glyceryl 2-linolenate | 55268-58-1

• 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: glyceryl 2-linolenate
• 英文别名: 2-monolinolenin；linolenic acid 2-hydroxy-1-(hydroxymethyl)ethyl ester；1,3-dihydroxypropan-2-yl (9Z,12Z,15Z)-octadeca-9,12,15-trienoate
• CAS: 55268-58-1
• 化学式: C₂₁H₃₆O₄
• 分子量: 352.514
• InChiKey: ZCCLDKGWJIREQF-PDBXOOCHSA-N

物化性质

• 沸点：
  484.8±45.0 °C(Predicted)
• 密度：
  0.993±0.06 g/cm3(Predicted)
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  25
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2916190090

反应信息

• 作为反应物：
  描述：

  glyceryl 2-linolenate 以 正己烷 为溶剂， 反应 24.0h， 生成 2,3-dihydroxypropyl (9Z,12Z,15Z)-9,12,15-octadecatrienoate
  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：

  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

文献信息

• Lubricating oil composition providing anti-wear protection
  申请人：TEXACO DEVELOPMENT CORPORATION

  公开号：EP0698657A1

  公开（公告）日：1996-02-28

  A lubricating oil additive which provides anti-wear properties to a lubricating oil, being the reaction product of 2,5-dimercapto-1,3,4-thiadiazole and a mixture of unsaturated mono-, di-, and tri-glycerides. The additive is preferably formed by reacting a mixture of unsaturated mono-, di-, and tri-glycerides with diethanolamine to provide an intermediate reaction product and reacting the intermediate reaction product with 2,5-dimercapto-1,3,4-thiadiazole.

  一种可为润滑油提供抗磨损性能的润滑油添加剂，是 2,5-二巯基-1,3,4-噻二唑与不饱和单甘酯、双甘酯和三甘酯混合物的反应产物。这种添加剂最好是通过将不饱和单甘酯、双甘酯和三甘酯混合物与二乙醇胺反应生成中间反应产物，再将中间反应产物与 2,5-二巯基-1,3,4-噻二唑反应而形成。
• Hair and/or scalp treatment compositions
  申请人：Unilever PLC

  公开号：EP1785130A2

  公开（公告）日：2007-05-16

  Hair and/or scalp treatment compositions comprise an antidandruff agent, an effective amount of a cannabinoid receptor (CBR) activating agent and a cosmetically acceptable diluent or carrier. Alternatively, the compositions may be shampoo compositions comprising from 3 to 50 wt% surfactant, a CB receptor activating agent and a cosmetically acceptable diluent or carrier, provided that the CB receptor activating agent is not palmitoylethanolamide. The compositions are useful in the treatment and/or prevention of the symptoms of dandruff and can reduce scalp itch, a symptom which is typically associated with dandruff.

  头发和/或头皮治疗组合物由去屑剂、有效量的大麻素受体（CBR）激活剂和化妆品可接受的稀释剂或载体组成。或者，这些组合物可以是洗发水组合物，包含 3 至 50 wt%的表面活性剂、CB 受体激活剂和化妆品上可接受的稀释剂或载体，前提是 CB 受体激活剂不是棕榈酰乙醇酰胺。这些组合物可用于治疗和/或预防头皮屑症状，并可减轻头皮瘙痒（头皮屑的典型症状）。
• A MIXTURE WITH STABILIZED TASTE AND/OR ODOR
  申请人：Symrise AG

  公开号：EP3777981A1

  公开（公告）日：2021-02-17

  Suggested is a mixture with stabilized taste and/or odor, comprising or consisting of: (a) [6]-paradol and (b) at least one mono- or polyunsaturated C8-C22 fatty acid or its monohydric or polyhydric C1-C18 aliphatic alcohols ester, wherein the composition comprises the component (a) in an amount from 0.0001 to 1 wt.-percent, based on the mixture.

  建议是一种具有稳定味道和/或气味的混合物，由以下物质组成或构成： (a) [6]-paradol 和 (b) 至少一种一元或多元不饱和 C8-C22 脂肪酸或其一元或多元 C1-C18 脂肪醇酯、 其中，该组合物包含的 (a) 组分的含量为 0.0001 至 1 wt.-%，以混合物为基础。
• Reduced friction lubricants comprising magnesium detergents and/or overbased magnesium detergents and molybdenum based friction modifiers
  申请人：LANXESS Corporation

  公开号：US11535807B2

  公开（公告）日：2022-12-27

  The addition of mixed thio acid amide molybdenum dithiocarbamates to lubricant compositions comprising magnesium detergents and/or overbased magnesium detergents, e.g., overbased magnesium sulfonate, provides lubricant compositions that suppress Low Speed Pre-Ignition and possess excellent low friction characteristics. Furthermore, the addition of molybdenum based friction reducing additives, e.g., mixed thio acid amide molybdenum dithiocarbamates, in combination with one or more fatty acid 2-hydroxyalkylamides, to lubricant compositions comprising magnesium detergents or overbased magnesium detergents provides lubricant compositions that suppress Low Speed Pre-ignition and possess excellent low friction characteristics.

  在包含镁洗涤剂和/或过基镁洗涤剂（如过基磺酸镁）的润滑油组合物中添加混合硫代酸酰胺钼二硫代氨基甲酸盐，可提供抑制低速预点火并具有优异低摩擦特性的润滑油组合物。此外，在包含镁洗涤剂或过基镁洗涤剂的润滑剂组合物中加入钼基减摩添加剂，例如混合硫代酸酰胺二硫代氨基甲酸钼，与一种或多种脂肪酸 2- 羟基烷基酰胺结合使用，可提供抑制低速预点火并具有优异低摩擦特性的润滑剂组合物。
• ANTIPERSPIRANT OR DEODORANT COMPOSITIONS
  申请人：Unilever Home & Personal Care USA, Division of Conopco, Inc.

  公开号：US20020182159A1

  公开（公告）日：2002-12-05

  Deodorant and antiperspirant compositions comprising an aluminum or aluminum-zirconium active can suffer from perceived irritancy when applied topically, which is generally manifested as an itch sensation. This irritancy can be ameliorated or overcome by incorporating within the composition a cannabanoid receptor (CBR) activating agent, and especially an amount selected in the range of from 0.25 to 10 wt %.

  含有铝或铝锆活性成分的除臭剂和止汗剂组合物在局部使用时会产生刺激感，通常表现为瘙痒感。 通过在组合物中加入大麻素受体（CBR）激活剂，尤其是在 0.25 至 10 wt % 的范围内加入一定量的大麻素受体激活剂，可以改善或克服这种刺激性。