491-80-5 Usage
Description
5,7-Dihydrox -4'-methoxyisoflavone, also known as Biochanin A (BCA), is a natural isoflavone with diverse biological actions, most notably as a phytoestrogen. It is synthesized in vitro from phloroglucinol and is catabolized to isoflavone genistein post ingestion. BCA can affect hormone levels by inhibiting 5α-reductase and 17β-hydroxysteroid dehydrogenase or altering aromatase (CYP19A1) activity. It also intersects with signaling through peroxisome proliferator-activated receptors (PPARs), as it activates PPARγ and has been shown to activate a PPARα promoter. Moreover, it increases the expression of the PPARγ coactivator PGC-1α, promoting mitochondrial biogenesis. BCA inhibits fatty acid amide hydrolase and acts as an agonist of the aryl hydrocarbon receptor (AhR). It is an off-white solid.
Uses
Used in Dietary Cancer Prophylaxis:
5,7-Dihydrox -4'-methoxyisoflavone is used as a chemopreventive agent for its putative benefits in dietary cancer prophylaxis. It inhibits metabolic activation of benzo[a]pyrene and has been found to induce sulfotransferases for xenobiotic detoxification, which has been proposed as a mechanism of its cancer preventive effects.
Used in Antineoplastic Applications:
5,7-Dihydrox -4'-methoxyisoflavone is used as an antineoplastic agent, acting as an inhibitor of cancer cell proliferation, differentiation, and chemoprevention. It is a selective agonist at ER-β estrogen receptors, which may have chemopreventive efficacy against breast cancer, while its low activity at ER-α estrogen receptors makes it essentially devoid of uterotrophic activity.
Used in Treatment of Diabetes Type 2:
5,7-Dihydrox -4'-methoxyisoflavone is used as a pharmacological agent for the treatment of diabetes type 2, as it acts as an agonist of PPARgamma, a nuclear receptor that is a current target for diabetes treatment.
Used in Cardiovascular Applications:
5,7-Dihydrox -4'-methoxyisoflavone is used as a cardiovascular agent, as it reduces arterial resistance and enhances microcirculation, potentially through effects on potassium and/or calcium ion channels.
Used in Apoptosis Induction and Nitric Oxide Synthase Inhibition:
5,7-Dihydrox -4'-methoxyisoflavone is used as an apoptosis inducer and nitric oxide synthase inhibitor, contributing to its potential therapeutic applications in various diseases and conditions.
Biochem/physiol Actions
Biochanin A is an isoflavone phytoestrogen found in red clover (Trifolium pratense) that is a selective agonist at ER-β estrogen receptors, and may have chemopreventive efficacy against breast cancer. In line with its low activity at ER-α estrogen receptors, it is essentially devoid of uterotrophic activity. Biochanin A is also a ligand for the aryl hydrocarbon receptor (AhR). It reduces arterial resistance and enhances microcirculation perhaps via effects on potassium and/or calcium ion channels. Induction of sulfotransferases for xenobiotic detoxification has been proposed as a mechanism of its cancer preventive effects.
Check Digit Verification of cas no
The CAS Registry Mumber 491-80-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,9 and 1 respectively; the second part has 2 digits, 8 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 491-80:
(5*4)+(4*9)+(3*1)+(2*8)+(1*0)=75
75 % 10 = 5
So 491-80-5 is a valid CAS Registry Number.
InChI:InChI=1/C16H12O5/c1-20-11-4-2-9(3-5-11)12-8-21-14-7-10(17)6-13(18)15(14)16(12)19/h2-8,17-18H,1H3
491-80-5Relevant articles and documents
Isoflavonoid glycosides from Dalbergia sissoo
Farag, Salwa F.,Ahmed, Amany S.,Terashima, Kenji,Takaya, Yoshiaki,Niwa, Masatake
, p. 1263 - 1268 (2001)
Two isoflavone glycosides, biochanin A 7-O-[β-D-apiofuranosyl-(1 → 5)-β-D-apiofuranosyl-(1 → 6)-β-D-glucopyranoside] and tectorigenin 7-O-[β-D-apiofuranosyl-(1 → 6)-β-D-glucopyranoside], were isolated from Dalbergia sissoo. Their structures were elucidate
Synthesis method of biochanin A
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Paragraph 0012; 0016; 0017; 0018, (2021/08/14)
The invention discloses a synthesis method of biochanin A. The synthesis method comprises the following steps: (1) carrying out condensation reaction on p-methoxyacetophenone and N-bromosuccinimide in the presence of absolute ethyl alcohol to obtain Alpha-bromo-4-methoxyacetophenone; and (2) by taking absolute ethyl alcohol as a reaction solvent, carrying out condensation reaction on 2, 4, 6-trihydroxy benzaldehyde and Alpha-bromo-4-methoxyacetophenone in the presence of a catalyst, evaporating reaction liquid, and separating and purifying a solid product by using column chromatography to obtain the biochanin A. The novel catalyst is adopted for catalysis, the product yield is high, reaction conditions are mild, and raw materials of the catalyst are easy to obtain and low in price. The synthesis method disclosed by the invention is simple in process, low in cost, time-saving, high in yield, low in equipment corrosion degree and suitable for industrial production.
Cytosine N-isoflavone compound as well as preparation method and application thereof
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, (2019/10/02)
The invention relates to a cytosine N-isoflavone compound as well as a preparation method and application thereof. The compound has a structural formula as shown in the specification, wherein R1 is selected from one of hydroxyl, alkoxy, amido or halo, R2 is selected from one of hydrogen, alkyl or aryl, and R3 is selected from one or a combination of several of hydroxyl, alkoxy, amido or halo. Compared with the prior art, the cytosine N-isoflavone compound has the characteristic that an isoflavone compound serving as a structural unit is spliced to N on the 12th position of cytosine by using acombined synthesis technology, so that a series of cytosine-isoflavone derivatives are synthesized, and a novel active pharmacological action is exerted.