Record Information
Version1.0
Creation date2015-05-07 20:19:00 UTC
Update date2019-11-26 03:21:55 UTC
Primary IDFDB030860
Secondary Accession NumbersNot Available
Chemical Information
FooDB Nameferulate
DescriptionFerulic acid, also known as 4-hydroxy-3-methoxycinnamic acid or 3-methoxy-4-hydroxy-trans-cinnamic acid, is a member of the class of compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated. Ferulic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Ferulic acid can be found in a number of food items such as flaxseed, pepper (c. chinense), chinese cinnamon, and wakame, which makes ferulic acid a potential biomarker for the consumption of these food products. Ferulic acid can be found primarily in blood, feces, and urine, as well as in human fibroblasts and stratum corneum tissues. Ferulic acid exists in all eukaryotes, ranging from yeast to humans. Ferulic acid is a hydroxycinnamic acid, a type of organic compound. It is an abundant phenolic phytochemical found in plant cell walls, covalently bonded as side chains to molecules such as arabinoxylans. As a component of lignin, ferulic acid is a precursor in the manufacture of other aromatic compounds. The name is derived from the genus Ferula, referring to the giant fennel (Ferula communis) .
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
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
trans-FerulateGenerator
FerulateGenerator
(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
Ferulic acid, (e)-isomerMeSH, HMDB
Ferulic acid, monosodium saltMeSH, HMDB
Sodium ferulateMeSH, HMDB
Ferulic acid, (Z)-isomerMeSH, HMDB
8,8'-Diferulic acidMeSH, HMDB
(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-Methoxy-4-hydroxycinnamic acidHMDB
4'-Hydroxy-3'-methoxycinnamic acidHMDB
Coniferic acidHMDB
Ferulaic acidHMDB
4’-Hydroxy-3’-methoxycinnamic acidPhytoBank
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
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0006-5900000000-8c81de6c352294475072Spectrum
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-d193da7a6efffdab2dbbSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00kr-7900000000-b5b8d28b28c8067c3932Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-002r-9000000000-d3616a5367a7a2a9b3c6Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positivesplash10-0006-1900000000-5dffac87fe7c815de4ceSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0006-0900000000-c173873ef0d975be6c34Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-001i-0900000000-0b9174ecaba08b2f01b9Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-001i-1900000000-eff77e27aef254928643Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-001r-9700000000-18946fad05ffb1f78a7dSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-001r-9300000000-e2221a73d3d078bf6e03Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0002-0900000000-653c9a454414dd8b8b50Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-002b-0900000000-62b2ee8bf9571be3d97fSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-001i-0900000000-a7cded21e6010eb8bce2Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-0900000000-c173873ef0d975be6c34Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-0900000000-0b9174ecaba08b2f01b9Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-1900000000-eff77e27aef254928643Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001r-9700000000-18946fad05ffb1f78a7dSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001r-9300000000-e2221a73d3d078bf6e03Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001i-0900000000-a7cded21e6010eb8bce2Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-002b-0900000000-cdced9ddbcdaedf2f1b9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0900000000-434fdd914ca34cd68f41Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0900000000-0dcbcad8bf6cb403f4f8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0g31-5900000000-4fa9ed831b4e0d1573e5Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-29c8691e15490f8d88acSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0900000000-e940f09e099b7acf3772Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00o1-1900000000-ee61087a069406e459c7Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
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 / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference