3-O-Dodecyl-sn-glycerin | 90904-23-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: 3-O-Dodecyl-sn-glycerin
• 英文别名: 3-O-dodecyl-sn-glycerol；(-)-3-dodecyloxy-propane-1,2-diol；(-)-O¹-Dodecyl-glycerin；(-)-3-Dodecyloxy-propan-1,2-diol；1-Monododecylglycerol；(2R)-3-dodecoxypropane-1,2-diol
• CAS: 90904-23-7
• 化学式: C₁₅H₃₂O₃
• 分子量: 260.417
• InChiKey: GBXRUYNQDDTQQS-OAHLLOKOSA-N

物化性质

• 沸点：
  390.5±22.0 °C(Predicted)
• 密度：
  0.937±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-O-Dodecyl-sn-glycerin 在 吡啶 、 甲醇 、 4-二甲氨基吡啶 、 sodium azide 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 四丁基氟化铵 、 sodium methylate 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 99.5h， 生成 2-deoxy-2-dodecanamido-1-O-dodecyl-3-O-β-D-galactopyranosyl-sn-glycerol
  参考文献：
  名称：

  Self-Organizing Properties of Natural and Related Synthetic Glycolipids

  摘要：

  In this article we report on the syntheses, self-organizing properties, and structures of a variety of cerebrosides and related synthetic glycolipids. The thermotropic and lyotropic liquid crystalline properties of the materials were evaluated in detail. All of the families of materials studied exhibited columnar mesophases. In the dry state the aliphatic chains were found to be located on the exterior of the columns, whereas in the wet state the reverse was the case with the polar headgroups on the exterior. Thus, the aliphatic chains, act almost like hydrocarbon solvents in the dry state.

  DOI：

  10.1021/ja020396+
• 作为产物：
  描述：

  溴代十二烷 在 四丁基溴化铵 作用下， 反应 20.0h， 生成 3-O-Dodecyl-sn-glycerin
  参考文献：
  名称：

  Self-Organizing Properties of Natural and Related Synthetic Glycolipids

  摘要：

  In this article we report on the syntheses, self-organizing properties, and structures of a variety of cerebrosides and related synthetic glycolipids. The thermotropic and lyotropic liquid crystalline properties of the materials were evaluated in detail. All of the families of materials studied exhibited columnar mesophases. In the dry state the aliphatic chains were found to be located on the exterior of the columns, whereas in the wet state the reverse was the case with the polar headgroups on the exterior. Thus, the aliphatic chains, act almost like hydrocarbon solvents in the dry state.

  DOI：

  10.1021/ja020396+

文献信息

• 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 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。
• Autotaxin structure–activity relationships revealed through lysophosphatidylcholine analogs
  作者：E. Jeffrey North、Daniel A. Osborne、Peter K. Bridson、Daniel L. Baker、Abby L. Parrill

  DOI：10.1016/j.bmc.2009.03.030

  日期：2009.5

  Autotaxin (ATX) catalyzes the hydrolysis of lysophosphatidylcholine (LPC) to form the bioactive lipid lysophosphatidic acid (LPA). LPA stimulates cell proliferation, cell survival, and cell migration and is involved in obesity, rheumatoid arthritis, neuropathic pain, atherosclerosis and various cancers, suggesting that ATX inhibitors have broad therapeutic potential. Product feedback inhibition of ATX by LPA has stimulated structure-activity studies focused on LPA analogs. However, LPA displays mixed mode inhibition, indicating that it can bind to both the enzyme and the enzyme-substrate complex. This suggests that LPA may not interact solely with the catalytic site. In this report we have prepared LPC analogs to help map out substrate structure-activity relationships. The structural variances include length and unsaturation of the fatty tail, choline and polar linker presence, acyl versus ether linkage of the hydrocarbon chain, and methylene and nitrogen replacement of the choline oxygen. All LPC analogs were assayed in competition with the synthetic substrate, FS-3, to show the preference ATX has for each alteration. Choline presence and methylene replacement of the choline oxygen were detrimental to ATX recognition. These findings provide insights into the structure of the enzyme in the vicinity of the catalytic site as well as suggesting that ATX produces rate enhancement, at least in part, by substrate destabilization. (C) 2009 Elsevier Ltd. All rights reserved.
• Prinz, Harald; Six, Lambert; Ruess, Klaus-Peter, Liebigs Annalen der Chemie, 1985, # 2, p. 217 - 225
  作者：Prinz, Harald、Six, Lambert、Ruess, Klaus-Peter、Lieflaender, Manfred

  DOI：——

  日期：——
• US8808703B2
  申请人：——

  公开号：US8808703B2

  公开（公告）日：2014-08-19