Record Information
Version1.0
Creation date2010-04-08 22:10:22 UTC
Update date2019-11-27 17:23:05 UTC
Primary IDFDB012802
Secondary Accession NumbersNot Available
Chemical Information
FooDB Nametrans-Ferulic acid
Descriptiontrans-Ferulic acid, also known as (e)-ferulic acid or (e)-ferulate, 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. trans-Ferulic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). trans-Ferulic acid exists in all living species, ranging from bacteria to humans. trans-Ferulic acid is found, on average, in the highest concentration in corns. trans-Ferulic acid has also been detected, but not quantified in, several different foods, such as burdocks, ginkgo nuts, persian limes, kiwis, and chickpea. This could make trans-ferulic acid a potential biomarker for the consumption of these foods.
CAS Number537-98-4
Structure
Thumb
Synonyms
SynonymSource
(e)-3-(4-Hydroxy-3-methoxyphenyl)-2-propenoic acidChEBI
(e)-4'-Hydroxy-3'-methoxycinnamic acidChEBI
(e)-4-Hydroxy-3-methoxycinnamic acidChEBI
(e)-Ferulic acidChEBI
3-(4-Hydroxy-3-methoxyphenyl)propenoic acidChEBI
3-Methoxy-4-hydroxy-trans-cinnamic acidChEBI
4-Hydroxy-3-methoxycinnamic acidChEBI
trans-4-Hydroxy-3-methoxycinnamic acidChEBI
Ferulic acidKegg
3-Methoxy-4-hydroxy-trans-cinnamateKegg
4-Hydroxy-3-methoxycinnamateKegg
(e)-3-(4-Hydroxy-3-methoxyphenyl)-2-propenoateGenerator
(e)-4'-Hydroxy-3'-methoxycinnamateGenerator
(e)-4-Hydroxy-3-methoxycinnamateGenerator
(e)-FerulateGenerator
3-(4-Hydroxy-3-methoxyphenyl)propenoateGenerator
trans-4-Hydroxy-3-methoxycinnamateGenerator
FerulateGenerator
trans-FerulateGenerator
8,8'-Diferulic acidHMDB
Ferulic acid, (e)-isomerHMDB
Ferulic acid, monosodium saltHMDB
Sodium ferulateHMDB
Ferulic acid, (Z)-isomerHMDB
(2E)-3-(4-Hydroxy-3-methoxyphenyl)-2-propenoateHMDB
(2E)-3-(4-Hydroxy-3-methoxyphenyl)-2-propenoic acidHMDB
(e)-4-Hydroxy-3-methoxy-cinnamateHMDB
(e)-4-Hydroxy-3-methoxy-cinnamic acidHMDB
trans-Ferulic acidChEBI
(2E)-3-(4-Hydroxy-3-methoxyphenyl)-2-acrylic acidHMDB
(2E)-3-(4-Hydroxy-3-methoxyphenyl)prop-2-enoic acidHMDB
(E)-3-(4-Hydroxy-3-methoxyphenyl)acrylic acidHMDB
Fumalic acidHMDB
3-(4-Hydroxy-3-methoxyphenyl)-2-propenoic acidHMDB
3-(4-Hydroxy-3-methoxyphenyl)acrylic acidHMDB
3-Methoxy-4-hydroxycinnamic acidHMDB
4'-Hydroxy-3'-methoxycinnamic acidHMDB
Coniferic acidHMDB
Ferulaic acidHMDB
(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acidbiospider
(E)-3-(4-Hydroxy-3-methoxyphenyl)-2-propenoatebiospider
(E)-3-(4-Hydroxy-3-methoxyphenyl)-2-propenoic acidbiospider
(E)-4-Hydroxy-3-methoxy-cinnamatebiospider
(E)-4-Hydroxy-3-methoxy-cinnamic acidbiospider
(E)-4-Hydroxy-3-methoxycinnamatebiospider
(E)-4-Hydroxy-3-methoxycinnamic acidbiospider
(E)-4'-Hydroxy-3'-methoxycinnamic acidbiospider
(E)-Ferulatebiospider
(E)-Ferulic acidbiospider
2-Propenoic acid, 3-(4-hydroxy-3-methoxyphenyl)-, (E)-biospider
4-Hydroxy-3-methoxy-(E)-cinnamic acidbiospider
Predicted Properties
PropertyValueSource
Water Solubility0.91 g/LALOGPS
logP1.58ALOGPS
logP1.67ChemAxon
logS-2.3ALOGPS
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
Polarizability19.18 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC10H10O4
IUPAC name(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid
InChI IdentifierInChI=1S/C10H10O4/c1-14-9-6-7(2-4-8(9)11)3-5-10(12)13/h2-6,11H,1H3,(H,12,13)/b5-3+
InChI KeyKSEBMYQBYZTDHS-HWKANZROSA-N
Isomeric SMILESCOC1=C(O)C=CC(\C=C\C(O)=O)=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-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 PointMp 174°DFC
    Boiling PointNot Available
    Experimental Water SolubilityNot Available
    Experimental logP1.51HANSCH,C ET AL. (1995)
    Experimental pKa4.7
    Isoelectric pointNot Available
    ChargeNot Available
    Optical RotationNot Available
    Spectroscopic UV Data322 () (EtOH) (Berdy)DFC
    DensityNot Available
    Refractive IndexNot Available
    Spectra
    Spectra
    Spectrum TypeDescriptionSplash Key
    GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-05g4-1978000000-1097d5b300514a0489dfView in MoNA
    GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00kv-2964000000-3d20d62c97c33247cfcfView in MoNA
    GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-00ku-1965000000-ebee2a916fe97f0270a1View in MoNA
    GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00di-9654000000-b3f1759076cffd2ac235View in MoNA
    GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-000m-3975000000-5a41c311d78f7219474cView in MoNA
    GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-1900000000-5dffac87fe7c815de4ceView in MoNA
    GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-2900000000-8db541bacfe47b9e0c8bView in MoNA
    GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-2900000000-a338415bd30d4e62e664View in MoNA
    GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-05g4-1978000000-1097d5b300514a0489dfView in MoNA
    GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00kv-2964000000-3d20d62c97c33247cfcfView in MoNA
    GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00ku-1965000000-ebee2a916fe97f0270a1View in MoNA
    GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9654000000-b3f1759076cffd2ac235View in MoNA
    GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-000m-3975000000-5a41c311d78f7219474cView in MoNA
    GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00kv-1954000000-9dae07505bd18466be87View in MoNA
    Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002e-0900000000-d76b7991f2d90cb58bd5View in MoNA
    Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-6094000000-b805979df23a0d890d7cView in MoNA
    LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-004i-0900000000-d193da7a6efffdab2dbbView in MoNA
    LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00kr-7900000000-b5b8d28b28c8067c3932View in MoNA
    LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-002r-9000000000-d3616a5367a7a2a9b3c6View in MoNA
    LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positivesplash10-0006-1900000000-5dffac87fe7c815de4ceView in MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0006-0900000000-c173873ef0d975be6c34View in MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-001i-0900000000-0b9174ecaba08b2f01b9View in MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-001i-1900000000-eff77e27aef254928643View in MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-001r-9700000000-18946fad05ffb1f78a7dView in MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-001r-9300000000-e2221a73d3d078bf6e03View in MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0002-0900000000-653c9a454414dd8b8b50View in MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-002b-0900000000-62b2ee8bf9571be3d97fView in MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-001i-0900000000-a7cded21e6010eb8bce2View in MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-0900000000-c173873ef0d975be6c34View in MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-0900000000-0b9174ecaba08b2f01b9View in MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-1900000000-eff77e27aef254928643View in MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001r-9700000000-18946fad05ffb1f78a7dView in MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001r-9300000000-e2221a73d3d078bf6e03View in MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001i-0900000000-a7cded21e6010eb8bce2View in MoNA
    LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-002b-0900000000-cdced9ddbcdaedf2f1b9View in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0900000000-434fdd914ca34cd68f41View in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0900000000-0dcbcad8bf6cb403f4f8View in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0g31-5900000000-4fa9ed831b4e0d1573e5View in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-29c8691e15490f8d88acView in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0900000000-e940f09e099b7acf3772View in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00o1-1900000000-ee61087a069406e459c7View in MoNA
    MSMass Spectrum (Electron Ionization)splash10-0006-5900000000-8c81de6c352294475072View in MoNA
    1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
    1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
    1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
    1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
    1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
    2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
    ChemSpider ID393368
    ChEMBL IDCHEMBL32749
    KEGG Compound IDC01494
    Pubchem Compound ID445858
    Pubchem Substance IDNot Available
    ChEBI IDNot Available
    Phenol-Explorer ID499
    DrugBank IDDB07767
    HMDB IDHMDB00954
    CRC / DFC (Dictionary of Food Compounds) IDHLG59-X:HLG60-R
    EAFUS IDNot Available
    Dr. Duke IDTRANS-FERULIC-ACID
    BIGG IDNot Available
    KNApSAcK IDNot Available
    HET IDFER
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    Flavornet IDNot Available
    GoodScent IDNot Available
    SuperScent IDNot Available
    Wikipedia IDNot Available
    Phenol-Explorer Metabolite IDNot Available
    Duplicate IDSNot Available
    Old DFC IDSNot Available
    Associated Foods
    FoodContent Range AverageReference
    FoodReference
    Biological Effects and Interactions
    Health Effects / Bioactivities
    DescriptorIDDefinitionReference
    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
    cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
    inhibitor35222 A substance that diminishes the rate of a chemical reaction.CHEBI
    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).