1.0 2010-04-08 22:05:29 UTC 2025-11-18 22:39:44 UTC FDB002700 Isoferulic acid It is used as a food additive; listed in the EAFUS Food Additive Database (Jan 2001) Isoferulic acid is a chlorogenic acid (CGA). CGAs are formed by the esterification of hydroxycinnamic acids, such as caffeic, ferulic, and {rho}-coumaric, with quinic acid. CGA are abundant phenolic compounds in coffee, with caffeoylquinic (CQA), feruloylquinic (FQA), and dicaffeoylquinic (diCQA) acids being the major subclasses, and coffee is the most consumed food product in the world. Isoferulic acid is present in normal human urine in concentrations of 0.05-2.07 umol/mmol creatinine at baseline, and reaches 0.2 - 9.6 umol/mmol creatinine in four hours after a cup of coffee, with a large inter-individual variation. (PMID: 17884997). Isoferulic acid is found in many foods, some of which are sunflower, peanut, common wheat, and vinegar. (2E)-3-(3-Hydroxy-4-methoxyphenyl)-2-propenoic acid 3-(3-Hydroxy-4-methoxyphenyl)-2-propenoate 3-(3-Hydroxy-4-methoxyphenyl)-2-propenoic acid 3-(3-Hydroxy-4-methoxyphenyl)-2-propenoic acid, 9CI 3-Hydroxy-4-methoxy-cinnamate 3-Hydroxy-4-methoxy-cinnamic acid 3-Hydroxy-4-methoxycinnamate 3-Hydroxy-4-methoxycinnamic acid Hesperetate Hesperetic acid Hesperetinic acid Isoferulate Isoferulic acid C10H10O4 194.184 194.057908808 (2E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoic acid isoferulic acid 537-73-5 COC1=C(O)C=C(\C=C\C(O)=O)C=C1 InChI=1S/C10H10O4/c1-14-9-4-2-7(6-8(9)11)3-5-10(12)13/h2-6,11H,1H3,(H,12,13)/b5-3+ QURCVMIEKCOAJU-HWKANZROSA-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 1-hydroxy-4-unsubstituted benzenoids Alkyl aryl ethers Anisoles Carbonyl compounds Carboxylic acids Cinnamic acids Coumaric acids and derivatives Hydrocarbon derivatives Methoxybenzenes Methoxyphenols Monocarboxylic acids and derivatives Organic oxides Phenoxy compounds Styrenes 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid Alkyl aryl ether Anisole Aromatic homomonocyclic compound Benzenoid Carbonyl group Carboxylic acid Carboxylic acid derivative Cinnamic acid Coumaric acid or derivatives Ether Hydrocarbon derivative Hydroxycinnamic acid Methoxybenzene Methoxyphenol Monocarboxylic acid or derivatives Monocyclic benzene moiety Organic oxide Organic oxygen compound Organooxygen compound Phenol Phenol ether Phenoxy compound Styrene ferulic acids Solid logp 1.56 ALOGPS logs -2.35 ALOGPS solubility 8.71e-01 g/l ALOGPS melting_point 228 - 233 oC logp 1.67 ChemAxon pka_strongest_acidic 3.77 ChemAxon pka_strongest_basic -4.9 ChemAxon iupac (2E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoic acid ChemAxon average_mass 194.184 ChemAxon mono_mass 194.057908808 ChemAxon smiles COC1=C(O)C=C(\C=C\C(O)=O)C=C1 ChemAxon formula C10H10O4 ChemAxon inchi InChI=1S/C10H10O4/c1-14-9-4-2-7(6-8(9)11)3-5-10(12)13/h2-6,11H,1H3,(H,12,13)/b5-3+ ChemAxon inchikey QURCVMIEKCOAJU-HWKANZROSA-N ChemAxon polar_surface_area 66.76 ChemAxon refractivity 51.5 ChemAxon polarizability 19.36 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::NmrOneD 1620 Specdb::NmrOneD 3900 Specdb::NmrOneD 4174 Specdb::EiMs 1635 Specdb::MsIr 990 Specdb::MsIr 991 Specdb::MsIr 992 Specdb::NmrTwoD 1561 Specdb::CMs 6015 Specdb::CMs 37863 Specdb::CMs 131757 Specdb::CMs 139491 Specdb::CMs 1082471 Specdb::CMs 1082472 Specdb::CMs 1082473 Specdb::CMs 1082474 Specdb::CMs 1082475 Specdb::MsMs 1351 Specdb::MsMs 1352 Specdb::MsMs 1353 Specdb::MsMs 4958 Specdb::MsMs 4959 Specdb::MsMs 4960 Specdb::MsMs 4961 Specdb::MsMs 4962 Specdb::MsMs 241558 Specdb::MsMs 241559 Specdb::MsMs 241560 Specdb::MsMs 243613 Specdb::MsMs 243614 Specdb::MsMs 243615 Specdb::MsMs 285549 Specdb::MsMs 285550 Specdb::MsMs 285551 Specdb::MsMs 285552 Specdb::MsMs 285553 Specdb::MsMs 285554 Specdb::MsMs 373974 Specdb::MsMs 373975 Specdb::MsMs 373976 Specdb::MsMs 373977 Specdb::MsMs 373978 HMDB00955 4FE #<Reference:0x000055ce320936d8> #<Reference:0x000055ce32093520> #<Reference:0x000055ce32093368> #<Reference:0x000055ce320931b0> #<Reference:0x000055ce32092ff8> #<Reference:0x000055ce32092e40> #<Reference:0x000055ce32092c88> Bilberry Type 1 specific Vaccinium myrtillus 180763 Common wheat Type 1 specific Triticum aestivum 4565 0.3 0.3 0.3 mg/100 g German camomile Type 1 specific Matricaria recutita 127986 Peanut Type 1 specific Arachis hypogaea 3818 0.02 0.02 0.02 mg/100 g Soy bean Type 1 specific Glycine max 3847 Sunflower Type 1 specific Helianthus annuus 4232 155.0 155.0 155.0 mg/100 g Vinegar Type 2 specific 0.045295 0.045294739 0.045294739 mg/100 g Anti-edemic 248 Anti-inflammatory 370 A substance that reduces or suppresses inflammation. Anti-oxidant 502 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324. Hypothermic 1023