115073-43-3

Basic information

• Product Name: (R)-3-methyl-2-cyclohexenyl acetate
• Synonyms: (R)-3-methyl-2-cyclohexenyl acetate
• CAS NO: 115073-43-3
• Molecular Weight: 154.209
• Mol File: 115073-43-3.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (R)-3-methyl-2-cyclohexenyl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-3-methyl-2-cyclohexenyl acetate(115073-43-3)
• EPA Substance Registry System: (R)-3-methyl-2-cyclohexenyl acetate(115073-43-3)

Safety Data

• Hazardous Substances Data: 115073-43-3(Hazardous Substances Data)

Upstream product

• 108-05-4 vinyl acetate 
• 21378-21-2 3-methylcyclohex-2-en-1-ol 
• 108-22-5 Isopropenyl acetate 
• 75411-49-3 3-methyl-2-cyclohexen-1-yl acetate 
• 108-82-7 2,6-dimethyl-4-heptanol 

Downstream Products

• 112837-26-0 (1R,2R,3S)-2,3-epoxy-3-methylcyclohexyl tosylate 
• 112837-29-3 (S)-(-)-1-methyl-2-cyclohexen-1-ol 
• 18890-22-7 (R)-3-methylcyclohex-2-en-1-ol 
• 60733-10-0 (S)-seudenol 

Relevant articles and documents

Enzymatic Kinetic Resolution of 2-Cyclohexen-1-ol Derivatives

Optically active (S)-2-cyclohexen-1-ol derivatives and their enantiomeric (R)-acetates have been obtained in high enantiomeric excesses by enzymatic kinetic acetylation catalyzed by lipase AK.

Discovery and Design of Family VIII Carboxylesterases as Highly Efficient Acyltransferases

Promiscuous acyltransferase activity is the ability of certain hydrolases to preferentially catalyze acyl transfer over hydrolysis, even in bulk water. However, poor enantioselectivity, low transfer efficiency, significant product hydrolysis, and limited substrate scope represent considerable drawbacks for their application. By activity-based screening of several hydrolases, we identified the family VIII carboxylesterase, EstCE1, as an unprecedentedly efficient acyltransferase. EstCE1 catalyzes the irreversible amidation and carbamoylation of amines in water, which enabled the synthesis of the drug moclobemide from methyl 4-chlorobenzoate and 4-(2-aminoethyl)morpholine (ca. 20 % conversion). We solved the crystal structure of EstCE1 and detailed structure–function analysis revealed a three-amino acid motif important for promiscuous acyltransferase activity. Introducing this motif into an esterase without acetyltransferase activity transformed a “hydrolase” into an “acyltransferase”.

Pheromone Synthesis, CXI. - An Enzyme-Mediated Synthesis of Both Enantiomers of Seudenol and 1-Methyl-2-cyclohexen-1-ol, the Aggregation Pheromones of Dendroctonus pseudotsugae

Enzymatic resolution of seudenol acetate by pig liver esterase has led to an efficient preparation of both the enantiomers of seudenol and 1-methyl-2-cyclohexen-1-ol, the aggregation pheromones of the Douglas-fir beetle Dendroctonus pseudotsugae Hopkins.