顺6,9,12,15-十八碳四烯酸 | 20290-75-9

• 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6,9,12,15-十八碳四烯酸
• 中文别名: 4,8,12,15-十八碳四烯酸；鰮油酸
• 英文名称: stearidonic acid
• 英文别名: (6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoic acid
• CAS: 20290-75-9
• 化学式: C₁₈H₂₈O₂
• 分子量: 276.419
• InChiKey: JIWBIWFOSCKQMA-LTKCOYKYSA-N

物化性质

• 熔点：
  200℃ (decomposition)
• 沸点：
  382.5±11.0 °C(Predicted)
• 密度：
  0.9334 g/cm3 (15 ºC)
• 闪点：
  17 °C
• 溶解度：
  可溶于氯仿（少许）
• LogP：
  5.890 (est)
• 物理描述：
  Liquid
• 保留指数：
  1951.7

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  20
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 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：
  F
• 危险类别码：
  R11
• 危险品运输编号：
  UN 1170 3/PG 2
• WGK Germany：
  3
• 储存条件：
  -20°C，密闭保存，并保持干燥。

制备方法与用途

Stearylidonic acid是一种含有18个碳原子、ω-3系列的脂肪酸，它是EPA和DHA的饮食前体。

反应信息

• 作为反应物：
  描述：

  顺6,9,12,15-十八碳四烯酸 在 soybean 15-lipoxygenase 作用下， 反应 0.5h， 生成 13-hydroxy SDA
  参考文献：
  名称：

  WO2007/90162

  摘要：

  公开号：
• 作为产物：
  描述：

  Γ-十八碳三烯酸 在 Saccharomyces cerevisiae expressing Δ6 fatty acid desaturase 作用下， 反应 48.0h， 生成 顺6,9,12,15-十八碳四烯酸
  参考文献：
  名称：

  Multiple genes for functional ∆6 fatty acyl desaturases (Fad) in Atlantic salmon (Salmo salar L.): Gene and cDNA characterization, functional expression, tissue distribution and nutritional regulation

  摘要：

  Fish are the primary source in the human food basket of the n-3 long-chain polyunsaturated fatty acids, eicosapentaenoate (EPA; 20:5n-3) and docosahexaenoate (DHA: 22:6n-3), that are crucial to the health of higher vertebrates. Atlantic salmon are able to synthesize EPA and DHA from 18:3n-3 through reactions catalyzed by fatty acyl desaturases (Fad) and elongases of very long chain fatty acids. Previously, two cDNAs encoding functionally distinct Delta 5 and Delta 6 Fads were isolated, but screening of a genomic DNA library revealed the existence of more putative fad genes in the Atlantic salmon genome. In the present study, we show that there are at least four genes encoding putative Fad proteins in Atlantic salmon. Two genes, Delta 6fad_a and Delta 5fad, corresponded to the previously cloned Delta 6 and Delta 5 Fad cDNAs. Functional characterization by heterologous expression in yeast showed that the cDNAs for both the two further putative fad genes, Delta 6fad_b and Delta 6fad_c, had only Delta 6 activity, converting 47% and 12% of 18:3n-3 to 18:4n-3, and 25 and 7% of 18:2n-6 to 18:3n-6, for Delta 6Fad_b and Delta 6fad_c, respectively. Both Delta 6fad_a and Delta 6fad_b genes were highly expressed in intestine (pyloric caeca), liver and brain, with Delta 6fad_b also highly expressed in gill, whereas Delta 6fad_c transcript was found predominantly in brain, with lower expression levels in all other tissues. The expression levels of the Delta 6fad_a gene in liver and the Delta 6fad_b gene in intestine were significantly higher in fish fed diets containing vegetable oil compared to fish fed fish oil suggesting up-regulation in response to reduced dietary EPA and DHA. In contrast, no significant differences were found between transcript levels for Delta 6fad_a in intestine, Delta 6fad_b in liver, or Delta 6fad_c in liver or intestine of fish fed vegetable oil compared to fish fed fish oil. The observed differences in tissue expression and nutritional regulation of the fad genes are discussed in relation to gene structures and fish physiology. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.bbalip.2010.04.007

文献信息

• [EN] BIOACTIVE CONJUGATES FOR OLIGONUCLEOTIDE DELIVERY<br/>[FR] CONJUGUÉS BIOACTIFS POUR L'ADMINISTRATION D'OLIGONUCLÉOTIDES
  申请人：UNIV MASSACHUSETTS

  公开号：WO2017030973A1

  公开（公告）日：2017-02-23

  Provided herein are self-delivering oligonucleotides that are characterized by efficient RISC entry, minimum immune response and off-target effects, efficient cellular uptake without formulation, and efficient and specific tissue distribution.

  本文提供的自递送寡核苷酸具有高效的RISC进入、最小的免疫反应和非靶效应、无需配方的高效细胞摄取，以及高效和特异的组织分布。
• 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。
• [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。
• [EN] TREATMENT OF NEURODEGENERATIVE CONDITIONS<br/>[FR] TRAITEMENT D'ETATS NEURODEGENERATIFS
  申请人：BTG INT LTD

  公开号：WO2005018632A1

  公开（公告）日：2005-03-03

  A method is provided for treating a patient in need of therapy for a neurodegenerative disease comprising administering to that patient a therapeutically effective dose of a lipid glyceride comprising a glycerol moiety and a fatty acid moiety, the fatty acid moiety being selected from the group consisting of Ϝ-linolenic acid, dihomo-Ϝ-linolenic acid and arachidonic acid characterised in that the selected fatty acid moiety is attached to the glycerol moiety at its sn-2 position. Preferably the method is that wherein the lipid is administered for a duration and at a dose sufficient to maintain or elevate TGF-β1 levels in the patient to therapeutic levels.

  提供了一种治疗神经退行性疾病患者的方法，包括向该患者施用含有甘油基团和脂肪酸基团的治疗有效剂量的脂质甘油酯，所述脂肪酸基团选自Ϝ-亚麻酸、二油酸和花生四烯酸组成的群体，其特点在于所选的脂肪酸基团附着在甘油基团的sn-2位置。最好的方法是，脂质被施用的持续时间和剂量足以维持或提高患者体内TGF-β1水平至治疗水平。
• 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。