Record Information
Creation date2010-04-08 22:04:30 UTC
Update date2019-11-26 02:54:37 UTC
Primary IDFDB000271
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name8-4'-Dehydrodiferulic acid
Description8-4'-dehydrodiferulic acid belongs to phenylpyruvic acid derivatives class of compounds. Those are compounds containing a phenylpyruvic acid moiety, which consists of a phenyl group substituted at the second position by an pyruvic acid. 8-4'-dehydrodiferulic acid is practically insoluble (in water) and a moderately acidic compound (based on its pKa). 8-4'-dehydrodiferulic acid can be found in a number of food items such as corn, semolina, common wheat, and hard wheat, which makes 8-4'-dehydrodiferulic acid a potential biomarker for the consumption of these food products.
CAS NumberNot Available
8-4'-Dehydrodiferulic acidmanual
8-O-4'-Dehydrodiferulic aciddb_source
Predicted Properties
Water Solubility0.01 g/LALOGPS
pKa (Strongest Acidic)2.55ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area122.52 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity101.2 m³·mol⁻¹ChemAxon
Polarizability38.13 ųChemAxon
Number of Rings2ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC20H18O8
IUPAC name(2E)-2-{4-[(1Z)-2-carboxyeth-1-en-1-yl]-2-methoxyphenoxy}-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid
InChI IdentifierInChI=1S/C20H18O8/c1-26-16-10-13(3-6-14(16)21)11-18(20(24)25)28-15-7-4-12(5-8-19(22)23)9-17(15)27-2/h3-11,21H,1-2H3,(H,22,23)(H,24,25)/b8-5-,18-11+
Isomeric SMILESCOC1=C(O)C=CC(\C=C(\OC2=C(OC)C=C(\C=C/C(O)=O)C=C2)C(O)=O)=C1
Average Molecular Weight386.3521
Monoisotopic Molecular Weight386.100167552
Description Belongs to the class of organic compounds known as phenylpyruvic acid derivatives. Phenylpyruvic acid derivatives are compounds containing a phenylpyruvic acid moiety, which consists of a phenyl group substituted at the second position by an pyruvic acid.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylpyruvic acid derivatives
Direct ParentPhenylpyruvic acid derivatives
Alternative Parents
  • Cinnamic acid
  • Cinnamic acid or derivatives
  • Coumaric acid or derivatives
  • Hydroxycinnamic acid
  • Hydroxycinnamic acid or derivatives
  • Enol-phenylpyruvate
  • Phenoxyacetate
  • Methoxyphenol
  • Methoxybenzene
  • Phenol ether
  • Styrene
  • Anisole
  • Phenoxy compound
  • Phenol
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Dicarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Carbonyl group
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
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
EI-MS/GC-MSNot Available
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-0209000000-fa29ab0f47e2db911354Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00my-0709000000-912c20ff6ffda4f4b22dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002b-0900000000-8db4c285b0c27ee052a0Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0119000000-f983c477f3424334631eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002o-0905000000-695a5127d215aa67302bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0900000000-263cd13cc63b4daaf92bSpectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID516
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNNB89-J:NNB89-J
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
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
MSDSNot Available
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.