91739-31-0

Basic information

• Product Name: (4SR,6SR,7SR)-7-hydroxy-4,6-dimethyl-3-nonanone
• CAS NO: 91739-31-0
• Molecular Weight: 186.294
• Mol File: 91739-31-0.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: (4SR,6SR,7SR)-7-hydroxy-4,6-dimethyl-3-nonanone(CAS DataBase Reference)
• NIST Chemistry Reference: (4SR,6SR,7SR)-7-hydroxy-4,6-dimethyl-3-nonanone(91739-31-0)
• EPA Substance Registry System: (4SR,6SR,7SR)-7-hydroxy-4,6-dimethyl-3-nonanone(91739-31-0)

Safety Data

• Hazardous Substances Data: 91739-31-0(Hazardous Substances Data)

Upstream product

• 72598-35-7 (-)-serricornin 
• 78433-62-2 (4RS,6S,7S)-7-t-butyldimethylsilyloxy-4,6-dimethyl-3-nonanone 
• 100235-81-2 methyl (2R,3R)-2-methyl-3-tetrahydropyranyloxypentenoate 
• 96-22-0 pentan-3-one 
• 78433-62-2 (6R,7R)-7-(tert-Butyl-dimethyl-silanyloxy)-4,6-dimethyl-nonan-3-one 
• 72522-40-8 (4RS,6SR,7SR)-Serricornin 
• 131026-16-9 (-)-(E)-(6S,7S)-4,6-dimethyl-7-hydroxy-4-nonen-3-one 
• 119460-81-0 (4SR,5SR)-5-O-acetyl-2,5-dihydroxy-2,4-dimethyl-2-O-trimethylsilylheptan-3-one 
• 119460-86-5 ethyl (4SR,5SR)-5-O-acetyl-5-hydroxy-2,4-dimethylhepten-2-oate 
• 119460-88-7 ethyl (4SR,5SR)-5-O-acetyl-5-hydroxy-2,4-dimethylheptanoate 
• 119460-82-1 (4SR,5SR)-5-O-acetyl-2,5-dihydroxy-2,4-dimethyl-heptan-3-one 
• 119460-83-2 (4SR,5SR)-5-O-acetyl-2,4-dimethyl-2,3,5-heptanotriol 
• 119460-84-3 (2SR,3SR)-3-O-acetyl-3-hydroxy-2-methylpetanal 
• 119460-80-9 (4SR,5SR)-2,5-dihydroxy-2,4-dimethyl-2-O-trimethylsilylheptan-3-one 

Downstream Products

• 72522-40-8 (4R,6S,7S)-7-hydroxy-4,6-dimethyl-3-nonanone 
• 72598-35-7 (-)-serricornin 
• 91660-58-1 (4S,6S,7S)-Serricornin 
• 72485-37-1 (4R^*,6R^*,7S^*)-7-acetyloxy-4,6-dimethyl-3-nonanone 
• 72485-37-1 (4R,6S,7S)-7-acetoxy-4,6-dimethyl-3-nonanone 

Relevant articles and documents

A new synthesis of serricornin [(4s,6s,7s)-7-hydroxy-4,6-dimethyl-3-nonanone], the sex pheromone of the cigarette beetle

Serricornin, the sex pheromone of Lasioderma serricorne F, was synthesised in 7.6% overall yield starting from methyl (R)-3-hydroxypentanoate of microbial origin. Its (4R,6S,7S)-isomer was also synthesised.

Synthesis of (4R,6S,7R)-7-hydroxy-4,6-dimethyl-3-nonanone and (3R,5S,6R)-6-hydroxy-3,5-dimethyl-2-octanone, the pheromone components of the bostrychid beetle, Dinoderus bifoveolatus

(4R,6S,7R)-7-Hydroxy-4,6-dimethyl-3-nonanone and (3R,5S,6R)-6-hydroxy-3,5- dimethyl-2-octanone, the pheromone components of the bostrychid beetle, Dinoderus bifoveolatus, as well as their (4R,6S,7S)-and (3R,5S,6S)-isomers were synthesized from (2R,4S,5R)- and (2R,4S,5S)2,4-dimethyl-5-heptanolide, respectively.

A practical enantioselective synthesis of the cigarette beetle sex pheromone serricornin

(4RS,6S,7S)-7-hydroxy-4,6-dimethyl-3-nonanone (serricornin and its C4- epimer) may be prepared from oxazolidinone 5 in 8 steps with an overall yield of 33%.