Record Information
Version1.0
Creation date2010-04-08 22:04:30 UTC
Update date2019-11-26 02:54:36 UTC
Primary IDFDB000264
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name5-8'-Dehydrodiferulic acid
Description5-8'-dehydrodiferulic acid is a member of the class of compounds known as stilbenes. Stilbenes are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. 5-8'-dehydrodiferulic acid is practically insoluble (in water) and a moderately acidic compound (based on its pKa). 5-8'-dehydrodiferulic acid can be found in a number of food items such as corn, common wheat, rye, and semolina, which makes 5-8'-dehydrodiferulic acid a potential biomarker for the consumption of these food products. 8,5'-Diferulic acid is a non cyclic type of diferulic acid. It is the predominant diferulic acid in sugar beet pulp. It is also found in barley, in maize bran and rye. 8-5'-Diferulic acid has also been identified to be covalently linked to carbohydrate moieties of the arabinogalactan-protein fraction of gum arabic .
CAS NumberNot Available
Structure
Thumb
Synonyms
SynonymSource
(2E)-2-[5-(2-Carboxyeth-1-en-1-yl)-2-hydroxy-3-methoxyphenyl]-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoateGenerator
5-8'-DehydrodiferulateGenerator
Predicted PropertiesNot Available
Chemical FormulaC20H18O8
IUPAC name
InChI IdentifierInChI=1S/C20H18O8/c1-27-16-9-11(3-5-15(16)21)8-14(20(25)26)13-7-12(4-6-18(22)23)10-17(28-2)19(13)24/h3-10,21,24H,1-2H3,(H,22,23)(H,25,26)/b6-4-,14-8+
InChI KeyDEPVSDIYICBTJE-FGDQGFBNSA-N
Isomeric SMILESCOC1=CC(\C=C/C(O)=O)=CC(\C(=C/C2=CC(OC)=C(O)C=C2)C(O)=O)=C1O
Average Molecular Weight386.3521
Monoisotopic Molecular Weight386.100167552
Classification
Description Belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassStilbenes
Sub ClassNot Available
Direct ParentStilbenes
Alternative Parents
Substituents
  • Stilbene
  • Cinnamic acid
  • Cinnamic acid or derivatives
  • Coumaric acid or derivatives
  • Hydroxycinnamic acid
  • Hydroxycinnamic acid or derivatives
  • Methoxyphenol
  • Anisole
  • Phenoxy compound
  • Methoxybenzene
  • Phenol ether
  • Styrene
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Dicarboxylic acid or derivatives
  • Monocyclic benzene moiety
  • Benzenoid
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
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-MSNot Available
MS/MSNot Available
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 ID508
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNNB85-F:NNB85-F
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— 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.