3-O-Tetradecyl-sn-glycerin | 82873-40-3

• 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-Tetradecyl-sn-glycerin
• 英文别名: (R)-tetradecylglycerol；3-tetradecyl-sn-glycerol；1-o-Tetradecylglycerol, (R)-；(2R)-3-tetradecoxypropane-1,2-diol
• CAS: 82873-40-3
• 化学式: C₁₇H₃₆O₃
• 分子量: 288.471
• InChiKey: JSSKAZULTFHXBH-QGZVFWFLSA-N

物化性质

• 沸点：
  418.3±25.0 °C(Predicted)
• 密度：
  0.927±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  20
• 可旋转键数：
  16
• 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-Tetradecyl-sn-glycerin 在 palladium on activated charcoal molecular sieve 、 三氟化硼 、 potassium tert-butylate 、 氢气 、 碘 、 sodium methylate 、 silver(l) oxide 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 、 叔丁醇 、 苯 为溶剂， 反应 126.5h， 生成 1-O-<4-O-(α-D-Glucopyranosyl)-β-D-glucopyranosyl>-3-O-tetradecyl-sn-glycerin
  参考文献：
  名称：

  Prinz, Harald; Six, Lambert; Ruess, Klaus-Peter, Liebigs Annalen der Chemie, 1985, # 2, p. 217 - 225

  摘要：

  DOI：
• 作为产物：
  描述：

  十四醇 在 氢氧化钾 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 17.0h， 生成 3-O-Tetradecyl-sn-glycerin
  参考文献：
  名称：

  Prinz, Harald; Six, Lambert; Ruess, Klaus-Peter, Liebigs Annalen der Chemie, 1985, # 2, p. 217 - 225

  摘要：

  DOI：

文献信息

• Certain phosphoric acid ester derivatives of 1,3-dioxy propane
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US04426525A1

  公开（公告）日：1984-01-17

  Tridecyloxy- or tetradecyloxy-propane derivatives of the formula: ##STR1## wherein R.sup.1 is tridecyl or tetradecyl, R.sup.2 is hydrogen or --OCH.sub.3, and R.sup.3, R.sup.4 and R.sup.5 independently represent hydrogen or C.sub.1-3 alkyl, or ##STR2## represents cyclic ammonio, and their salts, have inhibitory activity to multiplication of tumor cells and antimicrobial activity.

  Tridecyloxy-或tetradecyloxy-丙烷衍生物的公式为：##STR1##其中R.sup.1为十三烷基或十四烷基，R.sup.2为氢或--OCH.sub.3，R.sup.3、R.sup.4和R.sup.5独立地表示氢或C.sub.1-3烷基，或者##STR2##表示环氨基，它们的盐具有抑制肿瘤细胞增殖和抗微生物活性。
• Tridecyloxy- or tetradecyloxy-propane derivatives
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US04544512A1

  公开（公告）日：1985-10-01

  Tridecyloxy- or tetradecyloxy-propane derivatives of the formula: ##STR1## wherein R.sup.1 is tridecyl or tetradecyl, R.sup.2 is hydrogen or --OCH.sub.3, and R.sup.3, R.sup.4 and R.sup.5 independently represent hydrogen or C.sub.1-3 alkyl, or ##STR2## represents cyclic ammonio, and their salts, have inhibitory activity to multiplication of tumor cells and antimicrobial activity.

  Tridecyloxy-或tetradecyloxy-丙烷衍生物的公式为：##STR1##其中R.sup.1是三十三烷基或十四烷基，R.sup.2是氢或--OCH.sub.3，而R.sup.3，R.sup.4和R.sup.5分别表示氢或C.sub.1-3烷基，或##STR2##代表环状铵，它们的盐具有抑制肿瘤细胞增殖和抗微生物活性。
• Tridecyloxy- or tetradecyloxy-propane derivatives, and their use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP0050460A2

  公开（公告）日：1982-04-28

  Tridecyloxy- or tetradecyloxy-propane derivatives of the formula: wherein R1 is tridecyl or tetradecyl, R2 is hydrogen or -OCH3, and R3, R4 and R5 independently represent hydrogen or C1-3 alkyl, or represents cyclic ammonio, and their salts, have inhibitory activity to multiplication of tumor cells and antimicrobial activity.

  式中的十三烷氧基丙烷或十四烷氧基丙烷衍生物： 其中 R1 是十三烷基或十四烷基，R2 是氢或-OCH3，R3、R4 和 R5 独立地代表氢或 C1-3 烷基，或 代表环氨，它们及其盐类具有抑制肿瘤细胞繁殖的活性和抗菌活性。
• 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.
• US4426525A
  申请人：——

  公开号：US4426525A

  公开（公告）日：1984-01-17