deazaaminopterin was similarly prepared from 15. Biological evaluation of the 5-methyl-5-deaza analogues together with previously reported 5-deazaaminopterin and 5-deazamethotrexate for inhibition of dihydrofolate reductase (DHFR) isolated from L1210 cells and for their effect on cell growth inhibition, transport characteristics, and net accumulation of polyglutamate forms in L1210 cells revealed the analogues to have essentially the same properties as the appropriate parent compound, aminopterin or methotrexate (MTX), except that 20 and 21 were approximately 10 times more growth inhibitory than MTX. In in vivo tests against P388/0 and P388/MTX leukemia in mice, the analogues showed activity comparable to that of MTX, with the more potent 20 producing the same response in the P388/0 test as MTX but at one-fourth the dose; none showed activity against P388/MTX. Hydrolytic deamination of 12 and 20 produced 5-methyl-5-deazafolic acid and 5,10-dimethyl-5-deazafolic acid, respectively. In bacterial studies on

  13. Scalable synthesis of the unusual amino acid segment (ADMOA unit) of marine anti-inflammatory peptide: solomonamide A.

    PubMed

    Kavitha, Nerella; Chandrasekhar, Srivari

    2015-06-14

    The most abundantly available hexose sugar, d-glucose has been converted to protected 4-amino(2'amino-4'-hydroxy phenyl)-3,5-dihydroxy-2-methyl-6-oxo hexanoic acid (protected ADMOA, 3), the unusual amino acid present in marine natural product solomonamide A in gram quantities involving easy to operate chemical transformations. PMID:25960353

  14. 40 CFR 721.1725 - Benzoic acid, 3,3′-methyl-enebis [6 amino-, di-2-propenyl ester.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... Significant New Uses for Specific Chemical Substances § 721.1725 Benzoic acid, 3,3′-methyl-enebis [6 amino..., Benzoic acid, 3,3′-methylenebis [6 amino-, di-2-propenyl ester. (2) The significant new uses are: (i) Any... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Benzoic acid, 3,3â²-methyl-enebis...

  15. 40 CFR 721.1725 - Benzoic acid, 3,3′-methyl-enebis [6 amino-, di-2-propenyl ester.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... Significant New Uses for Specific Chemical Substances § 721.1725 Benzoic acid, 3,3′-methyl-enebis [6 amino..., Benzoic acid, 3,3′-methylenebis [6 amino-, di-2-propenyl ester. (2) The significant new uses are: (i) Any... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Benzoic acid, 3,3â²-methyl-enebis...

  16. 40 CFR 721.1725 - Benzoic acid, 3,3′-methyl-enebis [6 amino-, di-2-propenyl ester.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... Significant New Uses for Specific Chemical Substances § 721.1725 Benzoic acid, 3,3′-methyl-enebis [6 amino..., Benzoic acid, 3,3′-methylenebis [6 amino-, di-2-propenyl ester. (2) The significant new uses are: (i) Any... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Benzoic acid, 3,3â²-methyl-enebis...

  17. Preparation of fatty acid methyl esters for gas-liquid chromatography[S

    PubMed Central

    Ichihara, Ken'ichi; Fukubayashi, Yumeto

    2010-01-01

    A convenient method using commercial aqueous concentrated HCl (conc. HCl; 35%, w/w) as an acid catalyst was developed for preparation of fatty acid methyl esters (FAMEs) from sterol esters, triacylglycerols, phospholipids, and FFAs for gas-liquid chromatography (GC). An 8% (w/v) solution of HCl in methanol/water (85:15, v/v) was prepared by diluting 9.7 ml of conc. HCl with 41.5 ml of methanol. Toluene (0.2 ml), methanol (1.5 ml), and the 8% HCl solution (0.3 ml) were added sequentially to the lipid sample. The final HCl concentration was 1.2% (w/v). This solution (2 ml) was incubated at 45°C overnight or heated at 100°C for 1–1.5 h. The amount of FFA formed in the presence of water derived from conc. HCl was estimated to be <1.4%. The yields of FAMEs were >96% for the above lipid classes and were the same as or better than those obtained by saponification/methylation or by acid-catalyzed methanolysis/methylation using commercial anhydrous HCl/methanol. The method developed here could be successfully applied to fatty acid analysis of various lipid samples, including fish oils, vegetable oils, and blood lipids by GC. PMID:19759389

  18. DNA methylation patterns are associated with n-3 fatty acid intake in Yup'ik people.

    PubMed

    Aslibekyan, Stella; Wiener, Howard W; Havel, Peter J; Stanhope, Kimber L; O'Brien, Diane M; Hopkins, Scarlett E; Absher, Devin M; Tiwari, Hemant K; Boyer, Bert B

    2014-04-01

    A large body of evidence links a high dietary intake of n-3 (ω-3) polyunsaturated fatty acids (PUFAs) with improved cardiometabolic outcomes. Recent studies suggested that the biologic processes underlying the observed associations may involve epigenetic changes, specifically DNA methylation. To evaluate changes in methylation associated with n-3 PUFA intake, we conducted an epigenome-wide methylation association study of long-chain n-3 PUFA intake and tested associations between the diabetes- and cardiovascular disease-related traits. We assessed DNA methylation at ∼470,000 cytosine-phosphate-guanine (CpG) sites in a cross-sectional study of 185 Yup'ik Alaska Native individuals representing the top and bottom deciles of PUFA intake. Linear regression models were used to test for the associations of interest, adjusting for age, sex, and community group. We identified 27 differentially methylated CpG sites at biologically relevant regions that reached epigenome-wide significance (P < 1 × 10⁻⁷). Specifically, regions on chromosomes 3 (helicase-like transcription factor), 10 (actin α 2 smooth muscle/Fas cell surface death receptor), and 16 (protease serine 36/C16 open reading frame 67) each harbored 2 significant correlates of n-3 PUFA intake. In conclusion, we present promising evidence of association between several biologically relevant epigenetic markers and long-term intake of marine-derived n-3 PUFAs. PMID:24477300

  19. Influence of Organic Acids on Diltiazem HCl Release Kinetics from Hydroxypropyl Methyl Cellulose Matrix Tablets.

    PubMed

    Sateesha, Sb; Rajamma, Aj; Narode, Mk; Vyas, Bd

    2010-07-01

    The matrix tablets of diltiazem hydrochloride were prepared by direct compression using hydroxypropyl methyl cellulose (HPMC) and various amounts (2.5%, 5.0%, 10% and 20%) of citric acid, malic acid and succinic acid. The characterization of physical mixture of drug and organic acids was performed by Infra-red spectroscopy. An organic acid was incorporated to set up a system bringing about gradual release of this drug. The influence of organic acids on the release rate were described by the Peppas equation: M (t) /M(∞) = Kt (n) and Higuchi's equation: Q (t) = K(1)t(1/2). The addition of organic acids and the pH value of medium could notably influence the dissolution behavior and mechanism of drug-release from matrices. Increasing amounts of organic acid produced an increase in drug release rate, which showed a good linear relationship between contents of organic acid and drug accumulate release (%) in phosphate buffer, pH 7.4. The drug release increased significantly (P < 0.05) with use of succinic acid in tablet formulation. Increasing amounts of succinic acid above 10% produced decreasing values of n and increasing values of k, in a linear relationship, which indicated there was a burst release of drug from the matrix. Optimized formulations are found to be stable upon 3-month study. PMID:21042476

  20. Influence of Organic Acids on Diltiazem HCl Release Kinetics from Hydroxypropyl Methyl Cellulose Matrix Tablets

    PubMed Central

    Sateesha, SB; Rajamma, AJ; Narode, MK; Vyas, BD

    2010-01-01

    The matrix tablets of diltiazem hydrochloride were prepared by direct compression using hydroxypropyl methyl cellulose (HPMC) and various amounts (2.5%, 5.0%, 10% and 20%) of citric acid, malic acid and succinic acid. The characterization of physical mixture of drug and organic acids was performed by Infra-red spectroscopy. An organic acid was incorporated to set up a system bringing about gradual release of this drug. The influence of organic acids on the release rate were described by the Peppas equation: M t /M∞ = Kt n and Higuchi’s equation: Q t = K1t1/2. The addition of organic acids and the pH value of medium could notably influence the dissolution behavior and mechanism of drug-release from matrices. Increasing amounts of organic acid produced an increase in drug release rate, which showed a good linear relationship between contents of organic acid and drug accumulate release (%) in phosphate buffer, pH 7.4. The drug release increased significantly (P < 0.05) with use of succinic acid in tablet formulation. Increasing amounts of succinic acid above 10% produced decreasing values of n and increasing values of k, in a linear relationship, which indicated there was a burst release of drug from the matrix. Optimized formulations are found to be stable upon 3-month study. PMID:21042476

  1. 2-(2-Chloro-phen-yl)-5-methyl-1,3-dioxane-5-carboxylic acid.

    PubMed

    Jia, Guo-Kai; Yuan, Lin; Zhang, Min; Yuan, Xian-You

    2012-07-01

    In the title compound, C(12)H(13)ClO(4), the 1,3-dioxane ring adopts a chair conformation and the 2-chloro-benzene and methyl substituents occupy equatorial sites. The carboxyl group is in an axial inclination. In the crystal, carb-oxy-lic acid inversion dimers linked by pairs of O-H⋯O hydrogen bonds generate R(2) (2)(8) loops. PMID:22807863

  2. Complexation of NpO2+ with N-methyl-iminodiacetic Acid: in Comparison with Iminodiacetic and Dipicolinic Acids

    SciTech Connect

    Tian, Guoxin; Rao, Linfeng

    2010-10-01

    Complexation of Np(V) with N-methyl-iminodiacetic acid (MIDA) in 1 M NaClO{sub 4} solution was studied with multiple techniques including potentiometry, spectrophotometry, and microcalorimetry. The 1:2 complex, NpO{sub 2}(MIDA){sub 2}{sup 3-} was identified for the first time in aqueous solution. The correlation between its optical absorption properties and symmetry was discussed, in comparison with Np(V) complexes with two structurally related nitrilo-dicarboxylic acids, iminodiacetic acid (IDA) and dipicolinic acid (DPA). The order of the binding strength (DPA > MIDA > IDA) is explained by the difference in the structural and electronic properties of the ligands. In general, the nitrilo-dicarboxylates form stronger complexes with Np(V) than oxy-dicarboxylates due to a much more favorable enthalpy of complexation.

  3. Inhibition of vaccinia mRNA methylation by 2',5'-linked oligo(adenylic acid) triphosphate

    SciTech Connect

    Sharma, O.K.; Goswami, B.B.

    1981-04-01

    Extracts of interferon-treated cells synthesize unique 2',5'-linked oligo(adenylic acid) 5'-phosphates in the presence of ATP and double-stranded RNA. 2',5'-linked oligo(adenylic acid) 5'-triphosphate inhibits protein synthesis at nanomolar concentrations by activating RNase. We have observed that oligo(adenylic acid) 5'-monophosphate and 5'-triphosphate are potent inhibitors of vaccinia mRNA methylation in vitro. Both the methylation of the 5'-terminal guanine at the 7 position and the 2'-O-ribose methylation of the penultimate nucleoside are inhibited. Such inhibition of mRNA methylation is not due to degradation of the mRNA. Inhibition of the requisite modification of the 5' terminus of mRNA by 2',5'-linked oligo(adenylic acids) may be a mechanism of interferon action against both DNA and RNA viruses in which mRNAs derived from them are capped.

  4. Glycolaldehyde, methyl formate and acetic acid adsorption and thermal desorption from interstellar ices

    NASA Astrophysics Data System (ADS)

    Burke, Daren J.; Puletti, Fabrizio; Brown, Wendy A.; Woods, Paul M.; Viti, Serena; Slater, Ben

    2015-02-01

    We have undertaken a detailed investigation of the adsorption, desorption and thermal processing of the astrobiologically significant isomers glycolaldehyde, acetic acid and methyl formate. Here, we present the results of laboratory infrared and temperature programmed desorption (TPD) studies of the three isomers from model interstellar ices adsorbed on a carbonaceous dust grain analogue surface. Laboratory infrared data show that the isomers can be clearly distinguished on the basis of their infrared spectra, which has implications for observations of interstellar ice spectra. Laboratory TPD data also show that the three isomers can be distinguished on the basis of their thermal desorption behaviour. In particular, TPD data show that the isomers cannot be treated the same way in astrophysical models of desorption. The desorption of glycolaldehyde and acetic acid from water-dominated ices is very similar, with desorption being mainly dictated by water ice. However, methyl formate also desorbs from the surface of the ice, as a pure desorption feature, and therefore desorbs at a lower temperature than the other two isomers. This is more clearly indicated by models of the desorption on astrophysical time-scales corresponding to the heating rate of 25 and 5 M⊙ stars. For a 25 M⊙ star, our model shows that a proportion of the methyl formate can be found in the gas phase at earlier times compared to glycolaldehyde and acetic acid. This has implications for the observation and detection of these molecules, and potentially explains why methyl formate has been observed in a wider range of astrophysical environments than the other two isomers.

  5. Radioiodinated methyl-branched fatty acids: Evaluation of catabolites formed in vivo

    SciTech Connect

    Knapp, F.F. Jr.; Reske, S.N.; Kirsch, G.; Ambrose, K.R.; Blystone, S.L.; Goodman, M.M.

    1987-01-01

    Radioiodinated terminal iodophenyl-substituted long-chain fatty acids containing either racemic mono-methyl or geminal dimethyl-branching in the alkyl chain have been shown to exhibit delayed myocardial clearance properties which make these agents useful for the SPECT evaluation of myocardial fatty acid uptake patterns. Although the myocardial clearance rate of 15-(p-iodophenyl)-3-R,S- methylpentadecanoic acid (BMIPP) is considerably delayed, in comparison with the IPPA straight-chain analogue, analysis of the radioiodinated lipids present in the outflow tract of isolated rat hearts administered BMIPP have clearly demonstrated the presence of a polar metabolite. The synthesis of ..beta..-hydroxy fatty acids has been developed to allow investigation of the possible formation of ..beta..-hydroxy catabolites in vivo. The preparation of ..beta..-hydroxy BMIPP and ..beta..-hydroxy IPPA are described, and the possible significance of their formation in vivo discussed. 4 figs.

  6. Preparation of fatty acid methyl esters for gas-chromatographic analysis of marine lipids: insight studies.

    PubMed

    Carvalho, Ana P; Malcata, F Xavier

    2005-06-29

    Assays for fatty acid composition in biological materials are commonly carried out by gas chromatography, after conversion of the lipid material into the corresponding methyl esters (FAME) via suitable derivatization reactions. Quantitative derivatization depends on the type of catalyst and processing conditions employed, as well as the solubility of said sample in the reaction medium. Most literature pertinent to derivatization has focused on differential comparison between alternative methods; although useful to find out the best method for a particular sample, additional studies on factors that may affect each step of FAME preparation are urged. In this work, the influence of various parameters in each step of derivatization reactions was studied, using both cod liver oil and microalgal biomass as model systems. The accuracies of said methodologies were tested via comparison with the AOCS standard method, whereas their reproducibility was assessed by analysis of variance of (replicated) data. Alkaline catalysts generated lower levels of long-chain unsaturated FAME than acidic ones. Among these, acetyl chloride and BF(3) were statistically equivalent to each other. The standard method, which involves alkaline treatment of samples before acidic methylation with BF(3), provided equivalent results when compared with acidic methylation with BF(3) alone. Polarity of the reaction medium was found to be of the utmost importance in the process: intermediate values of polarity [e.g., obtained by a 1:1 (v/v) mixture of methanol with diethyl ether or toluene] provided amounts of extracted polyunsaturated fatty acids statistically higher than those obtained via the standard method. PMID:15969474

  7. 40 CFR 721.1645 - Benzenesulfonic acid, 4-methyl-, reaction products with oxirane mono[(C10-16-alkyloxy)methyl...

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... to reporting. (1) The chemical substance benzenesulfonic acid, 4-methyl-, reaction products with...-, reaction products with oxirane mono derivatives and 2,2,4(or 2,4,4)-trimethyl-1,6-hexanediamine. 721.1645... CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific...

  8. 40 CFR 721.1645 - Benzenesulfonic acid, 4-methyl-, reaction products with oxirane mono[(C10-16-alkyloxy)methyl...

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... to reporting. (1) The chemical substance benzenesulfonic acid, 4-methyl-, reaction products with...-, reaction products with oxirane mono derivatives and 2,2,4(or 2,4,4)-trimethyl-1,6-hexanediamine. 721.1645... CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific...

  9. Evaluation of eye irritation by S-(-)-10,11-dihydroxyfarnesic acid methyl ester secreted by Beauveria bassiana CS1029.

    PubMed

    Son, Hyeong-U; Lee, Sang-Han

    2013-10-01

    The aim of this study was to investigate whether S-(-)-10,11-dihydroxyfarnesic acid methyl ester produced by cell subtype Beauveria bassiana CS1029 causes acute toxicity when used for cosmetic purposes by performing an eye irritation test. New Zealand white (NZW) rabbits were treated with a 100 mg/dose of S-(-)-10,11-dihydroxyfarnesic acid methyl ester according to standard procedure guidelines. No significant changes in terms of ocular lesions of the cornea, turbidity of the cornea, swelling of the eyelid or ocular discharge were observed in the methyl ester-treated groups, while sodium dioctyl sulfosuccinate, a positive control, caused severe toxicity. The anatomical and pathological observations indicate that the methyl ester produced by Beauveria bassiana CS1029 did not induce eye irritation in the lenses of the rabbits. The data suggest that the methyl ester evaluated in this study has promising potential as a cosmetic ingredient that does not irritate the eye. PMID:24137288

  10. Evaluation of eye irritation by S-(-)-10,11-dihydroxyfarnesic acid methyl ester secreted by Beauveria bassiana CS1029

    PubMed Central

    SON, HYEONG-U; LEE, SANG-HAN

    2013-01-01

    The aim of this study was to investigate whether S-(-)-10,11-dihydroxyfarnesic acid methyl ester produced by cell subtype Beauveria bassiana CS1029 causes acute toxicity when used for cosmetic purposes by performing an eye irritation test. New Zealand white (NZW) rabbits were treated with a 100 mg/dose of S-(-)-10,11-dihydroxyfarnesic acid methyl ester according to standard procedure guidelines. No significant changes in terms of ocular lesions of the cornea, turbidity of the cornea, swelling of the eyelid or ocular discharge were observed in the methyl ester-treated groups, while sodium dioctyl sulfosuccinate, a positive control, caused severe toxicity. The anatomical and pathological observations indicate that the methyl ester produced by Beauveria bassiana CS1029 did not induce eye irritation in the lenses of the rabbits. The data suggest that the methyl ester evaluated in this study has promising potential as a cosmetic ingredient that does not irritate the eye. PMID:24137288

  11. Adsorption and Thermal Processing of Glycolaldehyde, Methyl Formate, and Acetic Acid on Graphite at 20 K.

    PubMed

    Burke, Daren J; Puletti, Fabrizio; Woods, Paul M; Viti, Serena; Slater, Ben; Brown, Wendy A

    2015-07-01

    We present the first detailed comparative study of the adsorption and thermal processing of the three astrophysically important C2O2H4 isomers glycolaldehyde, methyl formate, and acetic acid adsorbed on a graphitic grain analogue at 20 K. The ability of the individual molecule to form intermolecular hydrogen bonds is extremely important, dictating the growth modes of the ice on the surface and the measured desorption energies. Methyl formate forms only weak intermolecular bonds and hence wets the graphite surface, forming monolayer, bilayer, and multilayer ices, with the multilayer having a desorption energy of 35 kJ mol(-1). In contrast, glycolaldehyde and acetic acid dewet the surface, forming clusters even at the very lowest coverages. The strength of the intermolecular hydrogen bonding for glycolaldehyde and acetic acid is reflected in their desorption energies (46.8 and 55 kJ mol(-1), respectively), which are comparable to those measured for other hydrogen-bonded species such as water. Infrared spectra show that all three isomers undergo structural changes as a result of thermal processing. In the case of acetic acid and glycolaldehyde, this can be assigned to the formation of well-ordered, crystalline, structures where the molecules form chains of hydrogen-bonded moieties. The data reported here are of relevance to astrochemical studies of hot cores and star-forming regions and can be used to model desorption from interstellar ices during the warm up phase with particular importance for complex organic molecules. PMID:26057183

  12. Efficient transfer of information from hexitol nucleic acids to RNA during nonenzymatic oligomerization

    NASA Technical Reports Server (NTRS)

    Kozlov, I. A.; De Bouvere, B.; Van Aerschot, A.; Herdewijn, P.; Orgel, L. E.

    1999-01-01

    Hexitol nucleic acids (HNAs) are DNA analogues that contain the standard nucleoside bases attached to a phosphorylated 1,5-anhydrohexitol backbone. We find that HNAs support efficient information transfer in nonensymatic template-directed reactions. HNA heterosequences appeared to be superior to the corresponding DNA heterosequences in facilitating synthesis of complementary oligonucleotides from nucleoside-5'-phosphoro-2-methyl imidazolides.

  13. Anchoring the gas-phase acidity scale: From formic acid to methanethiol

    NASA Astrophysics Data System (ADS)

    Eyet, Nicole; Villano, Stephanie M.; Bierbaum, Veronica M.

    2009-06-01

    We have measured the gas-phase acidities of nine compounds: formic acid, acetic acid, 1,3-propanedithiol, 2-methyl-2-propanethiol, 3-methyl-1-butanethiol, 2-propanethiol, 1-propanethiol, ethanethiol, and methanethiol, with acidities ranging from 338.6 to 351.1 kcal mol-1 using proton transfer kinetics and the resulting equilibrium constants. These acids were anchored to the well-known acidity of hydrogen sulfide; the measured acidities are in good agreement with previous experimental values, but error bars are significantly reduced. The gas-phase acidity of 3-methyl-1-butanethiol was determined to be 347.1 (5) kcal mol-1; there were no previous measurements of this value. Entropies of deprotonation were calculated and enthalpies of deprotonation were determined.

  14. Light and acid dual-responsive organogel formation based on m-methyl red derivative.

    PubMed

    Cao, Xinhua; Gao, Aiping; Lv, Haiting; Wu, Yan; Wang, Xiuxiu; Fan, Yang

    2013-12-01

    A new gelator 1 that included m-methyl red was synthesized and fully characterized. It was found that the organogel of 1 was stable in DMSO even if the organogel was stimulated by acid or light. The organogel was thoroughly characterized using various microscopic techniques including field-emission scanning electron microscopy (FESEM), X-ray diffraction (XRD), UV-vis and Fourier transform infrared (FTIR) spectra. The organogel exhibited tunable structures and optical properties under different stimulation. The regular nanoring structure was turned into microspheres after the organogel in DMSO was stimulated at 254 nm light or acid. At the same time, the color of molecule 1 in gel state and solution state was all changed after stimulation by light or acid. The hydrogen bonding and π-π stacking were found to be the main driving forces for gel formation. This dual-responsive gel held promise for soft materials application in upscale smart responsive materials. PMID:24135789

  15. Thermal-induced conversion of maleic and fumaric acid anion radicals in poly(methyl methacrylate)

    SciTech Connect

    Torikai, A.; Fukumoto, M.

    1980-04-01

    Thermal-induced conversion of maleic and fumaric acid anion radicals produced by ..gamma.. irradiation at 77/sup 0/K in poly(methyl methacrylate) (PMMA) was studied by electron spin resonance (ESR) and optical absorption spectroscopic measurements. The ESR spectra of these acid anion radicals change into two-line spectra with a line separation of ca. 10 G by thermal annealing. This spectrum is assigned to a protonated radical of each acid anion radical. Anion radicals of the solutes are relatively stable below the ..gamma.. transition point of PMMA and the conversion reaction takes place near this point. This means that the molecular motion of matrix molecule affects the radical conversion reaction.

  16. Synthesis and characteristics of an aspartame analogue, L-asparaginyl L-3-phenyllactic acid methyl ester.

    PubMed

    Tao, Hu; Cui, Da-Fu; Zhang, You-Shang

    2004-06-01

    An aspartame analogue, L-asparaginyl L-3-phenyllactic acid methyl ester was synthesized with aspartic acid replaced by asparagine and peptide bond replaced by ester bond. The aspartic acid of aspartame could be replaced by asparagine as reported in the literature. In this analogue, the hydrogen of amide group could still form a hydrogen bond with the oxygen of ester bond and the ester bond was isosteric with peptide bond. However, the product was not sweet, showing that the peptide bond could not be replaced by ester bond. The peptide C-N bond behaves as a double bond that is not free to rotate and the C, O, N and H atoms are in the same plane. The replacement of peptide bond by ester bond destroyed the unique conformation of peptide bond, resulting in the loss of sweet taste. PMID:15188052

  17. The development of iodine-123-methyl-branched fatty acids and their applications in nuclear cardiology

    SciTech Connect

    Knapp, F.F. Jr.; Ambrose, K.R.; Kropp, J.; Biersack, H.J.; Goodman, M.M.; Franken, P.; Reske, S.N.; Som, P.; Sloof, G.W.; Visser, F.C.

    1993-06-01

    Continued Interest in the use of iodine-1 23-labeled fatty acids for myocardial Imaging results from observations from a variety of studies that in many types of cardiac disease, regional fatty acid myocardial uptake patterns are often different than regional distribution of flow tracers. These differences may reflect alterations in important parameters of metabolism which can be useful for patient management or therapeutic strategy decision making. In addition, use of iodine-I 23-labeled fatty acid distribution may represent a unique metabolic probe to relate some aspects of the metabolism of these substrates with the regional viability of cardiac tissue. The use of such viability markers could provide important prognostic information on myocardial salvage, helping to identify patients for revascularization or angioplasty. Clinical studies are currently in progress with the iodine-123-labeled 1 5-(p-iodophenyl)-3-R,S-methylpentadecanoic acid (BMIPP) fatty acid analogue at several institutions. The goals of this paper are to discuss development of the concept of metabolic trapping of fatty acids, to briefly review development and evaluation of various radioiodinated methyl-branched fatty acids and to discuss recent patient studies with iodine-123 (BMIPP) using single photon emission computerized tomography (SPECT).

  18. The development of iodine-123-methyl-branched fatty acids and their applications in nuclear cardiology

    SciTech Connect

    Knapp, F.F. Jr.; Ambrose, K.R. ); Kropp, J.; Biersack, H.J. . Inst. fuer Klinische und Experimentelle Nuklearmedizin); Goodman, M.M. . Dept. of Radiology); Franken, P. . Nuclear Medicine Dept.); Reske, S.N. (Ulm Univ. (Germany

    1993-01-01

    Continued Interest in the use of iodine-1 23-labeled fatty acids for myocardial Imaging results from observations from a variety of studies that in many types of cardiac disease, regional fatty acid myocardial uptake patterns are often different than regional distribution of flow tracers. These differences may reflect alterations in important parameters of metabolism which can be useful for patient management or therapeutic strategy decision making. In addition, use of iodine-I 23-labeled fatty acid distribution may represent a unique metabolic probe to relate some aspects of the metabolism of these substrates with the regional viability of cardiac tissue. The use of such viability markers could provide important prognostic information on myocardial salvage, helping to identify patients for revascularization or angioplasty. Clinical studies are currently in progress with the iodine-123-labeled 1 5-(p-iodophenyl)-3-R,S-methylpentadecanoic acid (BMIPP) fatty acid analogue at several institutions. The goals of this paper are to discuss development of the concept of metabolic trapping of fatty acids, to briefly review development and evaluation of various radioiodinated methyl-branched fatty acids and to discuss recent patient studies with iodine-123 (BMIPP) using single photon emission computerized tomography (SPECT).

  19. Accuracy, reproducibility, and interpretation of fatty acid methyl ester profiles of model bacterial communities

    USGS Publications Warehouse

    Kidd, Haack S.; Garchow, H.; Odelson, D.A.; Forney, L.J.; Klug, M.J.

    1994-01-01

    We determined the accuracy and reproducibility of whole-community fatty acid methyl ester (FAME) analysis with two model bacterial communities differing in composition by using the Microbial ID, Inc. (MIDI), system. The biomass, taxonomic structure, and expected MIDI-FAME profiles under a variety of environmental conditions were known for these model communities a priori. Not all members of each community could be detected in the composite profile because of lack of fatty acid 'signatures' in some isolates or because of variations (approximately fivefold) in fatty acid yield across taxa. MIDI- FAME profiles of replicate subsamples of a given community were similar in terms of fatty acid yield per unit of community dry weight and relative proportions of specific fatty acids. Principal-components analysis (PCA) of MIDI-FAME profiles resulted in a clear separation of the two different communities and a clustering of replicates of each community from two separate experiments on the first PCA axis. The first PCA axis accounted for 57.1% of the variance in the data and was correlated with fatty acids that varied significantly between communities and reflected the underlying community taxonomic structure. On the basis of our data, community fatty acid profiles can be used to assess the relative similarities and differences of microbial communities that differ in taxonomic composition. However, detailed interpretation of community fatty acid profiles in terms of biomass or community taxonomic composition must be viewed with caution until our knowledge of the quantitative and qualitative distribution of fatty acids over a wide variety of taxa and the effects of growth conditions on fatty acid profiles is more extensive.

  20. XAS and RIXS study of acetic acid and methyl formate in liquid

    NASA Astrophysics Data System (ADS)

    Takahashi, O.; Nishida, N.; Kanai, S.; Horikawa, Y.; Tokushima, T.

    2016-05-01

    Structure of acetic acid (AA) and methyl formate (MF) in the liquid phase is studied using X-ray absorption spectroscopy (XAS) and X-ray emission spectroscopy (XES) experimentally and theoretically. Two distinct XES spectra are observed by tuning photon energy for both molecules. Model structure in the liquid phase is constructed using the classical and first principle molecular dynamics simulations, and XES spectra are calculated using density functional theory. Calculated XES spectra are consistent with experimental ones. The effect of core-hole induced excited state molecular dynamics are discussed.

  1. Sterically controlled azomethine ylide cycloaddition polymerization of phenyl-C61-butyric acid methyl ester.

    PubMed

    Stephen, Meera; Ramanitra, Hasina H; Santos Silva, Hugo; Dowland, Simon; Bégué, Didier; Genevičius, Kristijonas; Arlauskas, Kęstutis; Juška, Gytis; Morse, Graham E; Distler, Andreas; Hiorns, Roger C

    2016-05-01

    Phenyl-C61-butyric acid methyl ester (PCBM) is polymerized simply using a one-pot reaction to yield soluble, high molecular weight polymers. The sterically controlled azomethine ylide cycloaddition polymerization (SACAP) is demonstrated to be highly adaptable and yields polymers with probable Mn≈ 24 600 g mol(-1) and Mw≈ 73 800 g mol(-1). Products are metal-free and of possible benefit to organic and hybrid photovoltaics and electronics as they form thin films from solution and have raised LUMOs. The promising electronic properties of this new polymer are discussed. PMID:27066898

  2. Radiation chemistry of salicylic and methyl substituted salicylic acids: Models for the radiation chemistry of pharmaceutical compounds

    NASA Astrophysics Data System (ADS)

    Ayatollahi, Shakiba; Kalnina, Daina; Song, Weihua; Turks, Maris; Cooper, William J.

    2013-11-01

    Salicylic acid and its derivatives are components of many medications and moieties found in numerous pharmaceutical compounds. They have been used as models for various pharmaceutical compounds in pharmacological studies, for the treatment of pharmaceuticals and personal care products (PPCPs), and, reactions with natural organic matter (NOM). In this study, the radiation chemistry of benzoic acid, salicylic acid and four methyl substituted salicylic acids (MSA) is reported. The absolute bimolecular reaction rate constants for hydroxyl radical reaction with benzoic and salicylic acids as well as 3-methyl-, 4-methyl-, 5-methyl-, and 6-methyl-salicylic acid were determined (5.86±0.54)×109, (1.07±0.07)×1010, (7.48±0.17)×109, (7.31±0.29)×109, (5.47±0.25)×109, (6.94±0.10)×109 (M-1 s-1), respectively. The hydrated electron reaction rate constants were measured (3.02±0.10)×109, (8.98±0.27)×109, (5.39±0.21)×109, (4.33±0.17)×109, (4.72±0.15)×109, (1.42±0.02)×109 (M-1 s-1), respectively. The transient absorption spectra for the six model compounds were examined and their role as model compounds for the radiation chemistry of pharmaceuticals investigated.

  3. pH dependence of methyl phosphonic acid, dipicolinic acid, and cyanide by surface-enhanced Raman spectroscopy

    NASA Astrophysics Data System (ADS)

    Farquharson, Stuart; Gift, Alan; Maksymiuk, Paul; Inscore, Frank E.; Smith, Wayne W.

    2004-03-01

    U.S. and Coalition forces fighting terrorism in Afghanistan and Iraq must consider a wide range of attack scenarios in addition to car bombings. Among these is the intentional poisoning of water supplies to obstruct military operations. To counter such attacks, the military is developing portable analyzers that can identify and quantify potential chemical agents in water supplies at microgram per liter concentrations within 10 minutes. To aid this effort we have been investigating the value of a surface-enhanced Raman spectroscopy based portable analyzer. In particular we have been developing silver-doped sol-gels to generate SER spectra of chemical agents and their hydrolysis products. Here we present SER spectra of methyl phosphonic acid and cyanide as a function of pH, an important factor affecting quantitation measurements, which to our knowledge has not been examined. In addition, dipicolinic acid, a chemical signature associated with anthrax-causing spores, is also presented.

  4. 21 CFR 172.225 - Methyl and ethyl esters of fatty acids produced from edible fats and oils.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... from edible fats and oils. 172.225 Section 172.225 Food and Drugs FOOD AND DRUG ADMINISTRATION... acids produced from edible fats and oils. Methyl esters and ethyl esters of fatty acids produced from edible fats and oils may be safely used in food, subject to the following prescribed conditions: (a)...

  5. 40 CFR 721.304 - Acetic acid, [(5-chloro-8-quinolinyl)oxy-], 1-methyl hexyl ester.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.304 Acetic acid, , 1-methyl hexyl ester. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as acetic acid, -, 1-methylhexyl ester (PMN...

  6. 40 CFR 721.304 - Acetic acid, [(5-chloro-8-quinolinyl)oxy-], 1-methyl hexyl ester.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.304 Acetic acid, , 1-methyl hexyl ester. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as acetic acid, -, 1-methylhexyl ester (PMN...

  7. 40 CFR 721.10188 - Fatty acids, tall-oil, reaction products with 4-methyl-2-pentanone and aliphatic polyamine...

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Fatty acids, tall-oil, reaction... SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.10188 Fatty acids, tall-oil, reaction products with 4-methyl-2-pentanone and aliphatic polyamine (generic)....

  8. 40 CFR 721.10188 - Fatty acids, tall-oil, reaction products with 4-methyl-2-pentanone and aliphatic polyamine...

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Fatty acids, tall-oil, reaction... SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.10188 Fatty acids, tall-oil, reaction products with 4-methyl-2-pentanone and aliphatic polyamine (generic)....

  9. 40 CFR 721.10188 - Fatty acids, tall-oil, reaction products with 4-methyl-2-pentanone and aliphatic polyamine...

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Fatty acids, tall-oil, reaction... SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.10188 Fatty acids, tall-oil, reaction products with 4-methyl-2-pentanone and aliphatic polyamine (generic)....

  10. 40 CFR 721.10188 - Fatty acids, tall-oil, reaction products with 4-methyl-2-pentanone and aliphatic polyamine...

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Fatty acids, tall-oil, reaction... SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.10188 Fatty acids, tall-oil, reaction products with 4-methyl-2-pentanone and aliphatic polyamine (generic)....

  11. 40 CFR 721.10188 - Fatty acids, tall-oil, reaction products with 4-methyl-2-pentanone and aliphatic polyamine...

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Fatty acids, tall-oil, reaction... SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.10188 Fatty acids, tall-oil, reaction products with 4-methyl-2-pentanone and aliphatic polyamine (generic)....

  12. Isolation and characterization of fatty acid methyl ester (FAME)-producing Streptomyces sp. S161 from sheep (Ovis aries) faeces.

    PubMed

    Lu, Y; Wang, J; Deng, Z; Wu, H; Deng, Q; Tan, H; Cao, L

    2013-09-01

    An actinomycete producing oil-like mixtures was isolated and characterized. The strain was isolated from sheep faeces and identified as Streptomyces sp. S161 based on 16S rRNA gene sequence analysis. The strain showed cellulase and xylanase activities. The (1) H nuclear magnetic resonance (NMR) spectra of the mixtures showed that the mixtures were composed of fatty acid methyl esters (52·5), triglycerides (13·7) and monoglycerides (9·1) (mol.%). Based on the gas chromatography-mass spectrometry (GC-MS) analysis, the fatty acid methyl esters were mainly composed of C14-C16 long-chain fatty acids. The results indicated that Streptomyces sp. S161 could produce fatty acid methyl esters (FAME) directly from starch. To our knowledge, this is the first isolated strain that can produce biodiesel (FAME) directly from starch. PMID:23692633

  13. Uric acid or 1-methyl uric acid in the urinary bladder increases serum glucose, insulin, true triglyceride, and total cholesterol levels in Wistar rats.

    PubMed

    Balasubramanian, T

    2003-10-01

    In animals deprived of food for a long period, a drop in the fat mass below 5% of the total body mass results in an increase in blood glucocorticoids and uric acid levels, followed by foraging activity. Since the glucocorticoids increase the uric acid excretion, an increase in the level of uric acid in the bladder urine could be the signal for this feeding behaviour and subsequent fat storage. Accumulation of fat is associated with hyperglycaemia, hyperinsulinaemia, hyperlipidaemia, and hypercholesterolaemia as seen in the metabolic syndrome or hibernation. It is hypothesized that uric acid or its structurally related compound, 1-methyl uric acid (one of the metabolites of the methyl xanthines namely caffeine, theophylline, and theobromine present in coffee, tea, cocoa, and some drugs), can act on the urinary bladder mucosa and increases the blood glucose, insulin, triglyceride, and cholesterol levels. In rats, perfusion of the urinary bladder with saturated aqueous solution of uric acid or 1-methyl uric acid results in a significant increase in the serum levels of glucose, insulin, true triglyceride, and total cholesterol in comparison with perfusion of the bladder with distilled water at 20, 40, and 80 min. The uric acid or the 1-methyl uric acid acts on the urinary bladder mucosa and increases the serum glucose, insulin, true triglyceride, and total cholesterol levels. PMID:15241498

  14. Methyl 2-(2-methyl-4-nitro-1H-imidazol-1-yl)acetate

    PubMed Central

    Zama, Sana; Bouraiou, Abdelmalek; Bouacida, Sofiane; Roisnel, Thierry; Belfaitah, Ali

    2013-01-01

    In the crystal of the title compound, C7H9N3O4, mol­ecules are linked by weak C—H⋯O hydrogen bonds into chains along the a-axis direction. The dihedral angle between the ring and the nitro group is 3.03 (6), while that between the ring and the acetate group is 85.01 (3)°. PMID:23795026

  15. Amonia gas: an improved reagent for chemical ionization mass spectrometry of bile acid methyl ester acetates

    SciTech Connect

    DeMark, B.R.; Klein, P.D.

    1981-01-01

    The ammonia chemical ionization mass spectra of 28 methyl ester acetate derivatives of bile acids and related compounds have been determined by gas-liquid chromatography-mass spectrometry. Advantages of ammonia ionization over the previously studied isobutane ionization include a 130 to 270% enhancement in the sensitivity of base peak monitoring, and direct determination of molecular weight from the base peak (M + NH/sub 4//sup +/) in the mass spectrum of any of the derivatives. Minor ions in the ammonia spectra also allow selective detection of 3-keto compounds and can indicate unsaturation or double bond conjugation in the molecule. The significance of these studies for the detection and quantitation of bile acids is discussed. 2 tables.

  16. A study of the autoxidation of some unsaturated fatty acid methyl esters using Fourier transform Raman spectroscopy

    NASA Astrophysics Data System (ADS)

    Agbenyega, J. K.; Claybourn, M.; Ellis, G.

    Near-infrared Fourier transform Raman and Fourier transform infrared spectroscopy have been used to investigate the chemical changes taking place during the curing reaction of several fatty acid methyl esters, which are used for modelling processes in the autoxidation of alkyd resin coatings. We have studied methyl oleate, methyl linoleate, and methyl linolenate in an attempt to monitor the degree of unsaturation within the fatty acid methyl esters (FAMES) during the complex autoxidation/polymerisation reaction that takes place once the paint system is coated onto a substrate and exposed to the atmosphere. The peaks around 1655 cm -1 have been assigned as follows: to the trans isomer at 1670 cm -1, the cis isomer at 1655 cm -1 and the conjugated structure at 1640 cm -1 [B. Schrader, Raman/Infrared Atlas of Organic Compounds (2nd Edn), VCH, Weinheim (1989); J. K. Abenyega, M. Claybourn and G. Ellis, in preparations]. Raman spectra for the cure of methyl linoleate after 24 h show several interesting features, suggesting the formation of a highly conjugated cyclic structure. Current theories about the mechanism for the autoxidation of methyl linoleate make no mention of this aromatic product.

  17. Neuroprotective Effect of Tauroursodeoxycholic Acid on N-Methyl-D-Aspartate-Induced Retinal Ganglion Cell Degeneration

    PubMed Central

    Fernández-Sánchez, Laura; Rondón, Netxibeth; Esquiva, Gema; Germain, Francisco; de la Villa, Pedro; Cuenca, Nicolás

    2015-01-01

    Retinal ganglion cell degeneration underlies the pathophysiology of diseases affecting the retina and optic nerve. Several studies have previously evidenced the anti-apoptotic properties of the bile constituent, tauroursodeoxycholic acid, in diverse models of photoreceptor degeneration. The aim of this study was to investigate the effects of systemic administration of tauroursodeoxycholic acid on N-methyl-D-aspartate (NMDA)-induced damage in the rat retina using a functional and morphological approach. Tauroursodeoxycholic acid was administered intraperitoneally before and after intravitreal injection of NMDA. Three days after insult, full-field electroretinograms showed reductions in the amplitudes of the positive and negative-scotopic threshold responses, scotopic a- and b-waves and oscillatory potentials. Quantitative morphological evaluation of whole-mount retinas demonstrated a reduction in the density of retinal ganglion cells. Systemic administration of tauroursodeoxycholic acid attenuated the functional impairment induced by NMDA, which correlated with a higher retinal ganglion cell density. Our findings sustain the efficacy of tauroursodeoxycholic acid administration in vivo, suggesting it would be a good candidate for the pharmacological treatment of degenerative diseases coursing with retinal ganglion cell loss. PMID:26379056

  18. A monolithic lipase reactor for biodiesel production by transesterification of triacylglycerides into fatty acid methyl esters

    PubMed Central

    Urban, Jiri; Svec, Frantisek; Fréchet, Jean M.J.

    2011-01-01

    An enzymatic reactor with lipase immobilized on a monolithic polymer support has been prepared and used to catalyze the transesterification of triacylglycerides into the fatty acid methyl esters commonly used for biodiesel. A design of experiments procedure was used to optimize the monolithic reactor with variables including control of the surface polarity of the monolith via variations in the length of the hydrocarbon chain in alkyl methacrylate monomer, time of grafting of 1-vinyl-4,4-dimethylazlactone used to activate the monolith, and time used for the immobilization of porcine lipase. Optimal conditions involved the use of a poly(stearyl methacrylate-co-ethylene dimethacrylate) monolith, grafted first with vinylazlactone, then treated with lipase for 2 h to carry out the immobilization of the enzyme. Best conditions for the transesterification of glyceryl tributyrate included a temperature of 37°C and a 10 min residence time of the substrate in the bioreactor. The reactor did not lose its activity even after pumping through it a solution of substrate equaling 1,000 reactor volumes. This enzymatic reactor was also used for the transesterification of triacylglycerides from soybean oil to fatty acid methyl esters thus demonstrating the ability of the reactor to produce biodiesel. PMID:21915852

  19. Supported phosphate and carbonate salts for heterogeneous catalysis of triglycerides to fatty acid methyl esters

    NASA Astrophysics Data System (ADS)

    Britton, Stephanie Lynne

    Fatty acid methyl esters made from vegetable oil, or biodiesel, have been identified as a substitute for diesel derived from crude oil. Biodiesel is currently made using a homogeneous base catalyst to perform the transesterification of triglycerides with methanol to generate fatty acid methyl esters (FAME). The use of a homogeneous catalyst necessitates additional purification of the product and byproducts before sale, and the catalyst is consumed and discarded. The development of a heterogeneous basic catalyst for the production of FAME is desirable. Tribasic phosphate salts and dibasic carbonate salts are active for the production of FAME but generally operate as homogeneous catalysts. Supporting these phosphate and carbonate salts on mesoporous MCM-41, microporous silica gel, and nonporous a-alumina proved successful to greater or lesser degrees depending on the identity of the support and pretreatment of the support. Although these salts were supported and were active for the production of FAME from canola oil, they proved to be operating as homogeneous catalysts due to leaching of the active species off the surface of the support. Further investigation of the active species present in the tribasic phosphate catalysts identified the active support as orthophosphate, and NMR studies revealed the phosphorus to be present as orthophosphate and diphosphate in varying proportions in each catalyst. Evaluation of the acid-washing support pretreatment process revealed that the exposure of the support to acid plays a large role in the development of activity on the surface of the catalyst, but manipulation of these parameters did not prevent leaching of the active site off the surface of the catalyst. Alternate methods of support pretreatment were no more effective in preventing leaching. Tribasic phosphate supported on silica gel is not effective as a heterogeneous catalyst for FAME production from triglycerides because of the lack of stability of the phosphate on the

  20. Genome-Wide Methylation and Gene Expression Changes in Newborn Rats following Maternal Protein Restriction and Reversal by Folic Acid

    PubMed Central

    Stupka, Elia; Clark, Adrian J. L.; Langley-Evans, Simon

    2013-01-01

    A large body of evidence from human and animal studies demonstrates that the maternal diet during pregnancy can programme physiological and metabolic functions in the developing fetus, effectively determining susceptibility to later disease. The mechanistic basis of such programming is unclear but may involve resetting of epigenetic marks and fetal gene expression. The aim of this study was to evaluate genome-wide DNA methylation and gene expression in the livers of newborn rats exposed to maternal protein restriction. On day one postnatally, there were 618 differentially expressed genes and 1183 differentially methylated regions (FDR 5%). The functional analysis of differentially expressed genes indicated a significant effect on DNA repair/cycle/maintenance functions and of lipid, amino acid metabolism and circadian functions. Enrichment for known biological functions was found to be associated with differentially methylated regions. Moreover, these epigenetically altered regions overlapped genetic loci associated with metabolic and cardiovascular diseases. Both expression changes and DNA methylation changes were largely reversed by supplementing the protein restricted diet with folic acid. Although the epigenetic and gene expression signatures appeared to underpin largely different biological processes, the gene expression profile of DNA methyl transferases was altered, providing a potential link between the two molecular signatures. The data showed that maternal protein restriction is associated with widespread differential gene expression and DNA methylation across the genome, and that folic acid is able to reset both molecular signatures. PMID:24391732

  1. DNA Methylation Profiling at Single-Base Resolution Reveals Gestational Folic Acid Supplementation Influences the Epigenome of Mouse Offspring Cerebellum

    PubMed Central

    Barua, Subit; Kuizon, Salomon; Brown, W. Ted; Junaid, Mohammed A.

    2016-01-01

    It is becoming increasingly more evident that lifestyle, environmental factors, and maternal nutrition during gestation can influence the epigenome of the developing fetus and thus modulate the physiological outcome. Variations in the intake of maternal nutrients affecting one-carbon metabolism may influence brain development and exert long-term effects on the health of the progeny. In this study, we investigated whether supplementation with high maternal folic acid during gestation alters DNA methylation and gene expression in the cerebellum of mouse offspring. We used reduced representation bisulfite sequencing to analyze the DNA methylation profile at the single-base resolution level. The genome-wide DNA methylation analysis revealed that supplementation with higher maternal folic acid resulted in distinct methylation patterns (P < 0.05) of CpG and non-CpG sites in the cerebellum of offspring. Such variations of methylation and gene expression in the cerebellum of offspring were highly sex-specific, including several genes of the neuronal pathways. These findings demonstrate that alterations in the level of maternal folic acid during gestation can influence methylation and gene expression in the cerebellum of offspring. Such changes in the offspring epigenome may alter neurodevelopment and influence the functional outcome of neurologic and psychiatric diseases. PMID:27199632

  2. Enzymatic Acylation of Anthocyanin Isolated from Black Rice with Methyl Aromatic Acid Ester as Donor: Stability of the Acylated Derivatives.

    PubMed

    Yan, Zheng; Li, Chunyang; Zhang, Lixia; Liu, Qin; Ou, Shiyi; Zeng, Xiaoxiong

    2016-02-10

    The enzymatic acylation of anthocyanin from black rice with aromatic acid methyl esters as acyl donors and Candida antarctica lipase B was carried out under reduced pressure. The highest conversion of 91% was obtained with benzoic acid methyl ester as acyl donor; cyanidin 3-(6″-benzoyl)-glucoside, cyanidin 3-(6″-salicyloyl)-glucoside, and cyanidin 3-(6″-cinnamoyl)-glucoside were successfully synthesized. This is the first report on the enzymatic acylation of anthocyanin from black rice with methyl aromatic esters as acyl donors and lipase as biocatalyst. Furthermore, the acylation with aromatic carboxylic acids enhanced both the thermostability and light resistivity of anthocyanin. In particular, cyanidin 3-(6″-cinnamoyl)-glucoside was the most stable among the three acylated anthocyanins synthesized. PMID:26766135

  3. Site-Directed Mutagenesis of HgcA and HgcB Reveals Amino Acid Residues Important for Mercury Methylation

    PubMed Central

    Smith, Steven D.; Bridou, Romain; Johs, Alexander; Parks, Jerry M.; Elias, Dwayne A.; Hurt, Richard A.; Brown, Steven D.; Podar, Mircea

    2015-01-01

    Methylmercury is a potent neurotoxin that is produced by anaerobic microorganisms from inorganic mercury by a recently discovered pathway. A two-gene cluster, consisting of hgcA and hgcB, encodes two of the proteins essential for this activity. hgcA encodes a corrinoid protein with a strictly conserved cysteine proposed to be the ligand for cobalt in the corrinoid cofactor, whereas hgcB encodes a ferredoxin-like protein thought to be an electron donor to HgcA. Deletion of either gene eliminates mercury methylation by the methylator Desulfovibrio desulfuricans ND132. Here, site-directed mutants of HgcA and HgcB were constructed to determine amino acid residues essential for mercury methylation. Mutations of the strictly conserved residue Cys93 in HgcA, the proposed ligand for the corrinoid cobalt, to Ala or Thr completely abolished the methylation capacity, but a His substitution produced measurable methylmercury. Mutations of conserved amino acids near Cys93 had various impacts on the methylation capacity but showed that the structure of the putative “cap helix” region harboring Cys93 is crucial for methylation function. In the ferredoxin-like protein HgcB, only one of two conserved cysteines found at the C terminus was necessary for methylation, but either cysteine sufficed. An additional, strictly conserved cysteine, Cys73, was also determined to be essential for methylation. This study supports the previously predicted importance of Cys93 in HgcA for methylation of mercury and reveals additional residues in HgcA and HgcB that facilitate the production of this neurotoxin. PMID:25724962

  4. Site-Directed Mutagenesis of HgcA and HgcB Reveals Amino Acid Residues Important for Mercury Methylation

    SciTech Connect

    Smith, Steven D.; Bridou, Romain; Johs, Alexander; Parks, Jerry M.; Elias, Dwayne A.; Hurt, Richard A.; Brown, Steven D.; Podar, Mircea; Wall, Judy D.

    2015-02-27

    Methylmercury is a potent neurotoxin that is produced by anaerobic microorganisms from inorganic mercury by a recently discovered pathway. A two-gene cluster, consisting of hgcA and hgcB, encodes two of the proteins essential for this activity. hgcA encodes a corrinoid protein with a strictly conserved cysteine proposed to be the ligand for cobalt in the corrinoid cofactor, whereas hgcB encodes a ferredoxin-like protein thought to be an electron donor to HgcA. Deletion of either gene eliminates mercury methylation by the methylator Desulfovibrio desulfuricans ND132. Here, site-directed mutants of HgcA and HgcB were constructed to determine amino acid residues essential for mercury methylation. Mutations of the strictly conserved residue Cys93 in HgcA, the proposed ligand for the corrinoid cobalt, to Ala or Thr completely abolished the methylation capacity, but a His substitution produced measurable methylmercury. Mutations of conserved amino acids near Cys93 had various impacts on the methylation capacity but showed that the structure of the putative “cap helix” region harboring Cys93 is crucial for methylation function. In the ferredoxin-like protein HgcB, only one of two conserved cysteines found at the C terminus was necessary for methylation, but either cysteine sufficed. An additional, strictly conserved cysteine, Cys73, was also determined to be essential for methylation. Ultimately, this study supports the previously predicted importance of Cys93 in HgcA for methylation of mercury and reveals additional residues in HgcA and HgcB that facilitate the production of this neurotoxin.

  5. Site-Directed Mutagenesis of HgcA and HgcB Reveals Amino Acid Residues Important for Mercury Methylation

    DOE PAGESBeta

    Smith, Steven D.; Bridou, Romain; Johs, Alexander; Parks, Jerry M.; Elias, Dwayne A.; Hurt, Richard A.; Brown, Steven D.; Podar, Mircea; Wall, Judy D.

    2015-02-27

    Methylmercury is a potent neurotoxin that is produced by anaerobic microorganisms from inorganic mercury by a recently discovered pathway. A two-gene cluster, consisting of hgcA and hgcB, encodes two of the proteins essential for this activity. hgcA encodes a corrinoid protein with a strictly conserved cysteine proposed to be the ligand for cobalt in the corrinoid cofactor, whereas hgcB encodes a ferredoxin-like protein thought to be an electron donor to HgcA. Deletion of either gene eliminates mercury methylation by the methylator Desulfovibrio desulfuricans ND132. Here, site-directed mutants of HgcA and HgcB were constructed to determine amino acid residues essential formore » mercury methylation. Mutations of the strictly conserved residue Cys93 in HgcA, the proposed ligand for the corrinoid cobalt, to Ala or Thr completely abolished the methylation capacity, but a His substitution produced measurable methylmercury. Mutations of conserved amino acids near Cys93 had various impacts on the methylation capacity but showed that the structure of the putative “cap helix” region harboring Cys93 is crucial for methylation function. In the ferredoxin-like protein HgcB, only one of two conserved cysteines found at the C terminus was necessary for methylation, but either cysteine sufficed. An additional, strictly conserved cysteine, Cys73, was also determined to be essential for methylation. Ultimately, this study supports the previously predicted importance of Cys93 in HgcA for methylation of mercury and reveals additional residues in HgcA and HgcB that facilitate the production of this neurotoxin.« less

  6. Methyl jasmonate stimulates biosynthesis of 2-phenylethylamine, phenylacetic acid and 2-phenylethanol in seedlings of common buckwheat.

    PubMed

    Horbowicz, Marcin; Wiczkowski, Wiesław; Sawicki, Tomasz; Szawara-Nowak, Dorota; Sytykiewicz, Hubert; Mitrus, Joanna

    2015-01-01

    Methyl jasmonate has a strong effect on secondary metabolizm in plants, by stimulating the biosynthesis a number of phenolic compounds and alkaloids. Common buckwheat (Fagopyrum esculentum Moench) is an important source of biologically active compounds. This research focuses on the detection and quantification of 2-phenylethylamine and its possible metabolites in the cotyledons, hypocotyl and roots of common buckwheat seedlings treated with methyl jasmonate. In cotyledons of buckwheat sprouts, only traces of 2-phenylethylamine were found, while in the hypocotyl and roots its concentration was about 150 and 1000-times higher, respectively. Treatment with methyl jasmonate resulted in a 4-fold increase of the 2-phenylethylamine level in the cotyledons of 7-day buckwheat seedlings, and an 11-fold and 5-fold increase in hypocotyl and roots, respectively. Methyl jasmonate treatment led also to about 4-fold increase of phenylacetic acid content in all examined seedling organs, but did not affect the 2-phenylethanol level in cotyledons, and slightly enhanced in hypocotyl and roots. It has been suggested that 2-phenylethylamine is a substrate for the biosynthesis of phenylacetic acid and 2-phenylethanol, as well as cinnamoyl 2-phenethylamide. In organs of buckwheat seedling treated with methyl jasmonate, higher amounts of aromatic amino acid transaminase mRNA were found. The enzyme can be involved in the synthesis of phenylpyruvic acid, but the presence of this compound could not be confirmed in any of the examined organs of common buckwheat seedling. PMID:25856561

  7. Methyl jasmonate, yeast extract and sucrose stimulate phenolic acids accumulation in Eryngium planum L. shoot cultures.

    PubMed

    Kikowska, Małgorzata; Kędziora, Izabela; Krawczyk, Aldona; Thiem, Barbara

    2015-01-01

    Eryngium planum L. has been reported as a medicinal plant used in traditional medicine in Europe. The tissue cultures may be an alternative source of the biomass rich in desired bioactive compounds. The purpose of this study was to investigate the influence of the biotechnological techniques on the selected phenolic acids accumulation in the agitated shoot cultures of E. planum. Qualitative and quantitative analyses of those compounds in 50% aqueous - methanolic extracts from the biomass were conducted by applying the HPLC method. Methyl jasmonate (MeJA), yeast extract (YE) and sucrose (Suc) stimulated accumulation of the phenolic acids: rosmarinic (RA), chlorogenic (CGA) and caffeic (CA) in in vitro shoot cultures. Cultivation of shoots in liquid MS media supplemented with 1.0 mg L(-1) 6-benzyladenine and 0.1 mg L(-1) indole-3-acetic acid in the presence of 100 µM MeJA for 48h was an optimum condition of elicitation and resulted in approximately 4.5-fold increased content of RA + CGA + CA in plant material compared to the control (19.795 mg g(-1) DW, 4.36 mg g(-1) DW, respectively). The results provide the first evidence that the selected phenolic acids can be synthesized in elicited shoot cultures of flat sea holly in higher amount than in untreated shoots. PMID:25856557

  8. Rapid Photodegradation of Methyl Orange (MO) Assisted with Cu(II) and Tartaric Acid

    PubMed Central

    Guo, Jing; Chen, Xue; Shi, Ying; Lan, Yeqing; Qin, Chao

    2015-01-01

    Cu(II) and organic carboxylic acids, existing extensively in soil and aquatic environments, can form complexes that may play an important role in the photodegradation of organic contaminants. In this paper, the catalytic role of Cu(II) in the removal of methyl orange (MO) in the presence of tartaric acid with light was investigated through batch experiments. The results demonstrate that the introduction of Cu(II) could markedly enhance the photodegradation of MO. In addition, high initial concentrations of Cu(II) and tartaric acid benefited the decomposition of MO. The most rapid removal of MO assisted by Cu(II) was achieved at pH 3. The formation of Cu(II)-tartaric acid complexes was assumed to be the key factor, generating hydroxyl radicals (•OH) and other oxidizing free radicals under irradiation through a ligand-to-metal charge-transfer pathway that was responsible for the efficient degradation of MO. Some intermediates in the reaction system were also detected to support this reaction mechanism. PMID:26241043

  9. DNA Methylation Perturbations in Genes Involved in Polyunsaturated Fatty Acid Biosynthesis Associated with Depression and Suicide Risk

    PubMed Central

    Haghighi, Fatemeh; Galfalvy, Hanga; Chen, Sean; Huang, Yung-yu; Cooper, Thomas B.; Burke, Ainsley K.; Oquendo, Maria A.; Mann, J. John; Sublette, M. Elizabeth

    2015-01-01

    Polyunsaturated fatty acid (PUFA) status has been associated with neuropsychiatric disorders, including depression and risk of suicide. Long-chain PUFAs (LC-PUFAs) are obtained in the diet or produced by sequential desaturation and elongation of shorter-chain precursor fatty acids linoleic acid (LA, 18:2n-6) and α-linolenic acid (ALA, 18:3n-3). We compared DNA methylation patterns in genes involved in LC-PUFA biosynthesis in major depressive disorder (MDD) with (n = 22) and without (n = 39) history of suicide attempt, and age- and sex-matched healthy volunteers (n = 59). Plasma levels of selected PUFAs along the LC-PUFA biosynthesis pathway were determined by transesterification and gas chromatography. CpG methylation levels for the main human LC-PUFA biosynthetic genes, fatty acid desaturases 1 (Fads1) and 2 (Fads2), and elongation of very long-chain fatty acids protein 5 (Elovl5), were assayed by bisulfite pyrosequencing. Associations between PUFA levels and diagnosis or suicide attempt status did not survive correction for multiple testing. However, MDD diagnosis and suicide attempts were significantly associated with DNA methylation in Elovl5 gene regulatory regions. Also the relative roles of PUFA levels and DNA methylation with respect to diagnostic and suicide attempt status were determined by least absolute shrinkage and selection operator logistic regression analyses. We found that PUFA associations with suicide attempt status were explained by effects of Elovl5 DNA methylation within the regulatory regions. The observed link between plasma PUFA levels, DNA methylation, and suicide risk may have implications for modulation of disease-associated epigenetic marks by nutritional intervention. PMID:25972837

  10. DNA methylation perturbations in genes involved in polyunsaturated Fatty Acid biosynthesis associated with depression and suicide risk.

    PubMed

    Haghighi, Fatemeh; Galfalvy, Hanga; Chen, Sean; Huang, Yung-Yu; Cooper, Thomas B; Burke, Ainsley K; Oquendo, Maria A; Mann, J John; Sublette, M Elizabeth

    2015-01-01

    Polyunsaturated fatty acid (PUFA) status has been associated with neuropsychiatric disorders, including depression and risk of suicide. Long-chain PUFAs (LC-PUFAs) are obtained in the diet or produced by sequential desaturation and elongation of shorter-chain precursor fatty acids linoleic acid (LA, 18:2n-6) and α-linolenic acid (ALA, 18:3n-3). We compared DNA methylation patterns in genes involved in LC-PUFA biosynthesis in major depressive disorder (MDD) with (n = 22) and without (n = 39) history of suicide attempt, and age- and sex-matched healthy volunteers (n = 59). Plasma levels of selected PUFAs along the LC-PUFA biosynthesis pathway were determined by transesterification and gas chromatography. CpG methylation levels for the main human LC-PUFA biosynthetic genes, fatty acid desaturases 1 (Fads1) and 2 (Fads2), and elongation of very long-chain fatty acids protein 5 (Elovl5), were assayed by bisulfite pyrosequencing. Associations between PUFA levels and diagnosis or suicide attempt status did not survive correction for multiple testing. However, MDD diagnosis and suicide attempts were significantly associated with DNA methylation in Elovl5 gene regulatory regions. Also the relative roles of PUFA levels and DNA methylation with respect to diagnostic and suicide attempt status were determined by least absolute shrinkage and selection operator logistic regression analyses. We found that PUFA associations with suicide attempt status were explained by effects of Elovl5 DNA methylation within the regulatory regions. The observed link between plasma PUFA levels, DNA methylation, and suicide risk may have implications for modulation of disease-associated epigenetic marks by nutritional intervention. PMID:25972837

  11. An improved synthesis for the (Z)-14-methyl-9-pentadecenoic acid and its topoisomerase I inhibitory activity

    PubMed Central

    Carballeira, Néstor M.; Sanabria, David; Oyola, Delise

    2006-01-01

    An improved synthesis for the (Z)-14-methyl-9-pentadecenoic acid was developed based on the appropriate use of (trimethylsilyl)acetylene as the key reagent in the synthesis. The reported synthesis started with commercially available 8-bromo-1-octanol and furnished the desired acid in seven steps and in a 16% overall yield, a significant improvement over the previous reported synthesis for this fatty acid. The synthesis reported herein afforded sufficient amounts to study the acid topoisomerase I inhibitory potential and it was found that the title acid inhibits the human placenta DNA topoisomerase I enzyme at concentrations of 500 μM. PMID:17680032

  12. Methyl esterification of 15-hydroperoxyabietic acid does not affect the patch-test result in colophonium allergic patients.

    PubMed

    Karlberg, Ann-Therese; Bråred-Christensson, Johanna; Börje, Anna; Harambasic, Elma; Matura, Mihàly

    2007-06-01

    Colophonium (gum rosin) consists of numerous compounds. We have previously shown that abietic acid (Fig. 1), the major compound in gum rosin, is oxidized to strong contact allergens at air exposure (1). The most potent allergen identified is 15-hydroperoxyabietic acid (15-HPA, Fig. 1), which was isolated as its methyl ester (Fig. 1) and used for patch testing (2, 3). The aim of this study was to confirm the previous postulate that methyl esterification of the carboxyl group in 15-HPA does not affect the allergenic activity. PMID:17577378

  13. The plastidial retrograde signal methyl erythritol cyclopyrophosphate is a regulator of salicylic acid and jasmonic acid crosstalk

    PubMed Central

    Lemos, Mark; Xiao, Yanmei; Bjornson, Marta; Wang, Jin-zheng; Hicks, Derrick; de Souza, Amancio; Wang, Chang-Quan; Yang, Panyu; Ma, Shisong; Dinesh-Kumar, Savithramma; Dehesh, Katayoon

    2016-01-01

    The exquisite harmony between hormones and their corresponding signaling pathways is central to prioritizing plant responses to simultaneous and/or successive environmental trepidations. The crosstalk between jasmonic acid (JA) and salicylic acid (SA) is an established effective mechanism that optimizes and tailors plant adaptive responses. However, the underlying regulatory modules of this crosstalk are largely unknown. Global transcriptomic analyses of mutant plants (ceh1) with elevated levels of the stress-induced plastidial retrograde signaling metabolite 2-C-methyl-D-erythritol cyclopyrophosphate (MEcPP) revealed robustly induced JA marker genes, expected to be suppressed by the presence of constitutively high SA levels in the mutant background. Analyses of a range of genotypes with varying SA and MEcPP levels established the selective role of MEcPP-mediated signal(s) in induction of JA-responsive genes in the presence of elevated SA. Metabolic profiling revealed the presence of high levels of the JA precursor 12-oxo-phytodienoic acid (OPDA), but near wild type levels of JA in the ceh1 mutant plants. Analyses of coronatine-insensitive 1 (coi1)/ceh1 double mutant plants confirmed that the MEcPP-mediated induction is JA receptor COI1 dependent, potentially through elevated OPDA. These findings identify MEcPP as a previously unrecognized central regulatory module that induces JA-responsive genes in the presence of high SA, thereby staging a multifaceted plant response within the environmental context. PMID:26733689

  14. Photoinduced amino-imino tautomerization reaction in 2-aminopyrimidine and its methyl derivatives with acetic acid.

    PubMed

    Kitamura, Teruyoshi; Hikita, Atushi; Ishikawa, Hironori; Fujimoto, Akira

    2005-12-01

    The electronic absorption and fluorescence spectra of 2-aminopyrimidine (2APM), 2-amino-4-methylpyrimidine (2A4MPM), and 2-amino-4,6-dimethylpyrimidine (2ADMPM) with acetic acid (AcOH) were measured in isooctane (2,2,4-trimethylpentane) at room temperature. From the absorption spectra, a hydrogen-bonded complex formation of the 2APM/AcOH, 2A4MPM/AcOH, and 2ADMPM/AcOH systems was recognized in isooctane. The enthalpy changes (-DeltaH) for the complex formation were estimated to be ca. 41.2-45.1 kJ mol-1 and increased in proportion to the numbers of the methyl group introduced into the 2APM. The -DeltaH values refer to the formation of the hydrogen-bonded 1:1 complex between the ring nitrogen atom and NH2 group of the aminopyrimidine and the OH and CO groups of AcOH, respectively. In the 2A4MPM/AcOH double hydrogen-bonded complex the OH group of AcOH is thought to be linked to the ring nitrogen at the 1-postion of 2A4MPM. The fluorescence spectral results indicate that the double proton transfer reaction takes place during the excited state, and gives rise to an imino-tautomer vibration emission, from analogy with the fluorescences of 1-methyl-2(1H)-pyrimidinimine (MPMI), 1,4-dimethyl-2(1H)-pyrimidinimine (DMPMI), and 1,4,6-trimethyl-2(1H)-pyrimidinimine (TMPMI). The fluorescence quantum yields of the imino-tautomers also increased in proportion to the numbers of the methyl group introduced into the 2APM. PMID:15978861

  15. Photoinduced amino-imino tautomerization reaction in 2-aminopyrimidine and its methyl derivatives with acetic acid

    NASA Astrophysics Data System (ADS)

    Kitamura, Teruyoshi; Hikita, Atushi; Ishikawa, Hironori; Fujimoto, Akira

    2005-12-01

    The electronic absorption and fluorescence spectra of 2-aminopyrimidine (2APM), 2-amino-4-methylpyrimidine (2A4MPM), and 2-amino-4,6-dimethylpyrimidine (2ADMPM) with acetic acid (AcOH) were measured in isooctane (2,2,4-trimethylpentane) at room temperature. From the absorption spectra, a hydrogen-bonded complex formation of the 2APM/AcOH, 2A4MPM/AcOH, and 2ADMPM/AcOH systems was recognized in isooctane. The enthalpy changes (-Δ H) for the complex formation were estimated to be ca. 41.2-45.1 kJ mol -1 and increased in proportion to the numbers of the methyl group introduced into the 2APM. The -Δ H values refer to the formation of the hydrogen-bonded 1:1 complex between the ring nitrogen atom and NH 2 group of the aminopyrimidine and the OH and C dbnd O groups of AcOH, respectively. In the 2A4MPM/AcOH double hydrogen-bonded complex the OH group of AcOH is thought to be linked to the ring nitrogen at the 1-postion of 2A4MPM. The fluorescence spectral results indicate that the double proton transfer reaction takes place during the excited state, and gives rise to an imino-tautomer vibration emission, from analogy with the fluorescences of 1-methyl-2(1H)-pyrimidinimine (MPMI), 1,4-dimethyl-2(1H)-pyrimidinimine (DMPMI), and 1,4,6-trimethyl-2(1H)-pyrimidinimine (TMPMI). The fluorescence quantum yields of the imino-tautomers also increased in proportion to the numbers of the methyl group introduced into the 2APM.

  16. Simultaneous determination of salicylic, 3-methyl salicylic, 4-methyl salicylic, acetylsalicylic and benzoic acids in fruit, vegetables and derived beverages by SPME-LC-UV/DAD.

    PubMed

    Aresta, Antonella; Zambonin, Carlo

    2016-03-20

    Salicylic and benzoic acid are phenolic acids occurring in plant cells, thus they can be present in fruit and vegetables at various levels. They possess anti-inflammatory and antimicrobial properties, however they may induce symptoms and health problems in a small percentage of the population. Therefore, a low phenolic acid diet may be of clinical benefit to such individuals. In order to achieve this goal, the concentration of these substances in different food and beverages should be assessed. The present work describes for the first time a new method, based on solid phase microextraction (polydimethylsiloxane-divinylbenzene fiber) coupled to liquid chromatography with UV diode array detection, for the simultaneous determination of salicylic acid, 3-methyl salicylic acid, 4-methyl salicylic acid, acetylsalicylic acid and benzoic acid in selected fruit, vegetables and beverages. All the aspects influencing fiber adsorption (time, temperature, pH, salt addition) and desorption (desorption and injection time, desorption solvent mixture composition) of the analytes have been investigated. An isocratic separation was performed using an acetonitrile-phosphate buffer (pH 2.8; 2 mM) mixture (70:30, v/v) as the mobile phase. The estimated LOD and LOQ values (μg/mL) were in the range 0.002-0.028 and 0.007-0.095. The within-day and day-to-day precision values (RSD%) were between 4.7-6.1 and 6.6-9.4, respectively. The method has been successfully applied to the analysis of fava beans, blueberries, kiwi, tangerines, lemons, oranges and fruit juice (lemon and blueberry) samples. The major advantage of the method is that it only requires simple homogenization and/or centrifugation and dilution steps prior to SPME and injection in the LC system. PMID:26775020

  17. The solvent extraction of Americium(III) by 2,6-bis[(diphenylphosphino)-methyl]pyridine N,P,P` trioxide from nitric acid and hydrochloric acid solutions

    SciTech Connect

    Bond, E.M.; Engelhardt, U.; Deere, T.P.; Rapko, B.M.; Paine, R.T.

    1997-12-31

    The liquid/liquid extractions of Am(III) from nitric acid and hydrochloric acid solutions with chloroform solutions of 2,6-bis[(diphenylphosphino)methyl]pyridine N,P,P{prime} trioxide will be described. Americium(III) extracts well from high concentration nitric acid solutions (D>3000 at 6M nitric acid) and can be back extracted from the organic phase at 0.01M Nitric Acid. Americium(III) exhibits modest extraction from hydrochloric acid solutions (D=2.2 at 5M hydrochloric acid) and can be back extracted from the organic phase at 0.1M hydrochloric acid. The ligand dependency data suggest that two ligand molecules are coordinated to americium in the nitric acid system and three ligand molecules are coordinated to the americium in the hydrochloric acid system.

  18. Synthesis of both enantiomers of 12-methyl-13-tridecanolide and 14-methyl-15-pentadecanolide (muscolide).

    PubMed

    Noda, Yoshihiro; Mamiya, Natsuki; Kashin, Hitoshi

    2013-07-01

    Both enantiomers of 12-methyl-13-tridecanolide{(R)-(+)-1, (S)-(-)-1} and 14-methyl-15-pentadecanolide (muscolide) {(R)-(+)-2, (S)-(-)-2} were synthesized from either (S)-(+)- or (R)-(-)-3-bromo-2-methyl-1-propanol 8 as a chiral building block. PMID:23980425

  19. 40 CFR 721.4486 - Propanoic acid, 2-methyl-, (1R,2R,4R)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl ester, rel-.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ...,4R)-1,7,7-trimethylbicyclo hept-2-yl ester, rel-. (a) Chemical substance and significant new uses...)-1,7,7-trimethylbicyclo hept-2-yl ester, rel-. 721.4486 Section 721.4486 Protection of Environment...,7-trimethylbicyclo hept-2-yl ester, rel- (PMNs P-98-0497 and P-98-0509; CAS No. 85586-67-0)...

  20. Determination of enthalpy of formation of methyl and ethyl esters of fatty acids.

    PubMed

    Lapuerta, Magín; Rodríguez-Fernández, José; Oliva, Fermín

    2010-02-01

    Biofuels composed by fatty acid methyl esters are widely used as partly substituting fuels for diesel fossil fuels. Additionally, it is expected that the diesel biofuel norms will be extended to ethyl esters produced from bioethanol in the upcoming years. A precise knowledge of the standard enthalpy of formation is necessary for the calculation of some parameters useful for the analysis of the combustion process and emissions of a diesel engine operating with different fuels, such as the heating value, the adiabatic flame temperature or the kinetic mechanisms. However, experimental data for this property are scarce, and only available for short-chain, saturated methyl esters. In this work, four estimation methods for the calculation of the enthalpy of formation are examined and compared. Three of them are simple methods based on groups or bonds contribution, and another one is a computational method (with Gaussian 03 software). After presenting the implementation rules for each of them, conclusions are stated based on the results attained. Gaussian and Benson-Groups methods seem to be more accurate in predicting the actual values of the enthalpy of formation, both methods considering the separation between double bonds and the edge effects in the molecule. However, only the Gaussian method considers the effect of the position of the double bond in the molecule for all the unsaturated esters. PMID:19917272

  1. Intraparticle diffusion limitations in the hydrogenation of monounsaturated edible oils and their fatty acid methyl esters

    SciTech Connect

    Jonker, G.H.; Veldsink, J.W.; Beenackers, A.A.C.M.

    1998-12-01

    Intraparticle diffusion limitation in the hydrogenation and isomerization of fatty acid methyl esters (FAMEs) and edible oils (triacylglycerol, TAG) in porous nickel catalyst was investigated both under reactive and under inert conditions. Under reactive conditions, the diffusion coefficients were determined from the best fits of the model simulations applying the intrinsic reacting kinetics of monounsaturated FAME hydrogenation to experiments under diffusion limited conditions. Due to the absence of reaction (hydrogenation of double bonds), the obtained effective H{sub z} diffusion coefficient (D{sub e}) with the HPLC technique is volume averaged and thereby determined by the larger intercrystalline pores (<30% of the total pore volume) only. Moreover, D{sub e} measured under reaction conditions reflected the influence of the micropores, resulting in a 10-fold lower value.

  2. Preparation of ultrafine poly(methyl methacrylate-co-methacrylic acid) biodegradable nanoparticles loaded with ibuprofen.

    PubMed

    Saade, Hened; Diaz de León-Gómez, Ramón; Enríquez-Medrano, Francisco Javier; López, Raúl Guillermo

    2016-08-01

    Ibuprofen-loaded polymeric particles with around 9.2 nm in mean diameter, as determined by electron microscopy, dispersed in an aqueous media containing up to 12.8% solids were prepared by semicontinuous heterophase polymerization. The polymeric material is a (2/1 mol/mol) methyl methacrylate-co-methacrylic acid copolymer similar to Eudragit S100, deemed safe for human consumption and used in the manufacturing of drug-loaded pills as well as micro- and nanoparticles. The loading efficiency was 100%, attaining around 10-12% in drug content. Release studies showed that the drug is released from the nanoparticles at a slower rate than that in the case of free IB. Given their size as well as the pH values required for their dissolution, it is believed that this type of particles could be used as a basis for preparing nanosystems loaded with a variety of drugs. PMID:27126476

  3. Identification of jasmonic acid and its methyl ester as gum-inducing factors in tulips.

    PubMed

    Skrzypek, Edyta; Miyamoto, Kensuke; Saniewski, Marian; Ueda, Junichi

    2005-02-01

    The purpose of this study was to identify endogenous factors that induce gummosis and to show their role in gummosis in tulip (Tulipa gesneriana L. cv. Apeldoorn) stems. Using procedures to detect endogenous factors that induce gum in the stem of tulips, jasmonic acid (JA) and methyl jasmonate (JA-Me) were successfully identified using gas-liquid chromatography-mass spectrometry. Total amounts of JA and JA-Me designated as jasmonates in tulip stems were also estimated at about 70-80 ng/g fresh weight, using deuterium-labeled jasmonates as internal standards. The application of JA and JA-Me as lanolin pastes substantially induced gums in tulip stems with ethylene production. The application of ethephon, an ethylene-generating compound, however, induced no gummosis although it slightly affected jasmonate content in tulip stems. These results strongly suggest that JA and JA-Me are endogenous factors that induce gummosis in tulip stems. PMID:15654503

  4. Determination of monomethylarsonous acid, a key arsenic methylation intermediate, in human urine.

    PubMed Central

    Le, X C; Ma, M; Cullen, W R; Aposhian, H V; Lu, X; Zheng, B

    2000-01-01

    In this study we report on the finding of monomethylarsonous acid [MMA(III)] in human urine. This newly identified arsenic species is a key intermediate in the metabolic pathway of arsenic biomethylation, which involves stepwise reduction of pentavalent to trivalent arsenic species followed by oxidative addition of a methyl group. Arsenic speciation was carried out using ion-pair chromatographic separation of arsenic compounds with hydride generation atomic fluorescence spectrometry detection. Speciation of the inorganic arsenite [As(III)], inorganic arsenate [As(V)], monomethylarsonic acid [MMA(V)], dimethylarsinic acid [DMA(V)], and MMA(III) in a urine sample was complete in 5 min. Urine samples collected from humans before and after a single oral administration of 300 mg sodium 2,3-dimercapto-1-propane sulfonate (DMPS) were analyzed for arsenic species. MMA(III) was found in 51 out of 123 urine samples collected from 41 people in inner Mongolia 0-6 hr after the administration of DMPS. MMA(III )in urine samples did not arise from the reduction of MMA(V) by DMPS. DMPS probably assisted the release of MMA(III) that was formed in the body. Along with the presence of MMA(III), there was an increase in the relative concentration of MMA(V) and a decrease in DMA(V) in the urine samples collected after the DMPS ingestion. PMID:11102289

  5. Microscale analysis of amino acids using gas chromatography-mass spectrometry after methyl chloroformate derivatization.

    PubMed

    Chen, Wen-Ping; Yang, Xiao-Yuan; Hegeman, Adrian D; Gray, William M; Cohen, Jerry D

    2010-08-15

    To conduct studies of stable isotope incorporation and dilution in growing plants, a rapid microscale method for determination of amino acid profiles from minute amounts of plant samples was developed. The method involves solid-phase ion exchange followed by derivatization and analysis by gas chromatography-mass spectrometry (GC-MS). The procedure allowed the eluent to be derivatized directly with methyl chloroformate without sample lyophilization or other evaporation procedures. Sample extraction and derivatization required only ca. 30min and quantification of the 19 amino acids eluted from the cation exchange solid-phase extraction step from a single cotyledon (0.4mg fresh weight) or three etiolated 7-day-old Arabidopsis seedlings (0.1mg fresh weight) was easily accomplished in the selected ion monitoring mode. This method was especially useful for monitoring mass isotopic distribution of amino acids as illustrated by Arabidopsis seedlings that had been labeled with deuterium oxide and (15)N salts. Sample preparation was facile, rapid, economical, and the method is easily modified for integration into robotic systems for analysis with large numbers of samples. PMID:20663719

  6. Influence of fatty acid methyl esters from hydroxylated vegetable oils on diesel fuel lubricity.

    PubMed

    Goodrum, John W; Geller, Daniel P

    2005-05-01

    Current and future regulations on the sulfur content of diesel fuel have led to a decrease in lubricity of these fuels. This decreased lubricity poses a significant problem as it may lead to wear and damage of diesel engines, primarily fuel injection systems. Vegetable oil based diesel fuel substitutes (biodiesel) have been shown to be clean and effective and may increase overall lubricity when added to diesel fuel at nominally low levels. Previous studies on castor oil suggest that its uniquely high level of the hydroxy fatty acid ricinoleic acid may impart increased lubricity to the oil and its derivatives as compared to other vegetable oils. Likewise, the developing oilseed Lesquerella may also increase diesel lubricity through its unique hydroxy fatty acid composition. This study examines the effect of castor and Lesquerella oil esters on the lubricity of diesel fuel using the High-Frequency Reciprocating Rig (HFRR) test and compares these results to those for the commercial vegetable oil derivatives soybean and rapeseed methyl esters. PMID:15607199

  7. Inactivation of lambda phage infectivity and lambda deoxyribonucleic acid transfection by N-methyl-isatin beta-thiosemicarbazone-copper complexes.

    PubMed

    Levinson, W; Helling, R

    1976-01-01

    The infectivity of intact lambda phage and transfection by lambda deoxyribonucleic acid were inactivated by exposure to the copper complexes of N-methyl-isatin beta-thiosemicarbazone, thiosemicarbazide, and semicarbazide, but not methyl-isatin. No inactivation was observed when these compounds were used in the absence of copper sulfate. This confirms our previous observation that the activity of N-methyl-isatin beta-thiosemicarbazone is mediated by its thiosemicarbazone moiety and that the presence of copper is required for action. This represents the first time, to our knowledge, that semicarbazide has been found to possess antiviral activity. It is clear that these compounds act directly on deoxyribonucleic acid; whether the compounds also act on proteins has not been determined. PMID:769669

  8. Improvement of holographic thermal stability in phenanthrenequinone-doped poly(methyl methacrylate-co-methacrylic acid) photopolymer

    NASA Astrophysics Data System (ADS)

    Yu, Dan; Liu, Hongpeng; Wang, Heng; Wang, Jian; Jiang, Yongyuan; Sun, Xiudong

    2011-08-01

    Experimental studies of holographic thermal stability in phenanthrenequinone (PQ)-doped poly(methyl methacrylate-co-methacrylic acid) [P(MMA-co-MAA)] photopolymers are presented. A possibility to improve the thermal stability of holograms is demonstrated by doping methacrylic acid (MAA) into the poly(methyl methacrylate) (PMMA) polymer matrix. MAA as a copolymerization monomer can form a more stable polymer matrix with methyl methacrylate (MMA) monomer and increase average molecular weight of photoproducts, which finally depress the diffusion of photoproduct. The optimized MAA concentration copolymerized into P(MMA-co-MAA) polymer matrix can bring nearly a month's lifetime of gratings, which is obviously an improvement over the usual PQ-PMMA material under thermal treatment.

  9. Stereospecific enzymatic transformation of alpha-ketoglutarate to (2S,3R)-3-methyl glutamate during acidic lipopeptide biosynthesis.

    PubMed

    Mahlert, Christoph; Kopp, Florian; Thirlway, Jenny; Micklefield, Jason; Marahiel, Mohamed A

    2007-10-01

    The acidic lipopeptides, including the calcium-dependent antibiotics (CDA), daptomycin, and A54145, are important macrocyclic peptide natural products produced by Streptomyces species. All three compounds contain a 3-methyl glutamate (3-MeGlu) as the penultimate C-terminal residue, which is important for bioactivity. Here, biochemical in vitro reconstitution of the 3-MeGlu biosynthetic pathway is presented, using exclusively enzymes from the CDA producer Streptomyces coelicolor. It is shown that the predicted 3-MeGlu methyltransferase GlmT and its homologues DptI from the daptomycin producer Streptomyces roseosporus and LptI from the A54145 producer Streptomyces fradiae do not methylate free glutamic acid, PCP-bound glutamate, or Glu-containing CDA in vitro. Instead, GlmT, DptI, and LptI are S-adenosyl methionine (SAM)-dependent alpha-ketoglutarate methyltransferases that catalyze the stereospecific methylation of alpha-ketoglutarate (alphaKG) leading to (3R)-3-methyl-2-oxoglutarate. Subsequent enzyme screening identified the branched chain amino acid transaminase IlvE (SCO5523) as an efficient catalyst for the transformation of (3R)-3-methyl-2-oxoglutarate into (2S,3R)-3-MeGlu. Comparison of reversed-phase HPLC retention time of dabsylated 3-MeGlu generated by the coupled enzymatic reaction with dabsylated synthetic standards confirmed complete stereocontrol during enzymatic catalysis. This stereospecific two-step conversion of alphaKG to (2S,3R)-3-MeGlu completes our understanding of the biosynthesis and incorporation of beta-methylated amino acids into the nonribosomal lipopeptides. Finally, understanding this pathway may provide new possibilities for the production of modified peptides in engineered microbes. PMID:17784761

  10. Determination of Total Lipids as Fatty Acid Methyl Esters (FAME) by in situ Transesterification: Laboratory Analytical Procedure (LAP)

    SciTech Connect

    Van Wychen, S.; Laurens, L. M. L.

    2013-12-01

    This procedure is based on a whole biomass transesterification of lipids to fatty acid methyl esters to represent an accurate reflection of the potential of microalgal biofuels. Lipids are present in many forms and play various roles within an algal cell, from cell membrane phospholipids to energy stored as triacylglycerols.

  11. 40 CFR 721.1725 - Benzoic acid, 3,3′-methyl-enebis [6 amino-, di-2-propenyl ester.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... amino-, di-2-propenyl ester. 721.1725 Section 721.1725 Protection of Environment ENVIRONMENTAL... Significant New Uses for Specific Chemical Substances § 721.1725 Benzoic acid, 3,3′-methyl-enebis [6 amino-, di-2-propenyl ester. (a) Chemical substance and significant new uses subject to reporting. (1)...

  12. Properties of amylose-oleic acid inclusion complexes from corn starch grafted with poly(methyl acrylate)

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Corn starch granules have been previously investigated as fillers in polymers. In this study, much smaller particles in the form of spherulites produced by steam jet-cooking high-amylose corn starch and oleic acid to form amylose inclusion complexes were graft polymerized with methyl acrylate, both ...

  13. Structure-function properties of amylose-oleic acid inclusion complexes grafted with poly(methyl acrylate)

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Spherulites, produced by steam jet-cooking high-amylose starch and oleic acid, were grafted with methyl acrylate, both before and after removal of un-complexed amylopectin. For comparison, granular high-amylose corn starch was graft polymerized in a similar manner. The amount of grafted and ungrafte...

  14. 40 CFR 721.1725 - Benzoic acid, 3,3′-methyl-enebis [6 amino-, di-2-propenyl ester.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... amino-, di-2-propenyl ester. 721.1725 Section 721.1725 Protection of Environment ENVIRONMENTAL... Significant New Uses for Specific Chemical Substances § 721.1725 Benzoic acid, 3,3′-methyl-enebis [6 amino-, di-2-propenyl ester. (a) Chemical substance and significant new uses subject to reporting. (1)...

  15. Evaluation of Peanut Fatty Acid Methyl Ester Sprays, Combustion, and Emissions, for Use in an Indirect Injection Diesel Engine

    Technology Transfer Automated Retrieval System (TEKTRAN)

    The paper provides an analysis of 100% peanut fatty acid methyl esters (FAMEs) and peanut FAME/ULSD#2 blends (P20, P35, and P50) in an indirect injection (IDI) diesel engine (for auxiliary power unit applications) in comparison to ultralow sulfur diesel no. 2 (ULSD#2) at various speeds and 100% load...

  16. Preparation of fatty acid methyl esters from hazelnut, high-oleic peanut and walnut oils and evaluation as biodiesel

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Hazelnut, walnut and high-oleic peanut oils were converted into fatty acid methyl esters using catalytic sodium methoxide and evaluated as potential biodiesel fuels. These feedstocks were of interest due to their adaptability to marginal lands and their lipid production potentials (780-1780 L ha-1 y...

  17. Fatty Acid Methyl Ester Profiles for Characterization of Glomalean Fungi and Their Endomycorrhizae

    PubMed Central

    Graham, J. H.; Hodge, N. C.; Morton, J. B.

    1995-01-01

    Arbuscule-forming fungi in the order Glomales form obligate endomycorrhizal associations with plants that make them difficult to quantify, and taxonomy of the group is only beginning to be objectively understood. Fatty acid methyl ester (FAME) profiles were analyzed to assess the diversity and quantity of fatty acids in 53 isolates of 24 glomalean species. Spores and endomycorrhizal roots of sudan grass (Sorghum sudanense) and the citrus rootstock Carrizo citrange (Poncirus trifoliata x Citrus sinensis) were examined. Spores yielded reproducible FAME profiles from replicate spore collections extracted from soil pot cultures despite being grown in association with a host plant and with contaminating microorganisms present. Unweighted pair group analysis revealed relatively tight clusters of groups at the intraspecific, specific, and generic levels; however, lipid profiles at the family level were convergent. Thus, FAME profile comparisons provided a robust measure of similarity below the family level. FAME profiles in sudan grass roots containing vesicles and/or spores of Glomus intraradices were more similar to spore profiles than to profiles from nonmycorrhizal roots. The FAME profiles for Gigaspora species, which do not form vesicles or spores in roots, were less distinct from nonmycorrhizal roots. G. intraradices and G. rosea produced fatty acids in roots that were distinguishable from each other as well as from the host root. Production in citrus roots of the fatty acid 16:1(inf(omega)5) cis by two Glomus species was correlated with the development of mycorrhizal colonization as measured by clearing and staining procedures and by estimates of total incidence and vesicle intensity. FAME analysis of roots not only provided a measure of colonization development but also served as an index of carbon allocated to intraradical fungal growth and lipid storage. PMID:16534923

  18. Fatty acid synthase methylation levels in adipose tissue: effects of an obesogenic diet and phenolic compounds

    Technology Transfer Automated Retrieval System (TEKTRAN)

    DNA methylation is an epigenetic mechanism that can inhibit gene transcription. The aim of this study was to assess changes induced by an obesogenic diet in the methylation profile of genes involved in adipose tissue triacylglycerol metabolism, and to determine whether this methylation pattern can b...

  19. MicroRNA Mediates DNA De-methylation Events Triggered By Retinoic Acid During Neuroblastoma Cell Differentiation

    PubMed Central

    Das, Sudipto; Foley, Niamh; Bryan, Kenneth; Watters, Karen M; Bray, Isabella; Murphy, Derek M; Buckley, Patrick G; Stallings, Raymond L

    2010-01-01

    Neuroblastoma is an often fatal pediatric cancer arising from precursor cells of the sympathetic nervous system. 13-Cis retinoic acid is included in the treatment regime for patients with high-risk disease, and a similar derivative, all-trans retinoic acid (ATRA) causes neuroblastoma cell lines to undergo differentiation. The molecular signaling pathways involved with ATRA induced differentiation are complex, and the role that DNA methylation changes might play are unknown. The purpose of this study was to evaluate the genome-wide effects of ATRA on DNA methylation using methylated DNA immunoprecipitation applied to microarrays representing all known promoter and CpG islands. 402 gene promoters became demethylated, while 88 were hypermethylated post-ATRA. mRNA expression microarrays revealed that 82 of the demethylated genes were over-expressed by >2 fold, while 13 of the hyper methylated genes were under-expressed. Gene ontology analysis indicated that de-methylated and re-expressed genes were enriched for signal transduction pathways, including NOS1, which is required for neural cell differentiation. As a potential mechanism for the DNA methylation changes, we demonstrate the down-regulation of methyltransferases, DNMT1 and DNMT3B, along with the up-regulation of endogenous microRNAs targeting them. Ectopic over-expression of miR-152, targeting DNMT1, also negatively impacted cell invasiveness and anchorage independent growth, contributing in part to the differentiated phenotype. We conclude that functionally important, miRNA-mediated DNA de-methylation changes contribute to the process of ATRA induced differentiation resulting in the activation of NOS1, a critical determinant of neural cell differentiation. Our findings illustrate the plasticity and dynamic nature of the epigenome during cancer cell differentiation. PMID:20841484

  20. Inhibition of irritation and contact hypersensitivity by phenoxyacetic acid methyl ester in mice.

    PubMed

    Wille, J J; Kydonieus, A; Kalish, R S

    2000-01-01

    New anti-irritant treatments are required to prevent irritation and sensitization reactions to consumer medicines and dermatological drugs. We report here that phenoxyacetic acid methyl ester (PAME) is an effective agent to prevent and treat irritant and allergic contact dermatitis. Balb/c mice skin-treated with 1% PAME do not lose weight relative to vehicle-treated mice, nor is it irritating to mouse skin. Topical PAME prevents skin irritation to a wide variety of irritants including: arachidonic acid, capsaicin, sodium lauryl sulfate (SLS), disodium laureth sulfosuccinate and tetradecanoylphorbol-13-acetate. Histological studies showed that 1% PAME greatly diminished dermal neutrophilic infiltration and dermal capillary vessel dilation, and prevented epidermal hyperproliferation and hyperkeratosis that accompanies detergent (SLS)-induced skin irritation. Topical PAME inhibited ear swelling following ear challenge during the elicitation phase of contact hypersensitivity in mice sensitized with 1-chloro-2, 4-dinitrochlorobenzene (DNCB), oxazolone and the hair coloring dye rho-phenylenediamine (PPD). Finally, topical administration of 1% PAME prior to PPD or DNCB sensitization prevented the induction phase of contact hypersensitivity. These results indicate that PAME represents a potential new category of potent topical anti-inflammatory agents. PMID:10754454