(S)-decylglycerol | 79679-85-9

• 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: (S)-decylglycerol
• 英文别名: 1-O-decyl-sn-glycerol；(S)-Glyceryl capryl ether；(2S)-3-decoxypropane-1,2-diol
• CAS: 79679-85-9
• 化学式: C₁₃H₂₈O₃
• 分子量: 232.364
• InChiKey: SHQRLYGZJPBYGJ-ZDUSSCGKSA-N

物化性质

• 沸点：
  361.7±22.0 °C(Predicted)
• 密度：
  0.948±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  12
• 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：

  (S)-decylglycerol 、 3-chloropropylphosphonic acid 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 生成 (R)-3-(decyloxy)-2-hydroxypropyl (3-chloropropyl)phosphonate
  参考文献：
  名称：

  Autotaxin structure–activity relationships revealed through lysophosphatidylcholine analogs

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2009.03.030
• 作为产物：
  描述：

  methanesulfonic acid decyl ester 在 盐酸 、 potassium hydroxide 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 88.0h， 生成 (S)-decylglycerol
  参考文献：
  名称：

  天然烷基甘油的对映体合成及其抗菌和抗生物膜活性

  摘要：

  摘要 烷基甘油（AKGs）是通过烷基链长和不饱和度而变化的生物活性的天然化合物，它们的绝对构型为2小号。三个 AKGs ( 5l – 5n ) 以对映体纯的形式合成，并首次与其他 12 个已知和天然存在的 AKGs ( 5a – 5k , 5o )一起表征。它们的结构是使用1 H 和13 C APT NMR 与 2D-NMR、ESI-MS 或 HRESI-MS 和旋光数据建立的，并测试了它们的抗菌和抗生物膜活性。AKG 5a – 5m和5o对五种临床分离株和铜绿假单胞菌ATCC 15442显示出活性，MIC 值在 15–125 µg/mL 范围内。此外，在 MIC 的一半时，大多数 AKG 减少了 23%–99% 范围内的金黄色葡萄球菌生物膜形成和14%–64% 范围内的铜绿假单胞菌ATCC 15442 生物膜形成。在这项工作中评估的 AKG 的抗生物膜活性以前没有被研究过。

  DOI：

  10.1080/14786419.2019.1686370

文献信息

• Antimicrobial fatty compositions
  申请人：Research Foundation for Mental Hygiene, Inc.

  公开号：EP0465423A2

  公开（公告）日：1992-01-08

  This invention is directed to an antimicrobial activity of fatty acids and monoglycerides. More particularly, this invention is directed to the inactivation of enveloped viruses and the killing of microorganisms by fatty acids and monoglycerides. The invention is also directed to antimicrobial pharmaceutical compositions consisting essentially of inert pharmaceutical carrier and an effective amount of one or more compounds selected from the group consisting of fatty acids and monoglycerides thereof.

  本发明涉及脂肪酸和单甘酯的抗菌活性。更具体地说，本发明涉及脂肪酸和单甘油酯对包膜病毒的灭活和对微生物的杀灭。本发明还涉及抗菌药物组合物，主要由惰性药物载体和有效量的一种或多种选自由脂肪酸及其单甘酯组成的组的化合物构成。
• REDUCING THE SPREAD OF INFECTION BY BLOOD HANDLING EQUIPMENT
  申请人：Research Foundation for Mental Hygiene, Inc.

  公开号：EP0429645A1

  公开（公告）日：1991-06-05
• EP0429645A4
  申请人：——

  公开号：EP0429645A4

  公开（公告）日：1992-05-13
• US5434182A
  申请人：——

  公开号：US5434182A

  公开（公告）日：1995-07-18
• US5466714A
  申请人：——

  公开号：US5466714A

  公开（公告）日：1995-11-14