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221054-79-1,MFCD09025608
Catalog No.:AA00BE72

221054-79-1 | (R)-Equol

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Purity
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1mg
≥98%
in stock  
$26.00   $18.00
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5mg
≥98%
in stock  
$105.00   $73.00
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10mg
≥98%
in stock  
$185.00   $129.00
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25mg
≥98%
in stock  
$398.00   $278.00
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA00BE72
Chemical Name:
(R)-Equol
CAS Number:
221054-79-1
Molecular Formula:
C15H14O3
Molecular Weight:
242.2699
MDL Number:
MFCD09025608
SMILES:
Oc1ccc(cc1)[C@@H]1COc2c(C1)ccc(c2)O
Properties
Computed Properties
 
Complexity:
273  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
1  
Heavy Atom Count:
18  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
2  
Rotatable Bond Count:
1  
XLogP3:
3  

Downstream Synthesis Route
486-66-8   
(+)-Equol 
  531-95-3 

[1]BioorganicandMedicinalChemistry,2004,vol.12,p.1559-1567

[2]Patent:JP2015/44770,2015,A

10499-17-9   
(+)-Equol 
  531-95-3 

[1]BioorganicandMedicinalChemistry,2004,vol.12,p.1559-1567

[1]CurrentPatentAssignee:BRIGHAMYOUNGUNIVERSITY;CINCINNATICHILDREN'SHOSPITALMEDICALCENTER;COLORADOSTATEUNIVERSITYSYSTEM-WO2008/20853,2008,A1Locationinpatent:Page/Pagecolumn38-39

[2]Locationinpatent:experimentalpartMinekawa,Takayuki;Kambegawa,Akira;Shindome,Kumiko;Ohkuma,Hiroshi;Abe,Katsushi;Maekawa,Hiroaki;Arakawa,Hidetoshi[ChemicalandPharmaceuticalBulletin,2011,vol.59,#1,p.84-87]

[3]Li,Yuanyuan;Li,Qiang;Zhu,Nan;Gao,Zhuxian;Ma,Yulong[Chirality,2018,vol.30,#8,p.996-1004]

(3S,4S)-4-hydroxyequol 
 
(+)-Equol 
  531-95-3 

[1]Patent:JP2015/44770,2015,A.Locationinpatent:Paragraph0079-0081

C29H26O3 
 
(+)-Equol 
  531-95-3 

[1]TetrahedronLetters,2018,vol.59,p.2407-2411

Literature

Title: Equol inhibits growth, induces atresia, and inhibits steroidogenesis of mouse antral follicles in vitro.

Journal: Toxicology and applied pharmacology 20160315

Title: The inhibitory effect of black soybean on hepatic cholesterol accumulation in high cholesterol and high fat diet-induced non-alcoholic fatty liver disease.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20131001

Title: Effects of the natural endocrine disruptor equol on the pituitary function in adult male rats.

Journal: Toxicology 20130208

Title: Interaction effects between genes involved in the AKT signaling pathway and phytoestrogens in gastric carcinogenesis: a nested case-control study from the Korean Multi-Center Cancer Cohort.

Journal: Molecular nutrition & food research 20121101

Title: Effect of 17β-estradiol and flavonoids on the regulation of expression of newly identified oestrogen responsive genes in a rat raphe nuclei-derived cell line.

Journal: Journal of cellular physiology 20121001

Title: Epigenetic modulation of BRCA1 and BRCA2 gene expression by equol in breast cancer cell lines.

Journal: The British journal of nutrition 20121001

Title: Endocrine disrupting chemicals in urine of Japanese male partners of subfertile couples: a pilot study on exposure and semen quality.

Journal: International journal of hygiene and environmental health 20120901

Title: Analysis of regulatory mechanisms of an insulin-inducible SHARP-2 gene by (S)-Equol.

Journal: Archives of biochemistry and biophysics 20120901

Title: Synergistic and Selective Cancer Cell Killing Mediated by the Oncolytic Adenoviral Mutant AdΔΔ and Dietary Phytochemicals in Prostate Cancer Models.

Journal: Human gene therapy 20120901

Title: The effect of equol injection in ovo on lipid metabolism and hepatic lipogenic gene expression in broilers.

Journal: Animal : an international journal of animal bioscience 20120901

Title: Dietary intakes and food sources of phytoestrogens in the European Prospective Investigation into Cancer and Nutrition (EPIC) 24-hour dietary recall cohort.

Journal: European journal of clinical nutrition 20120801

Title: [Microbial conversion of daidzein affects fecal equol concentration and bacterial composition of rats with or without ovariectomy].

Journal: Wei sheng wu xue bao = Acta microbiologica Sinica 20120704

Title: Photoimmune protective effect of the phytoestrogenic isoflavonoid equol is partially due to its antioxidant activities.

Journal: Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology 20120701

Title: Foetal exposure to phthalate esters and anogenital distance in male newborns.

Journal: International journal of andrology 20120601

Title: Equol production changes over time in postmenopausal women.

Journal: The Journal of nutritional biochemistry 20120601

Title: Does equol production determine soy endocrine effects?

Journal: European journal of nutrition 20120601

Title: Prostate cancer chemoprevention by soy isoflavones: role of intestinal bacteria as the 'second human genome'.

Journal: Cancer science 20120601

Title: Elucidation of the metabolic pathway of S-equol in rat, monkey and man.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20120601

Title: Editorial comment to involvement of estrogen receptors in prostatic diseases.

Journal: International journal of urology : official journal of the Japanese Urological Association 20120601

Title: Toxicokinetics and lack of uterotropic effect of orally administered S-equol.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20120501

Title: Equol production changes over time in pre-menopausal women.

Journal: The British journal of nutrition 20120401

Title: 2-Morpholinoisoflav-3-enes as flexible intermediates in the synthesis of phenoxodiol, isophenoxodiol, equol and analogues: vasorelaxant properties, estrogen receptor binding and Rho/RhoA kinase pathway inhibition.

Journal: Bioorganic & medicinal chemistry 20120401

Title: The effects of natural S-equol supplementation on skin aging in postmenopausal women: a pilot randomized placebo-controlled trial.

Journal: Menopause (New York, N.Y.) 20120201

Title: Urinary estrogen metabolites during a randomized soy trial.

Journal: Nutrition and cancer 20120201

Title: [Phytoestrogenes in menopause: working mechanisms and clinical results in 28 patients].

Journal: Ceska gynekologie 20120201

Title: Prostate cancer chemoprevention study: an investigative randomized control study using purified isoflavones in men with rising prostate-specific antigen.

Journal: Cancer science 20120101

Title: A natural S-equol supplement alleviates hot flushes and other menopausal symptoms in equol nonproducing postmenopausal Japanese women.

Journal: Journal of women's health (2002) 20120101

Title: Biochemical investigation and gene analysis of equol: a plant and soy-derived isoflavonoid with antiaging and antioxidant properties with potential human skin applications.

Journal: BioFactors (Oxford, England) 20120101

Title: The isoflavone metabolite 6-methoxyequol inhibits angiogenesis and suppresses tumor growth.

Journal: Molecular cancer 20120101

Title: Comparative activities of the S-enantiomer and racemic forms of equol on bone fragility in ovariectomized mice.

Journal: Bioscience, biotechnology, and biochemistry 20120101

Title: Experimentally induced mastitis and metritis modulate soy bean derived isoflavone biotransformation in diary cows.

Journal: Theriogenology 20111201

Title: Antioxidant effect of a phytoestrogen equol on cultured muscle cells of embryonic broilers.

Journal: In vitro cellular & developmental biology. Animal 20111201

Title: [Equol-producing phenotype and in relation to serum sex hormones among healthy adults in Beijing].

Journal: Wei sheng yan jiu = Journal of hygiene research 20111101

Title: Resistant starch promotes equol production and inhibits tibial bone loss in ovariectomized mice treated with daidzein.

Journal: Metabolism: clinical and experimental 20111001

Title: Apparent bioavailability of isoflavones in urinary excretions of postmenopausal Malay women consuming tempeh compared with milk.

Journal: International journal of food sciences and nutrition 20110901

Title: Soy isoflavones augment the effect of TRAIL-mediated apoptotic death in prostate cancer cells.

Journal: Oncology reports 20110901

Title: Anticancer mechanism of equol in 7,12-dimethylbenz(a)anthracene-treated animals.

Journal: International journal of oncology 20110901

Title: Effects of S-equol and natural S-equol supplement (SE5-OH) on the growth of MCF-7 in vitro and as tumors implanted into ovariectomized athymic mice.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20110901

Title: Emerging evidence of the health benefits of S-equol, an estrogen receptor β agonist.

Journal: Nutrition reviews 20110801

Title: S-equol and the fermented soy product SE5-OH containing S-equol similarly decrease ovariectomy-induced increase in rat tail skin temperature in an animal model of hot flushes.

Journal: Menopause (New York, N.Y.) 20110701

Title: Impact of perinatal exposure to equol enantiomers on reproductive development in rodents.

Journal: Reproductive toxicology (Elmsford, N.Y.) 20110701

Title: The role of soy isoflavones in menopausal health: report of The North American Menopause Society/Wulf H. Utian Translational Science Symposium in Chicago, IL (October 2010).

Journal: Menopause (New York, N.Y.) 20110701

Title: [Anti-invasion effects of R- and S-enantiomers of equol on prostate cancer PC3, DU145 cells].

Journal: Wei sheng yan jiu = Journal of hygiene research 20110701

Title: O-desmethylangolensin: the importance of equol's lesser known cousin to human health.

Journal: Advances in nutrition (Bethesda, Md.) 20110701

Title: [Effect of equol on breast tumors induced by 7, 12-dimethylbenz (α) anthracene in ovariectominzed rats].

Journal: Beijing da xue xue bao. Yi xue ban = Journal of Peking University. Health sciences 20110618

Title: Natural S-equol decreases bone resorption in postmenopausal, non-equol-producing Japanese women: a pilot randomized, placebo-controlled trial.

Journal: Menopause (New York, N.Y.) 20110501

Title: Lactobacillus rhamnosus JCM 2771: impact on metabolism of isoflavonoids in the fecal flora from a male equol producer.

Journal: Current microbiology 20110501

Title: Development of chiral liquid chromatography-tandem mass spectrometry isotope dilution methods for the determination of unconjugated and total S-equol in human plasma and urine.

Journal: Journal of pharmaceutical and biomedical analysis 20110428

Title: Equol-stimulated mitochondrial reactive oxygen species activate endothelial nitric oxide synthase and redox signaling in endothelial cells: roles for F-actin and GPR30.

Journal: Hypertension (Dallas, Tex. : 1979) 20110401

Title: Hippocampal responsiveness to 17β-estradiol and equol after long-term ovariectomy: implication for a therapeutic window of opportunity.

Journal: Brain research 20110316

Title: Urinary isoflavone phytoestrogens in German children and adolescents--a longitudinal examination in the DONALD cohort.

Journal: Molecular nutrition & food research 20110301

Title: Quantification of five isoflavones and coumestrol in various solid agroenvironmental matrices using ¹³c₃-labeled internal standards.

Journal: Journal of agricultural and food chemistry 20110209

Title: Is equol production beneficial to health?

Journal: The Proceedings of the Nutrition Society 20110201

Title: Single-dose and steady-state pharmacokinetic studies of S-equol, a potent nonhormonal, estrogen receptor β-agonist being developed for the treatment of menopausal symptoms.

Journal: Menopause (New York, N.Y.) 20110201

Title: Transcriptional activity of estrogen-related receptor γ (ERRγ) is stimulated by the phytoestrogen equol.

Journal: The Journal of steroid biochemistry and molecular biology 20110101

Title: Development of bioluminescent enzyme immunoassay for s-equol using firefly luciferase and its application to the assessment of equol-producer status.

Journal: Chemical & pharmaceutical bulletin 20110101

Title: Equol an isoflavonoid: potential for improved prostate health, in vitro and in vivo evidence.

Journal: Reproductive biology and endocrinology : RB&E 20110101

Title: Soy isoflavone equol perpetuates dextran sulfate sodium-induced acute colitis in mice.

Journal: Bioscience, biotechnology, and biochemistry 20110101

Title: Neuromodulation by soy diets or equol: anti-depressive & anti-obesity-like influences, age- & hormone-dependent effects.

Journal: BMC neuroscience 20110101

Title: [Equol induced apoptosis of human breast cancer MDA-MB-231 cell by inhibiting the expression of nuclear factor-kappaB].

Journal: Wei sheng yan jiu = Journal of hygiene research 20110101

Title: Distribution of isoflavones in samples of serum, liver and mammary glands of rats or pigs fed dietary isoflavones.

Journal: Annals of nutrition & metabolism 20110101

Title: Identification of two novel reductases involved in equol biosynthesis in Lactococcus strain 20-92.

Journal: Journal of molecular microbiology and biotechnology 20110101

Title: Modulation of monoamine neurotransmitters in fighting fish Betta splendens exposed to waterborne phytoestrogens.

Journal: Fish physiology and biochemistry 20101201

Title: Genotoxicity assessment of S-equol in bacterial mutation, chromosomal aberration, and rodent bone marrow micronucleus tests.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20101201

Title: Urinary phytoestrogens and risk of prostate cancer in Jamaican men.

Journal: Cancer causes & control : CCC 20101201

Title: Mammary gland differentiation by early life exposure to enantiomers of the soy isoflavone metabolite equol.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20101101

Title: Effects of a high dose, aglycone-rich soy extract on prostate-specific antigen and serum isoflavone concentrations in men with localized prostate cancer.

Journal: Nutrition and cancer 20101101

Title: [Research development on relation between equol and soy foods health effect].

Journal: Wei sheng yan jiu = Journal of hygiene research 20101101

Title: [Advances on the study of equol metabolism in human].

Journal: Wei sheng yan jiu = Journal of hygiene research 20101101

Title: Synthesis of isoflavone aglycones and equol in soy milks fermented by food-related lactic acid bacteria and their effect on human intestinal Caco-2 cells.

Journal: Journal of agricultural and food chemistry 20101013

Title: Topical isoflavonoids reduce experimental cutaneous inflammation in mice.

Journal: Immunology and cell biology 20101001

Title: Daidzein and the daidzein metabolite, equol, enhance adipocyte differentiation and PPARgamma transcriptional activity.

Journal: The Journal of nutritional biochemistry 20100901

Title: Dietary genistein and equol (4', 7 isoflavandiol) reduce oxidative stress and protect rats against focal cerebral ischemia.

Journal: American journal of physiology. Regulatory, integrative and comparative physiology 20100901

Title: Slackia equolifaciens sp. nov., a human intestinal bacterium capable of producing equol.

Journal: International journal of systematic and evolutionary microbiology 20100801

Title: Conversion of (3S,4R)-tetrahydrodaidzein to (3S)-equol by THD reductase: proposed mechanism involving a radical intermediate.

Journal: Biochemistry 20100706

Title: Daidzein-metabolising phenotypes in relation to serum lipids and uric acid in adults in Guangzhou, China.

Journal: The British journal of nutrition 20100701

Title: Effects of genistein and equol on human and rat testicular 3beta-hydroxysteroid dehydrogenase and 17beta-hydroxysteroid dehydrogenase 3 activities.

Journal: Asian journal of andrology 20100701

Title: Effects of isoflavones equol and genistein on bone quality in a rat osteopenia model.

Journal: Phytotherapy research : PTR 20100601

Title: Microbial equol production attenuates colonic methanogenesis and sulphidogenesis in vitro.

Journal: Anaerobe 20100601

Title: Delayed activation of extracellular-signal-regulated kinase 1/2 is involved in genistein- and equol-induced cell proliferation and estrogen-receptor-alpha-mediated transcription in MCF-7 breast cancer cells.

Journal: The Journal of nutritional biochemistry 20100501

Title: Evaluation of bone quality and quantity in osteoporotic mice--the effects of genistein and equol.

Journal: Phytomedicine : international journal of phytotherapy and phytopharmacology 20100501

Title: The chemopreventive action of equol enantiomers in a chemically induced animal model of breast cancer.

Journal: Carcinogenesis 20100501

Title: Isolation and characterization of the equol-producing bacterium Slackia sp. strain NATTS.

Journal: Archives of microbiology 20100401

Title: Comparative effects of R- and S-equol and implication of transactivation functions (AF-1 and AF-2) in estrogen receptor-induced transcriptional activity.

Journal: Nutrients 20100301

Title: Changes in the histomorphometric and biomechanical properties of the proximal femur of ovariectomized rat after treatment with the phytoestrogens genistein and equol.

Journal: Planta medica 20100201

Title: Comparison of urodynamic effects of phytoestrogens equol, puerarin and genistein with these of estradiol 17beta in ovariectomized rats.

Journal: Experimental gerontology 20100201

Title: The soy isoflavone equol enhances antigen-specific IgE production in ovalbumin-immunized BALB/c mice.

Journal: Journal of nutritional science and vitaminology 20100101

Title: [Prevalence of equol producer phenotype and its relations to lifestyle factors and dietary intakes among lifestyle factors and dietary intakes among healthy Chinese adults in Beijing].

Journal: Wei sheng yan jiu = Journal of hygiene research 20100101

Title: Prevalence of the equol-producer phenotype and its relationship with dietary isoflavone and serum lipids in healthy Chinese adults.

Journal: Journal of epidemiology 20100101

Title: GC-MS determined distribution of urinary equol producers as affected by age, gender, and repeated ingestions of soymilk.

Journal: Journal of food science 20100101

Title: The role of diet in the metabolism of daidzein by human faecal microbiota sampled from Italian volunteers.

Journal: The Journal of nutritional biochemistry 20091201

Title: Equol in milk of dairy cows is derived from forage legumes such as red clover.

Journal: The British journal of nutrition 20091201

Title: Dietary cholesterol lowers plasma and cecal equol concentrations in mice.

Journal: Nutrition research (New York, N.Y.) 20091201

Title: [Nutrition and bone health. Isoflavones in bone health].

Journal: Clinical calcium 20091001

Title: Transport and metabolism of equol by Caco-2 human intestinal cells.

Journal: Journal of agricultural and food chemistry 20090923

Title: Isoflavone supplements stimulated the production of serum equol and decreased the serum dihydrotestosterone levels in healthy male volunteers.

Journal: Prostate cancer and prostatic diseases 20090901

Title: Daidzein-metabolizing phenotypes in relation to mammographic breast density among premenopausal women in the United States.

Journal: Breast cancer research and treatment 20090801

Title: Chronic equol administration attenuates the antioxidant defense system and causes apoptosis in the mouse brain.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20090801

Title: Estrogenic activity of bovine milk high or low in equol using immature mouse uterotrophic responses and an estrogen receptor transactivation assay.

Journal: Cancer epidemiology 20090701

Title: Association between estrogen receptor alpha polymorphisms and equol production, and its relation to bone mass.

Journal: International journal of molecular medicine 20090601

Title: Biotransformation of daidzein to equol by crude enzyme from Asaccharobacter celatus AHU1763 required an anaerobic environment.

Journal: Bioscience, biotechnology, and biochemistry 20090601

Title: Effects of equol on oxidized low-density lipoprotein-induced apoptosis in endothelial cells.

Journal: Journal of atherosclerosis and thrombosis 20090601

Title: Prostatic soy isoflavone concentrations exceed serum levels after dietary supplementation.

Journal: The Prostate 20090515

Title: Respective contribution exerted by AF-1 and AF-2 transactivation functions in estrogen receptor alpha induced transcriptional activity by isoflavones and equol: consequence on breast cancer cell proliferation.

Journal: Molecular nutrition & food research 20090501

Title: Ileal and faecal digestibility of daidzein and genistein and plasma bioavailability of these isoflavones and their bioactive metabolites in the ovariectomised rat.

Journal: Molecular nutrition & food research 20090501

Title: Hepatoprotective effects of daidzein against 7,12-dimetylbenz[a]anthracene-induced oxidative stress in mice.

Journal: International journal of molecular medicine 20090501

Title: Effect of glycosidation of isoflavones on their bioavailability and pharmacokinetics in aged male rats.

Journal: Molecular nutrition & food research 20090501

Title: Equol but not genistein improves early metaphyseal fracture healing in osteoporotic rats.

Journal: Planta medica 20090401

Title: Equol is more active than soy isoflavone itself to compete for binding to thromboxane A(2) receptor in human platelets.

Journal: Thrombosis research 20090301

Title: Systemic administration of diarylpropionitrile (DPN) or phytoestrogens does not affect anxiety-related behaviors in gonadally intact male rats.

Journal: Hormones and behavior 20090201

Title: Equol induces apoptosis through cytochrome c-mediated caspases cascade in human breast cancer MDA-MB-453 cells.

Journal: Chemico-biological interactions 20090115

Title: Modulation of neurotoxicant-induced increases in intracellular calcium by phytoestrogens differ for amyloid beta peptide (Abeta) and 1-methyl-4-phenyl-pyridine (MPP(+)).

Journal: Journal of applied toxicology : JAT 20090101

Title: A preliminary study of the safety, feasibility and cognitive efficacy of soy isoflavone supplements in older men and women.

Journal: Age and ageing 20090101

Title: New equol supplement for relieving menopausal symptoms: randomized, placebo-controlled trial of Japanese women.

Journal: Menopause (New York, N.Y.) 20090101

Title: [Effect of equol of a isoflavone metabolite on menopausal symptoms].

Journal: Wei sheng yan jiu = Journal of hygiene research 20090101

Title: Daidzein-metabolizing phenotypes in relation to serum hormones and sex hormone binding globulin, and urinary estrogen metabolites in premenopausal women in the United States.

Journal: Cancer causes & control : CCC 20081201

Title: Effects of prior oral contraceptive use and soy isoflavonoids on estrogen-metabolizing cytochrome P450 enzymes.

Journal: The Journal of steroid biochemistry and molecular biology 20081201

Title: Receptor binding and transactivation activities of red clover isoflavones and their metabolites.

Journal: The Journal of steroid biochemistry and molecular biology 20081101

Title: Antioxidant effects of equol on bovine aortic endothelial cells.

Journal: Biochemical and biophysical research communications 20081024

Title: Concentrations of isoflavones and their metabolites in the blood of pregnant and non-pregnant heifers fed soy bean.

Journal: The Journal of reproduction and development 20081001

Title: Impact of soy supplementation on sex steroids and vascular inflammation markers in postmenopausal women using tibolone: role of equol production capability.

Journal: Climacteric : the journal of the International Menopause Society 20081001

Title: Isolation and characterization of a novel equol-producing bacterium from human feces.

Journal: Bioscience, biotechnology, and biochemistry 20081001

Title: Urinary isoflavonoid excretion is similar after consuming soya milk and miso soup in Japanese-American women.

Journal: The British journal of nutrition 20080801

Title: Acute and subchronic toxicity and genotoxicity of SE5-OH, an equol-rich product produced by Lactococcus garvieae.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20080801

Title: Comparative activities of daidzein metabolites, equol and O-desmethylangolensin, on bone mineral density and lipid metabolism in ovariectomized mice and in osteoclast cell cultures.

Journal: European journal of nutrition 20080801

Title: Biotransformation of C-glucosylisoflavone puerarin to estrogenic (3S)-equol in co-culture of two human intestinal bacteria.

Journal: Biological & pharmaceutical bulletin 20080801

Title: Effect of intestinal production of equol on menopausal symptoms in women treated with soy isoflavones.

Journal: International journal of gynaecology and obstetrics: the official organ of the International Federation of Gynaecology and Obstetrics 20080701

Title: Effect of sulphation on the oestrogen agonist activity of the phytoestrogens genistein and daidzein in MCF-7 human breast cancer cells.

Journal: The Journal of endocrinology 20080601

Title: Equol production capability is associated with favorable vascular function in postmenopausal women using tibolone; no effect with soy supplementation.

Journal: Atherosclerosis 20080501

Title: Isolation and identification of equol-producing bacterial strains from cultures of pig faeces.

Journal: FEMS microbiology letters 20080501

Title: Adlercreutzia equolifaciens gen. nov., sp. nov., an equol-producing bacterium isolated from human faeces, and emended description of the genus Eggerthella.

Journal: International journal of systematic and evolutionary microbiology 20080501

Title: Neonatal exposure to endocrine active compounds or an ERbeta agonist increases adult anxiety and aggression in gonadally intact male rats.

Journal: Hormones and behavior 20080401

Title: Topical isoflavones provide effective photoprotection to skin.

Journal: Photodermatology, photoimmunology & photomedicine 20080401

Title: Inhibition by soya isoflavones of human polymorphonuclear leukocyte function: possible relevance for the beneficial effects of soya intake.

Journal: The British journal of nutrition 20080201

Title: Effects of dietary equol administration on the mammary gland in ovariectomized Sprague-Dawley rats.

Journal: Menopause (New York, N.Y.) 20080101

Title: Age-stratified serum levels of isoflavones and proportion of equol producers in Japanese and Korean healthy men.

Journal: Prostate cancer and prostatic diseases 20080101

Title: Equol status modifies the association of soy intake and mammographic density in a sample of postmenopausal women.

Journal: Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20080101

Title: Dietary and lifestyle correlates of urinary excretion status of equol in Japanese women.

Journal: Nutrition and cancer 20080101

Title: Effects of a high daily dose of soy isoflavones on DNA damage, apoptosis, and estrogenic outcomes in healthy postmenopausal women: a phase I clinical trial.

Journal: Menopause (New York, N.Y.) 20080101

Title: Phase II trial of isoflavone in prostate-specific antigen recurrent prostate cancer after previous local therapy.

Journal: BMC cancer 20080101

Title: Individual differences in equol production capability modulate blood pressure in tibolone-treated postmenopausal women: lack of effect of soy supplementation.

Journal: Climacteric : the journal of the International Menopause Society 20071201

Title: Effects of dietary equol administration on ovariectomy induced bone loss in Sprague-Dawley rats.

Journal: Maturitas 20071120

Title: Equol, a metabolite of the soybean isoflavone daidzein, inhibits neoplastic cell transformation by targeting the MEK/ERK/p90RSK/activator protein-1 pathway.

Journal: The Journal of biological chemistry 20071109

Title: Isoflavonoid-based bone-sparing treatments exert a low activity on reproductive organs and on hepatic metabolism of estradiol in ovariectomized rats.

Journal: Toxicology and applied pharmacology 20071015

Title: Uterotropic effects of dietary equol administration in ovariectomized Sprague-Dawley rats.

Journal: Climacteric : the journal of the International Menopause Society 20071001

Title: Role of tyrosine phosphorylation in U46619-induced vasoconstriction of pulmonary vasculature and its modulation by genistein, daidzein, and equol.

Journal: Journal of cardiovascular pharmacology 20071001

Title: Soy and prostate cancer study results mixed.

Journal: Journal of the National Cancer Institute 20070919

Title: Chemical composition and biological activity of a new type of Brazilian propolis: red propolis.

Journal: Journal of ethnopharmacology 20070905

Title: Aza analogues of equol: novel ligands for estrogen receptor beta.

Journal: Bioorganic & medicinal chemistry 20070901

Title: Phyto-oestrogens and risk of prostate cancer in Scottish men.

Journal: The British journal of nutrition 20070801

Title: High levels of equol in organic skimmed Finnish cow milk.

Journal: Molecular nutrition & food research 20070701

Title: Bioavailability of soy isoflavones in rats Part I: application of accurate methodology for studying the effects of gender and source of isoflavones.

Journal: Molecular nutrition & food research 20070701

Title: Metabolism of dietary soy isoflavones to equol by human intestinal microflora--implications for health.

Journal: Molecular nutrition & food research 20070701

Title: Simultaneous determination of daidzein, equol, genistein and bisphenol A in human urine by a fast and simple method using SPE and GC-MS.

Journal: Molecular nutrition & food research 20070701

Title: Dietary isoflavones differentially induce gene expression changes in lymphocytes from postmenopausal women who form equol as compared with those who do not.

Journal: The Journal of nutritional biochemistry 20070601

Title: Does the effect of soy phytoestrogens on bone in postmenopausal women depend on the equol-producing phenotype?

Journal: Nutrition reviews 20070601

Title: Modulation of soy isoflavones bioavailability and subsequent effects on bone health in ovariectomized rats: the case for equol.

Journal: Osteoporosis international : a journal established as result of cooperation between the European Foundation for Osteoporosis and the National Osteoporosis Foundation of the USA 20070501

Title: Vasorelaxant and antioxidant activity of the isoflavone metabolite equol in carotid and cerebral arteries.

Journal: Brain research 20070413

Title: Monoclonal antibody-based time-resolved fluorescence immunoassays for daidzein, genistein, and equol in blood and urine: application to the Isoheart intervention study.

Journal: Clinical chemistry 20070401

Title: Equol inhibits nitric oxide production and inducible nitric oxide synthase gene expression through down-regulating the activation of Akt.

Journal: International immunopharmacology 20070401

Title: Effects of dietary equol on the pituitary of the ovariectomized rats.

Journal: Hormone and metabolic research = Hormon- und Stoffwechselforschung = Hormones et metabolisme 20070401

Title: Bioavailability and urinary excretion of isoflavones in humans: effects of soy-based supplements formulation and equol production.

Journal: Journal of pharmaceutical and biomedical analysis 20070312

Title: Urinary excretion of equol by postmenopausal women consuming soymilk fermented by probiotic bifidobacteria.

Journal: European journal of clinical nutrition 20070301

Title: Urinary isoflavonoid excretion and soy consumption in three generations of Japanese women in Hawaii.

Journal: European journal of clinical nutrition 20070201

Title: Production of phytoestrogen S-equol from daidzein in mixed culture of two anaerobic bacteria.

Journal: Archives of microbiology 20070201

Title: Rapid and convenient detection of urinary equol by thin-layer chromatography.

Journal: Journal of nutritional science and vitaminology 20070201

Title: Equol producer status, salivary estradiol profile and urinary excretion of isoflavones in Irish Caucasian women, following ingestion of soymilk.

Journal: Steroids 20070101

Title: Effects of dietary equol on body weight gain, intra-abdominal fat accumulation, plasma lipids, and glucose tolerance in ovariectomized Sprague-Dawley rats.

Journal: Menopause (New York, N.Y.) 20070101

Title: Possible role of equol status in the effects of isoflavone on bone and fat mass in postmenopausal Japanese women: a double-blind, randomized, controlled trial.

Journal: Menopause (New York, N.Y.) 20070101

Title: The effect of the phytoestrogens genistein, daidzein, and equol on the growth of tamoxifen-resistant T47D/PKC alpha.

Journal: Nutrition and cancer 20070101

Title: Isoflavones, equol and cardiovascular disease: pharmacological and therapeutic insights.

Journal: Current medicinal chemistry 20070101

Title: Behavioral changes in fish exposed to phytoestrogens.

Journal: Environmental pollution (Barking, Essex : 1987) 20061201

Title: Molecular signatures of soy-derived phytochemicals in androgen-responsive prostate cancer cells: a comparison study using DNA microarray.

Journal: Molecular carcinogenesis 20061201

Title: Phyto- and endogenous estrogens differently activate intracellular calcium ion mobilization in bovine endometrial cells.

Journal: The Journal of reproduction and development 20061201

Title: Total synthesis of (S)-equol.

Journal: Organic letters 20061123

Title: Associations among maternal soy intake, isoflavone levels in urine and blood samples, and maternal and umbilical hormone concentrations (Japan).

Journal: Cancer causes & control : CCC 20061101

Title: Phytoestrogens regulate transcription and translation of vitamin D receptor in colon cancer cells.

Journal: The Journal of endocrinology 20061101

Title: Consumption of Lactobacillus acidophilus and Bifidobacterium longum does not alter phytoestrogen metabolism and plasma hormones in men: a pilot study.

Journal: Journal of alternative and complementary medicine (New York, N.Y.) 20061101

Title: [Progress in research of equol: a metabolite of the isoflavone daidzein].

Journal: Sheng li ke xue jin zhan [Progress in physiology] 20061001

Title: The isoflavone Equol mediates rapid vascular relaxation: Ca2+-independent activation of endothelial nitric-oxide synthase/Hsp90 involving ERK1/2 and Akt phosphorylation in human endothelial cells.

Journal: The Journal of biological chemistry 20060915

Title: One-month exposure to soy isoflavones did not induce the ability to produce equol in postmenopausal women.

Journal: European journal of clinical nutrition 20060901

Title: Effects of high-dose soy isoflavones and equol on reproductive tissues in female cynomolgus monkeys.

Journal: Biology of reproduction 20060901

Title: Protective effect of the isoflavone equol against DNA damage induced by ultraviolet radiation to hairless mouse skin.

Journal: Journal of veterinary science 20060901

Title: Supplementation of difructose anhydride III enhanced elevation of plasma equol concentrations and lowered plasma total cholesterol in isoflavone-fed rats.

Journal: The British journal of nutrition 20060901

Title: Production of equol from daidzein by gram-positive rod-shaped bacterium isolated from rat intestine.

Journal: Journal of bioscience and bioengineering 20060901

Title: The prooxidant, rather than antioxidant, acts of daidzein in vivo and in vitro: daidzein suppresses glutathione metabolism.

Journal: European journal of pharmacology 20060807

Title: Soya isoflavones suppress phorbol 12-myristate 13-acetate-induced COX-2 expression in MCF-7 cells.

Journal: The British journal of nutrition 20060701

Title: Dietary modulation of p-nonylphenol-induced polycystic kidneys in male Sprague-Dawley rats.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20060601

Title: Validation and application of a robust yeast estrogen bioassay for the screening of estrogenic activity in animal feed.

Journal: Food additives and contaminants 20060601

Title: Identification of equol producers in a Japanese population by high-performance liquid chromatography with coulometric array for determining serum isoflavones.

Journal: Phytomedicine : international journal of phytotherapy and phytopharmacology 20060501

Title: Equol and para-ethyl-phenol stimulate prostaglandin F(2alpha) secretion in bovine corpus luteum: intracellular mechanisms of action.

Journal: Prostaglandins & other lipid mediators 20060501

Title: Antioxidant activity of isoflavones and their major metabolites using different in vitro assays.

Journal: Journal of agricultural and food chemistry 20060419

Title: Absorption of isoflavones in humans: effects of food matrix and processing.

Journal: The Journal of nutritional biochemistry 20060401

Title: Effects of dietary daidzein and its metabolite, equol, at physiological concentrations on the growth of estrogen-dependent human breast cancer (MCF-7) tumors implanted in ovariectomized athymic mice.

Journal: Carcinogenesis 20060401

Title: Cooperative effects of isoflavones and exercise on bone and lipid metabolism in postmenopausal Japanese women: a randomized placebo-controlled trial.

Journal: Metabolism: clinical and experimental 20060401

Title: Effects of phytoestrogens on testosterone secretion by Leydig cells from Biłgoraj ganders (Anser anser).

Journal: British poultry science 20060401

Title: Short-term phytoestrogen supplementation alters insulin-like growth factor profile but not lipid or antioxidant status.

Journal: The Journal of nutritional biochemistry 20060301

Title: Postmenopausal bone mineral density in relation to soy isoflavone-metabolizing phenotypes.

Journal: Maturitas 20060220

Title: Phytoestrogens and their metabolites inhibit the sensitivity of the bovine corpus luteum to luteotropic factors.

Journal: The Journal of reproduction and development 20060201

Title: Does genotype and equol-production status affect response to isoflavones? Data from a pan-European study on the effects of isoflavones on cardiovascular risk markers in post-menopausal women.

Journal: The Proceedings of the Nutrition Society 20060201

Title: Structural elucidation of hydroxylated metabolites of the isoflavan equol by gas chromatography-mass spectrometry and high-performance liquid chromatography-mass spectrometry.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20060101

Title: Phyto-oestrogen intake in Scottish men: use of serum to validate a self-administered food-frequency questionnaire in older men.

Journal: European journal of clinical nutrition 20060101

Title: Isoflavonoid photoprotection in mouse and human skin is dependent on metallothionein.

Journal: The Journal of investigative dermatology 20060101

Title: Serum cholesterol efflux potential in postmenopausal women treated with isolated isoflavones.

Journal: Menopause (New York, N.Y.) 20060101

Title: Genistein and 17beta-estradiol, but not equol, regulate vitamin D synthesis in human colon and breast cancer cells.

Journal: Anticancer research 20060101

Title: Equol: a comparison of the effects of the racemic compound with that of the purified S-enantiomer on the growth, invasion, and DNA integrity of breast and prostate cells in vitro.

Journal: Nutrition and cancer 20060101

Title: Detection of isoflavones in mouse tibia after feeding daidzein.

Journal: Journal of medicinal food 20060101

Title: Phytoestrogen action in Leydig cells of Biłgoraj ganders (Anser anser).

Journal: Reproductive biology 20060101

Title: Estrogen receptor-independent inhibition of tumor necrosis factor-alpha gene expression by phytoestrogen equol is mediated by blocking nuclear factor-kappaB activation in mouse macrophages.

Journal: Biochemical pharmacology 20051219

Title: Serum equol, bone mineral density and biomechanical bone strength differ among four mouse strains.

Journal: The Journal of nutritional biochemistry 20051201

Title: Soy-isoflavone-enriched foods and inflammatory biomarkers of cardiovascular disease risk in postmenopausal women: interactions with genotype and equol production.

Journal: The American journal of clinical nutrition 20051201

Title: High concordance of daidzein-metabolizing phenotypes in individuals measured 1 to 3 years apart.

Journal: The British journal of nutrition 20051201

Title: Effect of pure genistein on bone markers and hot flushes.

Journal: Climacteric : the journal of the International Menopause Society 20051201

Title: Sensitive high-performance liquid chromatographic method using coulometric electrode array detection for measurement of phytoestrogens in dried blood spots.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20051105

Title: Formononetin, a phyto-oestrogen, and its metabolites up-regulate interleukin-4 production in activated T cells via increased AP-1 DNA binding activity.

Journal: Immunology 20050901

Title: Estrogenic and genotoxic potential of equol and two hydroxylated metabolites of Daidzein in cultured human Ishikawa cells.

Journal: Toxicology letters 20050728

Title: X-ray single-crystal analysis of (-)-(S)-equol isolated from rat's feces.

Journal: Chemistry & biodiversity 20050701

Title: Gut bacterial metabolism of the soy isoflavone daidzein: exploring the relevance to human health.

Journal: Experimental biology and medicine (Maywood, N.J.) 20050301

Title: Isolation and characterisation of an equol-producing mixed microbial culture from a human faecal sample and its activity under gastrointestinal conditions.

Journal: Archives of microbiology 20050101

Title: Effect of a soymilk supplement containing isoflavones on urinary F2 isoprostane levels in premenopausal women.

Journal: Nutrition and cancer 20050101

Title: Protection against photoaging in the hairless mouse by the isoflavone equol.

Journal: Photochemistry and photobiology 20050101

Title: Consumption of Lactobacillus acidophilus and Bifidobacterium longum do not alter urinary equol excretion and plasma reproductive hormones in premenopausal women.

Journal: European journal of clinical nutrition 20041201

Title: Lactobacillus gasseri: effects on mouse intestinal flora enzyme activity and isoflavonoids in the caecum and plasma.

Journal: The British journal of nutrition 20041101

Title: Biotransformation of soy isoflavone-glycosides in laying hens: intestinal absorption and preferential accumulation into egg yolk of equol, a more estrogenic metabolite of daidzein.

Journal: Biochimica et biophysica acta 20040924

Title: Estrogenicity of the isoflavone metabolite equol on reproductive and non-reproductive organs in mice.

Journal: Biology of reproduction 20040901

Title: Synthesis of phytoestrogenic isoflavonoid disulfates.

Journal: Steroids 20040901

Title: Mammographic density in relation to daidzein-metabolizing phenotypes in overweight, postmenopausal women.

Journal: Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20040701

Title: Identification of puerarin and its metabolites in rats by liquid chromatography-tandem mass spectrometry.

Journal: Journal of agricultural and food chemistry 20040616

Title: Genotoxicity of the isoflavones genistein, daidzein and equol in V79 cells.

Journal: Toxicology letters 20040615

Title: Distribution of soy-derived phytoestrogens in human breast tissue and biological fluids.

Journal: Obstetrics and gynecology 20040501

Title: Isoflavones stimulate estrogen receptor-mediated core histone acetylation.

Journal: Biochemical and biophysical research communications 20040423

Title: Equol is a novel anti-androgen that inhibits prostate growth and hormone feedback.

Journal: Biology of reproduction 20040401

Title: Urinary isoflavone kinetics: the effect of age, gender, food matrix and chemical composition.

Journal: The British journal of nutrition 20040401

Title: Influence of soya-based infant formula consumption on isoflavone and gut microflora metabolite concentrations in urine and on faecal microflora composition and metabolic activity in infants and children.

Journal: The British journal of nutrition 20040401

Title: Serum steroid hormones, sex hormone-binding globulin concentrations, and urinary hydroxylated estrogen metabolites in post-menopausal women in relation to daidzein-metabolizing phenotypes.

Journal: The Journal of steroid biochemistry and molecular biology 20040401

Title: Equol, a natural estrogenic metabolite from soy isoflavones: convenient preparation and resolution of R- and S-equols and their differing binding and biological activity through estrogen receptors alpha and beta.

Journal: Bioorganic & medicinal chemistry 20040315

Title: Comparisons of percent equol producers between prostate cancer patients and controls: case-controlled studies of isoflavones in Japanese, Korean and American residents.

Journal: Japanese journal of clinical oncology 20040201

Title: The topical isoflavonoid NV-07alpha reduces solar-simulated UV-induced suppression of Mantoux reactions in humans.

Journal: Photochemistry and photobiology 20040101

Title: Measurement of isoflavones using liquid chromatography with multi-channel coulometric electrochemical detection.

Journal: BioFactors (Oxford, England) 20040101

Title: Oestrogenic compounds and oxidative stress (in human sperm and lymphocytes in the Comet assay).

Journal: Mutation research 20031101

Title: A toxicity identification evaluation approach to studying estrogenic substances in hog manure and agricultural runoff.

Journal: Environmental toxicology and chemistry 20031001

Title: Variations in metabolism of the soy isoflavonoid daidzein by human intestinal microfloras from different individuals.

Journal: Archives of microbiology 20030701

Title: Effects of the isoflavones genistein and equol on the gonadal development of Japanese medaka Oryzias latipes.

Journal: Environmental health perspectives 20030701

Title: Urinary equol excretion in relation to 2-hydroxyestrone and 16alpha-hydroxyestrone concentrations: an observational study of young to middle-aged women.

Journal: The Journal of steroid biochemistry and molecular biology 20030701

Title: The phytoestrogen equol increases nitric oxide availability by inhibiting superoxide production: an antioxidant mechanism for cell-mediated LDL modification.

Journal: Free radical biology & medicine 20030515

Title: Metabolism of isoflavones and lignans by the gut microflora: a study in germ-free and human flora associated rats.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20030501

Title: Quantification of isoflavones and lignans in urine using gas chromatography/mass spectrometry.

Journal: Analytical biochemistry 20030401

Title: Time-resolved fluoroimmunoassay for equol in plasma and urine.

Journal: The Journal of steroid biochemistry and molecular biology 20030401

Title: Soy-derived isoflavones exert opposing actions on Guinea pig ventricular myocytes.

Journal: The Journal of pharmacology and experimental therapeutics 20030301

Title: Soy isoflavonoid equol modulates the growth of benign and malignant prostatic epithelial cells in vitro.

Journal: The Prostate 20030101

Title: Identification of phytoestrogens in bovine milk using liquid chromatography/electrospray tandem mass spectrometry.

Journal: Rapid communications in mass spectrometry : RCM 20030101

Title: Effect of in utero-administered coumestrol, equol, and organic selenium on biomarkers for phase 2 enzyme capacity and redox status.

Journal: Nutrition and cancer 20030101

Title: Higher consumption of green tea may enhance equol production.

Journal: Asian Pacific journal of cancer prevention : APJCP 20030101

Title: Quantitative analysis of urinary daidzein and equol by gas chromatography after solid-phase extraction and high-performance liquid chromatography.

Journal: The International journal of biological markers 20020101

Title: Effects of phytoestrogens on DNA synthesis and creatine kinase activity in vascular cells.

Journal: American journal of hypertension 20011201

Title: Regulation of phenobarbital-mediated induction of CYP102 (cytochrome P450(BM-3)) in Bacillus megaterium by phytochemicals from soy and green tea.

Journal: Journal of agricultural and food chemistry 20011001

Title: Animal models impacted by phytoestrogens in commercial chow: implications for pathways influenced by hormones.

Journal: Laboratory investigation; a journal of technical methods and pathology 20010501

Title: Effect of phytoestrogen and antioxidant supplementation on oxidative DNA damage assessed using the comet assay.

Journal: Mutation research 20010307

Title: Assaying the estrogenicity of phytoestrogens in cells of different estrogen sensitive tissues.

Journal: Toxicology in vitro : an international journal published in association with BIBRA 20010101

Title: Setchell KD, et al. S-equol, a potent ligand for estrogen receptor beta, is the exclusive enantiomeric form of the soy isoflavone metabolite produced by human intestinal bacterial flora. Am J Clin Nutr. 2005 May;81(5):1072-9.

Title: Magee PJ, et al. Daidzein, R-(+)equol and S-(-)equol inhibit the invasion of MDA-MB-231 breast cancer cells potentially via the down-regulation of matrix metalloproteinase-2. Eur J Nutr. 2014 Feb;53(1):345-50.

Title: Brown NM, et al. The chemopreventive action of equol enantiomers in a chemically induced animal model of breast cancer. Carcinogenesis. 2010 May;31(5):886-93.

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Tags:221054-79-1 Molecular Formula|221054-79-1 MDL|221054-79-1 SMILES|221054-79-1 (R)-Equol