methyl 32-hydroxydotriacontanoate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 32-hydroxydotriacontanoate
• 化学式: C₃₃H₆₆O₃
• 分子量: 510.885
• InChiKey: GXYMJTHSRJHVJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.5
• 重原子数：
  36
• 可旋转键数：
  32
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 32-hydroxydotriacontanoate 在 sodium hydroxide 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 以88%的产率得到32-hydroxydotriacontanoic acid
  参考文献：
  名称：

  Scalable Synthesis of Human Ultralong Chain Ceramides

  摘要：

  Ceramides with ultralong chains (>30 carbons), also known as acylceramides, play a critical role in the survival of mammals on dry land. An efficient and scalable synthesis of four major classes of ultralong human skin ceramides is reported. The key approach involves the use of a succinimidyl ester that acts as a protective group, helps overcome the extremely low solubility, and simultaneously activates the fatty acid for its clean and high-yielding attachment to a sphingoid base.

  DOI：

  10.1021/acs.orglett.5b02816
• 作为产物：
  描述：

  16-溴-1-十六烷醇 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 草酰氯 、 palladium 10% on activated carbon 、 氢气 、 sodium hexamethyldisilazane 、 4-甲基苯磺酸吡啶 、 二甲基亚砜 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 氯仿 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 63.5h， 生成 methyl 32-hydroxydotriacontanoate
  参考文献：
  名称：

  Scalable Synthesis of Human Ultralong Chain Ceramides

  摘要：

  Ceramides with ultralong chains (>30 carbons), also known as acylceramides, play a critical role in the survival of mammals on dry land. An efficient and scalable synthesis of four major classes of ultralong human skin ceramides is reported. The key approach involves the use of a succinimidyl ester that acts as a protective group, helps overcome the extremely low solubility, and simultaneously activates the fatty acid for its clean and high-yielding attachment to a sphingoid base.

  DOI：

  10.1021/acs.orglett.5b02816

文献信息

• US5221757A
  申请人：——

  公开号：US5221757A

  公开（公告）日：1993-06-22
• Scalable Synthesis of Human Ultralong Chain Ceramides
  作者：Lukáš Opálka、Andrej Kováčik、Michaela Sochorová、Jaroslav Roh、Jiří Kuneš、Juraj Lenčo、Kateřina Vávrová

  DOI：10.1021/acs.orglett.5b02816

  日期：2015.11.6

  Ceramides with ultralong chains (>30 carbons), also known as acylceramides, play a critical role in the survival of mammals on dry land. An efficient and scalable synthesis of four major classes of ultralong human skin ceramides is reported. The key approach involves the use of a succinimidyl ester that acts as a protective group, helps overcome the extremely low solubility, and simultaneously activates the fatty acid for its clean and high-yielding attachment to a sphingoid base.