5,7-Dihydrox -4'-methoxyisoflavone
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5,7-Dihydrox -4'-methoxyisoflavone
- Name 5,7-Dihydrox -4'-methoxyisoflavone
- CAS 491-80-5
- Purity 99%
Product Details
Cost-effective and customizable 5,7-Dihydrox -4'-methoxyisoflavone 491-80-5 supplier
- Molecular Formula: C16H12O5
- Molecular Weight: 284.268
- Appearance/Colour: Off-white solid
- Vapor Pressure: 2.25E-11mmHg at 25°C
- Melting Point: 210-213 °C(lit.)
- Refractive Index: 1.668
- Boiling Point: 518.6 °C at 760 mmHg
- PKA: 6.50±0.20(Predicted)
- Flash Point: 198.2 °C
- PSA： 79.90000
- Density: 1.42 g/cm3
- LogP: 2.87980
5,7-Dihydrox -4'-methoxyisoflavone(Cas 491-80-5) Usage
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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. |
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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. |
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
491-80-5 Relevant articles
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...
Synthesis method of biochanin A
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Paragraph 0012; 0016; 0017; 0018, (2021/08/14)
The invention discloses a synthesis meth...
Identification of ortho catechol-containing isoflavone as a privileged scaffold that directly prevents the aggregation of both amyloid β plaques and tau-mediated neurofibrillary tangles and its in vivo evaluation
Do, Ji Min,Gee, Min Sung,Inn, Kyung-Soo,Kim, Jong-Ho,Kim, Nam Kwon,Kim, Nam-Jung,Lee, Hyun Woo,Lee, Jong Kil,Seo, Min-Duk,Seong, Ji Hye,Son, Seung Hwan,Yoo, Hyung-Seok,Yoo, Ji-Na
, (2021/07/01)
In this study, polyhydroxyisoflavones th...
Influence of Substrate Binding Residues on the Substrate Scope and Regioselectivity of a Plant O-Methyltransferase against Flavonoids
Tang, Qingyun,Vianney, Yoanes M.,Weisz, Klaus,Grathwol, Christoph W.,Link, Andreas,Bornscheuer, Uwe T.,Pavlidis, Ioannis V.
, p. 3721 - 3727 (2020/06/02)
Methylation of free hydroxyl groups is a...
Cytosine N-isoflavone compound as well as preparation method and application thereof
-
, (2019/10/02)
The invention relates to a cytosine N-is...
491-80-5 Process route
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15485-66-2
2,4,6-trihydroxy-4'-methoxydeoxybenzoin
-
-
68-12-2,33513-42-7
N,N-dimethyl-formamide
-
-
491-80-5
5,7-Dihydroxy-3-(4-methoxy-phenyl)-chromen-4-on
| Conditions | Yield |
|---|---|
|
N,N-dimethyl-formamide;
With
phosphorus pentachloride;
at 55 ℃;
for 0.333333h;
2,4,6-trihydroxy-4'-methoxydeoxybenzoin;
With
boron trifluoride diethyl etherate;
In
N,N-dimethyl-formamide;
at 20 ℃;
for 1h;
|
92%
|
|
2,4,6-trihydroxy-4'-methoxydeoxybenzoin;
With
boron trifluoride diethyl etherate;
In
N,N-dimethyl-formamide;
at 50 - 60 ℃;
Cooling with ice;
N,N-dimethyl-formamide;
With
methanesulfonyl chloride;
at 50 - 70 ℃;
|
91%
|
|
2,4,6-trihydroxy-4'-methoxydeoxybenzoin; N,N-dimethyl-formamide;
With
boron trifluoride diethyl etherate; methanesulfonyl chloride;
In
N,N-dimethyl-formamide;
at 100 ℃;
With
water;
|
71%
|
|
With
boron trifluoride diethyl etherate; trichlorophosphate;
In
N,N-dimethyl-formamide;
at 60 - 70 ℃;
for 2h;
|
61%
|
|
With
boron trifluoride diethyl etherate; methanesulfonyl chloride;
Yield given. Multistep reaction;
1.) irradiation, reflux, 15 s, 2.) irradiation, reflux, 1 min;
|
|
|
With
phosphorus pentachloride; boron trifluoride;
In
N,N-dimethyl-formamide;
|
|
|
With
boron trifluoride diethyl etherate; methanesulfonyl chloride;
at 100 ℃;
|
|
|
2,4,6-trihydroxy-4'-methoxydeoxybenzoin; N,N-dimethyl-formamide;
With
boron trifluoride;
With
methanesulfonyl chloride;
|
|
|
2,4,6-trihydroxy-4'-methoxydeoxybenzoin; N,N-dimethyl-formamide;
With
boron trifluoride diethyl etherate;
at 20 ℃;
With
methanesulfonyl chloride;
In
N,N-dimethyl-formamide;
at 80 ℃;
Further stages.;
|
|
|
With
boron trifluoride diethyl etherate; methanesulfonyl chloride;
at 50 - 80 ℃;
Inert atmosphere;
|
-
-
487-70-7
2,4,6-trihydroxybenzaldehyde
-
-
2632-13-5
2-Bromo-4'-methoxyacetophenone
-
-
491-80-5
5,7-Dihydroxy-3-(4-methoxy-phenyl)-chromen-4-on
| Conditions | Yield |
|---|---|
|
With
N-(2-methylbenzyl)-4,5-dihydro-1H-imidazol-2-amine;
In
ethanol;
at 50 ℃;
for 6h;
Reagent/catalyst;
Inert atmosphere;
|
82%
|
|
2-Bromo-4'-methoxyacetophenone;
With
thiamine hydrochloride;
In
ethanol;
at 20 ℃;
for 0.25h;
Green chemistry;
2,4,6-trihydroxybenzaldehyde;
In
ethanol;
at 20 ℃;
for 2h;
Green chemistry;
|
65%
|
491-80-5 Upstream products
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113029-08-6
2-carbethoxy-5,7-dihydroxy-4'-methoxyisoflavone
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54443-59-3
acetic acid 7-acetoxy-3-(4-methoxyphenyl)-4-oxo-4H-chromen-5-yl ester
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15485-66-2
2,4,6-trihydroxy-4'-methoxydeoxybenzoin
-
109-94-4
formic acid ethyl ester
491-80-5 Downstream products
-
54443-59-3
acetic acid 7-acetoxy-3-(4-methoxyphenyl)-4-oxo-4H-chromen-5-yl ester
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114600-14-5
5-hydroxy-3-(4-methoxy-phenyl)-7-(toluene-4-sulfonyloxy)-chromen-4-one
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1162-82-9
4',5,7-trimethoxyisoflavone
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34086-51-6
4',7-dimethoxy-5-hydroxyisoflavone
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