(8Z,11Z,14Z,17Z)-methyl icosa-8, 11, 14, 17-tetraenoate | 132712-70-0

• 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: (8Z,11Z,14Z,17Z)-methyl icosa-8, 11, 14, 17-tetraenoate
• 英文别名: 8Z,11Z,14Z,17Z-eicosatetraenoic acid methyl ester；omega-3 Arachidonic Acid methyl ester；methyl (8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoate
• CAS: 132712-70-0
• 化学式: C₂₁H₃₄O₂
• 分子量: 318.5
• InChiKey: OHQGIWOBGITZPC-GJDCDIHCSA-N

物化性质

• 沸点：
  403.9±24.0 °C(Predicted)
• 密度：
  0.901±0.06 g/cm3(Predicted)
• 溶解度：
  DMF：50 mg/ml； DMSO：50 mg/ml；乙醇：50 mg/ml；己烷：10 mg/ml； PBS（pH 7.2）：0.15 mg/ml
• 保留指数：
  2255.3

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  23
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

制备方法与用途

ω-3花生四烯酸甲酯主要由二十二碳六烯酸、二十碳五烯酸和α亚油酸等组成，是维持正常生长发育所需的必需膳食营养素。甲基ω-3花生四烯酸是一种中性脂溶性的稀有脂肪酸。对于整体而言，ω-3脂肪酸能够减少炎症和自身免疫活性，并降低血栓形成及血小板活化。

反应信息

• 作为反应物：
  描述：

  (8Z,11Z,14Z,17Z)-methyl icosa-8, 11, 14, 17-tetraenoate 在 lithium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 8.0h， 以62%的产率得到(8Z,11Z,14Z,17Z)-8,11,14,17-二十碳四烯酸
  参考文献：
  名称：

  Synthesis of Rare Polyunsaturated Fatty Acids: Stearidonic and ω-3 Arachidonic

  摘要：

  对具有潜在抗炎活性的稀有天然 ω-3 C18 和 C20 脂肪酸进行了全化学合成，以便对其生物活性进行后续研究。

  DOI：

  10.1007/s10600-015-1485-3
• 作为产物：
  描述：

  二十二碳六烯酸 在 六甲基磷酰三胺 、 copper(l) iodide 、 甲酸 、 碘 、 乙酸酐 、 二异丁基氢化铝 、 potassium hydrogencarbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 potassium iodide 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 82.75h， 生成 (8Z,11Z,14Z,17Z)-methyl icosa-8, 11, 14, 17-tetraenoate
  参考文献：
  名称：

  Concise syntheses of three ω-3 polyunsaturated fatty acids

  摘要：

  The synthesis of the three omega-3 polyunsaturated fatty acids, eicosatetraenoic acid (3), docosapentaenoic acid (4), and stearidonic acid (5) has been achieved using eicosapentaenoic acid or docosahexaenoic acid as the starting materials. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.08.009

文献信息

• [EN] ASCORBATE ESTERS OF OMEGA-3 FATTY ACIDS<br/>[FR] ESTERS D'ASCORBATE D'ACIDES GRAS OMÉGA 3
  申请人：JIVA PHARMA INC

  公开号：WO2014134053A1

  公开（公告）日：2014-09-04

  The present invention provides ascorbate esters of omega-3 fatty acids as their pharmaceutically-acceptable salts and pharmaceutically- acceptable formulations for use as dietary supplements with enhanced antioxidant properties, in improving the effectiveness of other drugs and in treatment of hypertriglyceridemia, hypercholestolemia, diabetes, psychiatric and neurological disorders, attention deficit and hyperactivity disorder, and as cosmeceuticals.

  本发明提供了抗坏血酸酯化的ω-3脂肪酸及其药学上可接受的盐和制剂，用作具有增强抗氧化性能的膳食补充剂，在提高其他药物的有效性以及治疗高三酰甘油血症、高胆固醇血症、糖尿病、精神和神经障碍、注意力缺陷和多动症以及作为化妆品成分。
• Chemical C2-elongation of polyunsaturated fatty acids
  作者：Dmitry V. Kuklev、William L. Smith

  DOI：10.1016/j.chemphyslip.2006.09.002

  日期：2006.11

  Three fatty acids were synthesized from commercially available alpha-linolenic, stearidonic and eicosapentaenoic acids by C2-elongation using a four step preparative technique. The parent fatty acid methyl esters were reduced to alcohols with LiAlH4, converted to bromides by treatment with triphenylphosphine dibromide, coupled with a lithiated C2-elongation block -2,4,4-trimethyl-2-oxazoline - to form the corresponding 2,2-dimethyloxazolines of C2-elongated fatty acids, and finally, converted to the target polyunsaturated fatty acids by acidic alcoholysis. Yields of more than 60% were achieved on a gram scale. The resulting 11Z, 14Z, 17Z-eicosatrienoic, 8Z, 11Z, 14Z, 17Z-eicosatetraenoic and 7Z, 10Z,13Z, 16Z, 19Z-docosapentaenoic acids were obtained as colorless oils with > 98% purity and could be used for biochemical investigations without additional purification. The elongated fatty acids were free of byproducts that could result from Z-E isomerization or migration of double bonds. (c) 2006 Elsevier Ireland Ltd. All rights reserved.
• Ascorbate Esters of Omega-3 Fatty Acids and Their Formulations and Uses
  申请人：JIVA PHARMA, INC.

  公开号：US20150374660A1

  公开（公告）日：2015-12-31

  The present invention provides ascorbate esters of omega-3 fatty acids as their pharmaceutically-acceptable salts and pharmaceutically-acceptable formulations for use as dietary supplements with enhanced antioxidant properties, in improving the effectiveness of other drugs and in treatment of hypertriglyceridemia, hypercholestolemia, diabetes, psychiatric and neurological disorders, attention deficit and hyperactivity disorder, and as cosmeceuticals.
• Concise syntheses of three ω-3 polyunsaturated fatty acids
  作者：Martin Gjerde Jakobsen、Anders Vik、Trond Vidar Hansen

  DOI：10.1016/j.tetlet.2012.08.009

  日期：2012.10

  The synthesis of the three omega-3 polyunsaturated fatty acids, eicosatetraenoic acid (3), docosapentaenoic acid (4), and stearidonic acid (5) has been achieved using eicosapentaenoic acid or docosahexaenoic acid as the starting materials. (C) 2012 Elsevier Ltd. All rights reserved.
• Synthesis of Rare Polyunsaturated Fatty Acids: Stearidonic and ω-3 Arachidonic
  作者：A. B. Golovanov、I. V. Ivanov、N. V. Groza、G. I. Myagkova

  DOI：10.1007/s10600-015-1485-3

  日期：2015.11

  Total chemical syntheses of the rare natural ω-3 C18 and C20 fatty acids, which possess potential antiinflammatory activity, were elaborated for subsequent studies of their biological activity.

  对具有潜在抗炎活性的稀有天然 ω-3 C18 和 C20 脂肪酸进行了全化学合成，以便对其生物活性进行后续研究。