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Chemical Compound Review

Hyacinthin     2-phenylethanal

Synonyms: Phenylethanal, a-Tolualdehyde, PubChem19675, AGN-PC-0CIVES, AG-D-49403, ...
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Disease relevance of Oxophenylethane


High impact information on Oxophenylethane

  • PAAS is a bifunctional enzyme that catalyzes the unprecedented efficient coupling of phenylalanine decarboxylation to oxidation, generating phenylacetaldehyde, CO2, ammonia, and hydrogen peroxide in stoichiometric amounts [4].
  • The enzyme required NADH as a cofactor and showed no activity with NADPH; therefore, it was defined as an NADH-dependent phenylacetaldehyde reductase [1].
  • Inhibition constants (Ki) for DPAB, estimated from Dixon plots, were 10 nM (propanal) and 77 nM (phenylacetaldehyde) for mouse ALDH and 3 nM (propanal) and 70 nM (phenylacetaldehyde) for human ALDH [5].
  • After incubation with human liver microsomes for 20 min, almost 50% of a 0.03 microM concentration of [3H]-fentanyl was metabolized to the [3H]N-dealkylated metabolite phenylacetaldehyde, which was then converted principally to [3H]2-phenylethanol and to a smaller extent to [3H]phenylacetic acid in microsomal incubates [6].
  • While AOR oxidized a wide range of aliphatic and aromatic aldehydes, those with the highest apparent kcat/Km values (> 10 microM-1S-1) were acetaldehyde, isovalerylaldehyde, and phenylacetaldehyde (Km values of < 100 microM) [7].

Chemical compound and disease context of Oxophenylethane

  • An aldehyde oxime O-methyl ether, phenylacetaldehyde O-methyloxime, was detected using solid-phase microextraction (SPME) and gas chromatography-mass spectrometry (GC-MS) in the headspace above grapefruit leaves infected with Xanthomonas axonopodis pv. citri, the causal agent of citrus bacterial canker disease (CBCD) [3].

Biological context of Oxophenylethane


Anatomical context of Oxophenylethane


Associations of Oxophenylethane with other chemical compounds


Gene context of Oxophenylethane


Analytical, diagnostic and therapeutic context of Oxophenylethane


  1. Purification and characterization of phenylacetaldehyde reductase from a styrene-assimilating Corynebacterium strain, ST-10. Itoh, N., Morihama, R., Wang, J., Okada, K., Mizuguchi, N. Appl. Environ. Microbiol. (1997) [Pubmed]
  2. Photon emission by bacteria challenged with phenylacetaldehyde. A possible distinction between gram-positive and gram-negative bacteria. Surpili, M.J., Faljoni-Alario, A., Cilento, G. Photochem. Photobiol. (1993) [Pubmed]
  3. Phenylacetaldehyde O-methyloxime: a volatile compound produced by grapefruit leaves infected with the citrus canker pathogen, Xanthomonas axonopodis pv. citri. Zhang, A., Hartung, J.S. J. Agric. Food Chem. (2005) [Pubmed]
  4. Plant phenylacetaldehyde synthase is a bifunctional homotetrameric enzyme that catalyzes phenylalanine decarboxylation and oxidation. Kaminaga, Y., Schnepp, J., Peel, G., Kish, C.M., Ben-Nissan, G., Weiss, D., Orlova, I., Lavie, O., Rhodes, D., Wood, K., Porterfield, D.M., Cooper, A.J., Schloss, J.V., Pichersky, E., Vainstein, A., Dudareva, N. J. Biol. Chem. (2006) [Pubmed]
  5. Identification of 4-(N,N-dipropylamino)benzaldehyde as a potent, reversible inhibitor of mouse and human class I aldehyde dehydrogenase. Russo, J., Chung, S., Contreras, K., Lian, B., Lorenz, J., Stevens, D., Trousdell, W. Biochem. Pharmacol. (1995) [Pubmed]
  6. Biotransformation of tritiated fentanyl in human liver microsomes. Monitoring metabolism using phenylacetic acid and 2-phenylethanol. Tateishi, T., Wood, A.J., Guengerich, F.P., Wood, M. Biochem. Pharmacol. (1995) [Pubmed]
  7. Purification, characterization, and metabolic function of tungsten-containing aldehyde ferredoxin oxidoreductase from the hyperthermophilic and proteolytic archaeon Thermococcus strain ES-1. Heider, J., Ma, K., Adams, M.W. J. Bacteriol. (1995) [Pubmed]
  8. Styrene oxide in blood, hemoglobin adducts, and urinary metabolites in human volunteers exposed to (13)C(8)-styrene vapors. Johanson, G., Ernstgård, L., Gullstrand, E., Löf, A., Osterman-Golkar, S., Williams, C.C., Sumner, S.C. Toxicol. Appl. Pharmacol. (2000) [Pubmed]
  9. Effects of styrene and its metabolites on different lung compartments of the mouse--cell proliferation and histomorphology. Kaufmann, W., Mellert, W., van Ravenzwaay, B., Landsiedel, R., Poole, A. Regul. Toxicol. Pharmacol. (2005) [Pubmed]
  10. Schiff base formation with amino acids enhances light emission and damage induced in neutrophils by phenylacetaldehyde. Nascimento, A.L., Cilento, G. Biochim. Biophys. Acta (1989) [Pubmed]
  11. Generation of electronically excited states in situ. Polymorphonuclear leukocytes treated with phenylacetaldehyde. Nascimento, A.L., Cilento, G. Photochem. Photobiol. (1987) [Pubmed]
  12. Identification and characterization of phenylpyruvate decarboxylase genes in Saccharomyces cerevisiae. Vuralhan, Z., Morais, M.A., Tai, S.L., Piper, M.D., Pronk, J.T. Appl. Environ. Microbiol. (2003) [Pubmed]
  13. Kinetic properties of the bovine corneal aldehyde dehydrogenase (BCP 54). Konishi, Y., Mimura, Y. Exp. Eye Res. (1992) [Pubmed]
  14. Learning, odour preference and flower foraging in moths. Cunningham, J.P., Moore, C.J., Zalucki, M.P., West, S.A. J. Exp. Biol. (2004) [Pubmed]
  15. Electrophysiological and behavioral responses of female Helicoverpa armigera to compounds identified in flowers of African marigold, Tagetes erecta. Bruce, T.J., Cork, A. J. Chem. Ecol. (2001) [Pubmed]
  16. Enzymatic oxidation of 2-phenylethylamine to phenylacetic acid and 2-phenylethanol with special reference to the metabolism of its intermediate phenylacetaldehyde. Panoutsopoulos, G.I., Kouretas, D., Gounaris, E.G., Beedham, C. Basic & clinical pharmacology & toxicology. (2004) [Pubmed]
  17. Floral scent emission and pollinator attraction in two species of Gymnadenia (Orchidaceae). Huber, F.K., Kaiser, R., Sauter, W., Schiestl, F.P. Oecologia (2005) [Pubmed]
  18. Relationship between potentiometric measurements, sensorial analysis, and some substances responsible for aroma degradation of white wines. Silva Ferreira, A.C., Oliveira, C., Hogg, T., Guedes de Pinho, P. J. Agric. Food Chem. (2003) [Pubmed]
  19. Cloning, sequence analysis, and expression in Escherichia coli of the gene encoding phenylacetaldehyde reductase from styrene-assimilating Corynebacterium sp. strain ST-10. Wang, J.C., Sakakibara, M., Liu, J.Q., Dairi, T., Itoh, N. Appl. Microbiol. Biotechnol. (1999) [Pubmed]
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