(1R,3S,4S)-3-(hydroxymethyl)-3-(2'-hydroxyethoxy)-p-menthane | 869305-57-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1R,3S,4S)-3-(hydroxymethyl)-3-(2'-hydroxyethoxy)-p-menthane
• 英文别名: 2-[(1S,2S,5R)-1-(hydroxymethyl)-5-methyl-2-propan-2-ylcyclohexyl]oxyethanol
• CAS: 869305-57-7
• 化学式: C₁₃H₂₆O₃
• 分子量: 230.348
• InChiKey: FAMRFDSQRAQJFX-FRRDWIJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (1R,2S,5R)-1-(allyloxy)-2-isopropyl-5-methyl-1-vinylcyclohexane 在 臭氧 、 sodium tetrahydroborate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 以7.4 g的产率得到(1R,3S,4S)-3-(hydroxymethyl)-3-(2'-hydroxyethoxy)-p-menthane
  参考文献：
  名称：

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

  摘要：

  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 diasteroisomers (-)-38 and (-)-42. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.10.022

文献信息

• P-menthan-3-ol alkylated derivatives and their use as refreshing agents
  申请人：Joulain Daniel

  公开号：US20090163733A1

  公开（公告）日：2009-06-25

  The invention concerns a 3-alkylated crystallized (1R,4S)-p-menthan-(3)-ol derivative, of formula A or B, wherein: either when R<2> represents hydrogen or a methyl radical, R<1> represents a —(CH2)n-OH where n can be 1, 2 and 3, or when R<2> represents a hydroxy radical, R<1> represents a methyl radical or a —(CH2)n-OH group where n can be 1, 2 and 3. The invention also concerns methods for preparing same, and perfume, cosmetic or food compositions containing said derivative.

  该发明涉及一种3-烷基化结晶(1R,4S)-p-薄荷烷-(3)-醇衍生物，化学式为A或B，其中：当R<2>代表氢或甲基基团时，R<1>代表—(CH2)n-OH，其中n可以是1、2和3；或者当R<2>代表羟基时，R<1>代表甲基基团或—( )n-OH基团，其中n可以是1、2和3。该发明还涉及制备该衍生物的方法，以及含有该衍生物的香水、化妆品或食品组合物。
• DÉRIVES ALKYLES DU P-MENTHAN-3-OL ET LEUR UTILISATION COMME AGENTS REFRAÎCHISSANTS
  申请人：Robertet S.A.

  公开号：EP1791801B1

  公开（公告）日：2015-11-11
• US7816566B2
  申请人：——

  公开号：US7816566B2

  公开（公告）日：2010-10-19