74161-25-4

Basic information

• Product Name: 3-(2,4-Dihydroxyphenyl)-5,7-dihydroxy-8-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one
• Synonyms: 2,3-Dehydrokievitone;3-(2,4-Dihydroxyphenyl)-5,7-dihydroxy-8-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one
• CAS NO: 74161-25-4
• Molecular Formula: C₂₀H₁₈O₆
• Molecular Weight: 354.3533
• Mol File: 74161-25-4.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 633°Cat760mmHg
• Flash Point: 229.8°C
• Appearance: /
• Density: 1.424g/cm³
• Vapor Pressure: 1.29E-16mmHg at 25°C
• Refractive Index: 1.69
• PKA: 6.46±0.20(Predicted)
• CAS DataBase Reference: 3-(2,4-Dihydroxyphenyl)-5,7-dihydroxy-8-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(2,4-Dihydroxyphenyl)-5,7-dihydroxy-8-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one(74161-25-4)
• EPA Substance Registry System: 3-(2,4-Dihydroxyphenyl)-5,7-dihydroxy-8-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one(74161-25-4)

Safety Data

• Hazardous Substances Data: 74161-25-4(Hazardous Substances Data)

Usage

General Description

3-(2,4-Dihydroxyphenyl)-5,7-dihydroxy-8-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one, most commonly known as gancaonin M, is a complex chemical compound found in licorice. It is classified as a flavanone, a type of flavonoid that is commonly found in many plants and constitutes a significant part of the human diet. Gancaonin M is known for its wide range of potential therapeutic applications. Generally, these compounds manifest considerable antibacterial, anti-inflammatory, anticancer, and antioxidant effects. However, the use and effects of this specific compound require more in-depth investigation for a conclusive understanding.

InChI:InChI=1/C20H18O6/c1-10(2)3-5-13-16(23)8-17(24)18-19(25)14(9-26-20(13)18)12-6-4-11(21)7-15(12)22/h3-4,6-9,21-24H,5H2,1-2H3

Upstream product

• 160154-76-7 2',4',5,7-tetrakis(benzoyloxy)-8-(3-methyl-2-butenyl)isoflavone 
• 115-19-5 2-methyl-but-3-yn-2-ol 
• 104691-93-2 2',4',5,7-tetrahydroxy-8-(3-hydroxy-3-methylbutyl)isoflavone 
• 160154-73-4 2',4',5,7-tetrakis(benzyloxy)-8-iodoisoflavone 
• 160154-74-5 2',4',5,7-tetrakis(benzyloxy)-8-(3-hydroxy-3-methyl-1-butynyl)isoflavone 
• 160154-75-6 2',4',5,7-tetrakis(benzoyloxy)-8-(3-hydroxy-3-methylbutyl)isoflavone 
• 160154-72-3 1-<2-acetoxy-4,6-bis(benzyloxy)-3-iodophenyl>-2-<2,4-bis(benzyloxy)phenyl>-3,3-dimethoxypropan-1-one 
• 160154-71-2 2'-acetoxy-2,4,4',6'-tetrakis(benzyloxy)-3'-iodochalcone 

Downstream Products

• 122551-73-9 7-O-methyl-2,3-dehydrokievitone 
• 111930-14-4 3-(2,4-Dihydroxy-phenyl)-5-hydroxy-8-(1-hydroxy-1-methyl-ethyl)-8,9-dihydro-furo[2,3-h]chromen-4-one 
• 122551-74-0 7-O-methyl-2,3-dehydrokievitone-(-)-epoxide 

Relevant articles and documents

Regioselective synthesis of prenylisoflavones. Syntheses of allolicoisoflavone A, 2,3-dehydrokievitone, and related compounds

The palladium-catalyzed coupling reaction of 2',4',5,7- tetrakis(benzyloxy)-5'-iodolsoflavone (12), synthesized from the 5- iodochalcone 9, with 2-methyl-3-butyn-2-ol gave the corresponding 5'-(3- hydroxy-3-methyl-1-butynyl)isoflavone 13. The catalytic hydrogenation of 13 gave 2',4',5,7-tetrahydroxy-5'-(3-hydroxy-3-methylbutyl)isoflavone (2). Dehydration of the benzoate 14 of 2 afforded a mixture of 5'-(3-methyl-2- butenyl)isoflavone 15 and the isomer 5'-(3-methyl-3-butenyl)isoflavone 16. The separation of 15 was accomplished by a treatment of the mixture (15 and 16) with mercury(II) nitrate. Hydrolysis of 15 afforded 2',4',5,7- tetrahydroxy-5'-prenylisoflavone (allolicoisoflavone A) (1). In a similar manner, 2',4',5,7-tetrahydroxy-8-prenylisoflavone (2,3-dehydrokievitone) (3) and 2',4',5,7-tetrahydroxy-8-(3-hydroxy-3-methylbutyl)isoflavone (2,3- dehydrokievitone hydrate) (4) were synthesized from the corresponding 8- iodoisoflavone 22. The tetramethyl ether 5 of 3 was also prepared from the 8- iodotetramethoxyisoflavone 32.