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
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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5,7-Dihydrox -4'-methoxyisoflavone Suppliers

Hangzhou FST Pharmaceutical Co., Ltd
Tel
0571-88938521 18667135863
Fax
+86-571-88938660
Email
ps.wu@eyougene.com
Country
China
ProdList
127
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60
Shanxi Yuning Biotechnology Co., Ltd.
Tel
13623677056
Email
1639455302@qq.com
Country
China
ProdList
265
Advantage
58
J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
96815
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3B Pharmachem (Wuhan) International Co.,Ltd.
Tel
821-50328103-801 18930552037
Fax
86-21-50328109
Email
3bsc@sina.com
Country
China
ProdList
15839
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Chembest Research Laboratories Limited
Tel
+86-21-20908456
Fax
021-58180499
Email
sales@BioChemBest.com
Country
China
ProdList
6005
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Alfa Aesar
Tel
400-6106006
Fax
021-67582001/03/05
Email
saleschina@alfa-asia.com
Country
China
ProdList
30123
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TCI (Shanghai) Development Co., Ltd.
Tel
021-67121386
Fax
021-67121385
Email
Sales-CN@TCIchemicals.com
Country
China
ProdList
24529
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81
Beijing HwrkChemical Technology Co., Ltd
Tel
010-89508211 18501085097
Fax
010-89508210
Email
sales.bj@hwrkchemical.com
Country
China
ProdList
8415
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Energy Chemical
Tel
021-021-58432009 400-005-6266
Fax
021-58436166
Email
sales8178@energy-chemical.com
Country
China
ProdList
44689
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Jia Xing Isenchem Co.,Ltd
Tel
0573-85285100 18627885956
Fax
0573-85285100
Email
isenchem@163.com
Country
China
ProdList
9414
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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:


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