8-8'-Dehydrodiferulic acid (CHEM022970)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 20:45:44 UTC
Update Date2016-11-09 01:17:36 UTC
Accession NumberCHEM022970
Identification
Common Name8-8'-Dehydrodiferulic acid
ClassSmall Molecule
Description8-8'-Dehydrodiferulic acid is a polyphenol compound found in foods of plant origin (PMID: 20428313)
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
8-8'-DehydrodiferulateGenerator
(2E)-Bis[(4-hydroxy-3-methoxyphenyl)methylidene]butanedioateHMDB
Chemical FormulaC20H18O8
Average Molecular Mass386.352 g/mol
Monoisotopic Mass386.100 g/mol
CAS Registry NumberNot Available
IUPAC Name(2Z,3E)-bis[(4-hydroxy-3-methoxyphenyl)methylidene]butanedioic acid
Traditional Name(2Z,3E)-bis[(4-hydroxy-3-methoxyphenyl)methylidene]butanedioic acid
SMILESCOC1=C(O)C=CC(\C=C(\C(O)=O)/C(=C/C2=CC(OC)=C(O)C=C2)/C(O)=O)=C1
InChI IdentifierInChI=1S/C20H18O8/c1-27-17-9-11(3-5-15(17)21)7-13(19(23)24)14(20(25)26)8-12-4-6-16(22)18(10-12)28-2/h3-10,21-22H,1-2H3,(H,23,24)(H,25,26)/b13-7-,14-8+
InChI KeySPKZMOSDXTYXLK-MFUUIURDSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as lignans, neolignans and related compounds. These are plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can also be described as micromolecules with two phenylpropanoid units coupled together. They can be attached in various manners, like C5-C5', C8-C8'. Most known natural lignans are oxidized at C9 and C9´ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed.
KingdomOrganic compounds
Super ClassLignans, neolignans and related compounds
ClassNot Available
Sub ClassNot Available
Direct ParentLignans, neolignans and related compounds
Alternative Parents
Substituents
  • Norlignan skeleton
  • Cinnamic acid
  • Cinnamic acid or derivatives
  • Coumaric acid or derivatives
  • Hydroxycinnamic acid or derivatives
  • Hydroxycinnamic acid
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Dicarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Ether
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.029 g/LALOGPS
logP3.24ALOGPS
logP2.79ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)2.79ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area133.52 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity100.72 m³·mol⁻¹ChemAxon
Polarizability37.13 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00ko-0409000000-73deae33c335e184e345Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0bt9-3000029000-fffb0377a23ea253dd4eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0109000000-9c7609ea8cc607bde9d8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ko-0229000000-2925758ef7b4b0f5d02cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052k-0694000000-2f7413d682542540c85dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-d891ff7c770d199a2495Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000l-0329000000-46cba6d908bc2a00a765Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004l-0904000000-16d0f7babfe6c40538dbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000b-0059000000-2afdeabfedfeb460ca2bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0049000000-f517195a4935f779254dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-003r-0169000000-923f6f6b34faa93da1f1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0209000000-db1ab7cae585ebe0c389Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0adi-1719000000-8f6f8555e16bde401fa8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-2879000000-51984780b51828710be4Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0029277
FooDB IDFDB000272
Phenol Explorer ID517
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID29336462
ChEBI ID175914
PubChem Compound ID131750840
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Neveu V, Perez-Jimenez J, Vos F, Crespy V, du Chaffaut L, Mennen L, Knox C, Eisner R, Cruz J, Wishart D, Scalbert A: Phenol-Explorer: an online comprehensive database on polyphenol contents in foods. Database (Oxford). 2010;2010:bap024. doi: 10.1093/database/bap024. Epub 2010 Jan 8.