Canmetcon
Record Information
Version1.0
Creation date2010-04-08 22:10:22 UTC
Update date2018-05-28 23:39:18 UTC
Primary IDFDB012801
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameFerulic acid
DescriptionFerulic acid, also known as ferulate, 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 synthesized from cis-cinnamic acid. Ferulic acid is also a parent compound for other transformation products, including but not limited to, (2S,3S)-cis-fertaric acid, (2R,3R)-cis-fertaric acid, and (Z)-4-hydroxy-3-methoxycinnamoylagmatine. Ferulic acid can be found in a number of food items such as pineapple, pear, evergreen huckleberry, and silver linden, which makes ferulic acid a potential biomarker for the consumption of these food products. 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 Number1135-24-6
Structure
Thumb
Synonyms
SynonymSource
4-Hydroxy-3-methoxycinnamic acid, 8CIdb_source
Caffeic acid 3-methyl etherdb_source
Ferulic aciddb_source
Predicted Properties
PropertyValueSource
Water Solubility0.91 g/LALOGPS
logP1.58ALOGPS
logP1.67ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)3.27ChemAxon
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
Polarizability18.8 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC10H10O4
IUPAC name(2Z)-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-HYXAFXHYSA-N
Isomeric SMILES[H]\C(=C(/[H])C1=CC(OC)=C(O)C=C1)C(O)=O
Average Molecular Weight194.184
Monoisotopic Molecular Weight194.057908808
Classification
DescriptionThis compound belongs to the class of organic compounds known as hydroxycinnamic acids. These 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
  • Hydroxycinnamic acid
  • Coumaric acid or derivatives
  • Cinnamic acid
  • Methoxyphenol
  • Phenylpropene
  • Methoxybenzene
  • Styrene
  • Phenol ether
  • Anisole
  • Phenol
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 61.85%; H 5.19%; O 32.96%DFC
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
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-000m-3975000000-b565cdbaaa5aa607842cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot AvailableView in JSpectraViewer
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID459
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDHLG59-X:HLG59-X
EAFUS IDNot Available
Dr. Duke ID4-HYDROXY-3-METHOXY-CINNAMIC-ACID|FERULIC-ACID
BIGG IDNot Available
KNApSAcK IDC00002743
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite ID459
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
allelopathicDUKE
analgesic35480 An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.DUKE
anti aggregantDUKE
anti allergic50857 A drug used to treat allergic reactions.DUKE
anti arrhythmic38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti cancer35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti carcinogenic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti dysmenorrheic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti estrogenic35222 A substance that diminishes the rate of a chemical reaction.DUKE
anti hepatotoxic62868 Any compound that is able to prevent damage to the liver.DUKE
anti herpetic22587 A substance that destroys or inhibits replication of viruses.DUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti leukemic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti mitoticDUKE
anti mutagenicDUKE
anti neoplastic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti nitrosaminicDUKE
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
anti radicularDUKE
anti serotonin48278 DUKE
anti spasmodic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti thrombic50248 Drug that acts on blood and blood-forming organs and those that affect the hemostatic system.DUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
antitumor promoter35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti viral22587 A substance that destroys or inhibits replication of viruses.DUKE
arteriodilatorDUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
candidicideDUKE
cardiac38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
cholagogueDUKE
cholereticDUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
hepatoprotective62868 Any compound that is able to prevent damage to the liver.DUKE
hepatotropicDUKE
herbicide24527 A substance used to destroy plant pests.DUKE
hydrocholerecticDUKE
hypolipidemicDUKE
immunostimulant50847 A substance that augments, stimulates, activates, potentiates, or modulates the immune response at either the cellular or humoral level. A classical agent (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contains bacterial antigens. It could also be endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Its mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy is related to its antigen-specific immunoadjuvanticity.DUKE
insectifuge24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
metal chelator38161 A ligand with two or more separate binding sites that can bind to a single metallic central atom, forming a chelate.DUKE
ornithine-decarboxylase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
phagocytoticDUKE
preservative65255 Substances which are added to food in order to prevent decomposition caused by microbial growth or by undesirable chemical changes.DUKE
prostaglandigenicDUKE
prostaglandin synthesis inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
sunscreen52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
uteros sedative52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— 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.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.