biochanin A
5,7-dihydroxy-3-(4-methoxy-phenyl)-chromen-4-one
Identification
| Name | biochanin A |
| IUPAC | 5,7-dihydroxy-3-(4-methoxyphenyl)chromen-4-one |
| CAS Number | 491-80-5 |
| EINECS | 207-744-7 |
| FDA UNII | U13J6U390T |
| Molecular Formula | C16 H12 O5 |
| Molecular Weight | 284.26764000 |
| MDL Number | MFCD00006839 |
| Nikkaji Number | J11.761G |
| Beilstein | 278107 |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Boiling Point | 518.57 °C. @ 760.00 mm Hg (est) |
| Flash Point | 389.00 °F. TCC ( 198.30 °C. ) (est) |
| logP (o/w) | 3.341 (est) |
| Soluble in | water, 71.1 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for biochanin A usage levels up to | not for fragrance use. |
| Recommendation for biochanin A flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
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
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 ¹³câ-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.