(11Z,14Z,17Z)-11,14,17-icosatrienoic acid methyl ester | 62472-96-2

• 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: (11Z,14Z,17Z)-11,14,17-icosatrienoic acid methyl ester
• 英文别名: all-cis-11,14,17-eicosatrienoic acid methyl ester；cis-11,14,17-eicosatrienoic acid methyl ester；11,14,17-eicosatrienoic acid methyl ester；Methyl (11Z,14Z,17Z)-icosa-11,14,17-trienoate
• CAS: 62472-96-2
• 化学式: C₂₁H₃₆O₂
• 分子量: 320.516
• InChiKey: XQAVRBUXEPJVRC-YSTUJMKBSA-N

物化性质

• 沸点：
  398.6±11.0 °C(Predicted)
• 密度：
  0.891±0.06 g/cm3(Predicted)
• 溶解度：
  0.1 M Na2CO3：1 mg/mL； DMF：100mg/mL；二甲基亚砜：100mg/mL；乙醇：100mg/mL
• 保留指数：
  2305.1

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  23
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (11Z,14Z,17Z)-11,14,17-icosatrienoic acid methyl ester 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 16.0h， 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
• 作为产物：
  描述：

  linolenyl bromide 在 正丁基锂 、 乙酰氯 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 12.08h， 生成 (11Z,14Z,17Z)-11,14,17-icosatrienoic acid methyl ester
  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

• [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。
• Methods for treating benign prostatic hypertrophy (BPH) symptoms using extract from Ageratum spp
  申请人：GE Nutrients, Inc.

  公开号：US11071763B2

  公开（公告）日：2021-07-27

  An herbal extract and constituents thereof for treatment of BPH and related aging symptoms in males and for addressing male health using extracts from Ageratum spp., including, but not limited to, Ageratum conyzoides, Ageratum coeruleum and Ageratum houstonianum, is disclosed herein. At least one compound of plants, and parts of plants, of Ageratum spp., such as, but not limited to, N,N-bis(trimethylsilyl)-2-phenyl-7-(trifluoromethyl)quinolon-4-amine, 3′,4′,5′,6′,7′,8-hexamethoxyflavone, Phytol, Precocene, caryophyllene, squalene, alpha-linolenic acid, (Z,Z)-9,12-octadecadienoic acid, Hexadecanoic acid, Hydrocoumarin, Encecaline-1-(7-methoxy-2,2-dimethyl-2H-chromen-6-yl)ethanone, Senensetin-3,4,5,6,7-pentamethoxy flavone, Beta selinene, Stigmasterol, Beta sitosterol, Quercetin, Quercetin-3-O-rhamnosylglucoside, Linoleic acid, or Conyzorigin can be extracted utilizing a Common Plant Extraction Approach (CPEA). The extraction of compounds can be performed utilizing an ethanol solvent and sterile water solvent and/or ethanol mixed with sterile water (i.e., hydro-alcoholic solvents) separately and the concentrated materials obtained as these solvents systems are pooled together (or maintained separately) in order to obtain an herbal extract for the treatment of BPH.

  本文公开了一种草本提取物及其成分，用于治疗男性良性前列腺增生症和相关衰老症状，并利用龙胆草属植物（包括但不限于Ageratum conyzoides、Ageratum coeruleum和Ageratum houstonianum）的提取物解决男性健康问题。本文公开了至少一种龙舌兰属植物和植物部分的化合物，如，但不限于，Ageratum conyzoides、Ageratum coeruleum 和 Ageratum houstonianum、例如，但不限于，N,N-双（三甲基硅基）-2-苯基-7-（三氟甲基）喹啉-4-胺、3′,4′,5′,6′,7′,8-六甲氧基黄酮、植物醇、前胡烯、叶黄素、角鲨烯、α-亚麻酸、(Z,Z)-9,12-十八碳二烯酸、十六烷酸、氢化香豆素、可利用普通植物提取方法 (CPEA) 提取 Encecaline-1-(7-methoxy-2,2-dimethyl-2H-chromen-6-yl)ethanone, Senensetin-3,4,5,6,7-pentamethoxy flavone, Beta selinene, Stigmasterol, Beta sitosterol, Quercetin, Quercetin-3-O-rhamnosylglucoside, Linoleic acid 或 Conyzorigin。化合物的提取可分别使用乙醇溶剂和无菌水溶剂和/或乙醇与无菌水混合溶剂（即水醇溶剂），然后将这些溶剂系统得到的浓缩物集中在一起（或分别保存），以获得用于治疗良性前列腺增生症的草药提取物。
• Herbal preparation for stimulation of hair growth, control of hair fall, dandruff and infections thereof using Ageratum spp
  申请人：GE Nutrients, Inc.

  公开号：US11357809B2

  公开（公告）日：2022-06-14

  This disclosure describes herbal preparations for the stimulation of hair growth, control of hair fall, control of dandruff, and control of dandruff-related infections thereof, using herbaceous plants, Ageratum spp. Processes for preparing the herbal preparations and methods for using them are also disclosed. Such an herbal preparation using plants, Ageratum spp. can be utilized as an efficient hair care solution in a wide range of hair growth related problems of humans in a cost-effective manner.

  本公开描述了使用草本植物龙葵属（Ageratum spp）刺激头发生长、控制头发脱落、控制头皮屑和控制头皮屑相关感染的草本制剂，还公开了制备该草本制剂的工艺及其使用方法。这种使用龙胆草属植物的草药制剂可作为一种高效的头发护理解决方案，以经济有效的方式解决人类各种与头发生长相关的问题。
• HERBAL PREPARATION FOR STIMULATION OF HAIR GROWTH, CONTROL OF HAIR FALL, DANDRUFF AND INFECTIONS THEREOF USING AGERATUM SPP
  申请人：GE Nutrients, Inc.

  公开号：EP4013438A1

  公开（公告）日：2022-06-22
• 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.