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Identification
YMDB IDYMDB01325
NameFerulic acid
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionFerulic acid is a hydroxycinnamic acid related to cinnamic acid, a type of polyphenol. It is an abundant phenolic phytochemical found in plant cell wall components. It is present in beer and wine. Ferulic acid is decarboxylated to 4-vinylguaiacol during wine fermentation by certain strains of yeast. Vinylphenols then spontaneously condensate with grape anthocyanins (mainly malvidin-3-O-glucoside) to form pigments important for the color of ageing wine. [PMID: 17303275]
Structure
Thumb
Synonyms
  • (2E)-3-(4-Hydroxy-3-methoxyphenyl)-2-propenoic acid
  • 2-Propenoic acid, 3-(4-hydroxy-3-methoxyphenyl)-
  • 3-(4-Hydroxy-3-methoxyphenyl)-2-propenoic acid
  • 3-(4-Hydroxy-3-methoxyphenyl)acrylic acid
  • 3-Methoxy-4-hydroxy-trans-cinnamate
  • 3-methoxy-4-hydroxy-trans-cinnamic acid
  • 3-Methoxy-4-hydroxycinnamic acid
  • 4-Hydroxy-3-methoxycinnamic acid
  • Cinnamic acid, 4-hydroxy-3-methoxy-
  • Ferulate
  • Ferulic acid
  • (e)-3-(4-Hydroxy-3-methoxyphenyl)-2-propenoic acid
  • (e)-4'-Hydroxy-3'-methoxycinnamic acid
  • (e)-4-Hydroxy-3-methoxycinnamic acid
  • (e)-Ferulic acid
  • 3-(4-Hydroxy-3-methoxyphenyl)propenoic acid
  • trans-4-Hydroxy-3-methoxycinnamic acid
  • 4-Hydroxy-3-methoxycinnamate
  • (e)-3-(4-Hydroxy-3-methoxyphenyl)-2-propenoate
  • (e)-4'-Hydroxy-3'-methoxycinnamate
  • (e)-4-Hydroxy-3-methoxycinnamate
  • (e)-Ferulate
  • 3-(4-Hydroxy-3-methoxyphenyl)propenoate
  • trans-4-Hydroxy-3-methoxycinnamate
  • trans-Ferulate
  • 8,8'-Diferulic acid
  • Ferulic acid, (e)-isomer
  • Ferulic acid, monosodium salt
  • Sodium ferulate
  • Ferulic acid, (Z)-isomer
  • (2E)-3-(4-Hydroxy-3-methoxyphenyl)-2-propenoate
  • (e)-4-Hydroxy-3-methoxy-cinnamate
  • (e)-4-Hydroxy-3-methoxy-cinnamic acid
  • trans-Ferulic acid
  • (2E)-3-(4-Hydroxy-3-methoxyphenyl)-2-acrylic acid
  • (2E)-3-(4-Hydroxy-3-methoxyphenyl)prop-2-enoic acid
  • (E)-3-(4-Hydroxy-3-methoxyphenyl)acrylic acid
  • Fumalic acid
  • 4'-Hydroxy-3'-methoxycinnamic acid
  • Coniferic acid
  • Ferulaic acid
CAS number1135-24-6
WeightAverage: 194.184
Monoisotopic: 194.057908808
InChI KeyKSEBMYQBYZTDHS-HWKANZROSA-N
InChIInChI=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+
IUPAC Name(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid
Traditional IUPAC Nameferulic acid
Chemical FormulaC10H10O4
SMILESCOC1=CC(\C=C\C(O)=O)=CC=C1O
Chemical Taxonomy
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
Physical Properties
StateSolid
Charge0
Melting point168-172 °C
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogP1.51 [HANSCH,C ET AL. (1995)]PhysProp
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
Biological Properties
Cellular Locations
  • extracellular
Organoleptic PropertiesNot Available
SMPDB Pathways
Beer ReactionsPW002719 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG PathwaysNot Available
SMPDB Reactions
4-Vinylguaiacol + Carbon dioxideFerulic acid + hydron
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-05g4-1978000000-1097d5b300514a0489dfJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00kv-2964000000-3d20d62c97c33247cfcfJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-00ku-1965000000-ebee2a916fe97f0270a1JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00di-9654000000-b3f1759076cffd2ac235JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-000m-3975000000-5a41c311d78f7219474cJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-1900000000-5dffac87fe7c815de4ceJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-2900000000-8db541bacfe47b9e0c8bJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-2900000000-a338415bd30d4e62e664JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-05g4-1978000000-1097d5b300514a0489dfJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00kv-2964000000-3d20d62c97c33247cfcfJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00ku-1965000000-ebee2a916fe97f0270a1JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9654000000-b3f1759076cffd2ac235JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-000m-3975000000-5a41c311d78f7219474cJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00kv-1954000000-9dae07505bd18466be87JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002e-0900000000-d76b7991f2d90cb58bd5JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-6094000000-b805979df23a0d890d7cJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-004i-0900000000-d193da7a6efffdab2dbbJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00kr-7900000000-b5b8d28b28c8067c3932JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-002r-9000000000-d3616a5367a7a2a9b3c6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positivesplash10-0006-1900000000-5dffac87fe7c815de4ceJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0006-0900000000-c173873ef0d975be6c34JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-001i-0900000000-0b9174ecaba08b2f01b9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-001i-1900000000-eff77e27aef254928643JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-001r-9700000000-18946fad05ffb1f78a7dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-001r-9300000000-e2221a73d3d078bf6e03JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0002-0900000000-653c9a454414dd8b8b50JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-002b-0900000000-62b2ee8bf9571be3d97fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-001i-0900000000-a7cded21e6010eb8bce2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-0900000000-c173873ef0d975be6c34JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-0900000000-0b9174ecaba08b2f01b9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-1900000000-eff77e27aef254928643JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001r-9700000000-18946fad05ffb1f78a7dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001r-9300000000-e2221a73d3d078bf6e03JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001i-0900000000-a7cded21e6010eb8bce2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-002b-0900000000-cdced9ddbcdaedf2f1b9JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0900000000-434fdd914ca34cd68f41JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0900000000-0dcbcad8bf6cb403f4f8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0g31-5900000000-4fa9ed831b4e0d1573e5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-29c8691e15490f8d88acJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0900000000-e940f09e099b7acf3772JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00o1-1900000000-ee61087a069406e459c7JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-0006-5900000000-8c81de6c352294475072JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • Okabe, Y., Katayama, N., Iwama, M., Watanabe, H., Ohgi, K., Irie, M., Nitta, K., Kawauchi, H., Takayanagi, Y., Oyama, F., et, a. l. .. (1991). "Comparative base specificity, stability, and lectin activity of two lectins from eggs of Rana catesbeiana and R. japonica and liver ribonuclease from R. catesbeiana." J Biochem 109:786-790.1917903
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID17620
HMDB IDHMDB0000954
Pubchem Compound ID709
Kegg IDC01494
ChemSpider ID23936140
FOODB IDFDB012802
WikipediaFerulic_acid
BioCyc IDNot Available

Enzymes

General function:
ferulate metabolic process
Specific function:
Catalyzes the reversible decarboxylation of aromatic carboxylic acids like ferulic acid, p-coumaric acid or cinnamic acid, producing the corresponding vinyl derivatives 4-vinylphenol, 4-vinylguaiacol, and styrene, respectively, which play the role of aroma metabolites (PubMed:20471595, PubMed:25647642). Not essential for ubiquinone synthesis (PubMed:20471595).
Gene Name:
FDC1
Uniprot ID:
Q03034
Molecular weight:
56163.39
Reactions