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Category:natural substances and extractives
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Physical Properties:
| Assay: | 95.00 to 100.00
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| Food Chemicals Codex Listed: | No |
| Melting Point: | 385.00 °C. @ 760.00 mm Hg
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| Boiling Point: | 406.00 °C. @ 760.00 mm Hg (est)
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| Flash Point: | 391.00 °F. TCC ( 199.30 °C. ) (est)
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| logP (o/w): | 2.940 (est) |
| Soluble in: |
| | water, 250.5 mg/L @ 25 °C (est) |
Organoleptic Properties:
| Odor and/or flavor descriptions from others (if found). |
Cosmetic Information:
Suppliers:
Safety Information:
| Preferred SDS: View |
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| Hazards identification |
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| Classification of the substance or mixture |
| GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) |
| None found. |
| GHS Label elements, including precautionary statements |
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| Pictogram | |
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| Hazard statement(s) |
| None found. |
| Precautionary statement(s) |
| None found. |
| Oral/Parenteral Toxicity: |
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Not determined
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| Dermal Toxicity: |
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Not determined
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| Inhalation Toxicity: |
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Not determined
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Safety in Use Information:
| Category: | | natural substances and extractives |
| Recommendation for coumestrol usage levels up to: | | | not for fragrance use.
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| Recommendation for coumestrol flavor usage levels up to: |
| | not for flavor use.
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Safety References:
References:
Other Information:
Potential Blenders and core components note
Potential Uses:
Occurrence (nature, food, other): note
Synonyms:
| 3- | benzofurancarboxylic acid, 2-(2,4-dihydroxyphenyl)-6-hydroxy-, delta-lactone (6CI) | | 6H- | benzofuro(3,2-c)(1)benzopyran-6-one, 3,9-dihydroxy- | | 6H- | benzofuro[3,2-c][1]benzopyran-6-one, 3,9-dihydroxy- | | | cumoesterol | | | cumoestrol | | | cumostrol | | 3,9- | dihydroxy-6H-benzofuro(3,2-c)(1)benzopyran-6-one | | 3,9- | dihydroxycoumestan | | 2-(2,4- | dihydroxyphenyl)-6-hydroxy-3-benzofurancarboxylic acid d-lactone |
Articles:
| PubMed:Occurrence of isoflavonoids in Brazilian common bean germplasm (Phaseolus vulgaris L.). |
| PubMed:Biodistribution evaluation of icaritin in rats by ultra-performance liquid chromatography-tandem mass spectrometry. |
| PubMed:Assessment of dietary phytoestrogen intake via plant-derived foods in China. |
| PubMed:Coumestrol induces mitochondrial biogenesis by activating Sirt1 in cultured skeletal muscle cells. |
| PubMed:Effect of phytoestrogens on basal and GnRH-induced gonadotropin secretion. |
| PubMed:The E-screen test and the MELN gene-reporter assay used for determination of estrogenic activity in fruits and vegetables in relation to pesticide residues. |
| PubMed:Urinary phytoestrogen levels related to idiopathic male infertility in Chinese men. |
| PubMed:Coumestrol induces senescence through protein kinase CKII inhibition-mediated reactive oxygen species production in human breast cancer and colon cancer cells. |
| PubMed:Determination of the variations in levels of phenolic compounds in soybean (Glycine max Merr.) sprouts infected by anthracnose (Colletotrichum gloeosporioides). |
| PubMed:Phytoestrogen and fiber intakes in relation to incident vasomotor symptoms: results from the Study of Women's Health Across the Nation. |
| PubMed:Dietary relevant mixtures of phytoestrogens inhibit adipocyte differentiation in vitro. |
| PubMed:Development of a food compositional database for the estimation of dietary intake of phyto-oestrogens in a group of postmenopausal women previously treated for breast cancer and validation with urinary excretion. |
| PubMed:[Simultaneous determination of four kinds of furocoumarins in cosmetics by high performance liquid chromatography]. |
| PubMed:Relationship between dietary phytoestrogens and development of urinary incontinence in midlife women. |
| PubMed:Effects of selected phytoestrogens and their mixtures on the function of the thyroid hormone and the aryl hydrocarbon receptor. |
| PubMed:Intakes and sources of isoflavones, lignans, enterolignans, coumestrol and soya-containing foods in the Norfolk arm of the European Prospective Investigation into Cancer and Nutrition (EPIC-Norfolk), from 7 d food diaries, using a newly updated database. |
| PubMed:Distribution of isoflavones and coumestrol in neglected tropical and subtropical legumes. |
| PubMed:Mammographic breast density and serum phytoestrogen levels. |
| PubMed:Dietary phytoestrogen intakes and cognitive function during the menopausal transition: results from the Study of Women's Health Across the Nation Phytoestrogen Study. |
| PubMed:Effect of Aspergillus oryzae-challenged germination on soybean isoflavone content and antioxidant activity. |
| PubMed:Development of an updated phytoestrogen database for use with the SWAN food frequency questionnaire: intakes and food sources in a community-based, multiethnic cohort study. |
| PubMed:Estimated intake of dietary phyto-oestrogens in Australian women and evaluation of correlates of phyto-oestrogen intake. |
| PubMed:Estimated dietary phytoestrogen intake and major food sources among women during the year before pregnancy. |
| PubMed:Soy isoflavones and other isoflavonoids activate the human bitter taste receptors hTAS2R14 and hTAS2R39. |
| PubMed:Occurrence and mass balance of isoflavones on an experimental grassland field. |
| PubMed:Adverse influence of coumestrol on secretory function of bovine luteal cells in the first trimester of pregnancy. |
| PubMed:Quantification of five isoflavones and coumestrol in various solid agroenvironmental matrices using ¹³c₃-labeled internal standards. |
| PubMed:Phytoestrogenic compounds in alfalfa sprout (Medicago sativa) beyond coumestrol. |
| PubMed:Dietary phytoestrogens and the risk of ovarian cancer in the women's lifestyle and health cohort study. |
| PubMed:Profiles of phytoestrogens in human urine from several Asian countries. |
| PubMed:Effects of nutrition relevant mixtures of phytoestrogens on steroidogenesis, aromatase, estrogen, and androgen activity. |
| PubMed:The adverse effect of phytoestrogens on the synthesis and secretion of ovarian oxytocin in cattle. |
| PubMed:[Exposure of phytoestrogens intake through diet in a sample of females]. |
| PubMed:Dietary intake of polyphenols, nitrate and nitrite and gastric cancer risk in Mexico City. |
| PubMed:Phytoestrogen content of cereals and cereal-based foods consumed in the UK. |
| PubMed:Phytoestrogen consumption and endometrial cancer risk: a population-based case-control study in New Jersey. |
| PubMed:Effect of forage on the content of phyto-oestrogens in bovine milk. |
| PubMed:Pleiotropic combinatorial transcriptomes of human breast cancer cells exposed to mixtures of dietary phytoestrogens. |
| PubMed:Lactational coumestrol exposure increases ovarian apoptosis in adult rats. |
| PubMed:Fluorescence and inmunohistological detection of estrogen receptors in dog testis and epidydimis after oral coumestrol administration. |
| PubMed:Phytoestrogen content of foods of animal origin: dairy products, eggs, meat, fish, and seafood. |
| PubMed:Phytoestrogen content of beverages, nuts, seeds, and oils. |
| PubMed:Dietary consumption of phytochemicals and breast cancer risk in Mexican women. |
| PubMed:Determination of phytoestrogens in dietary supplements by LC-MS/MS. |
| PubMed:Screening of synthetic and plant-derived compounds for (anti)estrogenic and (anti)androgenic activities. |
| PubMed:Lignan content of selected foods from Japan. |
| PubMed:Estrogenic activities of isoflavones and flavones and their structure-activity relationships. |
| PubMed:Dietary phytoestrogens, including isoflavones, lignans, and coumestrol, in nonvitamin, nonmineral supplements commonly consumed by women in Canada. |
| PubMed:Quantification of six phytoestrogens at the nanogram per liter level in aqueous environmental samples using 13C3-labeled internal standards. |
| PubMed:8-Prenylnaringenin, inhibits estrogen receptor-alpha mediated cell growth and induces apoptosis in MCF-7 breast cancer cells. |
| PubMed:Mixture effects of estrogenic compounds on proliferation and pS2 expression of MCF-7 human breast cancer cells. |
| PubMed:Effects of various plant polyphenols on bladder carcinogen benzidine-induced mutagenicity. |
| PubMed:Assessing phytochemical intake in a group of Mexican women. |
| PubMed:Estrogenic effects of mixtures of phyto- and synthetic chemicals on uterine growth of prepubertal rats. |
| PubMed:Estimated intakes of isoflavones and coumestrol in Korean population. |
| PubMed:Glyphosate-tolerant alfalfa is compositionally equivalent to conventional alfalfa (Medicago sativa L.). |
| PubMed:The influence of polychlorinated biphenyls (PCBs) and phytoestrogens in vitro on functioning of reproductive tract in cow. |
| PubMed:Dietary intake of phytoestrogens, estrogen receptor-beta polymorphisms and the risk of prostate cancer. |
| PubMed:Phytoestrogen content of foods consumed in Canada, including isoflavones, lignans, and coumestan. |
| PubMed:Polyphenols in wild and weedy Mexican common beans (Phaseolus vulgaris L.). |
| PubMed:Inverse association of antioxidant and phytoestrogen nutrient intake with adult glioma in the San Francisco Bay Area: a case-control study. |
| PubMed:LDL-antioxidant pterocarpans from roots of Glycine max (L.) Merr. |
| PubMed:Chemical components with health implications in wild and cultivated Mexican common bean seeds (Phaseolus vulgaris L.). |
| PubMed:Genotoxicity of phytoestrogens. |
| PubMed:The effect of two dietary and a synthetic phytoestrogen on transepithelial calcium transport in human intestinal-like Caco-2 cells. |
| PubMed:Rapid yeast estrogen bioassays stably expressing human estrogen receptors alpha and beta, and green fluorescent protein: a comparison of different compounds with both receptor types. |
| PubMed:Development and validation of fluorescent receptor assays based on the human recombinant estrogen receptor subtypes alpha and beta. |
| PubMed:Differential effects of isoflavones and lignans on invasiveness of MDA-MB-231 breast cancer cells in vitro. |
| PubMed:Phytoestrogens modulate binding response of estrogen receptors alpha and beta to the estrogen response element. |
| PubMed:The OECD program to validate the rat uterotrophic bioassay. Phase 2: dietary phytoestrogen analyses. |
| PubMed:Effect of in utero-administered coumestrol, equol, and organic selenium on biomarkers for phase 2 enzyme capacity and redox status. |
| PubMed:Identification of phytoestrogens in bovine milk using liquid chromatography/electrospray tandem mass spectrometry. |
| PubMed:Phyto-oestrogen levels in foods: the design and construction of the VENUS database. |
| PubMed:A case-control study of dietary phytoestrogens and testicular cancer risk. |
| PubMed:Ability of structurally diverse natural products and synthetic chemicals to induce gene expression mediated by estrogen receptors from various species. |
| PubMed:Comparison of the oestrogenic effects of infant milk formulae, oestradiol and the phytoestrogen coumestrol delivered continuously in the drinking water to ovariectomised mice. |
| PubMed:Estrogenic isoflavones in rodent diets. |
| PubMed:Reciprocal mutagenesis between human alpha(L349, M528) and rainbow trout (M317, I496) estrogen receptor residues demonstrates their importance in ligand binding and gene expression at different temperatures. |
| PubMed:Regulation of phenobarbital-mediated induction of CYP102 (cytochrome P450(BM-3)) in Bacillus megaterium by phytochemicals from soy and green tea. |
| PubMed:Pilot study of a specific dietary supplement in tumor-bearing mice and in stage IIIB and IV non-small cell lung cancer patients. |
| PubMed:Intake of dietary phytoestrogens is low in postmenopausal women in the United States: the Framingham study(1-4). |
| PubMed:Evaluation of the genotoxicity of the phytoestrogen, coumestrol, in AHH-1 TK(+/-) human lymphoblastoid cells. |
| PubMed:Differential estrogen receptor binding of estrogenic substances: a species comparison. |
| PubMed:Quantitative determination of isoflavones and coumestrol in soybean by column liquid chromatography. |
| PubMed:Induction of the soybean phytoalexins coumestrol and glyceollin by Aspergillus. |
| PubMed:Assessing phytoestrogen exposure in epidemiologic studies: development of a database (United States). |
| PubMed:The development of methods for assessing the in vivo oestrogen-like effects of xenobiotics in CD-1 mice. |
| PubMed:Phytoestrogen content of purified, open- and closed-formula laboratory animal diets. |
| PubMed:Phytoestrogen content in foods. |
| PubMed:The phytoestrogens coumoestrol and genistein induce structural chromosomal aberrations in cultured human peripheral blood lymphocytes. |
| PubMed:Safety evaluation of phytosterol esters. Part 1. Assessment of oestrogenicity using a combination of in vivo and in vitro assays. |
| PubMed:Effects of phytoestrogens on DNA synthesis in MCF-7 cells in the presence of estradiol or growth factors. |
| PubMed:Analysis of phytoestrogens and polyphenols in plasma, tissue, and urine using HPLC with coulometric array detection. |
| PubMed:Induction of micronuclei, DNA strand breaks and HPRT mutations in cultured Chinese hamster V79 cells by the phytoestrogen coumoestrol. |
| PubMed:Urinary phytoestrogen levels in young women from a multiethnic population. |
| PubMed:Phytoestrogen concentration determines effects on DNA synthesis in human breast cancer cells. |
| PubMed:Isotope dilution gas chromatographic-mass spectrometric method for the determination of isoflavonoids, coumestrol, and lignans in food samples. |
| PubMed:Phytoestrogen content of foods--a compendium of literature values. |
| PubMed:Recent acute and subacute mycotoxicoses recognized in France. |
| PubMed:The effects of phytoestrogens on neonatal rat uterine growth and development. |
| PubMed:Long-term reproductive tract alterations in female mice treated neonatally with coumestrol. |
| PubMed:Effects of coumestrol and equol on the developing reproductive tract of the rat. |
| PubMed:Rapid HPLC analysis of dietary phytoestrogens from legumes and from human urine. |
| PubMed:Lignans and flavonoids inhibit aromatase enzyme in human preadipocytes. |
| PubMed:The influence of steroidal and nonsteroidal estrogens on the 5 alpha-reduction of testosterone by the ventral prostate of the rat. |
| PubMed:High-performance liquid chromatographic analysis of phytoestrogens in soy protein preparations with ultraviolet, electrochemical and thermospray mass spectrometric detection. |
| PubMed:Naturally occurring oestrogens in foods--a review. |
| PubMed:Effect of whole and fractionated dietary alfalfa meal on zearalenone toxicosis and metabolism in rats and swine. |
| PubMed:Analysis of coumestrol, a phytoestrogen, in alfalfa tablets sold for human consumption. |
| PubMed:Oestrogenic activity of soya-bean products. |
| PubMed:Analysis of coumestrol, a plant estrogen, in animal feeds by high-performance liquid chromatography. |
| PubMed:Coumestrol content of fractions obtained during wet processing of alfalfa. |
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a daidzein derivative occurring naturally in forage crops which has some estrogenic activity. Isol. from Medicago spp., Glycine max (soybean), Pisum sativum (pea), Spinacia oleracea (spinach), Brassica oleracea (cabbage), Dolichos biflorus (papadi), Melilotus alba (white melilot), Phaseolus spp. (inc. lima beans, pinto beans) and Vigna unguiculata (all Leguminosae). Potential nutriceutical
Coumestrol is a natural organic compound in the class of phytochemicals known as coumestans. It has garnered research interest because of its estrogenic activity and its prevalence in some foods, such as soybeans and herbs such as Pueraria mirifica.; Coumestrol is a phytoestrogen, mimicking the biological activity of estrogens. The chemical shape of coumestrol orients its two hydroxy groups in the same position as the two hydroxy groups in estradiol, allowing it to inhibit the activity of aromatase and hydroxysteroid dehydrogenase. These enzymes are involved in the biosynthesis of steroid hormones, and inhibition of these enzymes results in the modulation of hormone production.; Coumestrol, a coumestan isoflavone, has estrogenic properties (phytoestrogens are compounds structurally and functionally similar to 17-estradiol) and is an isoflavonoid phytoalexin produced by soybeans, a low molecular weight antimicrobial compound that is synthesized de novo and accumulates in plants after exposure to microorganisms (i.e.: phytoalexin induction and accumulation in soybean cotyledon tissue is observed with four species of Aspergillus: A. sojae, A. oryzae, A. niger, and A. flavus.). (PMID: 10888516); Coumestrol is a naturally occurring plant coumarin that displays high affinity for the hormone-binding site of the human estrogen receptor (hER), for which it serves as a potent non-steroidal agonist. Coumestrol emits intense blue fluorescence when bound to this protein, making it ideally suited for use as a cytological stain to detect ER in fixed and intact cells. Such observations illustrate the potential for using coumestrol to investigate real-time effects of a variety of physiological stimuli on the subcellular distribution of hER in living cells. (PMID: 8315272)
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3D/inchi