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Showing Compound 4,4'-Dihydroxy-3,3'-dimethoxy-9,9'-epoxylignan (FDB015354)

Record Information
Version1.0
Creation date2010-04-08 22:11:48 UTC
Update date2019-11-26 03:11:30 UTC
Primary IDFDB015354
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name4,4'-Dihydroxy-3,3'-dimethoxy-9,9'-epoxylignan
Description4,4'-dihydroxy-3,3'-dimethoxy-9,9'-epoxylignan, also known as 34-divanillyltetrahydrofuran or dv-tetrahydrofuran, is a member of the class of compounds known as 9,9'-epoxylignans. 9,9'-epoxylignans are lignans with a structure based on the 9,9'-epoxylignan skeleton, which consists of a tetrahydrofuran that carries two benzyl groups at the 3- and 4-positions. Additionally they are oxygenated at the 2-position to form dibenzylbutyrolactones (oxo group) or a dibenzylbutyrolactols (hydroxyl group). 4,4'-dihydroxy-3,3'-dimethoxy-9,9'-epoxylignan is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 4,4'-dihydroxy-3,3'-dimethoxy-9,9'-epoxylignan can be found in sesame, which makes 4,4'-dihydroxy-3,3'-dimethoxy-9,9'-epoxylignan a potential biomarker for the consumption of this food product.
CAS Number34730-78-4
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.014 g/LALOGPS
logP3.13ALOGPS
logP3.49ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)9.96ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area68.15 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity95.78 m³·mol⁻¹ChemAxon
Polarizability36.55 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC20H24O5
IUPAC name4-({4-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-3-yl}methyl)-2-methoxyphenol
InChI IdentifierInChI=1S/C20H24O5/c1-23-19-9-13(3-5-17(19)21)7-15-11-25-12-16(15)8-14-4-6-18(22)20(10-14)24-2/h3-6,9-10,15-16,21-22H,7-8,11-12H2,1-2H3
InChI KeyROGUIJKVZZROIQ-UHFFFAOYSA-N
Isomeric SMILESCOC1=CC(CC2COCC2CC2=CC(OC)=C(O)C=C2)=CC=C1O
Average Molecular Weight344.4016
Monoisotopic Molecular Weight344.162373878
Classification
Description Belongs to the class of organic compounds known as 9,9'-epoxylignans. These are lignans with a structure based on the 9,9'-epoxylignan skeleton, which consists of a tetrahydrofuran that carries two benzyl groups at the 3- and 4-positions. Additionally they are oxygenated at the 2-position to form dibenzylbutyrolactones (oxo group) or a dibenzylbutyrolactols (hydroxyl group).
KingdomOrganic compounds
Super ClassLignans, neolignans and related compounds
ClassFuranoid lignans
Sub ClassTetrahydrofuran lignans
Direct Parent9,9'-epoxylignans
Alternative Parents
Substituents
  • 9,9p-epoxylignan
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Tetrahydrofuran
  • Oxacycle
  • Dialkyl ether
  • Ether
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0139000000-9b5cde4bdf7750c5f5382016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000b-0879000000-3b04e08fed00e3aafa492016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01p9-0911000000-2a01f7a82cef2ecc74682016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0009000000-8a090c10c263b11760682016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0019000000-5fccac7ae6f12bd474862016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-0293000000-583163ff7f6c6d498d672016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0009000000-3b82d92714c6cc6bd1b12021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01r6-0129000000-16b803836bfc9d2db8512021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-0579000000-f8394aee62e6aee8f6ca2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0029000000-4dc0fc2b0cfae72a19992021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002b-0539000000-d91961b5f691b33fd44d2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0abi-1393000000-d71da85d5e62bafef1842021-10-21View 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 ID624
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDJZS49-S:JZS49-S
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
Processing...
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.