(1S,3R,4S)-p-menthane-3,8-diol | 19956-48-0

• 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: (1S,3R,4S)-p-menthane-3,8-diol
• 英文别名: 1alpha,3beta,4beta-p-Menthane-3,8-diol；(1R,2S,5S)-2-(2-hydroxypropan-2-yl)-5-methylcyclohexan-1-ol
• CAS: 19956-48-0
• 化学式: C₁₀H₂₀O₂
• 分子量: 172.268
• InChiKey: LMXFTMYMHGYJEI-XHNCKOQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,3R,4S)-p-menthane-3,8-diol 在 吡啶 、 chromium(VI) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 以89%的产率得到(+)-(2R,5S)-2-(1-hydroxy-1-methylethyl)-5-methylcyclohexanone
  参考文献：
  名称：

  Chiral dioxomolybdenum(VI) complexes for enantioselective alkene epoxidation

  摘要：

  Chiral dioxomolybdenum(M) complexes of the type MoO2Cl2(L*) (L* = oxime), MoO2(THF)(2)L* (L* = cis-p-menthane-3,8-diol) and MoO2Cl(THF)L* (L* = 8-phenylthioneomenthol and 8-phenylthioisoneomenthol) have been prepared in good yields by reacting MoO2Cl2(THF)(2) with the appropriate chiral organic bidentate O,O-, O,N- and O,S-ligands. The complexes were characterised by solution NMR (H-1, C-13, Mo-95) and IR spectroscopy as well as elementary analysis, and were evaluated as catalysts in solution for the asymmetric epoxidation of cis-beta -methylstyrene by tert-butylhydroperoxide (TBHP). The cis-diol complex shows high catalytic activity and enantiomeric excesses of up to 25%. An attempt was made to immobilise the complex MoO2(THF)Cl[(-)-8-phenylthioneomenthol] within the channels of MCM-41 mesoporous silica by using a tethering ligand [L = NC(CH2)(3)Si(OEt)(3)]. The material was characterised by powder X-ray diffraction (XRD), IR spectroscopy and magic-angle-spinning (MAS) NMR (C-13, Si-29). Catalytic examinations demonstrated that it was active in the epoxidation of cyclooctene by TBHP. (C) 2001 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(00)00790-7
• 作为产物：
  描述：

  (-)-香茅醛 在 硫酸 作用下， 以 水 、 丙酮 为溶剂， 反应 7.0h， 以64%的产率得到(1S,3R,4S)-p-menthane-3,8-diol
  参考文献：
  名称：

  对-薄荷烷-3,8-二醇异构体的立体选择性对白纹伊蚊排斥的影响

  摘要：

  媒介传播疾病每年导致约 700,000 人死亡。驱虫剂是限制它们的策略之一。对薄荷烷-3,8-二醇 (PMD) 是一种天然化合物，是传统合成驱虫剂最有前途的替代品之一。这项工作描述了一种从对映体纯香茅醛合成 PMD 的每种非对映异构体的非对映发散方法，并研究了它们对白纹伊蚊的驱避活性。我们发现顺式-PMD是香茅醛环化的动力学控制产物，而反式-PMD是热力学控制产物。晶体的 X 射线衍射分析突出了顺式或反式之间氢键模式的一些差异异构体。本论文使用新的评估系统 24 小时证明 (1 R )-(+)- cis -PMD 具有最高的排斥指数。(1 S )-(-)- cis -PMD 略低，(1 S )-(+)- trans -PMD 和 (1 R )-(-)- trans -PMD 有轻微影响。志愿者测试表明 (1 R )-(+)- cis -PMD 是最有效的。这种效应可归因于 PMD/昆虫气味

  DOI：

  10.1021/acs.jafc.1c03897

文献信息

• Biotransformations of Terpenes by Fungi from Amazonian<i>Citrus</i>Plants
  作者：Maria Gabriela Moreno Rueda、Alessandra Guerrini、Pier Paolo Giovannini、Alessandro Medici、Alessandro Grandini、Gianni Sacchetti、Paola Pedrini

  DOI：10.1002/cbdv.201300112

  日期：2013.10

  The biotransformations of (RS)-linalool (1), (S)-citronellal (2), and sabinene (3) with fungi isolated from the epicarp of fruits of Citrus genus of the Amazonian forest (i.e., C. limon, C. aurantifolia, C. aurantium, and C. paradisiaca) are reported. The more active strains have been characterized, and they belong to the genus Penicillium and Fusarium. Different biotransformation products have been

  （RS）-芳樟醇（1），（S）-香茅醛（2）和sa香烯（3）的生物转化是从亚马逊森林柑橘类水果的果皮（即C. limon，C.报道了桔梗，极光梭菌和天堂梭状芽胞杆菌。已经鉴定了更具活性的菌株，它们属于青霉属和镰刀菌属。取决于真菌和底物，已经获得了不同的生物转化产物。（RS）-Linalool（1）与镰刀菌属（Fusarium sp。）一起提供了（E）-和（Z）-呋喃萘酚氧化物（分别为7和8，分别为39和37％的产率）。（1D2），6-甲基庚-5-烯-2-酮（4; 49％）与藤蔓镰刀菌和1-甲基-1-（4-甲基戊基）环氧乙烷甲醇（6; 42％）与同心镰刀菌。（S）-香茅醛（2）得到镰刀菌属物种的（S）-香茅酚（12; 36-76％）和（S）-香茅酸（11; 5-43％），而非对映异构体对薄荷脑3，与青霉一起获得了作为主要产物的8-二醇13和14（产率分别为20％和50％）。最后，镰刀菌属物种和P
• Synthesis of <i>p</i>-menthane-3,8-diol from citronellal over lignin-derived carbon acid catalysts
  作者：Irwan Kurnia、Akihiro Yoshida、Nichaboon Chaihad、Tirto Prakoso、Shasha Li、Xiao Du、Xiaogang Hao、Abuliti Abudula、Guoqing Guan

  DOI：10.1039/d0nj00919a

  日期：——

  Sustainable carbon acid catalysts exhibited high-performance in the conversion of citronellal to p-menthane-3,8-diol via a carbocation-hydration pathway.

  可持续的碳酸催化剂在柠檬醛转化为对薄荷醇-3,8-二醇的过程中表现出高性能，通过一个碳阳离子水合路径实现。
• P-MENTHANE-3,8-DIOL ISOMER MIXTURE, COOLING SENSATION COMPOSITION COMPRISING THE SAME, AND PRODUCT COMPRISING THE COOLING SENSATION COMPOSITION
  申请人：Komatsuki Yasuhiro

  公开号：US20140219931A1

  公开（公告）日：2014-08-07

  The present invention relates to a p-menthane-3,8-diol isomer mixture 50% by mass or more of which is constituted of (1S)-isomers and a cooling sensation composition containing this mixture. The present invention also relates to a flavor and/or fragrance composition, food, beverage, cosmetic, daily use product, oral cavity composition, or pharmaceutical containing the p-menthane-3,8-diol isomer mixture in an amount of 0.0001 to 90% by mass.

  本发明涉及一种p-薄荷烷-3,8-二醇异构体混合物，其中50%或更多的质量由(1S)-异构体构成，以及含有该混合物的冷感组合物。本发明还涉及一种口味和/或香料组合物、食品、饮料、化妆品、日常用品、口腔组合物或药物，其中p-薄荷烷-3,8-二醇异构体混合物的质量占0.0001至90%。
• Biotransformation of (−)- and (+)-neomenthols and isomenthol by Aspergillus niger
  作者：Hironobu Takahashi、Yoshiaki Noma、Masao Toyota、Yoshinori Asakawa

  DOI：10.1016/s0031-9422(00)86876-4

  日期：1994.4.19

  Three menthols, (+)- and(-)-neomenthols and(+)-isomenthol were biotransformed by Aspergillus niger which converted nonspecifically (-)- and (+)-neomenthols to mere hydroxylated compounds, whereas, (+)-isomenthol was smoothly converted into 1-hydroxyisomenthol and 6-hydroxyisomenthol by the same fungus.
• Biotransformation of Citronellal by <i>Solanum </i><i>a</i><i>viculare</i> Suspension Cultures:  Preparation of <i>p</i>-Menthane-3,8-diols and Determination of Their Absolute Configurations
  作者：Tomáš Vaněk、Michal Novotný、Radka Podlipná、David Šaman、Irena Valterová

  DOI：10.1021/np0301588

  日期：2003.9.1

  Citronellal was transformed by Solanum aviculare suspension cultures to menthane-3,8-diols. cis-Menthane-3,8-diol dominated over the trans-isomer (39% and 15%, respectively). Absolute configurations of menthane-3,8-diols were assigned by critical analysis of H-1 and F-19 NMR spectra of prepared esters with 2-methoxy-2-phenyl-3,3,3-trifluoropropanoic acid. Citronellol and isopulegol were other products of the transformation (23% and 17%, respectively). The reaction course was identical for both citronellal enantiomers.