1621-56-3

Basic information

• Product Name: 7-METHOXYISOFLAVONE
• Synonyms: 7-METHOXYISOFLAVONE;AURORA 15641;3-Phenyl-7-methoxy-4H-1-benzopyran-4-one;7-Methoxy-3-phenyl-4H-1-benzopyran-4-one
• CAS NO: 1621-56-3
• Molecular Formula: C₁₆H₁₂O₃
• Molecular Weight: 252.26
• Product Categories: Mono-substituted Flavones
• Mol File: 1621-56-3.mol
• Article Data: 16

Chemical Properties

• Melting Point: 156-158℃
• Boiling Point: 421.2°Cat760mmHg
• Flash Point: 200.3°C
• Appearance: /
• Density: 1.240
• Vapor Pressure: 2.66E-07mmHg at 25°C
• Refractive Index: 1.614
• CAS DataBase Reference: 7-METHOXYISOFLAVONE(CAS DataBase Reference)
• NIST Chemistry Reference: 7-METHOXYISOFLAVONE(1621-56-3)
• EPA Substance Registry System: 7-METHOXYISOFLAVONE(1621-56-3)

Safety Data

• Hazardous Substances Data: 1621-56-3(Hazardous Substances Data)

Usage

Uses

7-Methoxyisoflavone, is a derivative of Isoflavone (I816808), that inhibits the clonogenicity of human colon cancer cells. It is also an activator of adenosine monophosphate-activated protein kinase (AMPK).

InChI:InChI=1/C16H12O3/c1-18-12-7-8-13-15(9-12)19-10-14(16(13)17)11-5-3-2-4-6-11/h2-10H,1H3

Upstream product

• 18439-96-8 1-(2-hydroxy-4-methoxyphenyl)-2-phenylethanone 
• 77287-34-4 formamide 
• 109-94-4 formic acid ethyl ester 
• 21785-09-1 7-methoxyflavanone 
• 109442-55-9 2-Hydroxy-4'-methoxy-benzoin 
• 3669-41-8 1-(2,4-dihydroxyphenyl)-2-phenylethanone 
• 150-19-6 O-methylresorcine 
• 52923-29-2 1-(2-hydroxy-4-methoxyphenyl)-3-phenylprop-2-en-1-one 
• 552-41-0 1-(2-hydroxy-4-methoxyphenyl)ethanone 
• 73220-41-4 3-bromo-7-methoxy-4H-chromen-4-one 
• 960-16-7 tributylphenylstannane 
• 73220-33-4 3-(dimethylamino)-1-(4-ethoxy-2-hydroxyphenyl)prop-2-en-1-one 
• 98-80-6 phenylboronic acid 
• 89-84-9 2',4'-dihydroxy-4-acetophenone 

Downstream Products

• 13057-72-2 7-hydroxyisoflavone 
• 1225387-35-8 6-phenyl-7-(2-hydroxy-4-methoxyphenyl)pyrazolo[1,5-a]pyrimidine 
• 1427272-63-6 3-cyano-6-(2-hydroxy-4-methoxyphenyl)-5-phenylpyridine-2-(1H)-thione 
• 1456626-68-8 3-cyano-6-(2-hydroxy-4-methoxyphenyl)-5-phenylpyridin-2(1H)-one 
• 1606136-76-8 2-methyl-6-phenyl-7-(2-hydroxyl-4-methoxyphenyl)pyrazolo[1,5-a]pyrimidine 
• 18439-96-8 1-(2-hydroxy-4-methoxyphenyl)-2-phenylethanone 
• 1391033-45-6 C₁₆H₁₂O₄ 
• 1380484-09-2 8-carbamoyl-4-(2-hydroxy-4-methoxyphenyl)-3-phenylimidazo[1,5-a]pyrimidine 
• 4281-30-5 cis-7-methoxyisoflavan-4-ol 
• 4281-30-5 trans-7-methoxyisoflavan-4-ol 
• 5128-69-8 7-methoxyisoflavanone 
• 1357294-42-8 5-(2-hydroxy-4-methoxyphenyl)-6-phenylimidazo[1,2-a]pyrimidine 

Relevant articles and documents

Two-Step Laser Excitation Fluoresence Study of the Ground-and Excited-State Proton Transfer in Alcohol Solutions of 7-Hydroxyisoflavone

The intermolecular excited-state proton transfer and relaxation processes to the parent molecule were investigated for the alcohol solutions of 7-hydroxyisoflavone (7-HIF) by means of nanosecond and two-step laser excitation (TSLE) fluorescence spectrosco

Design, synthesis and the structure-activity relationship of agonists targeting on the ALDH2 catalytic tunnel

ALDH2, a key enzyme in the alcohol metabolism process, detoxifies several kinds of toxic small molecular aldehydes, which induce severe organ damages. The development of novel Alda-1 type ALDH2 activators was mostly relied on HTS but not rational design so far. To clarify the structure–activity relationship (SAR) of the skeleton of Alda-1 analogs by synthesis of the least number of analogs, we prepared 31 Alda-1 analogs and 3 isoflavone derivatives and evaluated for their ALDH2-activating activity. Among these, the ALDH2-activating activity of mono-halogen-substituted (Cl and Br) N-piperonylbenzamides 3b and 3 k, and non-aromatic amides 8a-8c, were 1.5–2.1 folds higher than that of Alda-1 at 20 μM. The relationship between binding affinity in computer aided molecular docking model and the ALDH2-activating activity assays were clarified as follows: for Alda-1 analogs, with the formation of halogen bonds, the enzyme-activating activity was found to follow a specific regression curve within the range between ?5 kcal/mol and ?4 kcal/mol. For isoflavone derivatives, the basic moiety on the B ring enhance the activating activity. These results provide a new direction of utilizing computer-aided modeling to design novel ALDH2 agonists in the future.

Development of a general approach to the synthesis of a library of isoflavonoid derivatives

Isoflavonoids are a class of organic compounds that act primarily as antioxidants. They are produced almost exclusively by various members of the bean family including soybeans, tofu, peanuts, chick peas, and alfalfa. The antioxidant characteristics that isoflavonoids exhibit help hinder the progression of certain cancers, primarily breast, prostate, and colon cancer. We have developed a three-five step synthesis for obtaining a suite of isoflavonoid derivatives. The synthesis involves an enamine formation, a ring closure and halogenation, a Suzuki coupling, and finally a global deprotection to obtain the respective isoflavonoid derivatives.