145679-16-9

Upstream product

• 145621-79-0 4-((S)-2-Acetoxy-1-methyl-ethyl)-benzoic acid methyl ester 
• 145621-74-5 (S)-(-)-p-(2-acetoxy-1-methylethyl)benzyl chloride 
• 145621-77-8 Acetic acid (S)-2-(4-formyl-phenyl)-propyl ester 
• 50373-50-7 acetic acid (S)-(-)-2-phenyl-1-propanol ester 
• 37778-99-7 (S)-2-phenyl-1-propanol 
• 28645-07-0 (S)-methyl 2-phenylpropanoate 
• 7782-24-3 (S)-2-Phenylpropionic acid 
• 145621-80-3 methyl (S)-(-)-p-(2-hydroxy-1-methylethyl)benzoate 
• 145621-78-9 4-((S)-2-Acetoxy-1-methyl-ethyl)-benzoic acid 
• 145621-75-6 (S)-(-)-p-(2-acetoxy-1-methylethyl)benzyl alcohol 

Relevant academic research and scientific papers

The enantioselective metabolism of p-cymene in rabbits

p-Cymene (1) was metabolized in rabbits and the following four optically active metabolites, 2-(p-tolyl)-1-propanol (3': R/S = 65:35), 2-(p-tolyl)propanoic acid (5': R/S = 0:100), p-(2-hydroxy-1-methylethyl)benzoic acid (6': R/S = 91:9) and p-(1-carboxyethyl)benzoic acid (8': R/S = 30:70), were isolated in addition to three optically inactive metabolites, 2-(p-tolyl)-2-propanol (2), p-isopropylbenzoic acid (4'), and p-(1-hydroxy-1-methylethyl)benzoic acid (7'). The presumed metabolic pathways of p-cymene in rabbits were confirmed by the administration of the intermediate metabolites (2, 3', 4', and 5'). The enantiomeric ratios of the metabolites, 3' and 6', suggested that ω-hydroxylations of the isopropyl group in 1 and 4' occurred preferentially at the pro-S methyl group. In the metabolism of 1, the S-isomers are predominant in the propanoic acid derivatives, but the R-isomers are rich in the propanol derivatives. It is of interest that the metabolism of 4', however, produced predominantly the corresponding propanol derivative (6'; R/S = 91:9) and propanoic acid derivative (8'; R/S = 80:20) possessing the same R-configuration. Some optically active p-cymene derivatives were also synthesized as standard compounds.