CAS 65253-04-5: (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexanol

Applications (-)-8-Phenylmenthol is used to prepare piperidine-based analogs of cocaine as monoamine reuptake inhibitors. It is also used to prepare quinuclidinyl (fluoroalkyl)benzilate as muscarinic receptor antagonist. References amiz, A., et al.: J. Med. Chem., 43, 1215 (2000); Kiesewetter, D., et al.: J. Med. Chem., 38, 1711 (1995)

This Thermo Scientific Chemicals brand product was originally part of the Acros Organics product portfolio. Some documentation and label information may refer to the legacy brand. The original Acros Organics product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

The product (-)-8-Phenylmenthol is an organic compound with the formula (CH3)2C6H3(OCH2CH3)2. This colorless solid is a chiral secondary alcohol and a popular flavoring agent. It is prepared by condensing menthol with benzaldehyde and hydrochloric acid in the presence of potassium carbonate. The yield of this reaction is typically multigram, depending on the ratio of reactants used. (-)-8-Phenylmenthol has been shown to react with halides, amines, and alkyl halides to form reactive intermediates that can undergo further reactions. Mechanistic studies have shown that these reactions are initiated by the transfer of a proton from the (-)-8-phenylmenthol to a nucleophile at an adjacent carbon atom in the molecule, forming telluronium ion intermediates. These intermediates then undergo chemical transformation to form products via cinnamic acid as well