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Chemical Compound Review

Zimtsaeure     (E)-3-phenylprop-2-enoic acid

Synonyms: CINNAMIC ACID, SureCN1332, PubChem13612, CHEMBL27246, NSC-9189, ...
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Disease relevance of cinnamic acid

  • Present studies demonstrate that treatment with the histone deacetylases inhibitor LAQ824, a cinnamic acid hydroxamate, increased the acetylation of histones H3 and H4, as well as induced p21(WAF1) in the human T-cell acute leukemia Jurkat, B lymphoblast SKW 6.4, and acute myelogenous leukemia HL-60 cells [1].
  • Heterologous expression of the encP gene under the control of the ermE* promoter in Streptomyces coelicolor furthermore led to the production of cinnamic acid in the fermented cultures, confirming that the encP gene indeed encodes a novel bacterial phenylalanine ammonia-lyase [2].
  • Cinnamic acid, a naturally occurring aromatic fatty acid of low toxicity, has a long history of human exposure [3].
  • Using melanoma cells as a model, we found that cinnamic acid induces cell differentiation as evidenced by morphological changes and increased melanin production [3].
  • Thirty compounds, including flavonoids, cinnamic acid derivatives, and terpenoids, were tested for the ability to inhibit GTFs B, C, and D from Streptococcus mutans and GTF from S. sanguinis (GTF Ss) [4].

Psychiatry related information on cinnamic acid


High impact information on cinnamic acid


Chemical compound and disease context of cinnamic acid


Biological context of cinnamic acid


Anatomical context of cinnamic acid


Associations of cinnamic acid with other chemical compounds


Gene context of cinnamic acid


Analytical, diagnostic and therapeutic context of cinnamic acid


  1. Cotreatment with histone deacetylase inhibitor LAQ824 enhances Apo-2L/tumor necrosis factor-related apoptosis inducing ligand-induced death inducing signaling complex activity and apoptosis of human acute leukemia cells. Guo, F., Sigua, C., Tao, J., Bali, P., George, P., Li, Y., Wittmann, S., Moscinski, L., Atadja, P., Bhalla, K. Cancer Res. (2004) [Pubmed]
  2. Inactivation, complementation, and heterologous expression of encP, a novel bacterial phenylalanine ammonia-lyase gene. Xiang, L., Moore, B.S. J. Biol. Chem. (2002) [Pubmed]
  3. Cinnamic acid: a natural product with potential use in cancer intervention. Liu, L., Hudgins, W.R., Shack, S., Yin, M.Q., Samid, D. Int. J. Cancer (1995) [Pubmed]
  4. Effects of compounds found in propolis on Streptococcus mutans growth and on glucosyltransferase activity. Koo, H., Rosalen, P.L., Cury, J.A., Park, Y.K., Bowen, W.H. Antimicrob. Agents Chemother. (2002) [Pubmed]
  5. Enhanced benzaldehyde formation by a monokaryotic strain of Pycnoporus cinnabarinus using a selective solid adsorbent in the culture medium. Lomascolo, A., Lesage-Meessen, L., Labat, M., Navarro, D., Delattre, M., Asther, M. Can. J. Microbiol. (1999) [Pubmed]
  6. Enzymatic synthesis of cinnamic Acid derivatives. Lee, G.S., Widjaja, A., Ju, Y.H. Biotechnol. Lett. (2006) [Pubmed]
  7. The substrate specificity-determining amino acid code of 4-coumarate:CoA ligase. Schneider, K., Hövel, K., Witzel, K., Hamberger, B., Schomburg, D., Kombrink, E., Stuible, H.P. Proc. Natl. Acad. Sci. U.S.A. (2003) [Pubmed]
  8. Ferulate-5-hydroxylase from Arabidopsis thaliana defines a new family of cytochrome P450-dependent monooxygenases. Meyer, K., Cusumano, J.C., Somerville, C., Chapple, C.C. Proc. Natl. Acad. Sci. U.S.A. (1996) [Pubmed]
  9. Biosynthesis and metabolism of salicylic acid. Lee, H.I., León, J., Raskin, I. Proc. Natl. Acad. Sci. U.S.A. (1995) [Pubmed]
  10. Photoaffinity labeling of Arabidopsis thaliana plasma membrane vesicles by 5-azido-[7-3H]indole-3-acetic acid: identification of a glutathione S-transferase. Zettl, R., Schell, J., Palme, K. Proc. Natl. Acad. Sci. U.S.A. (1994) [Pubmed]
  11. Effects of common forage phenolic acids on Escherichia coli O157:H7 viability in bovine feces. Wells, J.E., Berry, E.D., Varel, V.H. Appl. Environ. Microbiol. (2005) [Pubmed]
  12. Biochemical characterization of a prokaryotic phenylalanine ammonia lyase. Xiang, L., Moore, B.S. J. Bacteriol. (2005) [Pubmed]
  13. On the photobiological properties of chimeras combining quaternary ammonium derivatives of retinoic amides and psoralen. A study with cultured human keratinocytes. Lartillot, V., Risler, A., Andriamialisoa, Z., Giraud, M., Sá e Melo, T., Michel, L., Santus, R. Photochem. Photobiol. (2003) [Pubmed]
  14. 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]
  15. Liver function in protein-energy malnutrition measured by cinnamic acid tolerance and benzoic acid tolerance: effect of carnitine supplementation. Ahern, D.A., Mitchell, M.E. Br. J. Nutr. (1989) [Pubmed]
  16. Characterization of a mitochondrial transport system for branched chain alpha-keto acids. Hutson, S.M., Rannels, S.L. J. Biol. Chem. (1985) [Pubmed]
  17. Chromophoric cinnamic acid substrates as resonance Raman probes of the active site environment in native and unfolded alpha-chymotrypsin. Weber, J.A., Turpin, P., Bernhard, S.A., Peticolas, W.L. Biochemistry (1986) [Pubmed]
  18. Kinetic properties of crystalline enzymes. Carboxypeptidase A. Spilburg, C.A., Bethune, J.L., Valee, B.L. Biochemistry (1977) [Pubmed]
  19. Inhibition of the mutagenicity of bay-region diol-epoxides of polycyclic aromatic hydrocarbons by tannic acid, hydroxylated anthraquinones and hydroxylated cinnamic acid derivatives. Huang, M.T., Chang, R.L., Wood, A.W., Newmark, H.L., Sayer, J.M., Yagi, H., Jerina, D.M., Conney, A.H. Carcinogenesis (1985) [Pubmed]
  20. Novel aromatic ester from Piper longum and its analogues inhibit expression of cell adhesion molecules on endothelial cells. Kumar, S., Arya, P., Mukherjee, C., Singh, B.K., Singh, N., Parmar, V.S., Prasad, A.K., Ghosh, B. Biochemistry (2005) [Pubmed]
  21. Effects of cinnamic acid derivatives on in vitro growth of Plasmodium falciparum and on the permeability of the membrane of malaria-infected erythrocytes. Kanaani, J., Ginsburg, H. Antimicrob. Agents Chemother. (1992) [Pubmed]
  22. The active principles of plant extracts with antithyrotropic activity: oxidation products of derivatives of 3,4-dihydroxycinnamic acid. Auf'mkolk, M., Amir, S.M., Kubota, K., Ingbar, S.H. Endocrinology (1985) [Pubmed]
  23. A Na(+)-dependent mechanism is involved in mucosal uptake of cinnamic acid across the jejunal brush border in rats. Wolffram, S., Weber, T., Grenacher, B., Scharrer, E. J. Nutr. (1995) [Pubmed]
  24. 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]
  25. Phenylalanine ammonia-lyase. Induction and purification from yeast and clearance in mammals. Fritz, R.R., Hodgins, D.S., Abell, C.W. J. Biol. Chem. (1976) [Pubmed]
  26. Styrene formation by the decomposition by Pichia carsonii of trans-cinnamic acid added to a ground fish product. Shimada, K., Kimura, E., Yasui, Y., Tanaka, H., Matsushita, S., Hagihara, H., Nagakura, M., Kawahisa, M. Appl. Environ. Microbiol. (1992) [Pubmed]
  27. Novel syntheses of cis and trans isomers of combretastatin A-4. Gaukroger, K., Hadfield, J.A., Hepworth, L.A., Lawrence, N.J., McGown, A.T. J. Org. Chem. (2001) [Pubmed]
  28. Synthesis of PPAR agonist via asymmetric hydrogenation of a cinnamic acid derivative and stereospecific displacement of (S)-2-chloropropionic acid. Houpis, I.N., Patterson, L.E., Alt, C.A., Rizzo, J.R., Zhang, T.Y., Haurez, M. Org. Lett. (2005) [Pubmed]
  29. PAD1 encodes phenylacrylic acid decarboxylase which confers resistance to cinnamic acid in Saccharomyces cerevisiae. Clausen, M., Lamb, C.J., Megnet, R., Doerner, P.W. Gene (1994) [Pubmed]
  30. The STL1 gene of Saccharomyces cerevisiae is predicted to encode a sugar transporter-like protein. Zhao, S., Douglas, N.W., Heine, M.J., Williams, G.M., Winther-Larsen, H.C., Meaden, P.G. Gene (1994) [Pubmed]
  31. Inhibitory effects of polyphenolic compounds on human arylamine N-acetyltransferase 1 and 2. Kukongviriyapan, V., Phromsopha, N., Tassaneeyakul, W., Kukongviriyapan, U., Sripa, B., Hahnvajanawong, V., Bhudhisawasdi, V. Xenobiotica (2006) [Pubmed]
  32. Cinnamic acids as new inhibitors of 17beta-hydroxysteroid dehydrogenase type 5 (AKR1C3). Brozic, P., Golob, B., Gomboc, N., Rizner, T.L., Gobec, S. Mol. Cell. Endocrinol. (2006) [Pubmed]
  33. A blend of polyphenolic compounds explains the stimulatory effect of red wine on human endothelial NO synthase. Wallerath, T., Li, H., Gödtel-Ambrust, U., Schwarz, P.M., Förstermann, U. Nitric Oxide (2005) [Pubmed]
  34. Cinnamic acid 4-hydroxylase from cell cultures of the hornwort Anthoceros agrestis. Petersen, M. Planta (2003) [Pubmed]
  35. Cloning of three A-type cytochromes P450, CYP71E1, CYP98, and CYP99 from Sorghum bicolor (L.) Moench by a PCR approach and identification by expression in Escherichia coli of CYP71E1 as a multifunctional cytochrome P450 in the biosynthesis of the cyanogenic glucoside dhurrin. Bak, S., Kahn, R.A., Nielsen, H.L., Moller, B.L., Halkier, B.A. Plant Mol. Biol. (1998) [Pubmed]
  36. Phenolic content of various beverages determines the extent of inhibition of human serum and low-density lipoprotein oxidation in vitro: identification and mechanism of action of some cinnamic acid derivatives from red wine. Abu-Amsha, R., Croft, K.D., Puddey, I.B., Proudfoot, J.M., Beilin, L.J. Clin. Sci. (1996) [Pubmed]
  37. Determination of cinnamic acid and paeoniflorin in traditional Chinese medicinal preparations by high-performance liquid chromatography. Wen, K.C., Huang, C.Y., Liu, F.S. J. Chromatogr. (1992) [Pubmed]
  38. Determination of cinnamic acid in human urine by differential-pulse polarography. Ferreira, V.S., Melios, C.B., Zanoni, M.V., Stradiotto, N.R. The Analyst. (1996) [Pubmed]
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