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
Synonyms
SynonymSource
DV-TetrahydrofuranMeSH
34-DivanillyltetrahydrofuranChEMBL
4,4'-[(Tetrahydro-3,4-furandiyl)bis(methylene)]bis[2-methoxyphenol], 9CIdb_source
a,a'-[Tetrahydro-3,4-furandiyl]bis[2-methoxy-p-cresol], 8CIdb_source
Anhydrosecoisolariciresinoldb_source
Divanillyltetrahydrofurandb_source
Shonanindb_source
Predicted Properties
PropertyValueSource
Water Solubility0.013 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 - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 69.75%; H 7.02%; O 23.23%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]25D -52.2 (c, 1.4 in THF)DFC
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, Positivesplash10-0002-0139000000-9b5cde4bdf7750c5f538Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000b-0879000000-3b04e08fed00e3aafa49Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01p9-0911000000-2a01f7a82cef2ecc7468Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0009000000-8a090c10c263b1176068Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0019000000-5fccac7ae6f12bd47486Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-0293000000-583163ff7f6c6d498d67Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0009000000-3b82d92714c6cc6bd1b1Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01r6-0129000000-16b803836bfc9d2db851Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-0579000000-f8394aee62e6aee8f6caSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0029000000-4dc0fc2b0cfae72a1999Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002b-0539000000-d91961b5f691b33fd44dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0abi-1393000000-d71da85d5e62bafef184Spectrum
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
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.