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Chemical Compound Review

SureCN39220     3-phenylprop-2-en-1-ol

Synonyms: ACMC-1CK26, AG-C-93310, ANW-15081, KB-76100, KB-77822, ...
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Disease relevance of Styrylcarbinol


High impact information on Styrylcarbinol

  • Wild-type Arabidopsis has a guaiacyl-rich, syringyl-guaiacyl lignin typical of other dicots, with prominent beta-aryl ether (beta-O-4), phenylcoumaran (beta-5), resinol (beta-beta), biphenyl/dibenzodioxocin (5-5), and cinnamyl alcohol end-group structures [3].
  • Inheritance, gene expression, and lignin characterization in a mutant pine deficient in cinnamyl alcohol dehydrogenase [4].
  • The coordinated up-regulation of phenylalanine ammonia lyase, 4-coumarate:CoA ligase, caffeoyl-CoA O-methyltransferase, cinnamoyl-CoA reductase and cinnamyl alcohol dehydrogenase in the presence of increasing concentrations of Phe also indicates that these steps are not truly rate-limiting, because they are modulated according to metabolic demand [5].
  • These polymers arise from the oxidative coupling of three cinnamyl alcohols in a nonrandom reaction, in which cell wall polysaccharides appear to influence the freedom of cinnamyl alcohol radicals, giving rise to a highly orchestrated process [6].
  • One of the genes, CAD, common to both systems and encoding the lignin-related protein cinnamyl alcohol dehydrogenase, was immunolocalized to immature xylem cells of the vascular bundles in the strawberry receptacle [7].

Biological context of Styrylcarbinol


Anatomical context of Styrylcarbinol


Associations of Styrylcarbinol with other chemical compounds


Gene context of Styrylcarbinol


Analytical, diagnostic and therapeutic context of Styrylcarbinol


  1. Lignification in transgenic poplars with extremely reduced caffeic acid O-methyltransferase activity. Jouanin, L., Goujon, T., de Nadaï, V., Martin, M.T., Mila, I., Vallet, C., Pollet, B., Yoshinaga, A., Chabbert, B., Petit-Conil, M., Lapierre, C. Plant Physiol. (2000) [Pubmed]
  2. Characterization of cinnamyl alcohol dehydrogenase of Helicobacter pylori. An aldehyde dismutating enzyme. Mee, B., Kelleher, D., Frias, J., Malone, R., Tipton, K.F., Henehan, G.T., Windle, H.J. FEBS J. (2005) [Pubmed]
  3. NMR characterization of lignins in Arabidopsis altered in the activity of ferulate 5-hydroxylase. Marita, J.M., Ralph, J., Hatfield, R.D., Chapple, C. Proc. Natl. Acad. Sci. U.S.A. (1999) [Pubmed]
  4. Inheritance, gene expression, and lignin characterization in a mutant pine deficient in cinnamyl alcohol dehydrogenase. MacKay, J.J., O'Malley, D.M., Presnell, T., Booker, F.L., Campbell, M.M., Whetten, R.W., Sederoff, R.R. Proc. Natl. Acad. Sci. U.S.A. (1997) [Pubmed]
  5. Transcriptional control of monolignol biosynthesis in Pinus taeda: factors affecting monolignol ratios and carbon allocation in phenylpropanoid metabolism. Anterola, A.M., Jeon, J.H., Davin, L.B., Lewis, N.G. J. Biol. Chem. (2002) [Pubmed]
  6. Lignification in plant cell walls. Ros Barceló, A. Int. Rev. Cytol. (1997) [Pubmed]
  7. Novel insight into vascular, stress, and auxin-dependent and -independent gene expression programs in strawberry, a non-climacteric fruit. Aharoni, A., Keizer, L.C., Van Den Broeck, H.C., Blanco-Portales, R., Muñoz-Blanco, J., Bois, G., Smit, P., De Vos, R.C., O'Connell, A.P. Plant Physiol. (2002) [Pubmed]
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  9. Protein binding and metabolism influence the relative skin sensitization potential of cinnamic compounds. Elahi, E.N., Wright, Z., Hinselwood, D., Hotchkiss, S.A., Basketter, D.A., Pease, C.K. Chem. Res. Toxicol. (2004) [Pubmed]
  10. Cell differentiation, secondary cell-wall formation and transformation of callus tissue of Pinus radiata D. Don. Möller, R., McDonald, A.G., Walter, C., Harris, P.J. Planta (2003) [Pubmed]
  11. Kinetic resolution of alcohols using a 1,2-dihydroimidazo[1,2-a]quinoline enantioselective acylation catalyst. Birman, V.B., Jiang, H. Org. Lett. (2005) [Pubmed]
  12. Diverse range of gene activity during Arabidopsis thaliana leaf senescence includes pathogen-independent induction of defense-related genes. Quirino, B.F., Normanly, J., Amasino, R.M. Plant Mol. Biol. (1999) [Pubmed]
  13. High sulfotransferase activity for phenolic aromatic odorants present in the mouse olfactory organ. Tamura, H., Miyawaki, A., Inoh, N., Harada, Y., Mikoshiba, K., Matsui, M. Chem. Biol. Interact. (1997) [Pubmed]
  14. Cinnamic compound metabolism in human skin and the role metabolism may play in determining relative sensitisation potency. Cheung, C., Hotchkiss, S.A., Pease, C.K. J. Dermatol. Sci. (2003) [Pubmed]
  15. Cross-coupling of hydroxycinnamyl aldehydes into lignins. Kim, H., Ralph, J., Yahiaoui, N., Pean, M., Boudet, A.M. Org. Lett. (2000) [Pubmed]
  16. Purification and properties of cinnamoyl-CoA reductase and cinnamyl alcohol dehydrogenase from poplar stems (Populus X euramericana). Sarni, F., Grand, C., Boudet, A.M. Eur. J. Biochem. (1984) [Pubmed]
  17. Engineering yeast alcohol dehydrogenase. Replacing Trp54 by Leu broadens substrate specificity. Weinhold, E.G., Benner, S.A. Protein Eng. (1995) [Pubmed]
  18. Cross-sensitization patterns in guinea pigs between cinnamaldehyde, cinnamyl alcohol and cinnamic acid. Weibel, H., Hansen, J., Andersen, K.E. Acta Derm. Venereol. (1989) [Pubmed]
  19. LC/MS/MS identification of glycosides produced by biotransformation of cinnamyl alcohol in Rhodiola rosea compact callus aggregates. Tolonen, A., György, Z., Jalonen, J., Neubauer, P., Hohtola, A. Biomed. Chromatogr. (2004) [Pubmed]
  20. Characterization of a Saccharomyces cerevisiae NADP(H)-dependent alcohol dehydrogenase (ADHVII), a member of the cinnamyl alcohol dehydrogenase family. Larroy, C., Parés, X., Biosca, J.A. Eur. J. Biochem. (2002) [Pubmed]
  21. Human skin absorption and metabolism of the contact allergens, cinnamic aldehyde, and cinnamic alcohol. Smith, C.K., Moore, C.A., Elahi, E.N., Smart, A.T., Hotchkiss, S.A. Toxicol. Appl. Pharmacol. (2000) [Pubmed]
  22. Crystal structures and catalytic mechanism of the Arabidopsis cinnamyl alcohol dehydrogenases AtCAD5 and AtCAD4. Youn, B., Camacho, R., Moinuddin, S.G., Lee, C., Davin, L.B., Lewis, N.G., Kang, C. Org. Biomol. Chem. (2006) [Pubmed]
  23. Identification and characterisation of cDNA clones encoding cinnamyl alcohol dehydrogenase from tobacco. Knight, M.E., Halpin, C., Schuch, W. Plant Mol. Biol. (1992) [Pubmed]
  24. QTL analysis and comparative genomics of herbage quality traits in perennial ryegrass (Lolium perenne L.). Cogan, N.O., Smith, K.F., Yamada, T., Francki, M.G., Vecchies, A.C., Jones, E.S., Spangenberg, G.C., Forster, J.W. Theor. Appl. Genet. (2005) [Pubmed]
  25. Chiral capillary electrophoresis applied to the determination of phenylglycidol enantiomers obtained from cinnamyl alcohol by asymmetric epoxidation using new titanium(IV) alkoxide compounds as catalysts. Morante-Zarcero, S., Crego, A.L., Sierra, I., Fajardo, M., Marina, M.L. Electrophoresis (2004) [Pubmed]
  26. Molecular cloning and expression of a Eucalyptus gunnii cDNA clone encoding cinnamyl alcohol dehydrogenase. Grima-Pettenati, J., Feuillet, C., Goffner, D., Borderies, G., Boudet, A.M. Plant Mol. Biol. (1993) [Pubmed]
  27. Molecular cloning, sequence analysis and elicitor-/ozone-induced accumulation of cinnamyl alcohol dehydrogenase from Norway spruce (Picea abies L.). Galliano, H., Cabané, M., Eckerskorn, C., Lottspeich, F., Sandermann, H., Ernst, D. Plant Mol. Biol. (1993) [Pubmed]
  28. Simultaneous determination of phenylglycidol enantiomers and cinnamyl alcohol in asymmetric epoxidation processes by chiral liquid chromatography. Morante-Zarcero, S., Pérez, Y., del Hierro, I., Fajardo, M., Sierra, I. Journal of chromatography. A. (2004) [Pubmed]
  29. Gene silencing studies in the gymnosperm species Pinus radiata. Wagner, A., Phillips, L., Narayan, R.D., Moody, J.M., Geddes, B. Plant Cell Rep. (2005) [Pubmed]
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