三亚麻精 | 14465-68-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 中文名称: 三亚麻精
• 中文别名: Α-亚麻酸甘油三酯；十八碳三烯酸甘油三酯(CIS-9,12,15)；亚麻酸甘油酯
• 英文名称: trilinolenin
• 英文别名: 2,3-bis[[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyl]oxy]propyl (9Z,12Z,15Z)-octadeca-9,12,15-trienoate
• CAS: 14465-68-0
• 化学式: C₅₇H₉₂O₆
• 分子量: 873.354
• InChiKey: UBEIMDKGOYBUKT-FLIQGJDUSA-N

物化性质

• 熔点：
  -23-24 °C
• 沸点：
  814.4±65.0 °C(Predicted)
• 密度：
  0.94 g/mL at 20 °C(lit.)
• 溶解度：
  DMF：10mg/mL；乙醇：10mg/mL；乙醇:PBS(pH 7.2) (1:1): 500μg/ml
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  18.3
• 重原子数：
  63
• 可旋转键数：
  47
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  三亚麻精 在 Novozym 435 、 乙醇 作用下， 反应 4.0h， 以60.4%的产率得到glyceryl 2-linolenate
  参考文献：
  名称：

  脂肪酸去饱和对2-单酰基甘油自发酰基迁移的影响

  摘要：

  AbstractThe effect of desaturation from the C9 to the C15 carbon of 2‐monoacylglycerol (2‐MAG) fatty acids on spontaneous acyl migration is described. Three 2‐MAG species, 2‐monooleoylglycerol (C18:1 cis‐Δ9), 2‐monolinoleoylglycerol (C18:2 cis‐Δ9,12), and 2‐monolinolenoylglycerol (C18:3 cis‐Δ9,12,15) were synthesized by lipase‐catalyzed ethanolysis of their respective triacylglycerols and isolated in >60 % yield and at 2‐MAG purities of >95 % relative to 1‐monoacylglycerol (1‐MAG). 1H‐NMR spectroscopy was used to monitor the spontaneous acyl migration of the 2‐MAG species over a temperature range from 20 to 80 °C. The relative energies of activation calculated from the Arrhenius relationships of the 2‐MAG acyl migration rate constants were 73.3, 68.0, and 72.9 kJ mol−1 for the three 2‐MAG species, respectively. Density functional calculations performed using the B3LYP functional at the 6‐31+G* basis set on the three ketal ring intermediate of the three 2‐MAG species followed a similar trend with a lack of relative energetic preference associated with the degree of desaturation. The kinetically determined relative activation energies were approximately twofold higher than the theoretical relative Gibbs free energies of the intermediates, suggesting that other factors influence acyl migration. In general, increasing desaturation after the C9 carbon of 2‐MAG fatty acids had no appreciable effect on acyl migration rates.

  DOI：

  10.1007/s11746-012-2113-z
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 aluminum oxide 作用下， 生成 三亚麻精
  参考文献：
  名称：

  Walker; Mills, Journal of the Society of Chemical Industry, 1943, vol. 62, p. 107

  摘要：

  DOI：

文献信息

• 1H-NMR Characterization of Epoxides Derived from Polyunsaturated Fatty Acids
  作者：Wei Xia、Suzanne M. Budge、Mike D. Lumsden

  DOI：10.1007/s11746-016-2800-2

  日期：2016.4

  chemical shifts of epoxides derived from polyunsaturated fatty acids (PUFA) has also limited the use of 1H NMR in detecting and quantifying these products during both oxidative degradation and industrial epoxidation. In this study, 1H NMR was used to characterize the epoxides synthesized from trilinolein, trilinolenin, canola oil, and fish oils by reaction with formic acid and hydrogen peroxide. Assignments

  近年来，1 H NMR已用于研究脂质氧化和工业过程中的环氧化物，但单环氧化物和二环氧化物的峰分配不一致。对于衍生自多不饱和脂肪酸（PUFA）的环氧化物的化学位移缺乏明确的定义，这也限制了1 H NMR在氧化降解和工业环氧化过程中检测和定量这些产物的用途。在本研究中，11 H NMR用于表征通过与甲酸和过氧化氢反应从三油精，三油精，菜籽油和鱼油合成的环氧化物。在低芥酸菜子油和鱼油中，来自PUFA的环氧化物的分配在2.90-3.23 ppm和2.90-3.28 ppm之间，这与这些油中的其他化学基团不同。环氧基的化学位移随着脂肪酸链中环氧基数量的增加而向下游移动。因此，二环氧化合物的峰出现在3.00、3.09和3.14 ppm，三环氧化合物的峰出现在3.00、3.16和3.21 ppm。结果还表明，在本研究条件下，环氧化过程中形成了二环氧和三环氧的立体异构体。这些新的二环和三环氧化物立体异构体
• Regioisomeric Characterization of Triacylglycerols Using Silver-Ion HPLC/MS and Randomization Synthesis of Standards
  作者：Miroslav Lísa、Hana Velínská、Michal Holčapek

  DOI：10.1021/ac900150j

  日期：2009.5.15

  Silver-ion normal-phase high-performance liquid chromatography (HPLC) provides a superior separation selectivity for lipids differing in the number and position of double bonds in fatty acid chains including the resolution of triacylglycerol (TG) regioisomers under optimized conditions. Our silver-ion HPLC method is based on the coupling of three columns in the total length of 75 cm and a new mobile phase gradient consisting of hexane−acetonitrile−2-propanol which provides better resolution and also reproducibility in comparison to previously used mobile phases. In our work, the chemical interesterification (randomization) of single-acid TG standards is used for the generation of regioisomeric series of TGs, because it provides a random distribution of fatty acids in TGs at well-defined concentration ratios. The baseline separation of regioisomeric TG pairs containing up to three double bonds and the partial separation of TG regioisomers with four to seven double bonds are reported for the first time. Our silver-ion high-performance liquid chromatography/mass spectrometry (HPLC/MS) method is applied for the regioisomeric characterization of complex samples of plant oils and animal fat, where the results clearly demonstrate different preference of sn-2 occupation in plants (mainly unsaturated fatty acids) versus animal fat (mainly saturated fatty acids).

  银离子正相高效液相色谱（HPLC）为脂质提供了优越的分离选择性，这些脂质在脂肪酸链中双键的数量和位置上存在差异，包括在优化条件下对甘油三酯（TG）位置异构体的分辨。我们的银离子HPLC方法是基于三根总长度为75厘米的柱子耦合以及一个新的由己烷、乙腈和丙酮醇组成的移动相梯度，这相比于之前使用的移动相提供了更好的分辨率和重复性。在我们的工作中，利用单酸TG标准的化学酯交换（随机化）来生成TG的位置异构体系列，因为这可以在明确定义的浓度比下提供脂肪酸在TG中的随机分布。首次报道了含有最多三个双键的位置异构体TG对的基线分离以及含有四到七个双键的TG位置异构体的部分分离。我们的银离子高效液相色谱/质谱（HPLC/MS）方法应用于植物油和动物脂肪的复杂样品的位置异构体特性鉴定，结果清楚地展示了在植物（主要是不饱和脂肪酸）和动物脂肪（主要是饱和脂肪酸）中sn-2占位偏好的不同。
• [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。
• Site-Specific Deuteration of Polyunsaturated Alkenes
  作者：A. V. Smarun、M. Petković、M. S. Shchepinov、D. Vidović

  DOI：10.1021/acs.joc.7b02169

  日期：2017.12.15

  and expensive syntheses. In this report, we disclose a very efficient catalytic protocol for site-specific deuteration of PUFAs and analogous poly-alkenes under exceptional kinetic control. Deuterium oxide (D2O) has been identified not only as a deuterium source but also as a crucial component in the overall reaction mechanism responsible for averting the formation of thermodynamically favored side-products

  药物和生物学相关分子的选择性氘化在制药行业中变得越来越重要。多不饱和脂肪酸（PUFA）在其双烯丙基位点的位点选择性同位素增强已被认为是防止这些分子氧化损伤的一种独特方法，这种氧化损伤与神经元和视网膜疾病，动脉粥样硬化和衰老有关。用于制备位点选择性氘代PUFA的典型方法需要相当长，费力且昂贵的合成。在这份报告中，我们公开了非常有效的催化方案，用于在特殊动力学控制下对PUFA和类似聚烯烃进行位点特异性氘化。氧化氘（D 2O）不仅被认为是氘源，而且在整个反应机制中也起着至关重要的作用，该机制负责避免形成热力学上有利的副产物。
• Lipids for modulating immune response
  申请人：——

  公开号：US20040023922A1

  公开（公告）日：2004-02-05

  A product and the use thereof to stimulate and/or modulate immune response in animals and humans, comprising lipids having a glycerol backbone carrying at least one alkyl or acyl chain, wherein the lipid is phospholipid, glycolipid or neutral lipid, saturated or unsaturated, and the number of carbon atoms in the hydrocarbon tails lies between (10 and 22) inclusive, the lipids being defined as esters of glycerol (propane 1,2,3-triol) with fatty acids, also including 1,2-di-O-acylglycerol joined at oxygen (3) by a glycosidic linkage to a carbohydrate, also derivatives of glycerol in which one hydroxy group, commonly but not necessarly primary, is esterified with fatty acids, and execluding those organic compounds consisting of a trisaccharide repeating unit with oligosaccharide side chains and acyl or amine linked fatty acids.

  一种产品及其用途，用于刺激和/或调节动物和人类的免疫反应，包括具有甘油骨架的脂质，其携带至少一个烷基或酰基链，其中脂质为磷脂类、糖脂类或中性脂质，饱和或不饱和，碳原子数在(10和22)之间，脂质被定义为甘油(丙烷-1,2,3-三醇)与脂肪酸的酯，还包括通过氧(3)连接到碳水化合物的糖苷键的1,2-二-O-酰基甘油，以及甘油的衍生物，其中一个羟基团，通常但不一定是主要的，与脂肪酸酯化，不包括由三糖重复单元和寡糖侧链以及酰基或胺链脂肪酸组成的有机化合物。