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trans-Ferulic acid (FDB012802)

Record Information
Version1.0
Creation date2010-04-08 22:10:22 UTC
Update date2020-09-17 15:29:56 UTC
Primary IDFDB012802
Secondary Accession NumbersNot Available
Chemical Information
FooDB Nametrans-Ferulic acid
DescriptionFerulic acid, also known as (e)-ferulate or trans-ferulate, 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. Ferulic acid is a moderately weak acid (based on its pKa). Ferulic acid is a highly abundant phenolic phytochemical which is present in plant cell walls. In humans it can be readily absorbed by the small intestine and excreted through the urine. It is one of the most abundant phenolic acids in plants, varying from 5 g/kg in wheat bran to 9 g/kg in sugar-beet pulp and 50 g/kg in corn kernels. It occurs primarily in seeds and leaves both in its free form (albeit rarely) and covalently linked to lignin and other biopolymers. It is usually found as ester cross-links with polysaccharides in the cell wall, such as arabinoxylans in grasses, pectin in spinach and sugar beet, and xyloglucans in bamboo. It also can cross-link with a variety of plant proteins. Due to its phenolic nucleus and an extended side chain conjugation (carbohydrates and proteins), ferulic acid readily forms a resonance-stabilized phenoxy radical which accounts for its potent antioxidant potential. Food supplementation with curcumin and ferulic acid is considered a nutritional approach to reducing oxidative damage and amyloid pathology in Alzheimer’s disease (PMID: 17127365, 1398220, 15453708, 9878519). Ferulic acid can be produced by a number of microbes including Pseudomonas and Saccharomyces (PMID: 8395165). It possesses antioxidant, anti-aging and anti-inflammatory properties. It protects the skin from damage by UV light and is used in skin care, sun care, hair care and color cosmetics.
CAS Number537-98-4
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
    EI-MS/GC-MS
    TypeDescriptionSplash KeyView
    EI-MSMass Spectrum (Electron Ionization)splash10-0006-5900000000-8c81de6c3522944750722015-03-01View Spectrum
    GC-MStrans-Ferulic acid, 2 TMS, GC-MS Spectrumsplash10-05g4-1978000000-1097d5b300514a0489dfSpectrum
    GC-MStrans-Ferulic acid, 2 TMS, GC-MS Spectrumsplash10-00kv-2964000000-3d20d62c97c33247cfcfSpectrum
    GC-MStrans-Ferulic acid, non-derivatized, GC-MS Spectrumsplash10-00ku-1965000000-ebee2a916fe97f0270a1Spectrum
    GC-MStrans-Ferulic acid, 2 TMS, GC-MS Spectrumsplash10-00di-9654000000-b3f1759076cffd2ac235Spectrum
    GC-MStrans-Ferulic acid, 2 TMS, GC-MS Spectrumsplash10-000m-3975000000-5a41c311d78f7219474cSpectrum
    GC-MStrans-Ferulic acid, non-derivatized, GC-MS Spectrumsplash10-0006-1900000000-5dffac87fe7c815de4ceSpectrum
    GC-MStrans-Ferulic acid, non-derivatized, GC-MS Spectrumsplash10-0006-2900000000-8db541bacfe47b9e0c8bSpectrum
    GC-MStrans-Ferulic acid, non-derivatized, GC-MS Spectrumsplash10-0006-2900000000-a338415bd30d4e62e664Spectrum
    GC-MStrans-Ferulic acid, non-derivatized, GC-MS Spectrumsplash10-05g4-1978000000-1097d5b300514a0489dfSpectrum
    GC-MStrans-Ferulic acid, non-derivatized, GC-MS Spectrumsplash10-00kv-2964000000-3d20d62c97c33247cfcfSpectrum
    GC-MStrans-Ferulic acid, non-derivatized, GC-MS Spectrumsplash10-00ku-1965000000-ebee2a916fe97f0270a1Spectrum
    GC-MStrans-Ferulic acid, non-derivatized, GC-MS Spectrumsplash10-00di-9654000000-b3f1759076cffd2ac235Spectrum
    GC-MStrans-Ferulic acid, non-derivatized, GC-MS Spectrumsplash10-000m-3975000000-5a41c311d78f7219474cSpectrum
    GC-MStrans-Ferulic acid, non-derivatized, GC-MS Spectrumsplash10-00kv-1954000000-9dae07505bd18466be87Spectrum
    Predicted GC-MStrans-Ferulic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-002e-0900000000-d76b7991f2d90cb58bd5Spectrum
    Predicted GC-MStrans-Ferulic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-6094000000-b805979df23a0d890d7cSpectrum
    Predicted GC-MStrans-Ferulic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MStrans-Ferulic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MStrans-Ferulic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MStrans-Ferulic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MStrans-Ferulic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MStrans-Ferulic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MStrans-Ferulic acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    MS/MS
    TypeDescriptionSplash KeyView
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-004i-0900000000-d193da7a6efffdab2dbb2012-07-24View Spectrum
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00kr-7900000000-b5b8d28b28c8067c39322012-07-24View Spectrum
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-002r-9000000000-d3616a5367a7a2a9b3c62012-07-24View Spectrum
    MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positivesplash10-0006-1900000000-5dffac87fe7c815de4ce2012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0006-0900000000-c173873ef0d975be6c342012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-001i-0900000000-0b9174ecaba08b2f01b92012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-001i-1900000000-eff77e27aef2549286432012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-001r-9700000000-18946fad05ffb1f78a7d2012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-001r-9300000000-e2221a73d3d078bf6e032012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0002-0900000000-653c9a454414dd8b8b502012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-002b-0900000000-62b2ee8bf9571be3d97f2012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-001i-0900000000-a7cded21e6010eb8bce22012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-0900000000-c173873ef0d975be6c342017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-0900000000-0b9174ecaba08b2f01b92017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-1900000000-eff77e27aef2549286432017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001r-9700000000-18946fad05ffb1f78a7d2017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001r-9300000000-e2221a73d3d078bf6e032017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001i-0900000000-a7cded21e6010eb8bce22017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-002b-0900000000-cdced9ddbcdaedf2f1b92017-09-14View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0900000000-434fdd914ca34cd68f412016-09-12View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0900000000-0dcbcad8bf6cb403f4f82016-09-12View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0g31-5900000000-4fa9ed831b4e0d1573e52016-09-12View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-29c8691e15490f8d88ac2016-09-12View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0900000000-e940f09e099b7acf37722016-09-12View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00o1-1900000000-ee61087a069406e459c72016-09-12View Spectrum
    NMR
    TypeDescriptionView
    1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
    1D NMR1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)Spectrum
    1D NMR13C NMR Spectrum (1D, 25.16 MHz, DMSO-d6, experimental)Spectrum
    1D NMR1H NMR Spectrum (1D, DMSO, experimental)Spectrum
    1D NMR13C NMR Spectrum (1D, DMSO, experimental)Spectrum
    2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
    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).