86791-43-7

Basic information

• Product Name: ethyl 2-hydroxy-6-pentylbenzoate
• Synonyms: ethyl 2-hydroxy-6-pentylbenzoate
• CAS NO: 86791-43-7
• Molecular Weight: 236.311
• Mol File: 86791-43-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: ethyl 2-hydroxy-6-pentylbenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 2-hydroxy-6-pentylbenzoate(86791-43-7)
• EPA Substance Registry System: ethyl 2-hydroxy-6-pentylbenzoate(86791-43-7)

Safety Data

• Hazardous Substances Data: 86791-43-7(Hazardous Substances Data)

Upstream product

• 58497-40-8 3,5-dibromo-2,4-dihydroxy-6-n-pentylbenzoic acid ethyl ester 
• 38862-65-6 2,4-dihydroxy-6-n-pentylbenzoic acid ethyl ester 
• 86791-42-6 ethyl 2-hydroxy-6-pentyl-4-(1-phenyl-5-tetrazolyl)-oxybenzoate 

Downstream Products

• 83326-76-5 C_5:0-anacardic acid 

Relevant articles and documents

Inhibition of prostaglandin biosynthesis by 4-O-methylcryptochlorophaeic acid; synthesis of monomeric arylcarboxylic acids for inhibitory activity testing and X-ray analysis of 4-O-methylcryptochlorophaeic acid

In order to clarify the structure-activity relationship of 4-O-methylcryptochlorophaeic acid (1), which is a lichen meta-depside and a potent inhibitor of prostaglandin (PG) biosynthesis found in our previous screening work, arylcarboxylic acids (5-8) corresponding to the monomeric moieties of 4-O-methylcryptochlorophaeic acid (1) were synthesized and tested for inhibitory effect against PG biosynthesis by an enzyme system prepared from rabbit renal medulla. They were a hundred times less active that 4-O-methylcryptochlorophaeic acid (1), indicating that the dimeric structure of the meta-depside is essential for inhibitory activity against PG biosynthesis. Kinetic studies on the mechanism of inhibition revealed that 4-O-methylcryptochlorophaeic acid (1) inhibits PG biosynthesis competitively with respect to the substrate, arachidonic acid. The three dimensional structure of 4-O-methylcryptochlorophaeic acid (1), which is expected to have a molecular structure able to fit into an active site that accommodates arachidonic acid, was determined by single crystal X-ray analysis with the direct approach. The obtained structure reveals that 4-O-methylcryptochlorophaeic acid (1) maintains a rigid conformation by forming a strong hydrogen bond between a hydroxy group and a methoxy group. Based on these findings, a new active site model of fatty acid cylooxygenase is proposed in order to explain the inhibition by the meta-depside and acidic non-steroidal antiinflammatory drugs.