93796-20-4

Basic information

• Product Name: 3-Prenyl-2,4,6-trihydroxybenzophenone
• Synonyms: 3-Prenyl-2,4,6-trihydroxybenzophenone;Phenyl[2,4,6-trihydroxy-3-(3-methyl-2-buten-1-yl)phenyl]methanone;Phenyl(2,4,6-trihydroxy-3-(3-Methylbut-2-en-1-yl)phenyl)Methanone
• CAS NO: 93796-20-4
• Molecular Formula: C₁₈H₁₈O₄
• Molecular Weight: 298.33312
• Mol File: 93796-20-4.mol
• Article Data: 7

Chemical Properties

• Melting Point: 102–103°C
• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 3-Prenyl-2,4,6-trihydroxybenzophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Prenyl-2,4,6-trihydroxybenzophenone(93796-20-4)
• EPA Substance Registry System: 3-Prenyl-2,4,6-trihydroxybenzophenone(93796-20-4)

Safety Data

• Hazardous Substances Data: 93796-20-4(Hazardous Substances Data)

Usage

Preparation

Obtained by reaction of 2,4,6-tri-–hydroxy-benzophenone with prenyl-di-n-hexylsulfonium tetrafluoroborate salt (1 equiv) in the presence of Hünig’s base (1.1 equiv) in chloroform at r.t. for 7 h (42%).

Upstream product

• 115-18-4 2-methyl-3-buten-2-ol 
• 3555-86-0 2-benzoylphloroglucinol 
• 358-72-5 dimethylallyl diphosphate 
• 621-23-8 1,2,3-trimethoxybenzene 
• 98-88-4 benzoyl chloride 
• 870-63-3 prenyl bromide 
• 3770-80-7 2,4,6-trimethoxybenzophenone 
• 556-82-1 3-methyl-2-buten-1-ol 

Downstream Products

• 93796-23-7 2,4,6-trihydroxy-3-isopentylbenzophenone 
• 93796-30-6 2-benzoyl-3,5-dihydroxy-6-isopentyl-6-(3-methylbut-2-enyl)cyclohexa-2,4-dien-1-one 
• 93796-31-7 6-benzoyl-3,5-dihydroxy-2-isopentyl-6-(3-methylbut-2-enyl)cyclohexa-2,4-dien-1-one 
• 93796-29-3 2,4,6-trihydroxy-3-isopentyl-5-(3-methylbut-2-enyl)benzophenone 
• 93796-32-8 6-isopentyl-4-(3-methylbut-2-enyl)-2-benzoyl-3,5,6-trihydroxycyclohexa-2,4-dien-1-one 
• 93796-33-9 4-isopentyl-6-(3-methylbut-2-enyl)-2-benzoyl-3,5,6-trihydroxycyclohexa-2,4-dien-1-one 

Relevant articles and documents

PROCESSES FOR THE PREPARATION OF ORTHO-ALLYLATED HYDROXY ARYL COMPOUNDS

The present application describes process for preparing an ortho-allylated hydroxy aryl compounds such as compounds of Formula (I) by reacting an allylic alcohol with a hydroxy aryl compound in the presence of aluminum compound selected from alumina and aluminum alkoxides and in a non-protic solvent wherein at least one carbon atom ortho to the hydroxy group in the hydroxy aryl compound is unsubstituted. The present application also includes compounds of Formula (I).

Synthesis of 3-geranyl- and 3-prenyl-2,4,6-trihydroxybenzophenone

Biologically active phenyl[3-(3,7-dimethyl-2,6-octadienyl)-2,4,6-trihydroxyphenyl]methanone (2) and phenyl[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]methanone (3) were synthesized by an efficient and convenient synthetic sequence. The reaction steps of this synthesis included methylation, Friedel-Crafts acylation, demethylation and geranylation steps.

Friedel-Crafts Alkylation of Acylphloroglucinols Catalyzed by a Fungal Indole Prenyltransferase

Naturally occurring prenylated acylphloroglucinol derivatives are plant metabolites with diverse biological and pharmacological activities. Prenylation of acylphloroglucinols plays an important role in the formation of these intriguing natural products and is catalyzed in plants by membrane-bound enzymes. In this study, we demonstrate the prenylation of such compounds by a soluble fungal prenyltransferase AnaPT involved in the biosynthesis of prenylated indole alkaloids. The observed activities of AnaPT toward these substrates are much higher than that of a microsomal fraction containing an overproduced prenyltransferase from the plant hop.