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5-5'-Dehydrodiferulic acid (FDB000263)

Record Information
Version1.0
Creation date2010-04-08 22:04:30 UTC
Update date2019-11-26 02:54:36 UTC
Primary IDFDB000263
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name5-5'-Dehydrodiferulic acid
Description5-5'-dehydrodiferulic acid, also known as 8-O-4'-diferulic acid, belongs to biphenyls and derivatives class of compounds. Those are organic compounds containing to benzene rings linked together by a C-C bond. 5-5'-dehydrodiferulic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). 5-5'-dehydrodiferulic acid can be found in a number of food items such as corn, common wheat, semolina, and hard wheat, which makes 5-5'-dehydrodiferulic acid a potential biomarker for the consumption of these food products.
CAS NumberNot Available
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.011 g/LALOGPS
logP2.99ALOGPS
logP3.02ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)3.31ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area133.52 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity102.09 m³·mol⁻¹ChemAxon
Polarizability39.09 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC20H18O8
IUPAC name(2E)-3-(3-{5-[(1E)-2-carboxyeth-1-en-1-yl]-2-hydroxy-3-methoxyphenyl}-4-hydroxy-5-methoxyphenyl)prop-2-enoic acid
InChI IdentifierInChI=1S/C20H18O8/c1-27-15-9-11(3-5-17(21)22)7-13(19(15)25)14-8-12(4-6-18(23)24)10-16(28-2)20(14)26/h3-10,25-26H,1-2H3,(H,21,22)(H,23,24)/b5-3+,6-4+
InChI KeyLBQZVWQOPFFQJI-GGWOSOGESA-N
Isomeric SMILESCOC1=C(O)C(=CC(\C=C\C(O)=O)=C1)C1=CC(\C=C\C(O)=O)=CC(OC)=C1O
Average Molecular Weight386.3521
Monoisotopic Molecular Weight386.100167552
Classification
Description Belongs to the class of organic compounds known as biphenyls and derivatives. These are organic compounds containing to benzene rings linked together by a C-C bond.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBiphenyls and derivatives
Direct ParentBiphenyls and derivatives
Alternative Parents
Substituents
  • Biphenyl
  • Cinnamic acid
  • Cinnamic acid or derivatives
  • Coumaric acid or derivatives
  • Hydroxycinnamic acid
  • Hydroxycinnamic acid or derivatives
  • Methoxyphenol
  • Anisole
  • Phenoxy compound
  • Methoxybenzene
  • Styrene
  • Phenol ether
  • Alkyl aryl ether
  • Phenol
  • Dicarboxylic acid or derivatives
  • 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 Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties
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/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0009000000-d85c9cd7d779cbb13cd52016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00to-0019000000-424056ed345e5e27507d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05nb-1092000000-6e6087e1a0fe84a224b72016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-53f37140b678ecc220052016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000l-0409000000-8c55934149c7f7d6b5c02016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004l-2905000000-fc1ef99a4bce989279532016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-0009000000-fd497a558934a7ae9a742021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-0009000000-751294a3942fc89146982021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00te-0039000000-9abbf7d297c32e80c8042021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002k-0059000000-b0468f7e67b529055b512021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0095000000-3126232d3e36cd9329742021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004j-0079000000-21f7ca5e5f2d54b1cbe02021-10-21View Spectrum
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 ID507
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNPC86-Z:NPC86-Z
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.