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Enterolactone (PC001184)

Record Information
Version1.0
Creation date2018-05-02 12:14:01 UTC
Update date2018-05-04 14:23:46 UTC
FoodComEx IDPC001184
FoodDB RecordFDB002488
Chemical Information
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
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
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
3,4-Bis((3-hydroxyphenyl)methyl)dihydro-2-(3H)-furanonebiospider
BHMDFbiospider
dihydro-3,4-Bis((3-hydroxyphenyl)methyl)-2(3H)-furanoneHMDB
Dihydro-3,4-bis(3-hydroxyphenyl)methyl-2(3H)-furanone, 9CIdb_source
HPMFdb_source
trans-2,3-Bis(3-hydroxybenzyl)-gamma-butyrolactonebiospider
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
Chemical Taxonomy
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
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logPNot Available
Experimental Water SolubilityNot Available
Melting PointNot Available
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity Available1 to 2 mg
Delivery Time2 weeks
Storage Formpowder
Storage Conditions-18°C
StabilityNot Available
Purityunknown
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Augustin ScalbertInternational Agency for Research on Cancer (IARC), Biomarkers Group, 150 cours Albert Thomas, Lyon, FR, 69372scalberta@iarc.fr
Commercial Vendors
Not Available