485843-44-5

Basic information

• Product Name: Cyclohexanecarboxaldehyde, 5-methyl-2-(1-methylethyl)-, (1R,2S,5R)-rel- (9CI)
• Synonyms: Cyclohexanecarboxaldehyde, 5-methyl-2-(1-methylethyl)-, (1R,2S,5R)-rel- (9CI)
• CAS NO: 485843-44-5
• Molecular Formula: C11H20O
• Molecular Weight: 168.2759
• Product Categories: ISOPROPYL
• Mol File: 485843-44-5.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Cyclohexanecarboxaldehyde, 5-methyl-2-(1-methylethyl)-, (1R,2S,5R)-rel- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclohexanecarboxaldehyde, 5-methyl-2-(1-methylethyl)-, (1R,2S,5R)-rel- (9CI)(485843-44-5)
• EPA Substance Registry System: Cyclohexanecarboxaldehyde, 5-methyl-2-(1-methylethyl)-, (1R,2S,5R)-rel- (9CI)(485843-44-5)

Safety Data

• Hazardous Substances Data: 485843-44-5(Hazardous Substances Data)

Upstream product

• 39668-86-5 menthanecarboxylic acid 
• 343791-47-9 1-Isopropyl-2-[1-methoxy-meth-(E)-ylidene]-4-methyl-cyclohexane 
• 7647-01-0 hydrogenchloride 
• 28953-96-0 2-chloro-1-isopropyl-4-methyl-cyclohexane 
• 54556-12-6 2-isopropyl-5-methyl-cyclohexanecarbonitrile 
• 15356-60-2 (1S,2R,5S)-(+)-menthol 
• 142921-58-2 (1S,2R,5S)-(+)-menthol Mesylate 
• 1217664-77-1 (1R,2R,5S)-2-isopropyl-5-methylcyclohexane-1-carbonitrile 
• 4279-03-2 ethoxymethylmagnesium chloride 
• 17627-49-5 (-)-menthone 
• 289909-56-4 tert-Butyl-[(E)-(R)-4-isopropyl-6-((1S,2S,5R)-2-isopropyl-5-methyl-cyclohexyl)-4-methyl-hex-5-enyloxy]-dimethyl-silane 
• 80447-43-4 (2S,5R)-1-Methoxymethylen-2-isopropyl-5-methylcyclohexan 
• 10458-14-7 (2R,5S)-menthone 
• 184178-86-7 (1S,4S,7R)-4-isopropyl-7-methyl-1-oxaspiro[2.5]octane 

Downstream Products

• 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 
• 474380-45-5 (E)-(S)-1-((1R,2S,5R)-2-Isopropyl-5-methyl-cyclohexyl)-3-methyl-oct-2-en-1-ol 
• 474380-58-0 (E)-(R)-1-((1R,2S,5R)-2-Isopropyl-5-methyl-cyclohexyl)-3-methyl-oct-2-en-1-ol 
• 868744-85-8 (E)-(R)-1-((1R,2S,5R)-2-Isopropyl-5-methyl-cyclohexyl)-3-phenyl-prop-2-en-1-ol 
• 868744-93-8 (E)-(S)-1-((1R,2S,5R)-2-Isopropyl-5-methyl-cyclohexyl)-3-phenyl-prop-2-en-1-ol 
• 1207722-22-2 (1S,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexanecarbonyl Chloride 

Relevant articles and documents

A new approach to the stereoselective synthesis of trans-3-carbamoyl-β-lactam moieties

One-pot synthesis of optically active 1,4-disubstituted-3-carbamoyl-azetidinones from 5-[(N-arylamino)(hydroxyl)methylene]-2,2-dimethyl-1,3-dioxa-4,6-diones and chiral aldimines is achieved via thermal generation of carbamoyl ketenes and subsequent [2+2] cycloaddition. Three possible chiral induction approaches were tested and (R)-(+)-1-phenylethylamine was confirmed as the best chiral auxiliary. Among the four possible diastereoisomers, only two with significant excess of one were formed.

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.

COMPOUNDS USEFUL AS MODULATORS OF TRPM8

The present invention includes compounds useful as modulators of TRPM8, such as compounds of Formulae (Ia), (Ib) and (Ic), and the subgenus and species thereof; personal products containing those compounds; and the use of those compounds and the personal products, particularly the use of increasing or inducing chemesthetic sensations, such as cooling or cold sensations.