1.0 2020-03-18 23:27:38 UTC 2022-12-13 19:31:28 UTC CDB000177 (E)-p-Coumaric acid trans-4-Coumaric acid or (e)-p-Coumaric acid, the trans-isomer of 4-coumaric acid, also known as 4-hydroxycinnamic acid, belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing a cinnamic acid where the benzene ring is hydroxylated. 4-Hydroxycinnamic acid is a neutral compound. 4-Hydroxycinnamic acid exists in all living species, from bacteria to humans. 4-Hydroxycinnamic acid is found in highest concentrations in pepper (c. frutescens), pineapples, and sunflowers and in lower concentration in spinachs, kiwis, and sweet oranges. 4-Hydroxycinnamic acid has also been detected in wild rices, soursops, garden onions, hyssops, and avocado. This could make 4-hydroxycinnamic acid a potential biomarker for the consumption of these foods. 4-Hydroxycinnamic acid is also found in cannabis plants reported by Paris in 1973 ¬†(PMID: 6991645). (2E)-3-(4-Hydroxyphenyl)acrylic acid (e)-3-(4-Hydroxyphenyl)-2-propenoic acid (e)-p-Coumaric acid (e)-p-Hydroxycinnamic acid 4'-HYDROXYCINNAMIC ACID Naringeninic acid p-Coumaric acid trans-p-Coumaric acid trans-p-Coumarinic acid trans-p-Hydroxycinnamate trans-p-Hydroxycinnamic acid trans-4-Hydroxycinnamate 4-Hydroxycinnamate (2E)-3-(4-Hydroxyphenyl)acrylate (e)-3-(4-Hydroxyphenyl)-2-propenoate (e)-p-Coumarate (e)-p-Hydroxycinnamate 4'-HYDROXYCINNAMate Naringeninate p-Coumarate trans-p-Coumarate trans-p-Coumarinate 4-Coumaric acid, (e)-isomer 4-Coumaric acid, (Z)-isomer 4-Coumaric acid, disodium salt p-Coumaryl alcohol p-Hydroxycinnamic acid Para-coumaric acid trans-3-(4'-Hydroxyphenyl)-2-propenoic acid trans-HPPA 3-(4-Hydroxyphenyl)-2-propenoate 3-(4-Hydroxyphenyl)-2-propenoic acid 3-(4-Hydroxyphenyl)acrylate 3-(4-Hydroxyphenyl)acrylic acid 4-Coumarate 4-Hydroxy cinnamate 4-Hydroxy cinnamic acid 4-Hydroxyphenylpropenoate 4-Hydroxyphenylpropenoic acid b-[4-Hydroxyphenyl]acrylate b-[4-Hydroxyphenyl]acrylic acid beta-[4-Hydroxyphenyl]acrylate beta-[4-Hydroxyphenyl]acrylic acid cis-P-Coumarate Hydroxycinnamate Hydroxycinnamic acid P-Cumarate P-Cumaric acid P-Hydroxycinnamate P-Hydroxyphenylacrylate P-Hydroxyphenylacrylic acid Para coumarate Para coumaric acid Para-coumarate 4-Hydroxycinnamic acid trans-4-Coumarate (2E)-3-(4-Hydroxyphenyl)-2-propenoic acid (2E)-3-(4-Hydroxyphenyl)prop-2-enoic acid (E)-3-(4-Hydroxyphenyl)acrylic acid (E)-4-Hydroxycinnamic acid 4’-Hydroxycinnamic acid p-Cumaric acid p-Hydroxy-trans-cinnamic acid p-Hydroxyphenylacrylic acid p-trans-Coumaric acid trans-3-(4-Hydroxyphenyl)-2-propenoic acid trans-4-Coumaric acid β-[4-Hydroxyphenyl]acrylic acid C9H8O3 164.16 164.0473 (2E)-3-(4-hydroxyphenyl)prop-2-enoic acid coumaric acid 501-98-4 OC(=O)\C=C\C1=CC=C(O)C=C1 InChI=1S/C9H8O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-6,10H,(H,11,12)/b6-3+ NGSWKAQJJWESNS-ZZXKWVIFSA-N belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated. Hydroxycinnamic acids Organic compounds Phenylpropanoids and polyketides Cinnamic acids and derivatives Hydroxycinnamic acids and derivatives Aromatic homomonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids Carbonyl compounds Carboxylic acids Cinnamic acids Coumaric acids Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Styrenes 1-hydroxy-2-unsubstituted benzenoid Aromatic homomonocyclic compound Benzenoid Carbonyl group Carboxylic acid Carboxylic acid derivative Cinnamic acid Coumaric acid Coumaric acid or derivatives Hydrocarbon derivative Hydroxycinnamic acid Monocarboxylic acid or derivatives Monocyclic benzene moiety Organic oxide Organic oxygen compound Organooxygen compound Phenol Styrene 4-coumaric acid Paracoumaryl alcohol derivatives logp 1.79 SANGSTER (1994) melting_point 211.5 °C logp 1.74 ALOGPS logs -2.21 ALOGPS logp 1.83 ChemAxon pka_strongest_acidic 4 ChemAxon pka_strongest_basic -6 ChemAxon iupac (2E)-3-(4-hydroxyphenyl)prop-2-enoic acid ChemAxon average_mass 164.16 ChemAxon mono_mass 164.0473 ChemAxon smiles OC(=O)\C=C\C1=CC=C(O)C=C1 ChemAxon formula C9H8O3 ChemAxon inchi InChI=1S/C9H8O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-6,10H,(H,11,12)/b6-3+ ChemAxon inchikey NGSWKAQJJWESNS-ZZXKWVIFSA-N ChemAxon polar_surface_area 57.53 ChemAxon refractivity 45.04 ChemAxon polarizability 16.43 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB002593 C00811 DB04066 553148 637542 500 C00000152 32374 COUMARATE 36077 P-Coumaric_acid 6450 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645