1.0 2010-04-08 22:05:24 UTC 2025-11-18 22:37:49 UTC FDB002488 Enterolactone 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. 2,3-Bhbb 2,3-Bis(3-hydroxybenzyl)butyrolactone 2,3-bis(3'-hydroxybenzyl)butyrolactone 2(3H)-Furanone, dihydro-3,4-bis((3-hydroxyphenyl)methyl)- 3,4-Bis((3-hydroxyphenyl)methyl)dihydro-2-(3H)-furanone BHMDF dihydro-3,4-Bis((3-hydroxyphenyl)methyl)-2(3H)-furanone Dihydro-3,4-bis(3-hydroxyphenyl)methyl-2(3H)-furanone, 9CI HPMF trans-2,3-Bis(3-hydroxybenzyl)-gamma-butyrolactone C18H18O4 298.3331 298.120509064 (3R,4R)-3,4-bis[(3-hydroxyphenyl)methyl]oxolan-2-one enterolactone 76543-15-2 OC1=CC=CC(C[C@H]2COC(=O)[C@@H]2CC2=CC(O)=CC=C2)=C1 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 HVDGDHBAMCBBLR-WMLDXEAASA-N belongs to the class of organic compounds known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety. Dibenzylbutyrolactone lignans Organic compounds Lignans, neolignans and related compounds Furanoid lignans Tetrahydrofuran lignans Aromatic heteromonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Benzene and substituted derivatives Carbonyl compounds Carboxylic acid esters Gamma butyrolactones Hydrocarbon derivatives Lignan lactones Monocarboxylic acids and derivatives Organic oxides Oxacyclic compounds Tetrahydrofurans 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid Aromatic heteromonocyclic compound Benzenoid Carbonyl group Carboxylic acid derivative Carboxylic acid ester Dibenzylbutyrolactone Gamma butyrolactone Hydrocarbon derivative Lactone Lignan lactone Monocarboxylic acid or derivatives Monocyclic benzene moiety Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Phenol Tetrahydrofuran Solid logp 3.20 ALOGPS logs -4.12 ALOGPS solubility 2.24e-02 g/l ALOGPS logp 3.61 ChemAxon pka_strongest_acidic 9.16 ChemAxon pka_strongest_basic -6 ChemAxon iupac (3R,4R)-3,4-bis[(3-hydroxyphenyl)methyl]oxolan-2-one ChemAxon average_mass 298.3331 ChemAxon mono_mass 298.120509064 ChemAxon smiles OC1=CC=CC(C[C@H]2COC(=O)[C@@H]2CC2=CC(O)=CC=C2)=C1 ChemAxon formula C18H18O4 ChemAxon inchi 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 ChemAxon inchikey HVDGDHBAMCBBLR-WMLDXEAASA-N ChemAxon polar_surface_area 66.76 ChemAxon refractivity 82.71 ChemAxon polarizability 30.9 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon HMDB06101 #<Reference:0x000055ce3214a5b8> #<Reference:0x000055ce3214a400> #<Reference:0x000055ce3214a248> #<Reference:0x000055ce3214a090> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Breakfast cereal Type 2 specific Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Cereals and cereal products Unknown generic Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Milk (Cow) Type 2 specific 76.70474 130.056 0.0597 uM Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823