26564-75-0

Upstream product

• 26409-66-5 (1R,3R,4S)-3-ethoxycarbonylmethyl-p-menthan-3-ol 
• 51744-02-6 ((1R,2S,5R)-1-Hydroxy-2-isopropyl-5-methyl-cyclohexyl)-acetic acid tert-butyl ester 
• 10458-14-7 (2R,5S)-menthone 

Downstream Products

• 869305-59-9 C₁₆H₂₈O₅ 
• 1110772-38-7 (1R,3R,4S)-3-(2'-acetoxyethyl)-p-menthan-3-ol 
• 1110772-39-8 (1R,3R,4S)-3-(2'-acetoxyethyl)-p-menthan-3-yl acetate 

Relevant academic research and scientific papers

P-menthan-3-ol alkylated derivatives and their use as refreshing agents

The invention concerns a 3-alkylated crystallized (1R,4S)-p-menthan-(3)-ol derivative, of formula A or B, wherein: either when R represents hydrogen or a methyl radical, R represents a —(CH2)n-OH where n can be 1, 2 and 3, or when R represents a

3-Alkyl-p-menthan-3-ol derivatives: synthesis and evaluation of their physiological cooling activity

Different 3-alkyl-p-methan-3-ol derivatives provide a strong physiological cooling effect with potential application as food and cosmetic additives. In order to investigate the influence of the chemical structure on the cooling sensation, the stereoselective syntheses of 29 different 3-alkyl-p-methan-3-ol derivatives were accomplished. All the compounds obtained are odorless and were evaluated by taste, considering two sensations: a cooling effect and bitterness. The results of this structure-activity relationship study highlight that compounds with a (1R,4S)-configuration are the isomers with the more intense cooling effect and lower bitterness. In addition, the structure of the 3-alkyl chain affected the latter properties. Increasing the chain length over two carbon atoms does not change the cooling power, but enhances the bitterness with the additional feature that the branched isomers are considerably more bitter than the linear ones. Overall, the 3-alkyl-p-menthan-3-ol isomers with the best quality in terms of high cooling power and low bitterness are (1R,4S)-3-(hydroxymethyl)-p-menthan-3-ol diastereoisomers (-)-38 and (-)-42.