(7'R*,8'S*)-4,7'-Epoxy-3,8'-bilign-7-ene-4'-hydroxy-3',5-dimethoxy-9,9'-dioic acid (CHEM034407)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 04:53:41 UTC
Update Date2016-11-09 01:21:07 UTC
Accession NumberCHEM034407
Identification
Common Name(7'R*,8'S*)-4,7'-Epoxy-3,8'-bilign-7-ene-4'-hydroxy-3',5-dimethoxy-9,9'-dioic acid
ClassSmall Molecule
Description3-[3-Carboxy-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-5-benzofuranyl]-2-propenoic acid is found in cereals and cereal products. 3-[3-Carboxy-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-5-benzofuranyl]-2-propenoic acid is isolated by saponification from wheat bran, cocksfoot, switch grass and cultured corn cells. Antioxidant.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3-[3-Carboxy-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-5-benzofuranyl]-2-propenoateGenerator
3-[3-Carboxy-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-5-benzofuranyl]-2-propenoic acid, 9ciHMDB
5-(2-Carboxyvinyl)-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-3-benzofurancarboxylic acidHMDB
5-[(1Z)-2-Carboxyeth-1-en-1-yl]-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-2,3-dihydro-1-benzofuran-3-carboxylateGenerator
(7'R*,8's*)-4,7'-epoxy-3,8'-bilign-7-ene-4'-hydroxy-3',5-dimethoxy-9,9'-dioateGenerator
Chemical FormulaC20H18O8
Average Molecular Mass386.352 g/mol
Monoisotopic Mass386.100 g/mol
CAS Registry Number160169-55-1
IUPAC Name5-[(1Z)-2-carboxyeth-1-en-1-yl]-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-2,3-dihydro-1-benzofuran-3-carboxylic acid
Traditional Name5-[(1Z)-2-carboxyeth-1-en-1-yl]-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-2,3-dihydro-1-benzofuran-3-carboxylic acid
SMILESCOC1=CC(\C=C/C(O)=O)=CC2=C1OC(C2C(O)=O)C1=CC(OC)=C(O)C=C1
InChI IdentifierInChI=1S/C20H18O8/c1-26-14-9-11(4-5-13(14)21)18-17(20(24)25)12-7-10(3-6-16(22)23)8-15(27-2)19(12)28-18/h3-9,17-18,21H,1-2H3,(H,22,23)(H,24,25)/b6-3-
InChI KeyJTHPLBUVRLOJBB-UTCJRWHESA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
Class2-arylbenzofuran flavonoids
Sub ClassNot Available
Direct Parent2-arylbenzofuran flavonoids
Alternative Parents
Substituents
  • 2-arylbenzofuran flavonoid
  • Neolignan skeleton
  • Coumaric acid or derivatives
  • Methoxyphenol
  • Benzofuran
  • Coumaran
  • Phenoxy compound
  • Methoxybenzene
  • Anisole
  • Styrene
  • Phenol ether
  • Alkyl aryl ether
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Dicarboxylic acid or derivatives
  • Monocyclic benzene moiety
  • Oxacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organoheterocyclic compound
  • Ether
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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 Solubility0.042 g/LALOGPS
logP2.99ALOGPS
logP2.56ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)3.17ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area122.52 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity98.11 m³·mol⁻¹ChemAxon
Polarizability37.86 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kf-0309000000-3430f30bc375381be738Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-000i-2000190000-2a741d2e3e25061bad43Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0109000000-e0b585f21780151fd3ebSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gkc-0119000000-72f5f07bcc738dc87bdcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002r-1900000000-e3455fd2a3c777b30c17Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000l-0009000000-0e6a5f01ed2f3d7a4048Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00mx-0019000000-e0de8b213dd69f233706Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-1649000000-3e0a5de588bcc30027c8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0019000000-26c5c39e4fb9c7194df2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0029000000-0a490dfde23643a97e74Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ar0-0194000000-d73bee2952709d583c42Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0009000000-5d1c4f43bb3b859a1786Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0g6s-0039000000-7ea23dc0fa8f520267bfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f7t-0976000000-c5327ce2cfcc3d97e270Spectrum
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 IDHMDB0041277
FooDB IDFDB021189
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID35015143
ChEBI ID175915
PubChem Compound ID101088304
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.