花生四烯酸酐 | 55726-28-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 花生四烯酸酐
• 英文名称: arachidonic acid anhydride
• 英文别名: Arachidonic anhydride；[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyl] (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate
• CAS: 55726-28-8
• 化学式: C₄₀H₆₂O₃
• 分子量: 590.93
• InChiKey: FFBZPQRGHCBZJB-XCHUKFSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.9
• 重原子数：
  43
• 可旋转键数：
  30
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  花生四烯酸酐 、 红霉素 在 4-二甲氨基吡啶 作用下， 以 吡啶 为溶剂， 反应 8.0h， 以60%的产率得到2'-O-arachidonoylerythromycin A
  参考文献：
  名称：

  New fatty monoesters of erythromycin A.

  摘要：

  通过使用各种试剂（如酰基氯、羧酸酐和混合碳酐）合成了新的红霉素 A 脂肪多炔（亚油酸、亚麻酸、花生四烯酸和亚麻酸）单酯。测定了这些新酯对人体皮肤常住菌群的体外抗菌特性，并将其与红霉素 A 的抗菌特性进行了比较。双键的数量和立体化学似乎在体外抗菌活性的表现中起着至关重要的作用。

  DOI：

  10.1248/cpb.38.1672
• 作为产物：
  描述：

  花生四烯酸 在 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 生成 花生四烯酸酐
  参考文献：
  名称：

  Synthesis and characterization of novel PUFA esters exhibiting potential anticancer activities: An in vitro study

  摘要：

  Polyunsaturated fatty acids (PUFAs) have been reported to play a regulatory role in tumour growth progression. In the present study, we have synthesized ester derivatives of two important PUFA viz., linoleic acid (LA) and arachidonic acid (AA) with propofol, a widely used general anaesthetic-sedative agent. The novel propofol ester analogues have been found to inhibit various cancer cell lines in a dose-dependent manner. Moreover, the compounds have been found to induce apoptotic cell death by enhancing the release of cytochrome c and expression of caspase-3. The data of the present study suggest that novel propofol PUFA esters have strong potential to emerge as effective anticancer agents. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.07.044

文献信息

• Diacylnucleosides and process for preparing the same
  申请人：Asahi Kasei Kogyo Kabushiki Kaisha

  公开号：US04097665A1

  公开（公告）日：1978-06-27

  Compounds represented by formula (I) ##STR1## wherein one of Z.sub.1 ', Z.sub.2 ', Z.sub.3 ' and Z.sub.4 ' represents R, another one of Z.sub.1 ', Z.sub.2 ', Z.sub.3 ' and Z.sub.4 ' represents Z, and the remaining two moieties of Z.sub.1 ', Z.sub.2 ', Z.sub.3 ' and Z.sub.4 ' represents a hydrogen atom and/or a protective group, one of R and Z represents A.sub.1 and the other represents A.sub.2, A.sub.1 being an acyl group having 14 to 22 carbon atoms which does not contain a carboxylic group and A.sub.2 being an acyl group having 2 to 14 carbon atoms and having one carboxyl group, X represents a hydrogen atom or a halogen atom (hereinafter referred to as Compound Ia); a 2,2'-anhydro product of Compound Ia wherein Z.sub.2 ' represents a hydrogen atom (hereinafter referred to as Compound Ib); an arabinosylation product of Compound Ia (hereinafter referred to as Compound Ic); a deamination product of Compound Ia (hereinafter referred to as Compound Id); a 2'-deoxy product of Compound Id wherein Z.sub.2 ' represents a hydrogen atom (hereinafter referred to as Compound Ie); a salt of Compound Ia, Ib, Ic, or Id or Ie having an A.sub.2 group with a base (hereinafter referred to as Compound If); and a salt of Compound Ia, Ib or Ic wherein Z.sub.1 ' represents a hydrogen atom with an acid (hereinafter referred to as Compound Ih); and processes for preparing the same.

  化合物的化学式为（I）##STR1## 其中Z.sub.1'，Z.sub.2'，Z.sub.3'和Z.sub.4'中的一个代表R，Z.sub.1'，Z.sub.2'，Z.sub.3'和Z.sub.4'中的另一个代表Z，Z.sub.1'，Z.sub.2'，Z.sub.3'和Z.sub.4'的剩余两个基团代表氢原子和/或保护基，R和Z中的一个代表A.sub.1，另一个代表A.sub.2，其中A.sub.1是具有14至22个碳原子且不含羧基的酰基，A.sub.2是具有2至14个碳原子且具有一个羧基的酰基，X代表氢原子或卤素原子（以下简称化合物Ia）; 化合物Ia的2,2'-去水产物，其中Z.sub.2'代表氢原子（以下简称化合物Ib）; 化合物Ia的阿拉伯糖基化产物（以下简称化合物Ic）; 化合物Ia的脱氨产物（以下简称化合物Id）; 化合物Id的2'-去氧产物，其中Z.sub.2'代表氢原子（以下简称化合物Ie）; 具有碱的A.sub.2基团的化合物Ia，Ib，Ic，或Id或Ie的盐（以下简称化合物If）; 以及具有酸的化合物Ia，Ib或Ic的Z.sub.1'代表氢原子的盐（以下简称化合物Ih）; 以及制备它们的过程。
• PREPARATION OF AMINO ACID-FATTY ACID ANHYDRIDES
  申请人：MacDougall Joseph

  公开号：US20080200725A1

  公开（公告）日：2008-08-21

  The present invention describes compounds produced from an amino acid molecule and a fatty acid molecule. The compounds being in the form of amino-fatty acid compounds being bound by an anhydride linkage, or mixtures thereof made by reacting amino acids or derivatives thereof with an appropriate fatty acid previously reacted with a thionyl halide. The administration of such molecules provides supplemental amino acids with enhanced bioavailability and the additional benefits conferred by the specific fatty acid.

  本发明描述了由氨基酸分子和脂肪酸分子产生的化合物。这些化合物采用酐键连接的氨基-脂肪酸化合物形式存在，或者是由氨基酸或其衍生物与预先经过硫酰卤化物反应的适当脂肪酸混合物制成的。这些分子的使用提供了增强生物利用度的补充氨基酸以及特定脂肪酸所赋予的附加益处。
• Preparation of amino acid-fatty acid anhydrides
  申请人：MacDougall Joseph

  公开号：US20080281113A1

  公开（公告）日：2008-11-13

  The present invention describes compounds produced from an amino acid molecule and a fatty acid molecule. The compounds being in the form of amino-fatty acid compounds being bound by an anhydride linkage, or mixtures thereof made by reacting amino acids or derivatives thereof with an appropriate fatty acid previously reacted with a thionyl halide. The administration of such molecules provides supplemental amino acids with enhanced bioavailability and the additional benefits conferred by the specific fatty acid.

  本发明描述了由氨基酸分子和脂肪酸分子产生的化合物。这些化合物采用酐键连接，形成氨基脂肪酸化合物，或者由氨基酸或其衍生物与事先与硫酰卤反应的适当脂肪酸混合而成。这些分子的使用提供了增强生物利用度的补充氨基酸和特定脂肪酸所赋予的额外益处。
• Arachidonoyl ethanolamide-[1,2-14C] as a substrate for anandamide amidase
  作者：Romelda L. Omeir、Suzette Chin、Yang Hong、David G. Ahern、Dale G. Deutsch

  DOI：10.1016/0024-3205(95)00181-5

  日期：1995.5

  Arachidonoyl ethanolamide-[1,2-14C] was prepared and evaluated as a substrate for anandamide amidase in a radioenzymatic assay that does not require a thin layer chromatography separation step. Using this substrate the release of ethanolamine-[1,2-14C] is linear for approximately thirty minutes. Anandamide amidase exhibits maximal activity between pH 8 and pH 9 with a steep decline in activity at pH

  制备了花生四烯酰基乙醇酰胺-[1,2-14C]，并在不需要薄层色谱分离步骤的放射酶测定中将其评估为花生四烯酰胺酰胺酶的底物。使用该底物，乙醇胺-[1,2-14C]的释放线性发生约三十分钟。花生四烯酰胺酰胺酶在pH 8和pH 9之间显示最大活性，在pH值低于6和高于10时活性急剧下降。花生四烯酰乙醇酰胺-[1,2-14C]用于测定花生四烯酰胺酰胺酶的范围从10微克到100微克。牛脑匀浆中的蛋白质在0.2 ml的孵育混合物中。当绘制为稳态Michaelis-Menten方程的矩形双曲线时，每小时每毫克蛋白质匀浆形成的Km约为30 +/- 7 microM，Vmax为198 +/- 13 nmoles乙醇胺。
• Priller, Josef; Briley, Eileen M.; Mansouri, Jaleh, Molecular Pharmacology, 1995, vol. 48, # 2, p. 288 - 292
  作者：Priller, Josef、Briley, Eileen M.、Mansouri, Jaleh、Devane, William A.、Mackie, Ken、Felder, Christian C.

  DOI：——

  日期：——