2.0 2012-08-09 09:16:11 -0600 2015-09-13 15:15:33 -0600 ECMDB21422 M2MDB001817 Cinnamic acid Cinnamic acid has the formula C6H5CHCHCOOH and is an odorless white crystalline acid, which is slightly soluble in water. It has a melting point of 133 degree centigrade and a boiling point of 300 degree centigrade. It is an intermediate in the degradation of aromatic compounds in E. coli and is a substrate for several dioxygenases. (E)-3-phenyl-2-propenoate (E)-3-phenyl-2-propenoic acid 3-Phenyl-2-propenoate 3-Phenyl-2-propenoic acid 3-phenyl-acrylate 3-phenyl-acrylic acid 3-Phenylacrylate 3-Phenylacrylic acid 3-phenylpropenoate 3-phenylpropenoic acid b-Phenylacrylate b-Phenylacrylic acid Benzenepropenoate Benzenepropenoic acid Benzylideneacetate Benzylideneacetic acid beta-Phenylacrylate Beta-Phenylacrylic acid Cinnamate Cinnamylate Cinnamylic acid Phenylacrylate Phenylacrylic acid β-Phenylacrylate β-Phenylacrylic acid C9H8O2 148.1586 148.0524295 (2Z)-3-phenylprop-2-enoic acid cis-cinnamic acid 621-82-9 OC(=O)\C=C/C1=CC=CC=C1 InChI=1S/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6- WBYWAXJHAXSJNI-SREVYHEPSA-N Solid Membrane logp 2.38 ALOGPS logs -2.38 ALOGPS solubility 6.18e-01 g/l ALOGPS melting_point 132-135 oC logp 2.14 ChemAxon pka_strongest_acidic 4.01 ChemAxon iupac (2Z)-3-phenylprop-2-enoic acid ChemAxon average_mass 148.1586 ChemAxon mono_mass 148.0524295 ChemAxon smiles OC(=O)\C=C/C1=CC=CC=C1 ChemAxon formula C9H8O2 ChemAxon inchi InChI=1S/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6- ChemAxon inchikey WBYWAXJHAXSJNI-SREVYHEPSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 43.06 ChemAxon polarizability 15.03 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 18983 Specdb::CMs 37627 Specdb::CMs 135249 Specdb::CMs 142983 Specdb::CMs 1066146 Specdb::NmrOneD 1423 Specdb::NmrOneD 166573 Specdb::MsMs 791 Specdb::MsMs 792 Specdb::MsMs 793 Specdb::MsMs 308164 Specdb::MsMs 308165 Specdb::MsMs 308166 Specdb::MsMs 352285 Specdb::MsMs 352286 Specdb::MsMs 352287 Specdb::MsMs 2256590 Specdb::MsMs 2258010 Specdb::MsMs 2260015 Specdb::MsMs 2328531 Specdb::MsMs 2328532 Specdb::MsMs 2328533 Specdb::MsMs 2633720 Specdb::MsMs 2633721 Specdb::MsMs 2633722 Specdb::NmrTwoD 1368 HMDB00567 444539 10286933 C10438 27386 Cinnamic acid Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. 18331064 Kukongviriyapan V, Phromsopha N, Tassaneeyakul W, Kukongviriyapan U, Sripa B, Hahnvajanawong V, Bhudhisawasdi V: Inhibitory effects of polyphenolic compounds on human arylamine N-acetyltransferase 1 and 2. Xenobiotica. 2006 Jan;36(1):15-28. 16507510 An, Hong; He, Xifeng; Fu, Jing. Synthesis of cinnamic acid. Huagong Shikan (2005), 19(7), 32-33, 41. http://hmdb.ca/system/metabolites/msds/000/000/486/original/HMDB00567.pdf?1358463081 3-phenylpropionate/cinnamic acid dioxygenase subunit alpha P0ABR5 HCAE_ECOLI hcaE http://ecmdb.ca/proteins/P0ABR5.xml 3-phenylpropionate/cinnamic acid dioxygenase ferredoxin subunit P0ABW0 HCAC_ECOLI hcaC http://ecmdb.ca/proteins/P0ABW0.xml 3-phenylpropionate/cinnamic acid dioxygenase subunit beta Q47140 HCAF_ECOLI hcaF http://ecmdb.ca/proteins/Q47140.xml Cinnamic acid + NADH + Oxygen <> cis-3-(3-Carboxyethenyl)-3,5-cyclohexadiene-1,2-diol + NAD PW_R003835