1.02010-04-08 22:05:29 UTC2019-11-26 02:57:50 UTCFDB002700Isoferulic acidIt 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 acid3-(3-Hydroxy-4-methoxyphenyl)-2-propenoate3-(3-Hydroxy-4-methoxyphenyl)-2-propenoic acid3-(3-Hydroxy-4-methoxyphenyl)-2-propenoic acid, 9CI3-Hydroxy-4-methoxy-cinnamate3-Hydroxy-4-methoxy-cinnamic acid3-Hydroxy-4-methoxycinnamate3-Hydroxy-4-methoxycinnamic acidHesperetateHesperetic acidHesperetinic acidIsoferulateIsoferulic acidC10H10O4194.184194.057908808(2E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoic acidisoferulic acid537-73-5COC1=C(O)C=C(\C=C\C(O)=O)C=C1InChI=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 acidsOrganic compoundsPhenylpropanoids and polyketidesCinnamic acids and derivativesHydroxycinnamic acids and derivativesAromatic homomonocyclic compounds1-hydroxy-2-unsubstituted benzenoids1-hydroxy-4-unsubstituted benzenoidsAlkyl aryl ethersAnisolesCarbonyl compoundsCarboxylic acidsCinnamic acidsCoumaric acids and derivativesHydrocarbon derivativesMethoxybenzenesMethoxyphenolsMonocarboxylic acids and derivativesOrganic oxidesPhenoxy compoundsStyrenes1-hydroxy-2-unsubstituted benzenoid1-hydroxy-4-unsubstituted benzenoidAlkyl aryl etherAnisoleAromatic homomonocyclic compoundBenzenoidCarbonyl groupCarboxylic acidCarboxylic acid derivativeCinnamic acidCoumaric acid or derivativesEtherHydrocarbon derivativeHydroxycinnamic acidMethoxybenzeneMethoxyphenolMonocarboxylic acid or derivativesMonocyclic benzene moietyOrganic oxideOrganic oxygen compoundOrganooxygen compoundPhenolPhenol etherPhenoxy compoundStyreneferulic acidsSolidlogp1.56logs-2.35solubility8.71e-01 g/lmelting_point228 - 233 oClogp1.67pka_strongest_acidic3.77pka_strongest_basic-4.9iupac(2E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoic acidaverage_mass194.184mono_mass194.057908808smilesCOC1=C(O)C=C(\C=C\C(O)=O)C=C1formulaC10H10O4inchiInChI=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+inchikeyQURCVMIEKCOAJU-HWKANZROSA-Npolar_surface_area66.76refractivity51.5polarizability19.36rotatable_bond_count3acceptor_count4donor_count2physiological_charge-1formal_charge0Specdb::NmrTwoD1561Specdb::NmrOneD1620Specdb::NmrOneD3900Specdb::NmrOneD4174Specdb::EiMs1635Specdb::MsIr990Specdb::MsIr991Specdb::MsIr992Specdb::CMs6015Specdb::CMs37863Specdb::CMs131757Specdb::CMs139491Specdb::CMs1082471Specdb::CMs1082472Specdb::CMs1082473Specdb::CMs1082474Specdb::CMs1082475Specdb::MsMs1351Specdb::MsMs1352Specdb::MsMs1353Specdb::MsMs4958Specdb::MsMs4959Specdb::MsMs4960Specdb::MsMs4961Specdb::MsMs4962Specdb::MsMs241558Specdb::MsMs241559Specdb::MsMs241560Specdb::MsMs243613Specdb::MsMs243614Specdb::MsMs243615Specdb::MsMs285549Specdb::MsMs285550Specdb::MsMs285551Specdb::MsMs285552Specdb::MsMs285553Specdb::MsMs285554Specdb::MsMs373974Specdb::MsMs373975Specdb::MsMs373976Specdb::MsMs373977Specdb::MsMs373978HMDB009554FE#<Reference:0x000055567644bd18>#<Reference:0x000055567644bb10>#<Reference:0x000055567644b818>#<Reference:0x000055567644b480>#<Reference:0x000055567644b250>#<Reference:0x000055567644afd0>#<Reference:0x000055567644acb0>BilberryType 1specificVaccinium myrtillus180763Common wheatType 1specificTriticum aestivum45650.30.30.3mg/100 gGerman camomileType 1specificMatricaria recutita127986PeanutType 1specificArachis hypogaea38180.020.020.02mg/100 gSoy beanType 1specificGlycine max3847SunflowerType 1specificHelianthus annuus4232155.0155.0155.0mg/100 gVinegarType 2specific0.0452950.0452947390.045294739mg/100 ganti edemic248anti inflammatory370A substance that reduces or suppresses inflammation.antioxidant502A 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.hypothermic1023