28437-37-8

Basic information

• Product Name: 1-[2,4-dihydroxy-5-(3-methyl-2-butenyl)phenyl]ethanone
• Synonyms: 1-[2,4-dihydroxy-5-(3-methyl-2-butenyl)phenyl]ethanone
• CAS NO: 28437-37-8
• Molecular Formula: C₁₃H₁₆O₃
• Molecular Weight: 220.26434
• Mol File: 28437-37-8.mol
• Article Data: 18

Chemical Properties

• Melting Point: 146°C
• Appearance: /
• CAS DataBase Reference: 1-[2,4-dihydroxy-5-(3-methyl-2-butenyl)phenyl]ethanone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[2,4-dihydroxy-5-(3-methyl-2-butenyl)phenyl]ethanone(28437-37-8)
• EPA Substance Registry System: 1-[2,4-dihydroxy-5-(3-methyl-2-butenyl)phenyl]ethanone(28437-37-8)

Safety Data

• Hazardous Substances Data: 28437-37-8(Hazardous Substances Data)

Usage

Preparation

Preparation by reaction of 2-methylbut-3-en-2-ol with resacetophenone in the presence of boron trifluoride etherate.

Upstream product

• 89-84-9 2',4'-dihydroxy-4-acetophenone 
• 870-63-3 prenyl bromide 
• 35817-07-3 Acetic acid 5-acetoxy-2-acetyl-4-(3-methyl-but-2-enyl)-phenyl ester 
• 556-82-1 3-methyl-2-buten-1-ol 
• 108-46-3 recorcinol 
• 115-18-4 2-methyl-3-buten-2-ol 
• 71243-12-4 1-(2,4-dihydroxy-3-iodophenyl)ethanone 
• 157953-16-7 2',4'-bis(benzyloxy)-5'-iodoacetophenone 
• 1026247-18-6 1-[2,4-Dihydroxy-5-(3-hydroxy-3-methyl-butyl)-phenyl]-ethanone 
• 22877-01-6 2,4-bis(benzyloxy)acetophenone 
• 157953-27-0 C₂₇H₂₄O₅ 
• 157953-23-6 1-[2,4-Bis-benzyloxy-5-(3-hydroxy-3-methyl-but-1-ynyl)-phenyl]-ethanone 

Downstream Products

• 405261-82-7 7-methoxymethoxy-2-[4-methoxymethoxy-3-(3-methyl-but-2-enyl)-phenyl]-6-(3-methyl-but-2-enyl)-chroman-4-one 
• 405261-81-6 (E)-1-[2-Hydroxy-4-methoxymethoxy-5-(3-methyl-but-2-enyl)-phenyl]-3-[4-methoxymethoxy-3-(3-methyl-but-2-enyl)-phenyl]-propenone 
• 28448-83-1 2′-hydroxyl-4′-methoxyl-5′-isopentenylacetophenone 
• 20628-09-5 encecalin 
• 99217-73-9 (E)-3-(3,4-Bis-methoxymethoxy-phenyl)-1-[2-hydroxy-4-methoxymethoxy-5-(3-methyl-but-2-enyl)-phenyl]-propenone 
• 99217-68-2 broussochalcone A 
• 415921-46-9 8-[3-(3-methyl-2-butenyl)-4-hydroxyphenyl]-2,2-dimethyl-3,4,7,8-tetrahydro-2H,6H-benzo[1,2-b:5,4-b']dipyran-6-one 
• 118267-01-9 1-[7-hydroxy-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-6-yl]-3-(4-hydroxyphenyl)-2-propen-1-one 
• 415921-45-8 8-(4-hydroxyphenyl)-2,2-dimethyl-3,4,7,8-tetrahydro-2H,6H-benzo[1,2-b:5,4-b']dipyran-6-one 
• 78316-27-5 (+/-)-bavachin 

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Synthetic methods for prenylated chalcones and pyranochalcones

The inventors of the present invention invented a simple and effective way to synthesize compounds 1-9 of natural prenylated chalcones and pyrano chalcones by using Claisen-Schmidt condensation as a main step. In addition, an anti-inflammatory effect of synthetic compounds was evaluated in RAW 264.7 macrophages which were stimulated with a lipopolysaccharide. As a result, chalcone compounds having prenyl groups in a ring A (an acetophenone part) show weak inhibition or no inhibition on the generation of nitrogen oxide while chalcones (5, 6, 8, and 9) having no prenyl groups in the ring A show normal or good activity, and have no cytotoxicity.COPYRIGHT KIPO 2017