Home Other Building Blocks 7-Hydroxy-3-(4-hydroxyphenyl)chroman-4-one

7-Hydroxy-3-(4-hydroxyphenyl)chroman-4-one

CAS No.:
17238-05-0
Catalog Number:
AG00AE7D
Molecular Formula:
C15H12O4
Molecular Weight:
256.2534
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
5mg
≥98%
1 week
United States
$105
- +
10mg
≥98%
1 week
United States
$135
- +
25mg
≥98%
1 week
United States
$179
- +
50mg
≥98%
1 week
United States
$276
- +
Product Description
Catalog Number:
AG00AE7D
Chemical Name:
7-Hydroxy-3-(4-hydroxyphenyl)chroman-4-one
CAS Number:
17238-05-0
Molecular Formula:
C15H12O4
Molecular Weight:
256.2534
MDL Number:
MFCD00210494
IUPAC Name:
7-hydroxy-3-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
InChI:
InChI=1S/C15H12O4/c16-10-3-1-9(2-4-10)13-8-19-14-7-11(17)5-6-12(14)15(13)18/h1-7,13,16-17H,8H2
InChI Key:
JHYXBPPMXZIHKG-UHFFFAOYSA-N
SMILES:
Oc1ccc(cc1)C1COc2c(C1=O)ccc(c2)O
Properties
Complexity:
335  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
256.074g/mol
Formal Charge:
0
Heavy Atom Count:
19  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
2  
Isotope Atom Count:
0
Molecular Weight:
256.257g/mol
Monoisotopic Mass:
256.074g/mol
Rotatable Bond Count:
1  
Topological Polar Surface Area:
66.8A^2
Undefined Atom Stereocenter Count:
1  
Undefined Bond Stereocenter Count:
0
XLogP3:
2.4  
Literature
Title Journal
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Uterotropic effects of dietary equol administration in ovariectomized Sprague-Dawley rats. Climacteric : the journal of the International Menopause Society 20071001
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Soy and prostate cancer study results mixed. Journal of the National Cancer Institute 20070919
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High levels of equol in organic skimmed Finnish cow milk. Molecular nutrition & food research 20070701
Bioavailability of soy isoflavones in rats Part I: application of accurate methodology for studying the effects of gender and source of isoflavones. Molecular nutrition & food research 20070701
Metabolism of dietary soy isoflavones to equol by human intestinal microflora--implications for health. Molecular nutrition & food research 20070701
Simultaneous determination of daidzein, equol, genistein and bisphenol A in human urine by a fast and simple method using SPE and GC-MS. Molecular nutrition & food research 20070701
Quantitative determination of acetyl glucoside isoflavones and their metabolites in human urine using combined liquid chromatography-mass spectrometry. Journal of chromatography. A 20070622
Dietary isoflavones differentially induce gene expression changes in lymphocytes from postmenopausal women who form equol as compared with those who do not. The Journal of nutritional biochemistry 20070601
Does the effect of soy phytoestrogens on bone in postmenopausal women depend on the equol-producing phenotype? Nutrition reviews 20070601
Metabolism of daidzein by fecal bacteria in rats. Comparative medicine 20070601
Modulation of soy isoflavones bioavailability and subsequent effects on bone health in ovariectomized rats: the case for equol. Osteoporosis international : a journal established as result of cooperation between the European Foundation for Osteoporosis and the National Osteoporosis Foundation of the USA 20070501
Vasorelaxant and antioxidant activity of the isoflavone metabolite equol in carotid and cerebral arteries. Brain research 20070413
Monoclonal antibody-based time-resolved fluorescence immunoassays for daidzein, genistein, and equol in blood and urine: application to the Isoheart intervention study. Clinical chemistry 20070401
Equol inhibits nitric oxide production and inducible nitric oxide synthase gene expression through down-regulating the activation of Akt. International immunopharmacology 20070401
Effects of dietary equol on the pituitary of the ovariectomized rats. Hormone and metabolic research = Hormon- und Stoffwechselforschung = Hormones et metabolisme 20070401
Bioavailability and urinary excretion of isoflavones in humans: effects of soy-based supplements formulation and equol production. Journal of pharmaceutical and biomedical analysis 20070312
Urinary excretion of equol by postmenopausal women consuming soymilk fermented by probiotic bifidobacteria. European journal of clinical nutrition 20070301
Urinary isoflavonoid excretion and soy consumption in three generations of Japanese women in Hawaii. European journal of clinical nutrition 20070201
Production of phytoestrogen S-equol from daidzein in mixed culture of two anaerobic bacteria. Archives of microbiology 20070201
Isolation of an isoflavone-metabolizing, Clostridium-like bacterium, strain TM-40, from human faeces. Anaerobe 20070201
Rapid and convenient detection of urinary equol by thin-layer chromatography. Journal of nutritional science and vitaminology 20070201
Equol producer status, salivary estradiol profile and urinary excretion of isoflavones in Irish Caucasian women, following ingestion of soymilk. Steroids 20070101
Effects of dietary equol on body weight gain, intra-abdominal fat accumulation, plasma lipids, and glucose tolerance in ovariectomized Sprague-Dawley rats. Menopause (New York, N.Y.) 20070101
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. Menopause (New York, N.Y.) 20070101
The effect of the phytoestrogens genistein, daidzein, and equol on the growth of tamoxifen-resistant T47D/PKC alpha. Nutrition and cancer 20070101
Isoflavones, equol and cardiovascular disease: pharmacological and therapeutic insights. Current medicinal chemistry 20070101
Behavioral changes in fish exposed to phytoestrogens. Environmental pollution (Barking, Essex : 1987) 20061201
Molecular signatures of soy-derived phytochemicals in androgen-responsive prostate cancer cells: a comparison study using DNA microarray. Molecular carcinogenesis 20061201
Phyto- and endogenous estrogens differently activate intracellular calcium ion mobilization in bovine endometrial cells. The Journal of reproduction and development 20061201
Total synthesis of (S)-equol. Organic letters 20061123
Isoflavone metabolites and their in vitro dual functions: they can act as an estrogenic agonist or antagonist depending on the estrogen concentration. The Journal of steroid biochemistry and molecular biology 20061101
Associations among maternal soy intake, isoflavone levels in urine and blood samples, and maternal and umbilical hormone concentrations (Japan). Cancer causes & control : CCC 20061101
Phytoestrogens regulate transcription and translation of vitamin D receptor in colon cancer cells. The Journal of endocrinology 20061101
Consumption of Lactobacillus acidophilus and Bifidobacterium longum does not alter phytoestrogen metabolism and plasma hormones in men: a pilot study. Journal of alternative and complementary medicine (New York, N.Y.) 20061101
Phytoestrogen derivatives differentially inhibit arterial neointimal proliferation in a mouse model. European journal of pharmacology 20061024
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. The Journal of biological chemistry 20060915
One-month exposure to soy isoflavones did not induce the ability to produce equol in postmenopausal women. European journal of clinical nutrition 20060901
Effects of high-dose soy isoflavones and equol on reproductive tissues in female cynomolgus monkeys. Biology of reproduction 20060901
Protective effect of the isoflavone equol against DNA damage induced by ultraviolet radiation to hairless mouse skin. Journal of veterinary science 20060901
Supplementation of difructose anhydride III enhanced elevation of plasma equol concentrations and lowered plasma total cholesterol in isoflavone-fed rats. The British journal of nutrition 20060901
Production of equol from daidzein by gram-positive rod-shaped bacterium isolated from rat intestine. Journal of bioscience and bioengineering 20060901
The prooxidant, rather than antioxidant, acts of daidzein in vivo and in vitro: daidzein suppresses glutathione metabolism. European journal of pharmacology 20060807
Soya isoflavones suppress phorbol 12-myristate 13-acetate-induced COX-2 expression in MCF-7 cells. The British journal of nutrition 20060701
Dietary modulation of p-nonylphenol-induced polycystic kidneys in male Sprague-Dawley rats. Toxicological sciences : an official journal of the Society of Toxicology 20060601
Validation and application of a robust yeast estrogen bioassay for the screening of estrogenic activity in animal feed. Food additives and contaminants 20060601
Identification of equol producers in a Japanese population by high-performance liquid chromatography with coulometric array for determining serum isoflavones. Phytomedicine : international journal of phytotherapy and phytopharmacology 20060501
Equol and para-ethyl-phenol stimulate prostaglandin F(2alpha) secretion in bovine corpus luteum: intracellular mechanisms of action. Prostaglandins & other lipid mediators 20060501
Antioxidant activity of isoflavones and their major metabolites using different in vitro assays. Journal of agricultural and food chemistry 20060419
Absorption of isoflavones in humans: effects of food matrix and processing. The Journal of nutritional biochemistry 20060401
Prostatic fluid concentrations of isoflavonoids in soy consumers are sufficient to inhibit growth of benign and malignant prostatic epithelial cells in vitro. The Prostate 20060401
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. Carcinogenesis 20060401
Cooperative effects of isoflavones and exercise on bone and lipid metabolism in postmenopausal Japanese women: a randomized placebo-controlled trial. Metabolism: clinical and experimental 20060401
Effects of phytoestrogens on testosterone secretion by Leydig cells from Biłgoraj ganders (Anser anser). British poultry science 20060401
Short-term phytoestrogen supplementation alters insulin-like growth factor profile but not lipid or antioxidant status. The Journal of nutritional biochemistry 20060301
Postmenopausal bone mineral density in relation to soy isoflavone-metabolizing phenotypes. Maturitas 20060220
Phytoestrogens and their metabolites inhibit the sensitivity of the bovine corpus luteum to luteotropic factors. The Journal of reproduction and development 20060201
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. The Proceedings of the Nutrition Society 20060201
Structural elucidation of hydroxylated metabolites of the isoflavan equol by gas chromatography-mass spectrometry and high-performance liquid chromatography-mass spectrometry. Drug metabolism and disposition: the biological fate of chemicals 20060101
Phyto-oestrogen intake in Scottish men: use of serum to validate a self-administered food-frequency questionnaire in older men. European journal of clinical nutrition 20060101
Isoflavonoid photoprotection in mouse and human skin is dependent on metallothionein. The Journal of investigative dermatology 20060101
Serum cholesterol efflux potential in postmenopausal women treated with isolated isoflavones. Menopause (New York, N.Y.) 20060101
Genistein and 17beta-estradiol, but not equol, regulate vitamin D synthesis in human colon and breast cancer cells. Anticancer research 20060101
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. Nutrition and cancer 20060101
Detection of isoflavones in mouse tibia after feeding daidzein. Journal of medicinal food 20060101
Phytoestrogen action in Leydig cells of Biłgoraj ganders (Anser anser). Reproductive biology 20060101
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. Biochemical pharmacology 20051219
Serum equol, bone mineral density and biomechanical bone strength differ among four mouse strains. The Journal of nutritional biochemistry 20051201
High concordance of daidzein-metabolizing phenotypes in individuals measured 1 to 3 years apart. The British journal of nutrition 20051201
Effect of pure genistein on bone markers and hot flushes. Climacteric : the journal of the International Menopause Society 20051201
Sensitive high-performance liquid chromatographic method using coulometric electrode array detection for measurement of phytoestrogens in dried blood spots. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20051105
Formononetin, a phyto-oestrogen, and its metabolites up-regulate interleukin-4 production in activated T cells via increased AP-1 DNA binding activity. Immunology 20050901
Estrogenic and genotoxic potential of equol and two hydroxylated metabolites of Daidzein in cultured human Ishikawa cells. Toxicology letters 20050728
Antipyretic, analgesic and muscle relaxant activities of pueraria isoflavonoids and their metabolites from Pueraria lobata Ohwi-a traditional Chinese drug. Biological & pharmaceutical bulletin 20050701
X-ray single-crystal analysis of (-)-(S)-equol isolated from rat's feces. Chemistry & biodiversity 20050701
DPPH radical-scavenging compounds from dou-chi, a soybean fermented food. Bioscience, biotechnology, and biochemistry 20050501
Gut bacterial metabolism of the soy isoflavone daidzein: exploring the relevance to human health. Experimental biology and medicine (Maywood, N.J.) 20050301
Enhanced biosynthesis of dihydrodaidzein and dihydrogenistein by a newly isolated bovine rumen anaerobic bacterium. Journal of biotechnology 20050209
Isolation and characterisation of an equol-producing mixed microbial culture from a human faecal sample and its activity under gastrointestinal conditions. Archives of microbiology 20050101
A simple method for the characterization and quantification of soy isoflavone metabolites in the serum of MMTV-Neu mice using high-performance liquid chromatography/electrospray ionization mass spectrometry with multiple reaction monitoring. Rapid communications in mass spectrometry : RCM 20050101
Characterization and quantification of soy isoflavone metabolites in serum of renal transplanted patients by high-performance liquid chromatography/electrospray ionization mass spectrometry. Rapid communications in mass spectrometry : RCM 20050101
Effect of a soymilk supplement containing isoflavones on urinary F2 isoprostane levels in premenopausal women. Nutrition and cancer 20050101
Protection against photoaging in the hairless mouse by the isoflavone equol. Photochemistry and photobiology 20050101
Consumption of Lactobacillus acidophilus and Bifidobacterium longum do not alter urinary equol excretion and plasma reproductive hormones in premenopausal women. European journal of clinical nutrition 20041201
Lactobacillus gasseri: effects on mouse intestinal flora enzyme activity and isoflavonoids in the caecum and plasma. The British journal of nutrition 20041101
Biotransformation of soy isoflavone-glycosides in laying hens: intestinal absorption and preferential accumulation into egg yolk of equol, a more estrogenic metabolite of daidzein. Biochimica et biophysica acta 20040924
Estrogenicity of the isoflavone metabolite equol on reproductive and non-reproductive organs in mice. Biology of reproduction 20040901
Synthesis of phytoestrogenic isoflavonoid disulfates. Steroids 20040901
Mammographic density in relation to daidzein-metabolizing phenotypes in overweight, postmenopausal women. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20040701
Identification of puerarin and its metabolites in rats by liquid chromatography-tandem mass spectrometry. Journal of agricultural and food chemistry 20040616
Genotoxicity of the isoflavones genistein, daidzein and equol in V79 cells. Toxicology letters 20040615
Distribution of soy-derived phytoestrogens in human breast tissue and biological fluids. Obstetrics and gynecology 20040501
Isoflavones stimulate estrogen receptor-mediated core histone acetylation. Biochemical and biophysical research communications 20040423
Equol is a novel anti-androgen that inhibits prostate growth and hormone feedback. Biology of reproduction 20040401
Urinary isoflavone kinetics: the effect of age, gender, food matrix and chemical composition. The British journal of nutrition 20040401
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. The British journal of nutrition 20040401
Metabolism of daidzein by intestinal bacteria from rhesus monkeys (Macaca mulatta). Comparative medicine 20040401
Serum steroid hormones, sex hormone-binding globulin concentrations, and urinary hydroxylated estrogen metabolites in post-menopausal women in relation to daidzein-metabolizing phenotypes. The Journal of steroid biochemistry and molecular biology 20040401
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. Bioorganic & medicinal chemistry 20040315
Interactions of phytoestrogens with estrogen receptors alpha and beta (III). Estrogenic activities of soy isoflavone aglycones and their metabolites isolated from human urine. Biological & pharmaceutical bulletin 20040201
Comparisons of percent equol producers between prostate cancer patients and controls: case-controlled studies of isoflavones in Japanese, Korean and American residents. Japanese journal of clinical oncology 20040201
Plasma isoflavone levels versus self-reported soy isoflavone levels in Asian-American women in Los Angeles County. Carcinogenesis 20040101
The topical isoflavonoid NV-07alpha reduces solar-simulated UV-induced suppression of Mantoux reactions in humans. Photochemistry and photobiology 20040101
Measurement of isoflavones using liquid chromatography with multi-channel coulometric electrochemical detection. BioFactors (Oxford, England) 20040101
Oestrogenic compounds and oxidative stress (in human sperm and lymphocytes in the Comet assay). Mutation research 20031101
A toxicity identification evaluation approach to studying estrogenic substances in hog manure and agricultural runoff. Environmental toxicology and chemistry 20031001
Variations in metabolism of the soy isoflavonoid daidzein by human intestinal microfloras from different individuals. Archives of microbiology 20030701
Effects of the isoflavones genistein and equol on the gonadal development of Japanese medaka Oryzias latipes. Environmental health perspectives 20030701
Urinary equol excretion in relation to 2-hydroxyestrone and 16alpha-hydroxyestrone concentrations: an observational study of young to middle-aged women. The Journal of steroid biochemistry and molecular biology 20030701
The phytoestrogen equol increases nitric oxide availability by inhibiting superoxide production: an antioxidant mechanism for cell-mediated LDL modification. Free radical biology & medicine 20030515
Metabolism of isoflavones and lignans by the gut microflora: a study in germ-free and human flora associated rats. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20030501
Quantification of isoflavones and lignans in urine using gas chromatography/mass spectrometry. Analytical biochemistry 20030401
Time-resolved fluoroimmunoassay for equol in plasma and urine. The Journal of steroid biochemistry and molecular biology 20030401
Soy-derived isoflavones exert opposing actions on Guinea pig ventricular myocytes. The Journal of pharmacology and experimental therapeutics 20030301
Soy isoflavonoid equol modulates the growth of benign and malignant prostatic epithelial cells in vitro. The Prostate 20030101
Identification of phytoestrogens in bovine milk using liquid chromatography/electrospray tandem mass spectrometry. Rapid communications in mass spectrometry : RCM 20030101
Cardiovascular protective effects of synthetic isoflavone derivatives in apolipoprotein e-deficient mice. Journal of vascular research 20030101
Effect of in utero-administered coumestrol, equol, and organic selenium on biomarkers for phase 2 enzyme capacity and redox status. Nutrition and cancer 20030101
Higher consumption of green tea may enhance equol production. Asian Pacific journal of cancer prevention : APJCP 20030101
Liquid chromatographic-photodiode array mass spectrometric analysis of dietary phytoestrogens from human urine and blood. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20020925
Time-resolved fluoroimmunoassay of plasma and urine O-desmethylangolensin. The Journal of steroid biochemistry and molecular biology 20020801
Isolation of an anaerobic intestinal bacterium capable of cleaving the C-ring of the isoflavonoid daidzein. Archives of microbiology 20020701
Characterization of isoflavones and their conjugates in female rat urine using LC/MS/MS. Journal of agricultural and food chemistry 20020424
The correlation between dietary soy phytoestrogens and neuropathic pain behavior in rats after partial denervation. Anesthesia and analgesia 20020201
Quantitative analysis of urinary daidzein and equol by gas chromatography after solid-phase extraction and high-performance liquid chromatography. The International journal of biological markers 20020101
Regulation of phenobarbital-mediated induction of CYP102 (cytochrome P450(BM-3)) in Bacillus megaterium by phytochemicals from soy and green tea. Journal of agricultural and food chemistry 20011001
The vascular activity of some isoflavone metabolites: implications for a cardioprotective role. British journal of pharmacology 20010601
Animal models impacted by phytoestrogens in commercial chow: implications for pathways influenced by hormones. Laboratory investigation; a journal of technical methods and pathology 20010501
Effect of phytoestrogen and antioxidant supplementation on oxidative DNA damage assessed using the comet assay. Mutation research 20010307
Assaying the estrogenicity of phytoestrogens in cells of different estrogen sensitive tissues. Toxicology in vitro : an international journal published in association with BIBRA 20010101
Visual spatial memory is enhanced in female rats (but inhibited in males) by dietary soy phytoestrogens. BMC neuroscience 20010101
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