柳杉二醇 | 4666-84-6

• 物质功能分类: 天然产物 - 倍半萜
• 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
• 中文名称: 柳杉二醇
• 英文名称: cryptomeridiol
• 英文别名: 5αH-eudesmane-4α,11-diol；eudesmane-4α,11-diol；γ-eudesmol；cryptomeridol；proximadiol；(-)-Selina-4α,11-diol；(1R,4aR,7R,8aR)-7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-2,3,4,5,6,7,8,8a-octahydronaphthalen-1-ol
• CAS: 4666-84-6
• 化学式: C₁₅H₂₈O₂
• 分子量: 240.386
• InChiKey: LKKDASYGWYYFIK-QHSBEEBCSA-N

物化性质

• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。
• 熔点：
  137.5 °C(Solv: benzene (71-43-2))
• 沸点：
  317.3±10.0 °C(Predicted)
• 密度：
  1.019±0.06 g/cm3(Predicted)
• LogP：
  3.090 (est)
• 保留指数：
  1780

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• 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

安全信息

• 储存条件：
  储存条件：2-8℃，干燥处，密封保存。

制备方法与用途

Cryptomeridiol可以从Phaulopsis imbricata中分离获得。研究显示， Cryptomeridiol在α-MSH刺激的B16黑色素瘤细胞中具有显著的黑色素生成抑制活性。

反应信息

• 作为产物：
  描述：

  beta-桉叶醇 在 lithium aluminium tetrahydride 、 magnesium bis(monoperoxyphthalate)hexahydrate 作用下， 生成 柳杉二醇
  参考文献：
  名称：

  菊苣（Cichorium intybus）对（±）-4,8-​​二甲基环癸-3（E），7（E）-dien-1β-ol和（+）-hedycaryol的生物转化

  摘要：

  已经研究了新鲜菊苣的根悬浮液对合成的（E，E）-1,5-环癸二烯醇5和（+）-hedycaryol（11）的生物转化。孵育5具有根部悬浮液，得到一个2：差向异构eudesmanediols的1:1混合物图7a和7b中，而11被选择性地转化成cryptomeridiol（12）。建议对获得的结果进行解释。

  DOI：

  10.1016/0040-4020(94)00938-q

文献信息

• Structures and Spasmolytic Activities of Derivatives from Sesquiterpenes of Alpinia speciosa and Alpinia japonica.
  作者：Makoto MORITA、Hiroshi NAKANISHI、Hiroshi MORITA、Susumu MIHASHI、Hideji ITOKAWA

  DOI：10.1248/cpb.44.1603

  日期：——

  Sesquiterpenes isolated from Alpinia speciosa and Alpinia japonica, and their derivatives were found to inhibit histamine- or barium chloride-induced contraction of excised guinea pig ileum when tested by the Magnus method. Major spasmolytic principles contained in those extracts were the sesquiterpenes, β-eudesmol, nerolidol, humulene epoxide II and 4α-hydroxydihydroagarofuran. Relationships between the chemical structures of the sesquiterpenes and their derivatives, and their spasmolytic activities were discussed.

  通过马格努斯法测试发现，从白山药和白山药中分离出的倍半萜及其衍生物可抑制组胺或氯化钡引起的切除豚鼠回肠收缩。这些提取物所含的主要解痉成分是倍半萜、β-桉叶油醇、橙花叔醇、环氧化葎草烯 II 和 4α-羟基二氢豨莶草醚。讨论了倍半萜及其衍生物的化学结构与它们的解痉活性之间的关系。
• Sesquiterpenes from leaves of Cryptomeria japonica
  作者：Wen-Chiung Su、Jim-Min Fang、Yu-Shia Cheng

  DOI：10.1016/0031-9422(95)00013-w

  日期：1995.6

  Abstract Twenty-seven sesquiterpenes were isolated from leaves of Cryptomeria japonica . The new compounds included elem-1-en-4,11-diol, 11-acetoxyeudesman-4α-ol, eudesmane-5α,11-diol, 3-eudesmene-1β,11-diol, 1β-acetoxy-3-eudesmen-11-ol, 4-eudesmene-1β,11-diol, 1β-acetoxy-4-eudesmen-11-ol, 7-epi-γ-eudesmol, 7-epi-4-eudesmene-1β,11-diol, 1β-acetoxy-4(15)-eudesmen-11-ol. Their structures were determined

  摘要 从银杏叶中分离得到27个倍半萜。新化合物包括elem-1-en-4,11-diol、11-acetoxyeudesman-4α-ol、eudesmane-5α,11-diol、3-eudesmene-1β,11-diol、1β-acetoxy-3-eudesmen- 11-ol, 4-eudesmene-1β,11-diol, 1β-acetoxy-4-eudesmen-11-ol, 7-epi-γ-eudesmol, 7-epi-4-eudesmene-1β,11-diol, 1β- acetoxy-4(15)-eudesmen-11-ol。它们的结构是通过化学和光谱方法确定的。
• New Olefinic Cyclizations by Oxymetallation. Conversion of (?)-elemol to (?)-selina-4?, 11-diol (cryptomeridiol) and (?)-guai-1 (10)-ene-4?, 11-diol
  作者：Walter Renold、G�nther Ohloff、Torbj�rn Norin

  DOI：10.1002/hlca.19790620409

  日期：1979.6.8

  Acetoxythallation of (−)-elemol acetate (1b) yields a diacetate 2b which after treatment with lithium aluminium hydride gives (−)-guai-1 (10)-ene-4α, 11-diol (2a). (−)-Elemol (1a) is converted to (−)-selina-4α, 11-diol (9, cryptomeridiol) by hydroxymercuration followed by reductive demercuration. (+)-γg-Elemene (5) similarly yields (+)-selin-7(11)-en-4α-ol (11, juniper camphor). The stereochemistry

  （-）-醋酸乙烯酯（1b）的乙酰氧基化产生二乙酸酯2b，其在用氢化铝锂处理后得到（-）-guai-1（10）-ene-4α，11-二醇（2a）。（-）-Elemol（1a）通过羟基汞化然后还原性脱汞而被转化为（-）-selina-4α，11-二醇（9，隐美三醇）。（+）-γg-榄香烯（5）类似地产生（+）-selin-7（11）-en-4α-ol（11，杜松樟脑）。讨论了这些金属盐诱导的烯烃环化的立体化学，机理及其生物遗传学意义。
• Dry deodorant containing a sesquiterpene alcohol and zinc oxide
  申请人：Brahms John

  公开号：US20050191257A1

  公开（公告）日：2005-09-01

  A suspension product for reducing wetness under the arm which product comprises in % by weight based on the entire weight of the product: (a) 0.01-20% of a superabsorbent polymer with water absorbing capacity between 10-1000 g water/g superabsorber in the absence of added sodium chloride; (b) 0.05-10% of a sesquiterpene material; (c) 0.05-10% of a small particle size zinc oxide having a particle size range of 0.02-200 microns; (d) 2-88% of a volatile silicone, wherein the product is not made with any separately added water.

  一种用于减少腋下潮湿的悬浮产品，该产品按重量计，以产品总重量的百分比计， 包括：(a) 0.01-20%的超吸收聚合物，在不添加氯化钠的情况下，其吸水能力在 10-1000 克水/克超吸收剂之间；(b) 0.05-10%的倍半萜材料；(c) 0.05-10%的小粒径氧化锌，其粒径范围为 0.02-200 微米；(d) 2-88% 的挥发性有机硅，其中该产品不使用任何单独添加的水。
• Short and efficient hemisynthesis of α-eudesmol and cryptomeridiol
  作者：Mohamed Tebbaa、Ahmed El Hakmaoui、Ahmed Benharref、Mohamed Akssira

  DOI：10.1016/j.tetlet.2011.05.064

  日期：2011.7

  The aerial part of Dittrichia viscosa yielded two sesquiterpenes, isocostic acid (1) and ilicic acid (2), on multigram scale. These acids are appropriate starting materials for short and facile syntheses of a-eudesmol (5) and cryptomeridiol (6), natural products featuring anti-Alzheimer and anti-spasmodic properties. Compounds 5 and 6 were obtained in three steps in overall yields of 70% and 52%, respectively. (C) 2011 Elsevier Ltd. All rights reserved.