顺式-11,14,17-二十碳三烯酸 | 17046-59-2

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 顺式-11,14,17-二十碳三烯酸
• 中文别名: 11,14,17-二十碳三烯酸
• 英文名称: cis-11,14,17-eicosatrienoic acid
• 英文别名: Bishomo-a-linolenic acid；(11Z,14Z,17Z)-11,14,17-eicosatrienoic acid；11(Z),14(Z),17(Z)-eicosatrienoic acid；11Z,14Z,17Z-eicosatrienoic acid；11,14,17-eicosatrienoic acid；eicosatrienoic acid；(11Z,14Z,17Z)-icosa-11,14,17-trienoic acid
• CAS: 17046-59-2
• 化学式: C₂₀H₃₄O₂
• 分子量: 306.489
• InChiKey: AHANXAKGNAKFSK-PDBXOOCHSA-N

物化性质

• 沸点：
  432.7±14.0 °C(Predicted)
• 密度：
  0.917±0.06 g/cm3(Predicted)
• 溶解度：
  0.1 M Na2CO3：1.7 mg/mL； DMF：100mg/mL；二甲基亚砜：100mg/mL；乙醇：可混溶

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  22
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38

反应信息

• 作为反应物：
  描述：

  顺式-11,14,17-二十碳三烯酸 在 arachidonate 5-lipoxygenase 乙二胺四乙酸 、 sodium hydroxide 、 sodium tetrahydroborate 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 0.5h， 生成 11,18-dihydroxy-eicosatrienoic acid
  参考文献：
  名称：

  WO2008/103753

  摘要：

  公开号：
• 作为产物：
  描述：

  linolenyl bromide 在 氢氧化钾 、 正丁基锂 、 乙酰氯 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 为溶剂， 反应 28.08h， 生成 顺式-11,14,17-二十碳三烯酸
  参考文献：
  名称：

  Chemical C2-elongation of polyunsaturated fatty acids

  摘要：

  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.

  DOI：

  10.1016/j.chemphyslip.2006.09.002

文献信息

• UNSATURATED FATTY ACID MONOESTERS AND DIESTERS ON ASCORBIC ACID AND COSMETIC USES THEREOF
  申请人：Poigny Stéphane

  公开号：US20120076744A1

  公开（公告）日：2012-03-29

  The present invention relates to a compound with the following general formula (I): in which: R 1 is a hydrocarbon chain of an unsaturated fatty acid from C 12 to C 24 including at least one unsaturation; and R 2 and R 3 are, independently or simultaneously: a hydrogen or a C 1 -C 3 alkyl or a phenyl; and R 4 : a hydrogen atom or COR 1′ , where R 1′ is a hydrocarbon chain of an unsaturated fatty acid from C 12 to C 24 including at least one unsaturation, advantageously 1 to 6 and preferably 1 to 4.

  本发明涉及具有以下一般式（I）的化合物： 其中：R1是来自C12到C24的不饱和脂肪酸的烃链，包括至少一个不饱和度；而R2和R3是独立或同时的：氢或C1-C3烷基或苯基；而R4：氢原子或COR1'，其中R1'是来自C12到C24的不饱和脂肪酸的烃链，有利地为1到6，优选为1到4。
• Lipid-amino acid conjugates and methods of use
  申请人：Burstein H. Sumner

  公开号：US20060014820A1

  公开（公告）日：2006-01-19

  N-fatty acid-amino acid conjugates and J 2 prostanoid-amino acid conjugates are disclosed along with methods for making such conjugates and methods of using these conjugates in the treatment of conditions that involve dysfunctional lipid metabolism, insulin sensitivity, glucose homeostasis, and/or inflammation.

  N-脂肪酸-氨基酸共轭物和J2前列腺素-氨基酸共轭物被披露，以及制备这些共轭物的方法和在治疗涉及异常脂质代谢、胰岛素敏感性、葡萄糖稳态和/或炎症的疾病中使用这些共轭物的方法。
• [EN] LYMPHATIC SYSTEM-DIRECTING LIPID PRODRUGS<br/>[FR] PROMÉDICAMENTS LIPIDIQUES ORIENTANT VERS LE SYSTÈME LYMPHATIQUE
  申请人：ARIYA THERAPEUTICS INC

  公开号：WO2019046491A1

  公开（公告）日：2019-03-07

  The present invention provides lymphatic system-directing lipid prodrugs, pharmaceutical compositions thereof, methods of producing such prodrugs and compositions, as well as methods of improving the bioavailability or other properties of a therapeutic agent that comprises part of the lipid prodrug. The present invention also provides methods of treating a disease, disorder, or condition such as those disclosed herein, comprising administering to a patient in need thereof a provided lipid prodrug or a pharmaceutical composition thereof.

  本发明提供了淋巴系统定向脂质前药，其制药组合物，制备这种前药和组合物的方法，以及改善作为脂质前药一部分的治疗剂的生物利用度或其他性质的方法。本发明还提供了治疗疾病、紊乱或症状的方法，包括向需要的患者施用所提供的脂质前药或其制药组合物。
• FATTY ACID ANTIVIRAL CONJUGATES AND THEIR USES
  申请人：Catabasis Pharmaceuticals, Inc.

  公开号：US20160129122A1

  公开（公告）日：2016-05-12

  The invention relates to fatty acid antiviral conjugates; compositions comprising an effective amount of a fatty acid antiviral conjugate; and methods for treating or preventing a viral infection comprising the administration of an effective amount of a fatty acid antiviral conjugate.

  这项发明涉及脂肪酸抗病毒共轭物；包含有效量脂肪酸抗病毒共轭物的组合物；以及治疗或预防病毒感染的方法，包括给予有效量脂肪酸抗病毒共轭物。
• [EN] MACROCYCLIC COMPOUNDS FOR TREATMENT OF MEDICAL DISORDERS<br/>[FR] COMPOSÉS MACROCYCLIQUES DESTINÉS AU TRAITEMENT DE TROUBLES MÉDICAUX
  申请人：ACHILLION PHARMACEUTICALS INC

  公开号：WO2018160892A1

  公开（公告）日：2018-09-07

  Macrocyclic Complement Factor D inhibitors, pharmaceutical compositions, and uses thereof, as well as processes for their manufacture are provided. The compounds provided include Formula I, Formula II, Formula III, Formula IV, Formula V, Formula VI, Formula VII, and Formula VIII or a pharmaceutically acceptable salt, prodrug, isotopic analog, N-oxide, or isolated isomer thereof, optionally in a pharmaceutically acceptable composition. The inhibitors described herein target Factor D and inhibit or regulate the complement cascade.

  提供大环补体因子D抑制剂、药物组合物及其用途，以及它们的制造工艺。所提供的化合物包括公式I、公式II、公式III、公式IV、公式V、公式VI、公式VII和公式VIII或其药用可接受的盐、前药、同位素类似物、N-氧化物或孤立的同分异构体，可选地存在于药用可接受的组合物中。此处描述的抑制剂针对因子D并抑制或调节补体级联反应。