Showing Compound Enterolactone (FDB002488)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:24 UTC

Update date

2019-11-26 02:57:31 UTC

Primary ID

FDB002488

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Enterolactone

Description

Production 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 Number

76543-15-2

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
2,3-Bis(3'-hydroxybenzyl)butyrolactone	MeSH
2,3-Bis(3'-hydroxybenzyl)butyrolactone, (trans)-isomer	MeSH
trans-2,3-Bis(3-hydroxybenzyl)-gamma-butyrolactone	MeSH
BHMDF	MeSH
2,3-BHBB	MeSH
2,3-Bis(3'-hydroxybenzyl)butyrolactone, (trans)-(+-)-isomer	MeSH
3,4-Bis((3-hydroxyphenyl)methyl)dihydro-2-(3H)-furanone	MeSH
HPMF	MeSH
2,3-Bhbb	biospider
2,3-Bis(3-hydroxybenzyl)butyrolactone	db_source
2,3-bis(3'-hydroxybenzyl)butyrolactone	biospider
2(3H)-Furanone, dihydro-3,4-bis((3-hydroxyphenyl)methyl)-	biospider
dihydro-3,4-Bis((3-hydroxyphenyl)methyl)-2(3H)-furanone	HMDB
Dihydro-3,4-bis(3-hydroxyphenyl)methyl-2(3H)-furanone, 9CI	db_source

Predicted Properties

Property	Value	Source
Water Solubility	0.022 g/L	ALOGPS
logP	3.2	ALOGPS
logP	3.61	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	9.16	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	82.71 m³·mol⁻¹	ChemAxon
Polarizability	30.9 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C18H18O4

IUPAC name

(3R,4R)-3,4-bis[(3-hydroxyphenyl)methyl]oxolan-2-one

InChI Identifier

InChI=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 Key

HVDGDHBAMCBBLR-WMLDXEAASA-N

Isomeric SMILES

OC1=CC=CC(C[C@H]2COC(=O)[C@@H]2CC2=CC(O)=CC=C2)=C1

Average Molecular Weight

298.3331

Monoisotopic Molecular Weight

298.120509064

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.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Furanoid lignans

Sub Class

Tetrahydrofuran lignans

Direct Parent

Dibenzylbutyrolactone 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 Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Foods

Cocoa and cocoa products

Grains:

Cereal products:

Whole grain cereal products

Nuts and legumes:

Fruits and vegetables:

Fats and oils:

Oils:

Vegetable oils:

Olive oil

Beverages:

Coffee products

Alcohols:

Fermented alcohols:

Wine:

Red wine

Infusions:

Tea products

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 72.47%; H 6.08%; O 21.45%	DFC
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]20D -40.5 (c, 0.62 in CHCl3)	DFC
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available