5,7-Dihydrox -4'-methoxyisoflavone

ChemicalBook > CAS DataBase List > 5,7-Dihydrox -4'-methoxyisoflavone

5,7-Dihydrox -4'-methoxyisoflavone

Product Name: 5,7-Dihydrox -4'-methoxyisoflavone
CAS No.: 491-80-5
Chemical Name: 5,7-Dihydrox -4'-methoxyisoflavone
Synonyms: BIOCHANIN A;BIOCHANIN;BIOCHANIN A (AHP);OlMelin;Pratensol;Bilchanin A;Biochani,Olmelin;5,7-dihydroxy-3-(4-methoxyphenyl)chromen-4-one;5,7-Dihydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one;NSC 123538
CBNumber: CB8474490
Molecular Formula: C16H12O5
Formula Weight: 284.26
MOL File: 491-80-5.mol

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5,7-Dihydrox -4'-methoxyisoflavone Property

Melting point:: 210-213 °C(lit.)
Boiling point:: 340-355 °C(Press: 0.5 Torr)
Density: 1.420±0.06 g/cm3(Predicted)
storage temp.: 2-8°C
solubility: acetone: 10 mg/mL, clear, brown
form: Powder
pka: 6.50±0.20(Predicted)
color: Off-White to Beige
Water Solubility: Soluble in water (<1 mg/ml at 25°C), chloroform, methanol, DMSO (57 mg/ml at 25°C), and ethanol (9 mg/ml at 25°C).
λmax: 263nm(EtOH)(lit.)
BRN: 278107
LogP: 3.341 (est)
CAS DataBase Reference: 491-80-5(CAS DataBase Reference)
EPA Substance Registry System: 4H-1-Benzopyran-4-one, 5,7-dihydroxy-3-(4-methoxyphenyl)- (491-80-5)

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Safety

Safety Statements: 22-24/25
WGK Germany: 3
RTECS: DJ3002500
F: 10
TSCA: Yes
HS Code: 29329990

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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: PHL80012
Product name: Biochanin A
Purity: phyproof? Reference Substance
Packaging: 25MG
Price: $259
Updated: 2024/03/01

Sigma-Aldrich

Product number: 92142
Product name: Biochanin A
Purity: analytical standard
Packaging: 50mg
Price: $183
Updated: 2024/03/01

Sigma-Aldrich

Product number: 1071381
Product name: Biochanin A
Purity: United States Pharmacopeia (USP) Reference Standard
Packaging: 20mg
Price: $344
Updated: 2024/03/01

TCI Chemical

Product number: B4098
Product name: Biochanin A
Purity: >98.0%(HPLC)(T)
Packaging: 1g
Price: $217
Updated: 2024/03/01

TCI Chemical

Product number: B4098
Product name: Biochanin A
Purity: >98.0%(HPLC)(T)
Packaging: 5g
Price: $728
Updated: 2024/03/01

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5,7-Dihydrox -4'-methoxyisoflavone Chemical Properties,Usage,Production

Description

Biochanin A is a natural isoflavone with diverse biological actions, most notably as a phytoestrogen. It can affect hormone levels by inhibiting 5α-reductase and 17β-hydroxysteroid dehydrogenase or altering aromatase (CYP19A1) activity. Also known as 4’-methyl genistein, biochanin A can be metabolized in vivo to genistein , another phytoestrogen with diverse effects. Biochanin A also intersects with signaling through peroxisome proliferator-activated receptors (PPARs), as it activates PPARγ (EC₅₀ = 19 μM) and has also been shown to activate a PPARα promoter. Moreover, it increases the expression of the PPARγ coactivator PGC-1α, promoting mitochondrial biogenesis. Biochanin A also inhibits fatty acid amide hydrolase (IC₅₀ = 2.4 μM) and acts as an agonist of the aryl hydrocarbon receptor (EC₅₀ = 0.25 μM).

Chemical Properties

Off-White Solid

Uses

phytoestrogen

Uses

It has putative benefits in dietary cancer prophylaxis. It has also been found to inhibit fatty acid amide hydrolase and to act as agonist of PPARgamma, nuclear receptor that is current pharmacological target for the treatment of diabetes type 2. It acts as an antineoplastic agent. It 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. It is a nitric oxide synthase inhibitor and apoptosis inducer

Uses

An isoflavone with anticancer proliferation, differentiation and chemopreventitive properties. Inhibits metabolic activation of benzo[a]pyrene

Definition

ChEBI: Biochanin A is a member of the class of 7-hydroxyisoflavones that is 7-hydroxyisoflavone which is substituted by an additional hydroxy group at position 5 and a methoxy group at position 4'. A phytoestrogen, it has putative benefits in dietary cancer prophylaxis. It has a role as a phytoestrogen, a plant metabolite, an EC 3.5.1.99 (fatty acid amide hydrolase) inhibitor, a tyrosine kinase inhibitor and an antineoplastic agent. It is a member of 7-hydroxyisoflavones and a member of 4'-methoxyisoflavones. It is a conjugate acid of a biochanin A(1-).

General Description

Biochanin A (BCA) is synthesized in vitro from phloroglucinol. A series of steps involving Friedel?Crafts reaction results in an intermediate product 1-(2,4,6-trihydroxyphenyl)-2-(4 methoxyphenyl) ethanone, which post cyclization leads to BCA. It is catabolized to isoflavone genistein post ingestion.

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.

5,7-Dihydrox -4'-methoxyisoflavone Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from 5,7-Dihydrox -4'-methoxyisoflavone manufacturers

Shaanxi Dideu Medichem Co. Ltd

Product: 5,7-Dihydrox -4'-methoxyisoflavone 491-80-5
Price: US $1.00-100.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 4000KG
Release date: 2024-07-08

PNP Biotech Co. Ltd

Product: 5,7-Dihydrox -4'-methoxyisoflavone 491-80-5
Price: US $0.00/kg
Min. Order: 25kg
Purity: HPLC>99%
Supply Ability: Inquiry
Release date: 2022-09-16

Shanghai Standard Technology Co., Ltd.

Product: Biochanin A 491-80-5
Price: US $0.00/mg
Min. Order: 5mg
Purity: ≥98%(HPLC)
Supply Ability: 10 g
Release date: 2019-10-25

491-80-5, 5,7-Dihydrox -4'-methoxyisoflavoneRelated Search:

p-Anisidine Riboflavin Genistein Theaflavin 1-Hydroxyethylidene-1,1-diphosphonic acid Riboflavin 5'-Monophosphate Sodium Salt Anisole Bensulfuron methyl Kresoxim-methyl Methylparaben Aloe emodin p-Anisaldehyde Emodin Triclosan Thiophanate-methyl Methyl acrylate Curcumin (Trifluoromethoxy)benzene

Biochani,Olmelin

5,7-dihydroxy-3-(4-methoxyphenyl)chromen-4-one

BIOCHANIN A (AHP)

BIOCHANIN

5,7-DIHYDROXY-4''-METHOXYISOFLAVONE, 98% BIOCHANIN A

5,7-Dihydrox -4'-methoxyisoflavone

5,7-Dihydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one

Biochanin A, (5,7-Dihydroxy-4’-methoxyisoflavone)

Biochanin A，Genistein 4'-methyl ether，5,7-Dihydrox -4'-methoxyisoflavone

3-(4-Methoxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one

4'-Methylgenistein

Bilchanin A

NSC 123538

Biochanin A (4-Methylgenistein)

OlMelin

Pratensol

Biochanin A,5,7-Dihydroxy-4′-methoxyisoflavone, Genistein 4′-methyl ether

5,7-Dihydrox -4'-methoxyisoflavone 491-80-5

7-hydroxy-3-(4-methoxyphenyl)-4-oxo-1-benzopyran-5-olate

5,7-dihydroxy-3-(4-methoxyphenyl)-4h-1-benzopyran-4-on

5,7-dihydroxy-3-(4-methoxyphenyl)-4H-1-Benzopyran-4-one

APIGENIN 4-METHYL ETHER

BIOCHANIN A

5,7-DIHYDROXY-4'-METHOXYISOFLAVONE

5,7-DIHYDROXY-4-METHOXYISOFLAVONE

Genistein 4′-methyl ether

5,7-dihydroxy-3-p-methoxyphenyl-4H-chromen-4-one

4H-1-Benzopyran-4-one, 5,7-dihydroxy-3-(4-methoxyphenyl)-

5,7-Dihydroxy-4'-methoxyisoflavone Genistein 4'-methyl ether 5,7-Dihydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one

Biochanin A &gt

Genistein Methyl Ether

Chickpea bud A

5,7-Dihydroxy-4'-methoxyisoflavone (Biochanin A)

TIANFUCHEM--High purity 491-80-5 5,7-Dihydrox -4'-methoxyisoflavone

Chickpea sproutin A

Chickpea A

5,7- Dihydroxy - 4'- methoxy Isoflovone (or) Biochanin-A

Chickpea sprout extract

Biochanin A 98%min

Chickpea dentin A

5,7-Dihydrox -4'-methoxyisoflavone

4-Methylgenistein|||Olmelin

Biochanin A(P) (AHP Verified)

Biochanin A-RM

491-80-5

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