1-O-cis-9-octadecenyl isopropylideneglycerol | 22610-35-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-O-cis-9-octadecenyl isopropylideneglycerol
• 英文别名: 1-oleyl-2,3-isopropylidene glycerol；(Z)-2,2-Dimethyl-4-((octadec-9-en-1-yloxy)methyl)-1,3-dioxolane；2,2-dimethyl-4-[[(Z)-octadec-9-enoxy]methyl]-1,3-dioxolane
• CAS: 22610-35-1
• 化学式: C₂₄H₄₆O₃
• 分子量: 382.627
• InChiKey: ONGCAPZNZXGPGB-QXMHVHEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  27
• 可旋转键数：
  18
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-O-cis-9-octadecenyl isopropylideneglycerol 在 对甲苯磺酸 作用下， 以 四氢呋喃 、 水 为溶剂， 以869 mg的产率得到selachyl alcohol
  参考文献：
  名称：

  脂肪酶催化的顺序酯交换反应生成1- O-烷基甘油的动力学拆分

  摘要：

  通过对映选择性脂肪酶催化的酯交换反应制备1- O-烷基甘油类型的天然S-构型的Chimyl，batyl和selachyl醇。它们的外消旋体是分两步合成的，即外消旋的缩酮与相应的脂肪醇的溴化物反应，然后通过在酸性水溶液条件下进行脱保护将中间体转化为1- O-烷基甘油。的荧光假单胞菌的脂肪酶被用于动力学解析消旋的1- Ô通过连续二乙酰过程-alkylglycerols向他们提供实质上对映体纯。对于饱和的甲基E（E = 17–32）和batyl（E  = 14–38）醇在降低的温度下，而对于单不饱和selachyl（E  = 12–13）醇，则未观察到这种温度影响。

  DOI：

  10.1016/j.tetasy.2004.07.046
• 作为产物：
  描述：

  油醇 在 吡啶 、 氢氧化钾 作用下， 反应 11.0h， 生成 1-O-cis-9-octadecenyl isopropylideneglycerol
  参考文献：
  名称：

  Alunni-Bistocchi; Orvietani; Ricci, Il Farmaco, 1990, vol. 45, # 5, p. 499 - 509

  摘要：

  DOI：

文献信息

• Compositions containing lysophosphatidic acids which inhibit apoptosis and uses thereof
  申请人：Goddard John G.

  公开号：US06949528B1

  公开（公告）日：2005-09-27

  The invention provides anti-apoptotic compositions lysophosphatidic acids and methods for making and using the compositions. Such compositions can also contain LPA potentiating agents, including proteins, lipid membrane structures and polymers such as polyethylene glycols. The compositions can additionally contain other pharmaceutically effective agents such as drugs, antibiotics, wound healing agents and antioxidants.

  该发明提供了抗凋亡组合物溶磷脂酸及其制备和使用方法。这种组合物还可以包含增强LPA作用的剂，包括蛋白质、脂质膜结构和聚合物，如聚乙二醇。该组合物还可以额外含有其他药用有效剂，如药物、抗生素、伤口愈合剂和抗氧化剂。
• Process for the production of glyceryl ethers
  申请人：Kao Corporation

  公开号：US04465869A1

  公开（公告）日：1984-08-14

  The specification describes a process for the production of a 4-alkoxymethyl-1,3-dioxolan in good yield, in high purity and in a simple manner by reacting an alkyl glycidyl ether with a carbonyl compound in the presence of an acid catalyst. The 4-alkoxymethyl-1,3-dioxolan is useful as an intermediate for the production of an .alpha.-monoalkyl glyceryl ether by hydrolysis.

  该规范描述了一种生产4-烷氧甲基-1,3-二氧兰的方法，该方法通过在酸催化剂存在下将烷基环氧乙烷与羰基化合物反应，以高产率、高纯度和简单的方式生产。4-烷氧甲基-1,3-二氧兰可用作通过水解生产α-单烷基甘油醚的中间体。
• Sterol-Modified Phospholipids: Cholesterol and Phospholipid Chimeras with Improved Biomembrane Properties
  作者：Zhaohua Huang、Francis C. Szoka

  DOI：10.1021/ja8065557

  日期：2008.11.19

  We synthesized a family of sterol-modified glycerophospholipids (SML) in which the sn-1 or sn-2 position is covalently attached to cholesterol and the alternative position contains an aliphatic chain. The SML were used to explore how anchoring cholesterol to a phospholipid affects cholesterol behavior in a bilayer. Notably, cholesterol in the SML retains the membrane condensing properties of free cholesterol regardless of the chemistry or position of its attachment to the glycerol moiety of the phospholipid. SMLs by themselves formed liposomes upon hydration and in mixtures between an SML and diacylglycerophospholipids (C14 to C18 chain length) the thermotropic phase transition is eliminated at the SML equivalent of about 30 mol % free cholesterol. Osmotic-induced contents leakage from SML (C14-C18) liposomes depends upon the linkage and position of cholesterol but in general is similar to that observed in 3/2 diacylphosphatidylcholine/cholesterol (mole ratio) liposomes. SML liposomes are exceptionally resistant to contents release in the presence of serum at 37 degrees C. This is probably due to the fact that SML exchange between bilayers is more than 100 fold less than the exchange rate of free cholesterol in the same conditions. Importantly, SML liposomes containing doxorubicin are as effective in treating the murine C26 colon carcinoma as Doxil, a commercial liposome doxorubicin formulation. SMLs stabilize bilayers but do not exchange and hence provide a new tool for biophysical studies on membranes. They may improve liposomal drug delivery in organs predisposed to the extraction of free cholesterol from bilayers, such as the skin, lung, or blood.
• Kinetic resolution of 1-O-alkylglycerols by lipase
  作者：Gudmundur G Haraldsson、Pall Thordarson、Arnar Halldorsson、Bjorn Kristinsson

  DOI：10.1016/s0957-4166(99)00397-3

  日期：1999.9

  Pseudomonas sp. lipase was employed to resolve kinetically 1-O-alkylglycerols by a sequential diacylation process. Only low or moderate E-values were obtained, but at approximately 60% conversion enantiomerically pure monoacetates were obtained of the natural S-configuration for glyceryl ether lipids. (C) 1999 Elsevier Science Ltd. All rights reserved.
• [EN] COMPOSITION COMPRISING ETHER LIPID<br/>[FR] COMPOSITION COMPRENANT UN LIPIDE D'ETHER
  申请人：CAMURUS AB

  公开号：WO2005027976A3

  公开（公告）日：2005-12-01