丙二醇二月桂酸酯 | 22788-19-8

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 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: 丙二醇二月桂酸酯
• 英文名称: propylene glycol monolaurate
• 英文别名: propylene glycol dilaurate；propyleneglycol dilaurate；1,2-bis-lauroyloxy-propane；1,2-Bis-lauroyloxy-propan；Propylenglykol-dilaurat；propylene dilaurate；2-dodecanoyloxypropyl dodecanoate
• CAS: 22788-19-8
• 化学式: C₂₇H₅₂O₄
• 分子量: 440.707
• InChiKey: WITKSCOBOCOGSC-UHFFFAOYSA-N

物化性质

• 沸点：
  504.7±23.0 °C(Predicted)
• 密度：
  0.915±0.06 g/cm3(Predicted)
• 溶解度：
  几乎不溶于水，极易溶于酒精、甲醇和二氯甲烷。
• LogP：
  10.764 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  10.8
• 重原子数：
  31
• 可旋转键数：
  25
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2915900090

制备方法与用途

丙二醇二月桂酸酯是一种生物化学试剂，可用作生物材料或有机化合物，在生命科学研究中发挥重要作用。

反应信息

• 作为反应物：
  描述：

  丙二醇二月桂酸酯 、 硫酸 生成 月桂酸 、 1,2-bis-sulfooxy-propane 、 alkaline earth salt of/the/ methylsulfuric acid 、 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  The Reaction of Lauric Acid Esters with Sulfuric Acid

  摘要：

  DOI：

  10.1021/ja01516a028
• 作为产物：
  描述：

  月桂酸 、 1,2-丙二醇 在 lipase from Humicola lanuginosa No_. 3 phosphate buffer 作用下， 以 水 为溶剂， 反应 18.0h， 以18.4%的产率得到丙二醇二月桂酸酯
  参考文献：
  名称：

  Omar, Ibrahim Che; Nishio, Naomichi; Nagai, Shiro, Agricultural and Biological Chemistry, 1987, vol. 51, # 8, p. 2153 - 2160

  摘要：

  DOI：

文献信息

• Production of propylene glycol fatty acid monoesters by lipase‐catalyzed reactions in organic solvents
  作者：Jei‐Fu Shaw、Shian Lo

  DOI：10.1007/bf02541427

  日期：1994.7

  Fatty acid monoesters of propylene glycol (1,2‐propanediol) are good water‐in‐oil emulsifiers. These esters were synthesized enzymatically to overcome the problems associated with chemical processes. APseudomonas lipase was added to reaction mixtures containing propylene glycol and various acyl donors (fatty acids, fatty acid ethyl esters, fatty acid anhydrides and triglycerides) in organic solvents, and the mixtures were shaken at 30°C. The products were analyzed by gas chromatography. The yield of monoesters was affected by the acyl donors, organic solvents, temperature, water content, pH memory and reaction time. The anhydrous (lyophilized) enzyme and fatty acid anhydrides were best for monoester production. The optimum pH ranges were 4–5 and 8–10. The yields of propylene glycol monolaurate, monomyristate, monopalmitate, monostearate and monooleate with 50 mM fatty acid anhydrides as acyl donors were 97.2, 79.6, 83.7, 89.7 and 93.4 mM, respectively; those with 50 mM fatty acids as acyl donors were 37.3, 28.7, 28.7, 35.3 and 36.2 mM, respectively. The yields of propylene glycol monopalmitate, monostearate and monooleate with 50 mM triglycerides as acyl donors were 87.4, 65.1 and 83.2 mM, respectively.

  摘要 丙二醇（1,2-丙二醇）脂肪酸单酯是良好的油包水型乳化剂。这些酯类是通过酶法合成的，以克服与化学工艺相关的问题。在有机溶剂中含有丙二醇和各种酰基供体（脂肪酸、脂肪酸乙酯、脂肪酸酐和甘油三酯）的反应混合物中加入假单胞菌脂肪酶，然后在 30°C 下振荡混合物。产物通过气相色谱法进行分析。单酯的产量受酰基供体、有机溶剂、温度、含水量、pH 值记忆和反应时间的影响。无水（冻干）酶和脂肪酸酐最适合生产单酯。最佳 pH 值范围为 4-5 和 8-10。以 50 毫摩尔脂肪酸酐为酰基给体，丙二醇单月桂酸酯、单肉豆蔻酸酯、单棕榈酸酯、单硬脂酸酯和单油酸酯的产率分别为 97.2、79.6、83.7、89.7 和 93.4 毫摩尔；以 50 毫摩尔脂肪酸为酰基给体，丙二醇单月桂酸酯、单肉豆蔻酸酯、单棕榈酸酯、单硬脂酸酯和单油酸酯的产率分别为 37.3、28.7、28.7、35.3 和 36.2 毫摩尔。以 50 毫摩尔甘油三酯为酰基供体的丙二醇单棕榈酸酯、单硬脂酸酯和单油酸酯的产率分别为 87.4、65.1 和 83.2 毫摩尔。
• Reaction of ethylene oxide or propylene oxide with long‐chain fatty acids. Mono‐ and diester formation
  作者：A. N. Wrigley、F. D. Smith、A. J. Stirton

  DOI：10.1007/bf02540263

  日期：1959.1

  The alkali‐catalyzed reaction of ethylene oxide or propylene oxide with fatty acids was shown to be complex. Mono‐ and diesters were formed in comparable amounts even at an early stage when only about one equivalent of the cyclic ether had been condensed.

  The following compounds were isolated in a pure state: ethylene glycol monolaurate, ethylene glycol dilaurate, diethylene glycol dilaurate, ethylene glycol distearate, 1,2‐propylene glycol dilaurate, and 1,2‐propylene glycol distearate. A monoester from propylene oxide was shown to be a mixture of the 1‐and 2‐monolaurate [C₁₁H₂₃CO₂CH₂CHOHCH₃ and C₁₁H₂₃CO₂CH(CH₃)CH₂OH].

  摘要环氧乙烷或环氧丙烷与脂肪酸的碱催化反应十分复杂。分离出下列纯化合物：乙二醇单月桂酸酯、乙二醇二月桂酸酯、二乙二醇二月桂酸酯、乙二醇二硬脂酸酯、1,2-丙二醇二月桂酸酯和 1,2-丙二醇二硬脂酸酯。研究表明，环氧丙烷单酯是 1 和 2-单月桂酸酯[C11H23CO2CH2CHOHCH3 和 C11H23CO2CH(CH3)CH2OH]的混合物。
• COMPOUNDS (CYSTEIN BASED LIPOPEPTIDES) AND COMPOSITIONS AS TLR2 AGONISTS USED FOR TREATING INFECTIONS, INFLAMMATIONS, RESPIRATORY DISEASES ETC.
  申请人：Wu Tom Yao-Hsiang

  公开号：US20130065861A1

  公开（公告）日：2013-03-14

  The invention provides a novel class of compounds viz. generally lipopeptides like Pam3CSK4, immunogenic compositions and pharmaceutical compositions comprising such compounds and methods of using such compounds to treat or prevent diseases or disorders associated with Toll-Like Receptors 2. In one aspect, the compounds are useful as adjuvants for enhancing the effectiveness a vaccine.

  该发明提供了一类新型化合物，即通常为脂肽类似物Pam3CSK4的脂肽类化合物，以及包含这些化合物的免疫原组合物和药物组合物，以及使用这些化合物治疗或预防与Toll样受体2相关的疾病或紊乱的方法。在一个方面，这些化合物可用作增强疫苗有效性的佐剂。
• Compounds (cystein based lipopeptides) and compositions as TLR2 agonists used for treating infections, inflammations, respiratory diseases etc
  申请人：Wu Tom Yao-Hsiang

  公开号：US08808703B2

  公开（公告）日：2014-08-19

  The invention provides a novel class of compounds viz. generally lipopeptides like Pam3CSK4, immunogenic compositions and pharmaceutical compositions comprising such compounds and methods of using such compounds to treat or prevent diseases or disorders associated with Toll-Like Receptors 2. In one aspect, the compounds are useful as adjuvants for enhancing the effectiveness a vaccine.

  本发明提供了一类新型化合物，即通常类似于Pam3CSK4的脂肽类化合物，以及包括这些化合物的免疫原组合物和药物组合物，以及使用这些化合物治疗或预防与Toll-Like受体2相关的疾病或障碍的方法。在一个方面，这些化合物可用作佐剂，以增强疫苗的有效性。
• COMPOUNDS AND COMPOSITIONS AS TLR2 AGONISTS
  申请人：WU Tom Yao-Hsiang

  公开号：US20140323390A1

  公开（公告）日：2014-10-30

  The invention provides a novel class of compounds, immunogenic compositions and pharmaceutical compositions comprising such compounds and methods of using such compounds to treat or prevent diseases or disorders associated with Toll-Like Receptors 2. In one aspect, the compounds are useful as adjuvants for enhancing the effectiveness of a vaccine.

  本发明提供了一种新的化合物类别，免疫原组合物和包含这种化合物的药物组合物，以及使用这种化合物来治疗或预防与Toll样受体2相关的疾病或障碍的方法。在一个方面，这些化合物可用作佐剂，以增强疫苗的有效性。