The world's first wiki where authorship really matters (Nature Genetics, 2008). Due credit and reputation for authors. Imagine a global collaborative knowledge base for original thoughts. Search thousands of articles and collaborate with scientists around the globe.

wikigene or wiki gene protein drug chemical gene disease author authorship tracking collaborative publishing evolutionary knowledge reputation system wiki2.0 global collaboration genes proteins drugs chemicals diseases compound
Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
Chemical Compound Review

cinnamate     (E)-3-phenylprop-2-enoate

Synonyms: AC1NZCWE, CPD-674, CHEBI:15669, CHEBI:23248, STL299661, ...
This record was replaced with 444539.
Welcome! If you are familiar with the subject of this article, you can contribute to this open access knowledge base by deleting incorrect information, restructuring or completely rewriting any text. Read more.

Disease relevance of cinnamic acid


High impact information on cinnamic acid

  • The structure of the free enzyme shows a significant proportion of the active sites in the crystal to contain a naturally occurring, noncovalently bound tetrapeptide inhibitor [Dixon, M.M. & Matthews, B.W. (1989) Biochemistry 28, 7033-7038], even after cinnamate acylation and photolysis [6].
  • Visible light excitation of CdSe nanocrystals triggers the release of coumarin from cinnamate surface ligands [7].
  • Initial orientation and distances of ring protons to the iron do not explain the selective hydroxylation of cinnamate in the 4-position or the formation of single products from the thienyl compounds [8].
  • Paramagnetic relaxation effects of CYP73A1-Fe(III) on the 1H-NMR spectra of cinnamate and analogs indicate that their average initial orientation in the active site is parallel to the heme [8].
  • X-ray diffraction studies of photoactivation using a flow cell show that the cinnamate B acyl enzyme complex is fully capable of light-induced isomerization and regeneration of native enzyme in the crystalline state [9].

Chemical compound and disease context of cinnamic acid


Biological context of cinnamic acid

  • Substitution of a diethylamino group on the para position of the cinnamate ring causes a 1000-fold increase in the thermal stability of the inhibitor toward hydrolysis and deacylation [13].
  • With the aid of partial amino acid sequences determined for cinnamate 4-hydroxylase (P450C4H) purified from mung bean seedlings, two cDNA clones were isolated and their inserts were completely sequenced [14].
  • Mutagenic effects of racemic trans-epoxy cinnamate as well as the enantiomerically pure trans-epoxy cinnamates were observed in the Ames test with S. typhimurium strains TA1535, TA1537, TA1538 and TA100 without metabolic activation [15].
  • The kinetics of cinnamate transport in the absence or presence of a surplus of either unlabelled cinnamate or unlabelled butyrate indicates a reduction in the apparent affinity of the Na(+)-dependent mechanism involved in cinnamate uptake [16].
  • 4-Phenylbutyrate was a more effective inhibitor of histone deacetylase and inducer of histone acetylation than the structural analogs examined including 2- and 3-phenylbutyrate, cinnamate, methoxycinnamate, 2-phenoxybutyrate and phenoxyacetate [17].

Anatomical context of cinnamic acid


Associations of cinnamic acid with other chemical compounds


Gene context of cinnamic acid

  • Six novel halogenated soraphen analogues have been isolated from the wild-type producing organism using precursor directed biosyntheses; the best 'delivery vehicle' for the novel starter acids was cinnamate but ortho substituents were not tolerated by the soraphen PKS [27].
  • Molecular cloning and sequencing of a cDNA encoding mung bean cytochrome P450 (P450C4H) possessing cinnamate 4-hydroxylase activity [14].
  • Using an EDC/NHS conjugation method, collagen was chemically modified to incorporate a photosensitive cinnamate moiety [28].
  • Complex formation in aqueous solutions of trans-cinnamic acid or trans-cinnamate ion (the substrate, S) and alpha-cyclodextrin (the ligand, L) can be described quantiatively as the 1:1 and 1:2 complexes, SL and SL2 [29].
  • Results indicate that the microsomal system constituted by the overexpressed yeast P450 reductase and CA4H is characterized by a 1:1 coupling between NADPH oxidation and cinnamate hydroxylation and by one of the highest turnover numbers reported for an NADPH-dependent P450 reaction [30].

Analytical, diagnostic and therapeutic context of cinnamic acid

  • Significant immunosuppression also occurred at sites irradiated through the narrow-spectrum cinnamate-only sunscreen but was prevented by the two broad-spectrum sunscreens [31].
  • From its inhibition of the fluorimetric titration of chymotrypsin with 4-methylumbelliferyl-p-trimethylammonium cinnamate it was shown to combine with chymotrypsin in a 1:1 molar ratio and thus to retain its biological activity [32].
  • These data demonstrate that derivatization of collagen with photosensitive cinnamate moieties provides a facile route for solid-state crosslinking, thereby improving the mechanical properties of collagen and enhancing the potential applicability of collagen-based materials in tissue engineering and drug delivery [28].
  • Importance of using solid lipid microspheres as carriers for UV filters on the example octyl methoxy cinnamate [33].
  • A cDNA clone was generated from the elicited transcripts and assigned to cinnamate 4-monooxygenase based on sequence alignments and functional expression in yeast cells [34].


  1. Naturally occurring proteasome inhibitors from mate tea (Ilex paraguayensis) serve as models for topical proteasome inhibitors. Arbiser, J.L., Li, X.C., Hossain, C.F., Nagle, D.G., Smith, D.M., Miller, P., Govindarajan, B., DiCarlo, J., Landis-Piwowar, K.R., Dou, Q.P. J. Invest. Dermatol. (2005) [Pubmed]
  2. On the formation of 3-phenylpropionate and the different stereo-chemical course of the reduction of cinnamate by Clostridium sporogenes and Peptostreptococcus anaerobius. Giesel, H., Machacek, G., Bayerl, J., Simon, H. FEBS Lett. (1981) [Pubmed]
  3. Anaerobic degradation of trans-cinnamate and omega-phenylalkane carboxylic acids by the photosynthetic bacterium Rhodopseudomonas palustris: evidence for a beta-oxidation mechanism. Elder, D.J., Morgan, P., Kelly, D.J. Arch. Microbiol. (1992) [Pubmed]
  4. Methyl cinnamate derivatives enhance UV-induced mutagenesis due to the inhibition of DNA excision repair in Escherichia coli B/r. Shimoi, K., Nakamura, Y., Noro, T., Tomita, I., Fukushima, S., Inoue, T., Kada, T. Mutat. Res. (1985) [Pubmed]
  5. Degradation of cinnamate via beta-oxidation to benzoate by a defined, syntrophic consortium of anaerobic bacteria. Defnoun, S., Ambrosio, M., Garcia, J.L., Traoré, A., Labat, M. Curr. Microbiol. (2003) [Pubmed]
  6. Observation of the light-triggered binding of pyrone to chymotrypsin by Laue x-ray crystallography. Stoddard, B.L., Koenigs, P., Porter, N., Petratos, K., Petsko, G.A., Ringe, D. Proc. Natl. Acad. Sci. U.S.A. (1991) [Pubmed]
  7. Visible light excitation of CdSe nanocrystals triggers the release of coumarin from cinnamate surface ligands. Wijtmans, M., Rosenthal, S.J., Zwanenburg, B., Porter, N.A. J. Am. Chem. Soc. (2006) [Pubmed]
  8. Engineering of a water-soluble plant cytochrome P450, CYP73A1, and NMR-based orientation of natural and alternate substrates in the active site. Schoch, G.A., Attias, R., Belghazi, M., Dansette, P.M., Werck-Reichhart, D. Plant Physiol. (2003) [Pubmed]
  9. Photolysis and deacylation of inhibited chymotrypsin. Stoddard, B.L., Bruhnke, J., Koenigs, P., Porter, N., Ringe, D., Petsko, G.A. Biochemistry (1990) [Pubmed]
  10. Combinatorial biosynthesis of flavones and flavonols in Escherichia coli. Miyahisa, I., Funa, N., Ohnishi, Y., Martens, S., Moriguchi, T., Horinouchi, S. Appl. Microbiol. Biotechnol. (2006) [Pubmed]
  11. Cloning of a gene encoding cinnamoyl ester hydrolase from the ruminal bacterium Butyrivibrio fibrisolvens E14 by a novel method. Dalrymple, B.P., Swadling, Y., Cybinski, D.H., Xue, G.P. FEMS Microbiol. Lett. (1996) [Pubmed]
  12. Phenylalanine ammonia lyase in the management of phenylketonuria: the relationship between ingested cinnamate and urinary hippurate in humans. Hoskins, J.A., Gray, J. Res. Commun. Chem. Pathol. Pharmacol. (1982) [Pubmed]
  13. Structure and activity of two photoreversible cinnamates bound to chymotrypsin. Stoddard, B.L., Bruhnke, J., Porter, N., Ringe, D., Petsko, G.A. Biochemistry (1990) [Pubmed]
  14. Molecular cloning and sequencing of a cDNA encoding mung bean cytochrome P450 (P450C4H) possessing cinnamate 4-hydroxylase activity. Mizutani, M., Ward, E., DiMaio, J., Ohta, D., Ryals, J., Sato, R. Biochem. Biophys. Res. Commun. (1993) [Pubmed]
  15. Glutathione conjugation and bacterial mutagenicity of racemic and enantiomerically pure cis- and trans-methyl epoxycinnamates. Rietveld, E.C., van Gastel, F.J., Seutter-Berlage, F., Zwanenburg, B. Arch. Toxicol. (1988) [Pubmed]
  16. Cinnamate uptake by rat small intestine: transport kinetics and transepithelial transfer. Ader, P., Grenacher, B., Langguth, P., Scharrer, E., Wolffram, S. Exp. Physiol. (1996) [Pubmed]
  17. Induction of histone acetylation and growth regulation in eryrthroleukemia cells by 4-phenylbutyrate and structural analogs. Lea, M.A., Randolph, V.M., Hodge, S.K. Anticancer Res. (1999) [Pubmed]
  18. Recombinant Saccharomyces cerevisiae expressing P450 in artificial digestive systems: a model for biodetoxication in the human digestive environment. Blanquet, S., Meunier, J.P., Minekus, M., Marol-Bonnin, S., Alric, M. Appl. Environ. Microbiol. (2003) [Pubmed]
  19. Entrapment of phenylalanine ammonia-lyase in silk fibroin for protection from proteolytic attack. Inoue, S., Matsunaga, Y., Iwane, H., Sotomura, M., Nose, T. Biochem. Biophys. Res. Commun. (1986) [Pubmed]
  20. Catalytic properties of the plant cytochrome P450 CYP73 expressed in yeast. Substrate specificity of a cinnamate hydroxylase. Pierrel, M.A., Batard, Y., Kazmaier, M., Mignotte-Vieux, C., Durst, F., Werck-Reichhart, D. Eur. J. Biochem. (1994) [Pubmed]
  21. Effects of alpha-cyano-4-hydroxycinnamic acid on fatigue and recovery of isolated mouse muscle. Clarke, P.D., Clift, D.L., Dooldeniya, M., Burnett, C.A., Curtin, N.A. J. Muscle Res. Cell. Motil. (1995) [Pubmed]
  22. Investigation of the early stages in soraphen A biosynthesis. Hill, A.M., Thompson, B.L., Harris, J.P., Segret, R. Chem. Commun. (Camb.) (2003) [Pubmed]
  23. Induction and characterization of a microsomal flavonoid 3'-hydroxylase from parsley cell cultures. Hagmann, M.L., Heller, W., Grisebach, H. Eur. J. Biochem. (1983) [Pubmed]
  24. Distinct roles of cinnamate 4-hydroxylase genes in Populus. Lu, S., Zhou, Y., Li, L., Chiang, V.L. Plant Cell Physiol. (2006) [Pubmed]
  25. Myrianthiphyllin, The First Lignan Cinnamate from Myrianthus arboreus. Ngounou, F.N., Lontsi, D., Sondengam, B.L., Tsoupras, M.G., Tabacchi, R. Planta Med. (1990) [Pubmed]
  26. Rubrivivax benzoatilyticus sp. nov., an aromatic, hydrocarbon-degrading purple betaproteobacterium. Ramana, C.h.V., Sasikala, C.h., Arunasri, K., Anil Kumar, P., Srinivas, T.N., Shivaji, S., Gupta, P., Süling, J., Imhoff, J.F. Int. J. Syst. Evol. Microbiol. (2006) [Pubmed]
  27. Novel soraphens from precursor directed biosynthesis. Hill, A.M., Thompson, B.L. Chem. Commun. (Camb.) (2003) [Pubmed]
  28. Photomediated crosslinking of C6-cinnamate derivatized type I collagen. Dong, C.M., Wu, X., Caves, J., Rele, S.S., Thomas, B.S., Chaikof, E.L. Biomaterials (2005) [Pubmed]
  29. trans-Cinnamic acid--alpha-cyclodextrin system as studied by solubility, spectral, and potentiometric techniques. Connors, K.A., Rosanske, T.W. Journal of pharmaceutical sciences. (1980) [Pubmed]
  30. Characterization of recombinant plant cinnamate 4-hydroxylase produced in yeast. Kinetic and spectral properties of the major plant P450 of the phenylpropanoid pathway. Urban, P., Werck-Reichhart, D., Teutsch, H.G., Durst, F., Regnier, S., Kazmaier, M., Pompon, D. Eur. J. Biochem. (1994) [Pubmed]
  31. Broad-spectrum sunscreens provide greater protection against ultraviolet-radiation-induced suppression of contact hypersensitivity to a recall antigen in humans. Damian, D.L., Halliday, G.M., Barnetson, R.S. J. Invest. Dermatol. (1997) [Pubmed]
  32. The purification of alpha 1-antichymotrypsin from human serum using DNA-cellulose chromatography. Abdullah, M., Siddiqui, A.A., Hill, J.A., Davies, R.J. Arch. Biochem. Biophys. (1983) [Pubmed]
  33. Importance of using solid lipid microspheres as carriers for UV filters on the example octyl methoxy cinnamate. Yener, G., Incegül, T., Yener, N. International journal of pharmaceutics. (2003) [Pubmed]
  34. Functional expression of cinnamate 4-hydroxylase from Ammi majus L. Hübner, S., Hehmann, M., Schreiner, S., Martens, S., Lukacin, R., Matern, U. Phytochemistry (2003) [Pubmed]
WikiGenes - Universities