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Chemical Compound Review

benzylacetate     3-phenylpropanoic acid

Synonyms: hydrocinnamate, CHEMBL851, PubChem8185, SureCN3419, AGN-PC-005JV4, ...
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Disease relevance of Benzylacetic acid


High impact information on Benzylacetic acid


Chemical compound and disease context of Benzylacetic acid


Biological context of Benzylacetic acid


Anatomical context of Benzylacetic acid


Associations of Benzylacetic acid with other chemical compounds


Gene context of Benzylacetic acid

  • Sequence comparisons revealed that while hcaA1A2CD genes encode the four subunits of the 3-phenylpropionate dioxygenase, the hcaB gene codes for the corresponding cis-dihydrodiol dehydrogenase [23].
  • Optically active phenylpropanoic acid derivatives [(S)-5, and (R)-5] were prepared, and their affinities for peroxisome proliferator-activated receptor (PPAR)alpha and PPAR gamma were evaluated [14].
  • Remarkably, the expression of hcaA in the presence of 3-phenylpropionate was sharply and transiently induced at the end of the exponential growth phase [24].
  • The effects of laser fluence on ion formation in MALDI were studied using a tandem TOF mass spectrometer with a Nd-YAG laser and alpha-cyano hydrocinnamic acid matrix [25].
  • PCI was the most effective inhibitor, with a K(i) in the nM region, and no inhibition was shown with 3-phenylpropionic acid [26].

Analytical, diagnostic and therapeutic context of Benzylacetic acid


  1. Catalytic mechanism of C-C hydrolase MhpC from Escherichia coli: kinetic analysis of His263 and Ser110 site-directed mutants. Li, C., Montgomery, M.G., Mohammed, F., Li, J.J., Wood, S.P., Bugg, T.D. J. Mol. Biol. (2005) [Pubmed]
  2. Hepatic beta-oxidation of 3-phenylpropionic acid and the stereospecific dehydration of (R)- and (S)-3-hydroxy-3-phenylpropionyl-CoA by different enoyl-CoA hydratases. Mao, L.F., Chu, C., Schulz, H. Biochemistry (1994) [Pubmed]
  3. Evidence for a gem-Diol Reaction Intermediate in Bacterial C-C Hydrolase Enzymes BphD and MhpC from (13)C NMR Spectroscopy. Li, J.J., Li, C., Blindauer, C.A., Bugg, T.D. Biochemistry (2006) [Pubmed]
  4. Production of indole-3-propanoic acid and 3-(p-hydroxyphenyl)propanoic acid by Clostridium sporogenes: a convenient thin-layer chromatography detection system. Jellet, J.J., Forrest, T.P., Macdonald, I.A., Marrie, T.J., Holdeman, L.V. Can. J. Microbiol. (1980) [Pubmed]
  5. Experience with the 3-phenylpropionic acid loading test for diagnosis of medium-chain acyl-CoA dehydrogenase deficiency (MCADD). Lehnert, W. Pädiatrie und Pädologie. (1993) [Pubmed]
  6. Design, synthesis, and evaluation of substituted phenylpropanoic acid derivatives as human peroxisome proliferator activated receptor activators. Discovery of potent and human peroxisome proliferator activated receptor alpha subtype-selective activators. Nomura, M., Tanase, T., Ide, T., Tsunoda, M., Suzuki, M., Uchiki, H., Murakami, K., Miyachi, H. J. Med. Chem. (2003) [Pubmed]
  7. Rhodococcus L-phenylalanine dehydrogenase: kinetics, mechanism, and structural basis for catalytic specificity. Brunhuber, N.M., Thoden, J.B., Blanchard, J.S., Vanhooke, J.L. Biochemistry (2000) [Pubmed]
  8. Beta-substituted beta-phenylpropionyl chymotrypsins. Structural and stereochemical features in stable acyl enzymes. Reed, P.E., Katzenellenbogen, J.A. J. Med. Chem. (1991) [Pubmed]
  9. Synthesis and antifolate properties of 9-alkyl-10-deazaminopterins. DeGraw, J.I., Christie, P.H., Kisliuk, R.L., Gaumont, Y., Sirotnak, F.M. J. Med. Chem. (1990) [Pubmed]
  10. Cultivation of Escherichia coli with mixtures of 3-phenylpropionic acid and glucose: steady-state growth kinetics. Kovárová, K., Käch, A., Zehnder, A.J., Egli, T. Appl. Environ. Microbiol. (1997) [Pubmed]
  11. Chloridazon-catechol dioxygenases, a distinct group of meta-cleaving enzymes. Schmitt, S., Müller, R., Wegst, W., Lingens, F. Hoppe-Seyler's Z. Physiol. Chem. (1984) [Pubmed]
  12. Production and characterization of monoclonal anti-idiotypic antibody exhibiting a catalytic activity similar to carboxypeptidase A. Hu, R., Xie, G.Y., Zhang, X., Guo, Z.Q., Jin, S. J. Biotechnol. (1998) [Pubmed]
  13. 3-phenylpropionate catabolism and the Escherichia coli oxidative stress response. Turlin, E., Sismeiro, O., Le Caer, J.P., Labas, V., Danchin, A., Biville, F. Res. Microbiol. (2005) [Pubmed]
  14. Enantio-dependent binding and transactivation of optically active phenylpropanoic acid derivatives at human peroxisome proliferator-activated receptor alpha. Miyachi, H., Nomura, M., Tanase, T., Suzuki, M., Murakami, K., Awano, K. Bioorg. Med. Chem. Lett. (2002) [Pubmed]
  15. Phenylpropanoid interconversion in Anigozanthos preissii observed by high-performance liquid chromatography-nuclear magnetic resonance spectroscopy. Schmitt, B., Schneider, B. Phytochemical analysis : PCA. (2001) [Pubmed]
  16. Phenylpropionic acid-based cyclic prodrugs of opioid peptides that exhibit metabolic stability to peptidases and excellent cellular permeation. Gudmundsson, O.S., Nimkar, K., Gangwar, S., Siahaan, T., Borchardt, R.T. Pharm. Res. (1999) [Pubmed]
  17. Esterase-sensitive cyclic prodrugs of peptides: evaluation of a phenylpropionic acid promoiety in a model hexapeptide. Pauletti, G.M., Gangwar, S., Wang, B., Borchardt, R.T. Pharm. Res. (1997) [Pubmed]
  18. The Disposition and Metabolism of Naveglitazar, a Peroxisome Proliferator-Activated Receptor {alpha}-{gamma} Dual, {gamma}-Dominant Agonist in Mice, Rats, and Monkeys. Yi, P., Hadden, C.E., Annes, W.F., Jackson, D.A., Peterson, B.C., Gillespie, T.A., Johnson, J.T. Drug Metab. Dispos. (2007) [Pubmed]
  19. Antinociceptive effect of some carboxypeptidase A inhibitors in comparison with D-phenylalanine. Giusti, P., Carrara, M., Cima, L., Borin, G. Eur. J. Pharmacol. (1985) [Pubmed]
  20. Photosensitization by anticancer agents--10. ortho-semiquinone and superoxide radicals produced during anthrapyrazole-sensitized oxidation of catechols. Reszka, K., Lown, J.W., Chignell, C.F. Photochem. Photobiol. (1992) [Pubmed]
  21. The origin of urinary aromatic compounds excreted by ruminants. 2. The metabolism of phenolic cinnamic acids to benzoic acid. Martin, A.K. Br. J. Nutr. (1982) [Pubmed]
  22. Chemical constituents of the aquatic plant Schoenoplectus lacustris: evaluation of phytotoxic effects on the green alga Selenastrum capricornutum. D'Abrosca, B., Dellagreca, M., Fiorentino, A., Isidori, M., Monaco, P., Pacifico, S. J. Chem. Ecol. (2006) [Pubmed]
  23. Characterization of the hca cluster encoding the dioxygenolytic pathway for initial catabolism of 3-phenylpropionic acid in Escherichia coli K-12. Díaz, E., Ferrández, A., García, J.L. J. Bacteriol. (1998) [Pubmed]
  24. Regulation of the early steps of 3-phenylpropionate catabolism in Escherichia coli. Turlin, E., Perrotte-piquemal, M., Danchin, A., Biville, F. J. Mol. Microbiol. Biotechnol. (2001) [Pubmed]
  25. Fragmentation of Leucine Enkephalin as a Function of Laser Fluence in a MALDI TOF-TOF. Campbell, J.M., Vestal, M.L., Blank, P.S., Stein, S.E., Epstein, J.A., Yergey, A.L. J. Am. Soc. Mass Spectrom. (2007) [Pubmed]
  26. Ostrich (Struthio camelus) carboxypeptidase B: purification, kinetic properties and characterization of the pancreatic enzyme. Bradley, G., Naudé, R.J., Muramoto, K., Yamauchi, F., Oelofsen, W. Int. J. Biochem. Cell Biol. (1996) [Pubmed]
  27. When do gut flora in the newborn produce 3-phenylpropionic acid? Implications for early diagnosis of medium-chain acyl-CoA dehydrogenase deficiency. Bennett, M.J., Bhala, A., Poirier, S.F., Ragni, M.C., Willi, S.M., Hale, D.E. Clin. Chem. (1992) [Pubmed]
  28. Determination of phenylpropionic acid in fermentation medium by chromatographic techniques. Panos, J. Folia Microbiol. (Praha) (1991) [Pubmed]
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