80482-64-0

Basic information

• Product Name: (1S,2S,5R)-2-isopropyl-5-methylcyclohexanecarboxaldehyde
• Synonyms: (1S,2S,5R)-2-isopropyl-5-methylcyclohexanecarboxaldehyde
• CAS NO: 80482-64-0
• Molecular Weight: 168.279
• Mol File: 80482-64-0.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (1S,2S,5R)-2-isopropyl-5-methylcyclohexanecarboxaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2S,5R)-2-isopropyl-5-methylcyclohexanecarboxaldehyde(80482-64-0)
• EPA Substance Registry System: (1S,2S,5R)-2-isopropyl-5-methylcyclohexanecarboxaldehyde(80482-64-0)

Safety Data

• Hazardous Substances Data: 80482-64-0(Hazardous Substances Data)

Upstream product

• 2216-51-5 (-)-menthol 
• 61548-81-0 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl methanesulfonate 
• 184178-86-7 (1S,4S,7R)-4-isopropyl-7-methyl-1-oxaspiro[2.5]octane 
• 180978-26-1 (1S,2S,5R)-1-cyano-2-isopropyl-5-methylcyclohexane 
• 1217664-77-1 (1R,2R,5S)-2-isopropyl-5-methylcyclohexane-1-carbonitrile 
• 142921-58-2 (1S,2R,5S)-(+)-menthol Mesylate 
• 15356-60-2 (1S,2R,5S)-(+)-menthol 

Downstream Products

• 70985-58-9 (1S,2S,5R)-2-isopropyl-5-methylcyclohexane-1-carboxylic acid 
• 1207722-22-2 (1S,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexanecarbonyl Chloride 
• 485843-44-5 (1S,2R,5S)-2-isopropyl-5-methylcyclohexane-1-carboxaldehyde 
• 62309-29-9 (1S,2R,5S)-2-isopropyl-5-methylcyclohexane-1-carboxylic acid 
• 108235-79-6 (1S,2R,5S)-2-isopropyl-5-methylcyclohexane-1-carbonyl chloride 

Relevant articles and documents

Synthesis, characterization and hplc analysis of the (1S,2S,5R)-diastereomer and the enantiomer of the clinical candidate ar-15512

AR-15512 (formerly known as AVX-012 and WS-12) is a TRPM8 receptor agonist currently in phase 2b clinical trials for the treatment of dry eye. This bioactive compound with menthol-like cooling activity has three stereogenic centers, and its final structure and absolute configuration, (1R,2S,5R), have been previously solved by cryo-electron microscopy. The route of synthesis of AR-15512 has also been reported, revealing that epimerization processes at the C-1 can occur at specific stages of the synthesis. In order to confirm that the desired configuration of AR-15512 does not change throughout the process and to discard the presence of the enantiomer in the final product due to possible contamination of the initial starting material, both the enantiomer of AR-15512 and the diastereomer at the C-1 were synthesized and fully characterized. In addition, the absolute configuration of the (1S,2S,5R)-diastereomer was determined by X-ray crystallographic analysis, and new HPLC methods were designed and developed for the identification of the two stereoisomers and their comparison with the clinical candidate AR-15512.

Process for making neo-enriched p-menthane compounds

A process for making neo-enriched p-menthane intermediates is disclosed. Lewis acid-catalyzed rearrangement of an oxaspiro compound provides an aldehyde mixture comprising normal (II) and neo (III) p-menthane-3-aldehydes: with the neo aldehyde (III) as the major product. The aldehyde mixture is readily oxidized to provide the corresponding carboxylic acids, and the acids are easily converted to a host of neo-enriched p-menthane esters or amides. The esters and amides are valuable as physiological coolants.