Record Information
Version1.0
Creation date2010-04-08 22:05:24 UTC
Update date2019-11-26 02:57:31 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
BioavailabilityYesChemAxon
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
Description belongs to the class of organic compounds known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety.
KingdomOrganic compounds
Super ClassLignans, neolignans and related compounds
ClassFuranoid lignans
Sub ClassTetrahydrofuran 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
  • Tetrahydrofuran
  • 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
Foods
  • Cocoa and cocoa products
  • Grains:

    Nuts and legumes:

    Fruits and vegetables:

    Fats and oils:

    Beverages:

    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
    Food Biomarker OntologyNot Available
    VMH 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