ENTERODIOL

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C18H22O4
Molecular Weight	302.3649
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC[C@H](CC1=CC=CC(O)=C1)[C@H](CO)CC2=CC=CC(O)=C2

InChI

InChIKey=DWONJCNDULPHLV-HOTGVXAUSA-N

InChI=1S/C18H22O4/c19-11-15(7-13-3-1-5-17(21)9-13)16(12-20)8-14-4-2-6-18(22)10-14/h1-6,9-10,15-16,19-22H,7-8,11-12H2/t15-,16-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C18H22O4
Molecular Weight	302.3649
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Approval Year

PubMed

Title	Date	PubMed
Sesame supplementation does not improve cardiovascular disease risk markers in overweight men and women.	2009-12	19346113
Weekly excretion of the mammalian lignan enterolactone in milk of dairy cows fed flaxseed meal.	2009-11	19638265
Gastrointestinal microflora, food components and colon cancer prevention.	2009-10	19716282
Quantitative aspects of the metabolism of lignans in pigs fed fibre-enriched rye and wheat bread.	2009-10	19393112
Occurrence of phytoestrogens in municipal wastewater and surface waters.	2009-08	19657531
Milk concentration of the mammalian lignan enterolactone, milk production, milk fatty acid profile, and digestibility in dairy cows fed diets containing whole flaxseed or flaxseed meal.	2009-08	19250577
Biotransformation of sesaminol triglucoside to mammalian lignans by intestinal microbiota.	2009-07-22	19537732
Urinary phytoestrogen excretion and prostate cancer risk: a nested case-control study in the Multiethnic Cohort.	2009-07-07	19536097
Tissue distribution and elimination of sesaminol triglucoside and its metabolites in rat.	2009-07	19517453
Bacterial conversion of secoisolariciresinol and anhydrosecoisolariciresinol.	2009-07	19302311
Plasma phyto-oestrogens and prostate cancer in the European Prospective Investigation into Cancer and Nutrition.	2009-06-02	19436304
Lignans and breast cancer risk in pre- and post-menopausal women: meta-analyses of observational studies.	2009-05-05	19337250
Plasma enterolignans are not associated with nonfatal myocardial infarction risk.	2009-03	18687435
Phytoestrogens and phytoestrogen metabolites differentially modulate immune parameters in human leukocytes.	2008-12	18929616
Fecal and urinary lignans, intrafollicular estradiol, and endometrial receptors in lactating dairy cows fed diets supplemented with hydrogenated animal fat, flaxseed or sunflower seed.	2008-12	18762721
Effect of the form of the sesame-based diet on the absorption of lignans.	2008-12	18430262
Phytoestrogen content of foods of animal origin: dairy products, eggs, meat, fish, and seafood.	2008-11-12	18922017
Lack of prospective associations between plasma and urinary phytoestrogens and risk of prostate or colorectal cancer in the European Prospective into Cancer-Norfolk study.	2008-10	18843034
Dietary lariciresinol attenuates mammary tumor growth and reduces blood vessel density in human MCF-7 breast cancer xenografts and carcinogen-induced mammary tumors in rats.	2008-09-01	18528864
Flaxseed lignan attenuates high-fat diet-induced fat accumulation and induces adiponectin expression in mice.	2008-09	18252024
An amphioxus orthologue of the estrogen receptor that does not bind estradiol: insights into estrogen receptor evolution.	2008-07-25	18655705
Metabolism of the lignan macromolecule into enterolignans in the gastrointestinal lumen as determined in the simulator of the human intestinal microbial ecosystem.	2008-06-25	18494490
Effects of metabolites of the lignans enterolactone and enterodiol on osteoblastic differentiation of MG-63 cells.	2008-06	18520031
Effects of dietary flaxseed lignan extract on symptoms of benign prostatic hyperplasia.	2008-06	18358071
Dietary flaxseed lignan extract lowers plasma cholesterol and glucose concentrations in hypercholesterolaemic subjects.	2008-06	18053310
Genome analysis of food grade lactic Acid-producing bacteria: from basics to applications.	2008-05	19440514
Enterodiol and enterolactone, two major diet-derived polyphenol metabolites have different impact on ERalpha transcriptional activation in human breast cancer cells.	2008-05	18457947
Urinary excretion of 13 dietary flavonoids and phenolic acids in free-living healthy subjects - variability and possible use as biomarkers of polyphenol intake.	2008-04	17426744
Plasma enterolignan concentrations and colorectal cancer risk in a nested case-control study.	2008-03-15	18192676
Dietary lignans and postmenopausal breast cancer risk by oestrogen receptor status: a prospective cohort study of Swedish women.	2008-02-12	18212757
Lignan content of selected foods from Japan.	2008-01-23	18163563
Determination of urinary phytoestrogens by HPLC-MS/MS: a comparison of atmospheric pressure chemical ionization (APCI) and electrospray ionization (ESI).	2008-01-01	18068558
Breast cancer risk in relation to urinary and serum biomarkers of phytoestrogen exposure in the European Prospective into Cancer-Norfolk cohort study.	2008	18419813
Effects of a flaxseed-derived lignan supplement in type 2 diabetic patients: a randomized, double-blind, cross-over trial.	2007-11-07	17987126
Enantioselective oxidation of enterodiol to enterolactone by human intestinal bacteria.	2007-11	17978502
Enantioselective dehydroxylation of enterodiol and enterolactone precursors by human intestinal bacteria.	2007-11	17978485
Metabolism of isoflavones, lignans and prenylflavonoids by intestinal bacteria: producer phenotyping and relation with intestinal community.	2007-08	17506823
Can the combination of flaxseed and its lignans with soy and its isoflavones reduce the growth stimulatory effect of soy and its isoflavones on established breast cancer?	2007-07	17579892
Role of dietary lignans in the reduction of breast cancer risk.	2007-07	17576639
Determination of mammalian lignans in biological samples by modified gas chromatography/mass spectrometry.	2007-06-22	17580615
High throughput quantification of phytoestrogens in human urine and serum using liquid chromatography/tandem mass spectrometry (LC-MS/MS).	2007-06-15	17403619
Tissue distribution of lignans in rats in response to diet, dose-response, and competition with isoflavones.	2007-06-13	17497882
Isolation and characterization of a human intestinal bacterium, Eubacterium sp. ARC-2, capable of demethylating arctigenin, in the essential metabolic process to enterolactone.	2007-05	17473433
Flaxseed and its lignans inhibit estradiol-induced growth, angiogenesis, and secretion of vascular endothelial growth factor in human breast cancer xenografts in vivo.	2007-02-01	17289903
Validation of a phytoestrogen food frequency questionnaire with urinary concentrations of isoflavones and lignan metabolites in premenopausal women.	2007-02	17353586
Urinary phytoestrogen excretion of rats bearing methylnitrosourea-induced mammary carcinoma in response to treatment with 2-methoxyestradiol.	2007-02	17081745
Pilot study of urinary biomarkers of phytoestrogens, phthalates, and phenols in girls.	2007-01	17366830
Clostridium saccharogumia sp. nov. and Lactonifactor longoviformis gen. nov., sp. nov., two novel human faecal bacteria involved in the conversion of the dietary phytoestrogen secoisolariciresinol diglucoside.	2007-01	17196483
Lignans and human health.	2007	17943494
Phytoestrogen exposure, polymorphisms in COMT, CYP19, ESR1, and SHBG genes, and their associations with prostate cancer risk.	2006	17176215

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:56:05 GMT 2025` Edited by `admin` on `Mon Mar 31 19:56:05 GMT 2025`
Record UNII	BZF4X2AWRP
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ENTERODIOL

Common Name

English

(-)-ENTERODIOL

Preferred Name

English

(2R,3R)-2,3-BIS((3-HYDROXYPHENYL)METHYL)BUTANE-1,4-DIOL

Systematic Name

English

Code System Code Type Description

PUBCHEM

115089