Record Information
Version1.0
Creation date2010-04-08 22:05:29 UTC
Update date2019-11-26 02:57:50 UTC
Primary IDFDB002700
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameIsoferulic acid
DescriptionIt 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.
CAS Number537-73-5
Structure
Thumb
Synonyms
SynonymSource
3-Hydroxy-4-methoxycinnamic acidChEBI
Hesperetic acidChEBI
3-Hydroxy-4-methoxycinnamateGenerator
IsoferulateGenerator
3-(3-Hydroxy-4-methoxyphenyl)-2-propenoateHMDB
3-(3-Hydroxy-4-methoxyphenyl)-2-propenoic acidHMDB
3-Hydroxy-4-methoxy-cinnamateHMDB
3-Hydroxy-4-methoxy-cinnamic acidHMDB
(2E)-3-(3-Hydroxy-4-methoxyphenyl)-2-propenoic acidHMDB
(e)-3-Hydroxy-4-methoxycinnamic acidHMDB
(e)-4-Methoxycaffeic acidHMDB
(e)-4-O-Methylcaffeic acidHMDB
(e)-Hesperetic acidHMDB
(e)-Isoferulic acidHMDB
4-Methoxycaffeic acidHMDB
4-O-Methylcaffeic acidHMDB
trans-3-Hydroxy-4-methoxycinnamic acidHMDB
trans-4-Methoxycaffeic acidHMDB
trans-4-O-Methylcaffeic acidHMDB
trans-Hesperetic acidHMDB
trans-Isoferulic acidHMDB
(2E)-3-(3-Hydroxy-4-methoxyphenyl)prop-2-enoateHMDB
3'-Hydroxy-4'-methoxycinnamic acidHMDB
(e)-3-(3-Hydroxy-4-methoxyphenyl)-2-propenoic acidHMDB
(2E)-3-(3-Hydroxy-4-methoxyphenyl)prop-2-enoic acidHMDB
3-(3-Hydroxy-4-methoxyphenyl)-2-propenoic acid, 9CIdb_source
Hesperetatebiospider
Hesperetinic aciddb_source
Isoferulic aciddb_source
Predicted Properties
PropertyValueSource
Water Solubility0.87 g/LALOGPS
logP1.56ALOGPS
logP1.67ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)3.77ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity51.5 m³·mol⁻¹ChemAxon
Polarizability19.36 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H10O4
IUPAC name(2E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoic acid
InChI IdentifierInChI=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+
InChI KeyQURCVMIEKCOAJU-HWKANZROSA-N
Isomeric SMILESCOC1=C(O)C=C(\C=C\C(O)=O)C=C1
Average Molecular Weight194.184
Monoisotopic Molecular Weight194.057908808
Classification
Description 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.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassHydroxycinnamic acids and derivatives
Direct ParentHydroxycinnamic acids
Alternative Parents
Substituents
  • Cinnamic acid
  • Coumaric acid or derivatives
  • Hydroxycinnamic acid
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Styrene
  • Phenol ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Ether
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Foods
  • Cocoa and cocoa products
  • Grains:

    Nuts and legumes:

    Fruits and vegetables:

    Fats and oils:

    Beverages:

    Physico-Chemical Properties - Experimental
    Physico-Chemical Properties - Experimental
    PropertyValueReference
    Physical stateSolid
    Physical DescriptionNot Available
    Mass CompositionC 61.85%; H 5.19%; O 32.96%DFC
    Melting Point228 - 233 oC
    Boiling PointNot Available
    Experimental Water SolubilityNot Available
    Experimental logPNot Available
    Experimental pKaNot Available
    Isoelectric pointNot Available
    ChargeNot Available
    Optical RotationNot Available
    Spectroscopic UV Data322 (e 27500) (MeOH) (Derep)DFC
    DensityNot Available
    Refractive IndexNot Available
    Spectra
    Spectra
    EI-MS/GC-MS
    TypeDescriptionSplash KeyView
    EI-MSMass Spectrum (Electron Ionization)splash10-0006-5900000000-db5f99d89dd9e349c86c2015-03-01View Spectrum
    Predicted GC-MSIsoferulic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-002e-0900000000-b51b390a0727d3838cabSpectrum
    Predicted GC-MSIsoferulic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-7094000000-6021a908fd1b4eec8f00Spectrum
    Predicted GC-MSIsoferulic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSIsoferulic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSIsoferulic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSIsoferulic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSIsoferulic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSIsoferulic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSIsoferulic acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    MS/MS
    TypeDescriptionSplash KeyView
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-004l-0900000000-ab3320c9d0dfcba00b6e2012-07-24View Spectrum
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-001i-0900000000-2b9775043a4af5fdc0642012-07-24View Spectrum
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-001i-0900000000-29fd32eacfaa527045592012-07-24View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0006-0900000000-d26e8f9f43c25710a04d2012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-003r-0900000000-25d10f2b53d4679375242012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-001i-0900000000-b2f1dd5274585c5f6b0b2012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-001i-3900000000-2e21dbcbb598dba645252012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-001i-2900000000-7a28000b74f8c4f5b27f2012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-01p9-0920000000-7aaa9640d85177e2e6b52017-08-14View Spectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-01p9-0920000000-7aaa9640d85177e2e6b52017-08-14View Spectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-01p9-0920000000-7aaa9640d85177e2e6b52017-08-14View Spectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-01p9-0920000000-7aaa9640d85177e2e6b52017-08-14View Spectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-005l-0902100000-6fc8730bd28daa779b662017-08-14View Spectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-005l-0902100000-6fc8730bd28daa779b662017-08-14View Spectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-001i-0900000000-623ecba5385a03e0406b2017-09-12View Spectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0900000000-205ebeb435685d894bcf2017-09-12View Spectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-001i-0900000000-97eb2cfc1a86c4933f762017-09-12View Spectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-001i-0900000000-49f1d1fd82311df297132017-09-12View Spectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-005l-0902100000-6fc8730bd28daa779b662017-09-12View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0900000000-eaa8fbddbddb5c585ea42017-06-28View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002b-1900000000-c2fa54dcd41f9ab16b8e2017-06-28View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00fs-5900000000-a969ea13d0a4ad63b2a62017-06-28View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-6b2f8b891907a56146d62017-06-28View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0900000000-6139186c0691cc7b95bb2017-06-28View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00o0-2900000000-8d4f500b0c438df01f412017-06-28View Spectrum
    NMR
    TypeDescriptionView
    1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
    1D NMR1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)Spectrum
    1D NMR13C NMR Spectrum (1D, 22.53 MHz, DMSO-d6, experimental)Spectrum
    2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
    ChemSpider ID643318
    ChEMBL IDCHEMBL233295
    KEGG Compound IDC10470
    Pubchem Compound ID736186
    Pubchem Substance IDNot Available
    ChEBI IDNot Available
    Phenol-Explorer ID485
    DrugBank IDDB07109
    HMDB IDHMDB00955
    CRC / DFC (Dictionary of Food Compounds) IDCMK09-G:CND07-C
    EAFUS IDNot Available
    Dr. Duke IDISOFERULIC-ACID
    BIGG IDNot Available
    KNApSAcK IDC00002752
    HET ID4FE
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    Flavornet IDNot Available
    GoodScent IDNot Available
    SuperScent IDNot Available
    Wikipedia IDNot Available
    Phenol-Explorer Metabolite ID485
    Duplicate IDSNot Available
    Old DFC IDSNot Available
    Associated Foods
    FoodContent Range AverageReference
    FoodReference
    Biological Effects and Interactions
    Health Effects / Bioactivities
    DescriptorIDDefinitionReference
    anti edemicDUKE
    anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
    antioxidant22586 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.DUKE
    hypothermicDUKE
    EnzymesNot Available
    PathwaysNot Available
    MetabolismNot Available
    BiosynthesisNot Available
    Organoleptic Properties
    FlavoursNot Available
    Files
    MSDSshow
    References
    Synthesis ReferenceNot Available
    General ReferenceNot Available
    Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
    — Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.