cyclopentyl hexadecanoate | 737813-20-6

• 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: cyclopentyl hexadecanoate
• 英文别名: cyclopentyl-palmitate；Cyclopentyl palmitate
• CAS: 737813-20-6
• 化学式: C₂₁H₄₀O₂
• 分子量: 324.547
• InChiKey: BIUHJRCKXQFHTJ-UHFFFAOYSA-N

物化性质

• 沸点：
  379.9±10.0 °C(Predicted)
• 密度：
  0.90±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  23
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  环戊醇 、 棕榈酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以0.85%的产率得到cyclopentyl hexadecanoate
  参考文献：
  名称：

  USE OF ENDOCANNABINOID-LIKE COMPOUNDS FOR TREATING CNS DEGENERATIVE DISORDERS

  摘要：

  公开号：

  EP1592418B1

文献信息

• New endocannabinoid-like compounds and their use
  申请人：RESEARCH & INNOVATION SOC. COOP. A R.L.

  公开号：EP1900365A2

  公开（公告）日：2008-03-19

  The present invention describes compounds deriving from chemical reactions between saturated or monounsaturated acyl derivatives and primary amines or primary alcohols that display specific cannabinoid-like pharmacological activity without exhibiting the central unwanted side effects typical of synthetic cannabinoids or endocannabinoids acting on central cannabinoid (CB1) receptors. These compounds, having this pharmacological activity, may be utilised to prevent or to treat pathological conditions and diseases in mammals, including human subjects, that may undergo a clinical improvement upon their administration.

  本发明描述了由饱和或单不饱和酰基衍生物与伯胺或伯醇之间的化学反应所产生 的化合物，这些化合物显示出类似大麻素的特殊药理活性，而不会表现出合成大麻 素或作用于中枢大麻素（CB1）受体的内源性大麻素所特有的中枢性不良副作用。这些具有这种药理活性的化合物可用于预防或治疗哺乳动物（包括人类）的病理状况和疾病，服用后可改善临床症状。
• Synthesis and biological evaluation of new potential inhibitors of N-acylethanolamine hydrolyzing acid amidase
  作者：Carmela Saturnino、Stefania Petrosino、Alessia Ligresti、Chiara Palladino、Giovanni De Martino、Tiziana Bisogno、Vincenzo Di Marzo

  DOI：10.1016/j.bmcl.2009.11.134

  日期：2010.2

  N-Acylethanolamines, including N-palmitoyl-ethanolamine (PEA), are hydrolyzed to the corresponding fatty acids and ethanolamine by fatty acid amide hydrolase (FAAH). Recently, N-acylethanolamine-hydrolyzing acid amidase (NAAA) was identified as being able to specifically hydrolyze PEA. In order to find selective and effective inhibitors of this enzyme, we synthesized and screened several amides, retroamides, esters, retroesters and carbamates of palmitic acid (1-21) and esters with C15 and C17 alkyl chains (22-27). Cyclopentylhexadecanoate (13) exhibited the highest inhibitory activity on NAAA (IC50 = 10.0 mu M), without inhibiting FAAH up to 50 mu M. Compound 13 may become a useful template to design new NAAA inhibitors. (C) 2009 Elsevier Ltd. All rights reserved.
• USE IN THERAPY OF ENDOCANNABINOID-LIKE COMPOUNDS
  申请人：Research & Innovation Soc. Coop. A R.L.

  公开号：EP1592418A2

  公开（公告）日：2005-11-09
• Endocannabinoid-like compounds and their use for treating dermatitis
  申请人：Research & Innovation S.p.A.

  公开号：EP1900365B1

  公开（公告）日：2011-03-30
• OZONOLYSIS REACTIONS IN LIQUID CO2 AND CO2-EXPANDED SOLVENTS
  申请人：University Of Kansas

  公开号：EP2209547A2

  公开（公告）日：2010-07-28