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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 |
| Boiling Point: | 518.57 °C. @ 760.00 mm Hg (est)
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| Flash Point: | 389.00 °F. TCC ( 198.30 °C. ) (est)
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| logP (o/w): | 3.341 (est) |
| Soluble in: |
| | water, 71.1 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 biochanin A usage levels up to: | | | not for fragrance use.
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| Recommendation for biochanin A flavor usage levels up to: |
| | not for flavor use.
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Safety References:
European Food Safety Authority (EFSA) reference(s):
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Preparatory work to support the risk assessment for peri- and postmenopausal women taking food supplements containing isolated isoflavones
View page or View pdf
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Risk assessment for peri- and post-menopausal women taking food supplements containing isolated isoflavones
View page or View pdf
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| EPI System: View |
| Chemical Carcinogenesis Research Information System:Search |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA Substance Registry Services (TSCA):491-80-5 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :5280373 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:3 |
| 5,7-dihydroxy-3-(4-methoxyphenyl)chromen-4-one |
| Chemidplus:0000491805 |
References:
Other Information:
Potential Blenders and core components note
Potential Uses:
Occurrence (nature, food, other): note
Synonyms:
| 4H-1- | benzopyran-4-one, 5,7-dihydroxy-3-(4-methoxyphenyl)- | | | biochanine A | | 5,7- | dihydrox -4'-methoxyisoflavone | | 5,7- | dihydroxy-3-(4-methoxy-phenyl)-chromen-4-one | | 5,7- | dihydroxy-3-(4-methoxyphenyl)-4H-1-benzopyran-4-one | | 5,7- | dihydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one | | 5,7- | dihydroxy-3-(4-methoxyphenyl)chromen-4-one | | 5,7- | dihydroxy-3-p-methoxyphenyl-4H-chromen-4-one | | 5,7- | dihydroxy-3-para-methoxyphenyl-4H-chromen-4-one | | 5,7- | dihydroxy-4'-methoxy-isoflavone | | 5,7- | dihydroxy-4'-methoxy-isoflavone (8CI) | | 5,7- | dihydroxy-4'-methoxyisoflavone | | iso | flavone, 5,7-dihydroxy-4'-methoxy- | | | genistein 4-methyl ether | | | genistein 4'-methyl ether | | 4'- | methoxy-5,7-dihydroxy isoflavone | | 4'- | methylgenistein |
Articles:
| PubMed:Natural product agonists of peroxisome proliferator-activated receptor gamma (PPARγ): a review. |
| PubMed:Identification and quantification of the main isoflavones and other phytochemicals in soy based nutraceutical products by liquid chromatography-orbitrap high resolution mass spectrometry. |
| PubMed:Biochanin A and prunetin improve epithelial barrier function in intestinal CaCo-2 cells via downregulation of ERK, NF-κB, and tyrosine phosphorylation. |
| PubMed:Isoflavonoids in the Amaryllidaceae family. |
| PubMed:The isoflavone irilone contributes to the estrogenic potential of dietary supplements containing red clover. |
| PubMed:Biochanin A affects steroidogenesis and estrogen receptor-β expression in porcine granulosa cells. |
| PubMed:MLK3 is a direct target of biochanin A, which plays a role in solar UV-induced COX-2 expression in human keratinocytes. |
| PubMed:Inhibitory effect of phloretin and biochanin A on IgE-mediated allergic responses in rat basophilic leukemia RBL-2H3 cells. |
| PubMed:[A memoir of my researches on xenobiotic metabolism for 48 years--researches on Kanemi Yusho and endocrine disrupting chemicals]. |
| PubMed:Methylation of genistein and kaempferol improves their affinities for proteins. |
| 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:A modified QuEChERS method as sample treatment before the determination of isoflavones in foods by ultra-performance liquid chromatography-triple quadrupole mass spectrometry. |
| PubMed:Phytotoxic effect, uptake, and transformation of biochanin A in selected weed species. |
| PubMed:Distribution of isoflavones and coumestrol in neglected tropical and subtropical legumes. |
| PubMed:Germination dramatically increases isoflavonoid content and diversity in chickpea (Cicer arietinum L.) seeds. |
| PubMed:Effects of sodium metavanadate and germination on the sprouting of chickpeas and its content of vanadium, formononetin and biochanin A in the sprouts. |
| PubMed:Effects of sodium selenite and germination on the sprouting of chickpeas (Cicer arietinum L.) and its content of selenium, formononetin and biochanin A in the sprouts. |
| PubMed:Red clover and soy isoflavones--an in vitro safety assessment. |
| PubMed:Association between dietary phyto-oestrogens and bone density in men and postmenopausal women. |
| PubMed:Occurrence and mass balance of isoflavones on an experimental grassland field. |
| PubMed:Phytoestrogen intake and cardiovascular risk markers in Bangladeshi postmenopausal women. |
| PubMed:HPLC/DAD/MS and antioxidant activity of isoflavone-based food supplements. |
| PubMed:Quantification of five isoflavones and coumestrol in various solid agroenvironmental matrices using ¹³c₃-labeled internal standards. |
| PubMed:In Vitro Synergy of Biochanin A and Ciprofloxacin against Clinical Isolates of Staphylococcus aureus. |
| PubMed:Yeast α-glucosidase inhibition by isoflavones from plants of Leguminosae as an in vitro alternative to acarbose. |
| PubMed:Red clover (Trifolium pratense L.) isoflavones: root phenolic compounds affected by biotic and abiotic stress factors. |
| PubMed:Breast, colorectal, and prostate cancer risk in the European Prospective Investigation into Cancer and Nutrition-Norfolk in relation to phytoestrogen intake derived from an improved database. |
| PubMed:Cellular DNA breakage by soy isoflavone genistein and its methylated structural analogue biochanin A. |
| PubMed:Inhibition of angiogenesis and inflammation by an extract of red clover (Trifolium pratense L.). |
| PubMed:Equol in milk of dairy cows is derived from forage legumes such as red clover. |
| PubMed:Effect of an isoflavones-containing red clover preparation and alkaline supplementation on bone metabolism in ovariectomized rats. |
| PubMed:Phytoestrogen content of cereals and cereal-based foods consumed in the UK. |
| PubMed:Oregano: a source for peroxisome proliferator-activated receptor gamma antagonists. |
| PubMed:Phytoestrogen content of foods of animal origin: dairy products, eggs, meat, fish, and seafood. |
| PubMed:Effect of frequency and duration of ultrasonication on the extraction efficiency of selected isoflavones and trans-resveratrol from peanuts (Arachis hypogaea). |
| PubMed:Sodium borohydride/chloranil-based assay for quantifying total flavonoids. |
| PubMed:Effects of clover-grass silages and concentrate supplementation on the content of phytoestrogens in dairy cow milk. |
| PubMed:Determination of phytoestrogens in dietary supplements by LC-MS/MS. |
| PubMed:Estrogenic activities of isoflavones and flavones and their structure-activity relationships. |
| PubMed:Changes in the phytochemical composition and profile of raw, boiled, and roasted peanuts. |
| PubMed:Quantification of six phytoestrogens at the nanogram per liter level in aqueous environmental samples using 13C3-labeled internal standards. |
| PubMed:Analysis of flavonoid phytoestrogens in botanical and ephedra-containing dietary supplements. |
| PubMed:High levels of equol in organic skimmed Finnish cow milk. |
| PubMed:(Anti)estrogenic effects of phytochemicals on human primary mammary fibroblasts, MCF-7 cells and their co-culture. |
| PubMed:Biochanin A protects dopaminergic neurons against lipopolysaccharide-induced damage through inhibition of microglia activation and proinflammatory factors generation. |
| PubMed:Effects of the flavonoid biochanin A on gene expression in primary human hepatocytes and human intestinal cells. |
| PubMed:Comparison of extraction methods for the quantification of selected phytochemicals in peanuts (Arachis hypogaea). |
| PubMed:Estimated intakes of isoflavones and coumestrol in Korean population. |
| PubMed:Flavonoids modulate monocarboxylate transporter-1-mediated transport of gamma-hydroxybutyrate in vitro and in vivo. |
| PubMed:An accurate and reproducible method for the quantitative analysis of isoflavones and their metabolites in rat plasma using liquid chromatography/mass spectrometry combined with photodiode array detection. |
| PubMed:Analysis of isoflavones in foods and dietary supplements. |
| PubMed:Isoflavone profiles of red clovers and their distribution in different parts harvested at different growing stages. |
| PubMed:The isoflavone content of commercially-available feline diets in New Zealand. |
| PubMed:Inverse association of antioxidant and phytoestrogen nutrient intake with adult glioma in the San Francisco Bay Area: a case-control study. |
| PubMed:Isoflavonoids are present in Arabidopsis thaliana despite the absence of any homologue to known isoflavonoid synthases. |
| PubMed:Antioxidant activity of isoflavones and their major metabolites using different in vitro assays. |
| PubMed:Thermal degradation kinetics of isoflavone aglycones from soy and red clover. |
| PubMed:Seasonal variation of red clover (Trifolium pratense L., Fabaceae) isoflavones and estrogenic activity. |
| PubMed:Determination of isoflavones in dietary supplements containing soy, Red Clover and kudzu: extraction followed by basic or acid hydrolysis. |
| PubMed:Suppression of arachidonic acid metabolism and nitric oxide formation by kudzu isoflavones in murine macrophages. |
| PubMed:Red clover Trifolium pratense L. phytoestrogens: UV-B radiation increases isoflavone yield, and postharvest drying methods change the glucoside conjugate profiles. |
| PubMed:Biochanin A stimulates osteoblastic differentiation and inhibits hydrogen peroxide-induced production of inflammatory mediators in MC3T3-E1 cells. |
| PubMed:Supercritical fluid extraction of isoflavones from biological samples with ultra-fast high-performance liquid chromatography/mass spectrometry. |
| PubMed:Effects of the environment, cultivar, maturity, and preservation method on red clover isoflavone concentration. |
| PubMed:Comparison of the in vitro estrogenic activities of compounds from hops (Humulus lupulus) and red clover (Trifolium pratense). |
| PubMed:Isoflavones modulate the glucuronidation of estradiol in human liver microsomes. |
| PubMed:Evaluation of isoflavone aglycon and glycoside distribution in soy plants and soybeans by fast column high-performance liquid chromatography coupled with a diode-array detector. |
| PubMed:Differential modulation of ochratoxin A absorption across Caco-2 cells by dietary polyphenols, used at realistic intestinal concentrations. |
| PubMed:Phytoestrogens derived from red clover: an alternative to estrogen replacement therapy? |
| PubMed:Phytoestrogens possess a weak antioxidant activity on low density lipoprotein in contrast to the flavonoid quercetin in vitro in postmenopausal women. |
| PubMed:Determination of unusual soya and non-soya phytoestrogen sources in beer, fish products and other foods. |
| PubMed:Identification of urinary metabolites of the red clover isoflavones formononetin and biochanin A in human subjects. |
| PubMed:Inhibition of extrahepatic human cytochromes P450 1A1 and 1B1 by metabolism of isoflavones found in Trifolium pratense (red clover). |
| PubMed:Assessment of the reactivity of selected isoflavones against proteins in comparison to quercetin. |
| PubMed:Combined effects of multiple flavonoids on breast cancer resistance protein (ABCG2)-mediated transport. |
| PubMed:Effects of plant flavonoids on fecundity, survival, and feeding of the Formosan subterranean termite. |
| 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:Oxidative metabolism and genotoxic potential of major isoflavone phytoestrogens. |
| PubMed:Metabolism of biochanin A and formononetin by human liver microsomes in vitro. |
| PubMed:Inhibition of thyroid type 1 deiodinase activity by flavonoids. |
| PubMed:Intake of dietary phytoestrogens by Dutch women. |
| PubMed:Regulation of phenobarbital-mediated induction of CYP102 (cytochrome P450(BM-3)) in Bacillus megaterium by phytochemicals from soy and green tea. |
| PubMed:Intake of dietary phytoestrogens is low in postmenopausal women in the United States: the Framingham study(1-4). |
| PubMed:[Selected phytoestrogens with potential beneficial effects on risk of certain environmental diseases]. |
| PubMed:Quantitative determination of isoflavones and coumestrol in soybean by column liquid chromatography. |
| PubMed:Estrogenic activity of flavonoids in mice. The importance of estrogen receptor distribution, metabolism and bioavailability. |
| PubMed:Assessing phytoestrogen exposure in epidemiologic studies: development of a database (United States). |
| PubMed:LC-ESI-MS study of the flavonoid glycoside malonates of red clover (Trifolium pratense). |
| PubMed:Synthesis of haptens and conjugates for ELISAs of phytoestrogens. Development of the immunological tests. |
| PubMed:Development of a simple method for the determination of genistein, daidzein, biochanin A, and formononetin (biochanin B) in human urine. |
| PubMed:Phytoestrogen content of purified, open- and closed-formula laboratory animal diets. |
| PubMed:Phytoestrogen content in foods. |
| PubMed:Isoflavones in human breast milk and other biological fluids. |
| PubMed:Dietary flavonoids interact with trace metals and affect metallothionein level in human intestinal cells. |
| PubMed:Detection of weak estrogenic flavonoids using a recombinant yeast strain and a modified MCF7 cell proliferation assay. |
| PubMed:Isoflavone content of infant foods and formulas. |
| PubMed:Phytoestrogen concentration determines effects on DNA synthesis in human breast cancer cells. |
| PubMed:Interaction of 5,7-dihydroxy-4'-methoxyflavone with a multisubunit protein, carmin: thermodynamics and kinetics of interaction. |
| 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:Rapid HPLC analysis of dietary phytoestrogens from legumes and from human urine. |
| PubMed:Flavonoid inhibition of aromatase enzyme activity in human preadipocytes. |
| PubMed:Antimutagenic effects of flavonoids, chalcones and structurally related compounds on the activity of 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) and other heterocyclic amine mutagens from cooked food. |
| PubMed:Modifying role of dietary factors on the mutagenicity of aflatoxin B1: in vitro effect of plant flavonoids. |
| PubMed:High-performance liquid chromatographic analysis of phytoestrogens in soy protein preparations with ultraviolet, electrochemical and thermospray mass spectrometric detection. |
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phytoestrogen. Widespread isoflavone found in alfalfa (Medicago sativa), chick peas (Cicer arietinum) and white clover (Trifolium repens). Glycosides also widespread. Potential nutriceutical
The phytoestrogen biochanin A is an isoflavone derivative isolated from red clover Trifolium pratense with anticarcinogenic properties. Treating MCF-7 human breast carcinoma cells with biochanin A alone caused the accumulation of CYP1A1 mRNA and an increase in CYP1A1-specific 7-ethoxyresorufin O-deethylase (EROD) activity in a dose dependent manner. Biochanin A may be a natural ligand to bind on aryl hydrocarbon receptor acting as an antagonist/agonist of the pathway. (PMID: 16903077); Biochanin A suppress nuclear factor-kappaB-driven interleukin-6 (IL6) expression. In addition to its physiologic immune function as an acute stress cytokine, sustained elevated expression levels of IL6 promote chronic inflammatory disorders, aging frailty, and tumorigenesis. (PMID: 16651441); Biochanin A induces a decrease in invasive activity of U87MG cells in a dose-related manner. (PMID: 16598420); Biochanin A activates peroxisome proliferator-activated receptors (PPAR) PPARalpha, PPARgamma, and adipocyte differentiation in vitro of 3T3-L1 preadipocytes, suggesting potential value of isoflavones, especially biochanin A and their parent botanicals, as antidiabetic agents and for use in regulating lipid metabolism. (PMID: 16549448)
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