72598-35-7

Basic information

• Product Name: Serricornin
• Synonyms: (-)-Serricornine;(4S,6S,7S)-7-Hydroxy-4,6-dimethyl-3-nonanone;7-Hydroxy-4,6-dimethylnonan-3-one
• CAS NO: 72598-35-7
• Molecular Formula: C11H22O2
• Molecular Weight: 186.29
• Product Categories: insect pheromone
• Mol File: 72598-35-7.mol
• Article Data: 19

Chemical Properties

• Boiling Point: 291.5±13.0 °C(Predicted)
• Appearance: /
• Density: 0.904±0.06 g/cm3(Predicted)
• PKA: 15.01±0.20(Predicted)
• CAS DataBase Reference: Serricornin(CAS DataBase Reference)
• NIST Chemistry Reference: Serricornin(72598-35-7)
• EPA Substance Registry System: Serricornin(72598-35-7)

Safety Data

• Hazardous Substances Data: 72598-35-7(Hazardous Substances Data)

Upstream product

• 74-96-4 ethyl bromide 
• 117248-20-1 (3R,5S,6S)-6-Ethyl-3,5-dimethyltetrahydro-2H-pyran-2-on 
• 90270-02-3 (2R,4S)-1-hydroxy-2,4-dimethylpentyl acetate 
• 100757-47-9 (2S,3S)-3-t-butyldimethylsilyloxy-2-methyl-1-(4-methylbenzenesulfonyloxy)pentane 
• 149-31-5 (2S,3S)-2-methylpentane-1,3-diol 
• 86535-14-0 (2S,3S)-2-methyl-1-(4-methylbenzenesulfonyloxy)-3-pentanol 
• 86535-09-3 (2S,3R)-2-methyl-3-tetrahydropyranyloxy-1-pentanol 
• 78433-57-5 (2S,3R)-2-methylpentane-1,3-diol 1-benzyl ether 
• 86535-07-1 (2S,3S)-threo-2-methylpentane-1,3-diol 1-benzyl ether 
• 100699-14-7 (2S,3S)-3-t-butyldimethylsilyloxy-2-methylpentane-1-ol 1-benzyl ether 
• 86535-08-2 (2S,3R)-2-methylpentane-1,3-diol 1-benzyl,3-THP-ether 
• 137909-90-1 1,4-dioxa-8-thiaspiro<4.5>decane-6-carboxaldehyde 
• 62673-87-4 3-Formyltetrahydrothiopyran-4-one enol 
• 76291-47-9 diethylketone hydrazone 

Downstream Products

• 83997-86-8 serricornin acetate <(4S,6S,7S)-4,6-dimethyl-7-acetoxy-3-nonanone> 
• 72485-37-1 (4R,6S,7S)-7-acetoxy-4,6-dimethyl-3-nonanone 
• 72522-40-8 (4R,6S,7S)-7-hydroxy-4,6-dimethyl-3-nonanone 
• 91660-58-1 (4S,6S,7S)-Serricornin 
• 72485-37-1 (4R^*,6R^*,7S^*)-7-acetyloxy-4,6-dimethyl-3-nonanone 

Relevant articles and documents

New synthesis of serricornin, the sex pheromone of the cigarette beetle (Lasioderma serricorne)

A new approach to the total synthesis of serricornin, the sex pheromone of the cigarette beetle, based on readily available (4S,5E)-4-methyhept-5-enenitrile was implemented.

Thiopyran route to polypropionates: An efficient synthesis of serricornin

The synthesis of serricornin [(4S,6S,7S)-7-hydroxy-4,6-dimethylnonan-3-one] , a sex pheromone produced by the female cigarette beetle (Lasioderma serricorne F.), in seven steps from readily available racemic 1,4-dioxa-8-thiaspiro-[4.5] decane-6-carboxaldehyde (6) is described. The key steps include enantioselective aldol reaction of 6 with tetrahydrothiopyran-4-one catalyzed by 5-[(2S)-pyrrolidine-2-yl]-1H-tetrazole to fabricate the tetrapropionate skeleton, stereoselective LisBu3BH reduction of the resulting aldol adduct, Barton-McCombie deoxygenation, and Raney nickel desulfurization.

Synthesis of (4R,6S,7R)-7-hydroxy-4,6-dimethyl-3-nonanone and (3R,5S,6R)-6-hydroxy-3,5-dimethyl-2-octanone

The synthesis of (4R,6S,7R)-7-hydroxy-4,6-dimethyl-3-nonanone and (3R,5S,6R)-6-hydroxy-3,5-dimethyl-2-octanone is described as their acetates using a desymmetrization strategy as well as an Evans syn aldol strategy.