204326-53-4

Basic information

• Product Name: 4-((2R,1S,5S)-2-isopropyl-5-methylcyclohexyloxy)-4-oxobutanoic acid
• Synonyms: 4-((2R,1S,5S)-2-isopropyl-5-methylcyclohexyloxy)-4-oxobutanoic acid
• CAS NO: 204326-53-4
• Molecular Weight: 256.342
• Mol File: 204326-53-4.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 4-((2R,1S,5S)-2-isopropyl-5-methylcyclohexyloxy)-4-oxobutanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-((2R,1S,5S)-2-isopropyl-5-methylcyclohexyloxy)-4-oxobutanoic acid(204326-53-4)
• EPA Substance Registry System: 4-((2R,1S,5S)-2-isopropyl-5-methylcyclohexyloxy)-4-oxobutanoic acid(204326-53-4)

Safety Data

• Hazardous Substances Data: 204326-53-4(Hazardous Substances Data)

Upstream product

• 108-30-5 succinic acid anhydride 
• 15356-60-2 (1S,2R,5S)-(+)-menthol 
• 6070-20-8 dl-menthyl succinate 
• 15356-70-4 menthol 

Downstream Products

• 1415314-31-6 3-benzyl-4-((2R,1S,5S)-2-isopropyl-5-methylcyclohexyloxy)-4-oxobutanoic acid 

Relevant articles and documents

Production of l-menthyl acetate through kinetic resolution by?Candida cylindracea lipase: effects of alkaloids as additives

Abstract: Enzymatic transesterification of dl-menthol with vinyl acetate in tert-Butyl methyl ether (TBME) catalyzed by Candida cylindracea lipase (CCL) was carried out in the presence of cinchona alkaloid as additive. The effects of various reaction parameters, such as lipase nature and loading, acylating agent, molecular sieves, solvents and various additives, on the reactivity as well as on the enantioselectivity were investigated. A significant improvement of CCL reactivity has been recorded after using cinchona alkaloid as additive in TBME. A high enantiomeric ratio (E = 80) was achieved when 30?mol% of quinidine was added, and l-(-)-menthyl acetate was obtained with 93% optical purity and 49% conversion. This process was easily applied to gram-scale quantities, using commercially inexpensive lipase, providing high yield optically active menthol under mild experimental conditions. Graphical abstract: [Figure not available: see fulltext.].

Enzymatic production of l-menthol by a high substrate concentration tolerable esterase from newly isolated Bacillus subtilis ECU0554

Enzymatic preparation of l-menthol has been attracting much attention in the flavor and fragrance industry. A new ideal strain, Bacillus subtilis ECU0554, which exhibited high hydrolytic activity and excellent enantioselectivity towards l-menthyl ester, has been successfully isolated from soil samples through enrichment culture and identified as Bacillus subtilis by 16S rDNA gene sequencing. The esterase extracted from B. subtilis ECU0554 (BSE) showed the best catalytic properties (E > 200) for dl-menthyl acetate among the five menthyl esters examined. Enantioselective hydrolysis of 100 mM dl-menthyl acetate at 30°C and pH 7.0, using crude BSE as biocatalyst and 10% ethanol (v/v) as cosolvent, resulted in 49.0% conversion (3 h) and 98.0% ee for the l-menthol produced, which were much better than those using commercial enzymes tested. Moreover, BSE exhibited strong tolerance against high substrate concentration (up to 500 mM), and the concentration of l-menthol produced could reach as high as 182 mM, and more importantly, the optical purity of l-menthol produced was kept above 97% ee, which were not found in previous reports. These results imply that BSE is a potentially promising bio-catalyst for the large-scale enzymatic preparation of l-menthol. Using this excellent biocatalyst, the enzymatic production of l-menthol will become a mild, efficient, inexpensive and easy-to-use "green chemistry" methodology.