72522-40-8

Basic information

• Product Name: SERRICORNIN
• Synonyms: SERRICORNIN;4,6-Dimethyl-7-hydroxy-nonan-3-one;(4S,6S,7S)-7-Hydroxy-4,6-dimethylnonan-3-one
• CAS NO: 72522-40-8
• Molecular Formula: C11H22O2
• Molecular Weight: 186.29
• Product Categories: All Aliphatics;Aliphatics
• Mol File: 72522-40-8.mol

Chemical Properties

• Boiling Point: 291.5°C at 760 mmHg
• Flash Point: 122.6°C
• Appearance: /
• Density: 0.904g/cm³
• Vapor Pressure: 0.000209mmHg at 25°C
• Refractive Index: 1.441
• Storage Temp.: Refrigerator
• Solubility: Benzene (Slightly), Chloroform (Slightly), Methanol (Slightly)
• PKA: 15.01±0.20(Predicted)
• CAS DataBase Reference: SERRICORNIN(CAS DataBase Reference)
• NIST Chemistry Reference: SERRICORNIN(72522-40-8)
• EPA Substance Registry System: SERRICORNIN(72522-40-8)

Safety Data

• Hazardous Substances Data: 72522-40-8(Hazardous Substances Data)

Usage

Uses

Used in Pest Control Industry:
SERRICORNIN is used as a pheromone for attracting and controlling the population of Cigarette Beetles. The application reason is that it mimics the natural sex pheromone of the beetle, enabling effective pest management and reducing the need for chemical pesticides.
Used in Chemical Research:
SERRICORNIN is used as a research compound for studying the chemical properties and behavior of pheromones in insects. The application reason is to gain a deeper understanding of insect communication and develop new strategies for pest control and environmental management.
Used in Perfumery and Fragrance Industry:
SERRICORNIN is used as a component in the creation of synthetic pheromone-based fragrances. The application reason is to harness the unique properties of the compound to develop novel scents and enhance the overall sensory experience of perfumes and fragrances.

InChI:InChI=1/C11H22O2/c1-5-10(12)8(3)7-9(4)11(13)6-2/h8-10,12H,5-7H2,1-4H3

Upstream product

• 131026-16-9 (-)-(E)-(6S,7S)-4,6-dimethyl-7-hydroxy-4-nonen-3-one 
• 72598-35-7 (-)-serricornin 
• 78433-62-2 (4RS,6S,7S)-7-t-butyldimethylsilyloxy-4,6-dimethyl-3-nonanone 
• 72522-40-8 (4RS,6SR,7SR)-Serricornin 
• 74-96-4 ethyl bromide 
• 117248-20-1 (3R,5S,6S)-6-Ethyl-3,5-dimethyltetrahydro-2H-pyran-2-on 
• 631918-29-1 (2R,4S,5S)-2,4-dimethyl-1,5-heptanediol 
• 631918-27-9 (2R,4S,5S)-1-(tert-butyl(dimethyl)silyloxy)-5-hydroxy-2,4-dimethylheptane 
• 631918-22-4 (2R,4S,5RS)-1-(tert-butyl(dimethyl)silyloxy)-5-hydroxy-2,4-dimethylheptane 
• 90270-02-3 (2R,4S)-1-hydroxy-2,4-dimethylpentyl acetate 
• 147782-80-7 (2S,4R)-5-(tert-butyl(dimethyl)silyloxy)-2,4-dimethyl-1-pentanol 
• 147782-81-8 (2S,4R)-1-<(tert-Butyldimethylsilyl)oxy>-2,4-dimethylpentanal 
• 335060-49-6 (2S,4R)-5-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-2,4-dimethylpentyl acetate 
• 77302-11-5 [2R,3S]-(-)-3-hydroxy-2-methylpentanoic acid 

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,6S,7S)-7-acetoxy-4,6-dimethyl-3-nonanone 
• 72485-37-1 (4R^*,6R^*,7S^*)-7-acetyloxy-4,6-dimethyl-3-nonanone 

Relevant articles and documents

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.

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.

Versatile enantioselective synthesis of four diastereomers of serricornin, a sex pheromone of the cigarette beetle, using the SAMP/RAMP-hydrazone method

Serricornin is a female-produced sex pheromone of the cigarette beetle (Lasioderma serricorne), which is a pest of dried foodstuffs and tobacco. We report a versatile and short synthesis of all possible 6,7-syn-isomers of serricornin, including the natura

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%.

Facile synthesis of (-)-serricornin by means of palladium-catalyzed hydrogenolysis of alkenyloxiranes

Chiral synthesis of (-)-serricornin by using palladium-catalyzed stereoselective hydrogenolysis of the alkenyloxirane to the homoallylic alcohol with formic acid as a key step was carried out.

A short stereoselective synthesis of (-)-serricornin

Palladium-catalyzed reduction of (+)-(E)-(6S,7S)-4,6-dimethyl-6,7-epoxy-4-nonen-3-one with formic acid gave (-)-(E)-(6S,7S)-4,6-dimethyl-7-hydroxy-4-nonen-3-one, which was hydrogenated to give (-)-serricornin.

AN EFFICIENT AND STEREOSELECTIVE TOTAL SYNTHESIS OF (+/-)-SERRICORNINE

An efficient and stereoselective total synthesis of (+/-)-serricornine (1) the sex pheromone produced by the female cigarette beetle Lasioderma serricorne F, is described. (3SR,5SR,6SR)-6-Ethyltetrahydro-3,5-dimethyl-2H-pyran-2-one (10) is prepared in 65percent yield through lactonization of a 1:1 mixture of C-2 epimrs of the corresponding esters.

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.

DETERMINATION OF THE ABSOLUTE CONFIGURATION AT C-6 AND C-7 SERRICORNIN (4,6-DIMETHYL-7-HYDROXY-3-NONANONE), THE SEX PHEROMONE OF THE CIGARETTE BEETLE

The absolute configuration at C-6 and C-7 of serricornin was established as (6S, 7S) by synthesizing its (6R, 7S)-erythro and (6R, 7R)-threo isomers.