Record Information
Version1.0
Creation date2010-04-08 22:05:24 UTC
Update date2018-05-28 22:40:47 UTC
Primary IDFDB002488
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameEnterolactone
DescriptionProduction of intestinal flora acting on lignans present in cereal Enterolactone is a mammalian lignan that have a similar biphenolic structure to lignans from plants. Lignans are compounds with estrogenic properties and are probably the most important source of phytoestrogens in western diets. Mammalian lignans are formed from precursors that are contained mainly in vegetables, whole grain products and berries, via action of intestinal microflora. Enterolactone is produced in the colon by the action of bacteria on secoisolariciresinol, matairesinol and its glycosides. Secoisolariciresinol is converted to enterodiol which is subsequently converted to enterolactone as it passes through the colon. Matairesinol is converted directly to enterolactone. Enterolactone have been shown to possess weakly estrogenic and antiestrogenic activities, and it has been suggested that the high production of this antiestrogenic mammalian lignans in the gut may serve to protect against breast cancer in women and prostate cancer in men; however epidemiological evidence to date is conflicting. (PMID: 16168401, 12270221, 11216511, 12107024). Enterolactone is a biomarker for the consumption of soy beans and other soy products. Enterolactone is found in cereals and cereal products.
CAS Number76543-15-2
Structure
Thumb
Synonyms
SynonymSource
2,3-Bis(3'-hydroxybenzyl)butyrolactoneMeSH
2,3-Bis(3'-hydroxybenzyl)butyrolactone, (trans)-isomerMeSH
trans-2,3-Bis(3-hydroxybenzyl)-gamma-butyrolactoneMeSH
BHMDFMeSH
2,3-BHBBMeSH
2,3-Bis(3'-hydroxybenzyl)butyrolactone, (trans)-(+-)-isomerMeSH
3,4-Bis((3-hydroxyphenyl)methyl)dihydro-2-(3H)-furanoneMeSH
HPMFMeSH
2,3-Bhbbbiospider
2,3-Bis(3-hydroxybenzyl)butyrolactonedb_source
2,3-bis(3'-hydroxybenzyl)butyrolactonebiospider
2(3H)-Furanone, dihydro-3,4-bis((3-hydroxyphenyl)methyl)-biospider
dihydro-3,4-Bis((3-hydroxyphenyl)methyl)-2(3H)-furanoneHMDB
Dihydro-3,4-bis(3-hydroxyphenyl)methyl-2(3H)-furanone, 9CIdb_source
Predicted Properties
PropertyValueSource
Water Solubility0.022 g/LALOGPS
logP3.2ALOGPS
logP3.61ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)9.16ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity82.71 m³·mol⁻¹ChemAxon
Polarizability30.9 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC18H18O4
IUPAC name(3R,4R)-3,4-bis[(3-hydroxyphenyl)methyl]oxolan-2-one
InChI IdentifierInChI=1S/C18H18O4/c19-15-5-1-3-12(8-15)7-14-11-22-18(21)17(14)10-13-4-2-6-16(20)9-13/h1-6,8-9,14,17,19-20H,7,10-11H2/t14-,17+/m0/s1
InChI KeyHVDGDHBAMCBBLR-WMLDXEAASA-N
Isomeric SMILESOC1=CC=CC(C[C@H]2COC(=O)[C@@H]2CC2=CC(O)=CC=C2)=C1
Average Molecular Weight298.3331
Monoisotopic Molecular Weight298.120509064
Classification
DescriptionThis compound belongs to the class of chemical entities known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety.
KingdomChemical entities
Super ClassOrganic compounds
ClassLignans, neolignans and related compounds
Sub ClassFuranoid lignans
Direct ParentDibenzylbutyrolactone lignans
Alternative Parents
Substituents
  • Dibenzylbutyrolactone
  • Lignan lactone
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Gamma butyrolactone
  • Benzenoid
  • Oxolane
  • Carboxylic acid ester
  • Lactone
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Ontology TermNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 72.47%; H 6.08%; O 21.45%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]20D -40.5 (c, 0.62 in CHCl3)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
SpectraNot Available
ChemSpider ID110448
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID123917
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB06101
CRC / DFC (Dictionary of Food Compounds) IDCMB83-F:CMB83-F
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00000703
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDEnterolactone
Phenol-Explorer Metabolite ID1010
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
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference