Cis-p-menthane-3,8-diol | 92471-23-3

• 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: Cis-p-menthane-3,8-diol
• 英文别名: 8-hydroxy-(+)-neomenthol；(1R,3S,4R)-p-menthane-3,8-diol；(1S,2R,5R)-2-(2-hydroxypropan-2-yl)-5-methylcyclohexan-1-ol
• CAS: 92471-23-3
• 化学式: C₁₀H₂₀O₂
• 分子量: 172.268
• InChiKey: LMXFTMYMHGYJEI-HLTSFMKQSA-N

物化性质

• 熔点：
  57 - 61°C
• 沸点：
  267.6±8.0 °C(Predicted)
• 密度：
  1.009±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

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：

  Cis-p-menthane-3,8-diol 生成 [(1S,2R,5R)-2-(2-hydroxypropan-2-yl)-5-methylcyclohexyl] 2-methylpropanoate
  参考文献：
  名称：

  摘要：

  DOI：
• 作为产物：
  描述：

  (+)-香茅醛 在 硫酸 作用下， 生成 Cis-p-menthane-3,8-diol
  参考文献：
  名称：

  挥发性化合物CLXXXIX Sur薄荷醇和少量丙烯酸† ‡

  摘要：

  香茅醛的环化（我）C 10 ħ 18，通过硫酸水溶液O的表达式新-异胡薄荷醇与异胡薄荷醇Ç 10 ħ 18 neomenthoglycol（11）和menthoglycol（111）C 10 H ^ 18 Ò 2，和香茅醇缩醛Ç 20 ħ 36 o 2个这些二醇。

  DOI：

  10.1002/hlca.19640470109

文献信息

• Preparation of biologically active substances and animal and microbial metabolites from menthols, cineoles and kauranes
  作者：Yoshinori Asakawa、Reiko Matsuda、Motoo Tori、Toshihiro Hashimoto

  DOI：10.1016/0031-9422(88)83033-4

  日期：1988.1

  and their structures elucidated by NMR spectroscopy. Some hydroxylated menthols showed plant growth inhibitory and strong mosquito repellent activity. Among the hydroxylated cineoles, microbial and animal metabolites of cineoles were included. From ent-kauranes, a plant growth inhibitory diterpene alcohol, (−)-16α-hydroxy kaurane was obtained along with 16α-kauran-13α-ol.

  摘要 间氯过苯甲酸或干臭氧氧化了六种单萜类化合物 l-薄荷醇、l-乙酸薄荷酯、异薄荷醇、新薄荷醇、1,4-桉树脑和 1,8-桉树脑和一种双萜烃 ent-kaurene。得到各种羟基化产物及其核磁共振谱阐明的结构。一些羟基化薄荷醇显示出植物生长抑制和强烈的驱蚊活性。在羟基化桉树脑中，包括桉树脑的微生物和动物代谢物。从 ent-kaurane 中获得了植物生长抑制性二萜醇 (-)-16α-羟基 kaurane 以及 16α-kauran-13α-ol。
• [EN] 3'-KETOGLYCOSIDE COMPOUND FOR THE SLOW RELEASE OF A VOLATILE ALCOHOL<br/>[FR] COMPOSÉ 3'-CÉTOGLYCOSIDE POUR LA LIBÉRATION LENTE D'UN ALCOOL VOLATIL
  申请人：GLYCOSCIENCE S L

  公开号：WO2021160670A1

  公开（公告）日：2021-08-19

  The present invention relates to a 3'-ketoglycoside compound defined by formula (I) and its use for controlled release of alcohols, in particular alcohols showing an insect repellent effect. It relates also to a process for preparing the 3'-ketoglycoside compound of formula (I). It further relates to a composition comprising a 3'- ketoglycoside compound of formula (I). It relates also to the use of a 3'-ketoglycoside compound of formula (I) for the controlled release of alcohols. It related also to a method of use of such composition.

  本发明涉及由式(I)定义的3'-酮基糖苷化合物及其用于控制释放醇，特别是显示驱虫效果的醇。它还涉及制备式(I)的3'-酮基糖苷化合物的方法。此外，它还涉及包含式(I)的3'-酮基糖苷化合物的组合物。它还涉及使用式(I)的3'-酮基糖苷化合物来控制释放醇。它还涉及使用这种组合物的方法。
• Synthesis ofAristotelia-Type Alkaloids. Part III. (3R,4R)- and (3R,4S)-1-p-menthene-3,8-diol and the corresponding racemates: Preparation and assignment of configuration
  作者：Stefan Burkard、Martin Looser、Hans-J�rg Borschberg

  DOI：10.1002/hlca.19880710122

  日期：1988.2.3

  from 3-methyl-2-cyclohexen-1-one. The relative configuration of the diols, purified via the corresponding cyclocarbonates, was assigned by 1H-NMR spectroscopy and found to be at variance with tentative claims in the literature. Optically active samples of 3 and 4 were prepared by resolution of the racemates with (R)-1-phenylethylamine. The absolute configuration of the resulting diols was determined

  A 1：1混合物中的外消旋的反式-和顺式-1- p -menthene -3,8-二醇（（±） - 3及（±） - 4，RESP）在3个步骤中很容易地制备由3-甲基-2-环己烯-1-酮。通过1 H-NMR光谱法确定了通过相应的环碳酸酯纯化的二醇的相对构型，发现其与文献中的初步主张不符。的光学活性的样品3和4是由（与拆分外消旋物制备ř）-1-苯基乙胺。通过与已知绝对构型的标准品的化学相关性确定所得二醇的绝对构型。
• Eucalyptus as biomass. Novel compounds from microbial conversion of 1,8-cineole.
  作者：Hiroyuki NISHIMURA、Yoshiaki NOMA、Junya MIZUTANI

  DOI：10.1271/bbb1961.46.2601

  日期：——

  Conversion of 1, 8-cineole (1) by a strain of Aspergillus niger was investigated in connection with the biomass utilization of Eucalyptus plants. Two novel alcohols, 3-exo-(5) and 3-endo-hydroxycineole (6) were isolated from the culture broth and identified by interpretations of their spectral data. Furthermore, hydrogenolysis of 6 afforded p-methane-3, 8-e"-diol (8) which has been isolated as a plant growth inhibitor from Eucalyptus citriodora.

  研究了黑曲霉菌株对 1, 8-桉树脑 (1) 的转化与桉树植物的生物质利用的关系。从培养液中分离出两种新型醇：3-exo-(5) 和 3-endo-羟基桉树脑 (6)，并通过对其光谱数据的解释进行鉴定。此外，6 的氢解得到对-甲烷-3, 8-e"-二醇 (8)，它已作为植物生长抑制剂从柠檬桉中分离出来。
• Effect of the Stereoselectivity of <i>para</i>-Menthane-3,8-diol Isomers on Repulsion toward <i>Aedes albopictus</i>
  作者：Lorenzo G. Borrego、Niryhasinandrianina Ramarosandratana、Erwann Jeanneau、Estelle Métay、Voahangy V. Ramanandraibe、Mbolatiana T. Andrianjafy、Marc Lemaire

  DOI：10.1021/acs.jafc.1c03897

  日期：2021.9.22

  hydrogen-bond patterns between cis or trans isomers. The present paper demonstrates that (1R)-(+)-cis-PMD has the highest repellency index using a new evaluation system for 24 h. (1S)-(−)-cis-PMD has somewhat lower and (1S)-(+)-trans-PMD and (1R)-(−)-trans-PMD have a slight effect. Volunteer tests show that (1R)-(+)-cis-PMD is the most efficient. This effect could be ascribed to the interaction of PMD/insect

  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