2-羟基-3-(膦酰氧基)丙基硬脂酸酯 | 22002-86-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油磷脂
• 中文名称: 2-羟基-3-(膦酰氧基)丙基硬脂酸酯
• 英文名称: 1-Stearoyl-lysophosphatidic acid
• 英文别名: stearoyl-lysophosphatidic acid；lysophosphatidic acid；LysoPA(18:0)；18:0 LPA；2-hydroxy-3-(phosphonooxy)propyl stearate；stearyl-LPA；(2-hydroxy-3-phosphonooxypropyl) octadecanoate
• CAS: 22002-86-4
• 化学式: C₂₁H₄₃O₇P
• 分子量: 438.542
• InChiKey: LAYXSTYJRSVXIH-UHFFFAOYSA-N

物化性质

• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  29
• 可旋转键数：
  22
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  7

安全信息

• 海关编码：
  2931900090

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  单硬脂酸甘油酯	1-monostearoyl-rac-glycerol	123-94-4	C21H42O4	358.562

反应信息

• 作为反应物：
  描述：

  2-羟基-3-(膦酰氧基)丙基硬脂酸酯 、 4-N-3'-O-bis(tert-butoxycarbonyl)gemcitabine 在 吡啶 、 2,4,6-三异丙基苯磺酰氯 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 26.0h， 生成 2'-2'-difluoro-2'-deoxycytidine 5'-(3-stearoyloxy-2-rac-chloropropyl)phosphate
  参考文献：
  名称：

  Synthesis and in vitro evaluation of novel lipophilic monophosphorylated gemcitabine derivatives and their nanoparticles

  摘要：

  Gemcitabine hydrochloride (HCl) is approved for the treatment of a wide spectrum of solid tumors. However, the rapid development of resistance often makes gemcitabine less efficacious. In the present study, we synthesized several novel lipophilic monophosphorylated gemcitabine derivatives, incorporated them into solid lipid nanoparticles, and then evaluated their ability to overcome major known gemcitabine resistance mechanisms by evaluating their in vitro cytotoxicities in cancer cells that are deficient in deoxycytidine kinase (dCK), deficient in human equilibrative nucleoside transporter (hENT1), over-expressing ribonucleotide reductase M1 subunit (RRM1), or over-expressing RRM2. In dCK deficient cells, the monophosphorylated gemcitabine derivatives and their nanoparticles were up to 86-fold more cytotoxic than gemcitabine HCl. The majority of the gemcitabine derivatives and their nanoparticles were more cytotoxic than gemcitabine HCl in cells that over-expressing RRM1 or RRM2, and the gemcitabine derivatives in nanoparticles were also resistant to deamination by deoxycytidine deaminase. The gemcitabine derivatives (in nanoparticles) hold a great potential in overcoming gemcitabine resistance. (c) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ijpharm.2012.03.014
• 作为产物：
  描述：

  单硬脂酸甘油酯 在 三乙胺 、 三氯氧磷 、 碳酸氢钠 、 盐酸 、 水 作用下， 以 二氯甲烷 、 甲醇 、 氯仿 为溶剂， 反应 18.0h， 以59%的产率得到2-羟基-3-(膦酰氧基)丙基硬脂酸酯
  参考文献：
  名称：

  Synthesis and in vitro evaluation of novel lipophilic monophosphorylated gemcitabine derivatives and their nanoparticles

  摘要：

  Gemcitabine hydrochloride (HCl) is approved for the treatment of a wide spectrum of solid tumors. However, the rapid development of resistance often makes gemcitabine less efficacious. In the present study, we synthesized several novel lipophilic monophosphorylated gemcitabine derivatives, incorporated them into solid lipid nanoparticles, and then evaluated their ability to overcome major known gemcitabine resistance mechanisms by evaluating their in vitro cytotoxicities in cancer cells that are deficient in deoxycytidine kinase (dCK), deficient in human equilibrative nucleoside transporter (hENT1), over-expressing ribonucleotide reductase M1 subunit (RRM1), or over-expressing RRM2. In dCK deficient cells, the monophosphorylated gemcitabine derivatives and their nanoparticles were up to 86-fold more cytotoxic than gemcitabine HCl. The majority of the gemcitabine derivatives and their nanoparticles were more cytotoxic than gemcitabine HCl in cells that over-expressing RRM1 or RRM2, and the gemcitabine derivatives in nanoparticles were also resistant to deamination by deoxycytidine deaminase. The gemcitabine derivatives (in nanoparticles) hold a great potential in overcoming gemcitabine resistance. (c) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ijpharm.2012.03.014

文献信息

• Osteoblast-specific mitogens and drugs containing such compounds
  申请人：Esswein Angelika

  公开号：US20050014723A1

  公开（公告）日：2005-01-20

  Osteoblast-specific mitogens and drugs containing such compounds can be used for treating metabolic bone diseases. Novel compounds for this treatment include lysophosphatidylic acid derivatives selected from the group consisting of compounds of formula: wherein R 1 =alkenyl or alkynyl having from 6 to 24 carbon atoms; n=0-12; X=oxygen; the compounds (all-cis-5,8,11,14)-eicosatetraenoic acid 2-hydroxy-3-phosphonooxypropyl ester; cis-9, cis-12-octadecadienoic acid 2-hydroxy-3-phosphonooxypropyl ester; (all-cis-9,12,15)-octadecatrienoic acid 2-hydroxy-3-phosphonooxypropyl ester; cis-9-octadecenoic acid 2-hydroxy-3-phosphonooxypropyl ester; and erucic acid 2-hydroxy-3-phosphonooxypropylester being excluded, and the physiologically tolerable salts, esters, optically active forms, and racemates of said compounds.

  骨母细胞特异性促进因子和含有这种化合物的药物可用于治疗代谢性骨疾病。用于此治疗的新化合物包括从以下化合物组中选择的溶血磷脂酸衍生物：式中，R1 = 具有6至24个碳原子的烯基或炔基；n = 0-12；X = 氧；化合物（全顺式-5,8,11,14）-二十碳四烯酸2-羟基-3-膦酸氧丙基酯；顺-9，顺-12-十八碳二烯酸2-羟基-3-膦酸氧丙基酯；（全顺式-9,12,15）-十八碳三烯酸2-羟基-3-膦酸氧丙基酯；顺-9-十八碳烯酸2-羟基-3-膦酸氧丙基酯；和芥子酸2-羟基-3-膦酸氧丙基酯被排除，以及所述化合物的生理上可耐受的盐，酯，光学活性形式和外消旋体。
• Semi-biosynthetic production of fatty alcohols and fatty aldehydes
  申请人：Provivi, Inc.

  公开号：US11214818B2

  公开（公告）日：2022-01-04

  The present application relates to methods of producing one or more fatty alcohols and/or one or more fatty aldehydes from one or more unsaturated lipid moieties by combining the obtainment or production of the one or more unsaturated lipid moieties from a biological source with conversion by non-biological means of the one or more unsaturated lipid moieties to one or more fatty alcohols and/or one or more fatty aldehydes. The present application also relates to recombinant microorganisms having a biosynthesis pathway for the production of one or more unsaturated lipid moieties. The one or more fatty alcohols can further be chemically converted to one or more corresponding fatty acetates. The one or more fatty alcohols, one or more fatty aldehydes and/or one or more fatty acetates produced by the methods described herein may be one or more insect pheromones, one or more fragrances, one or more flavoring agents, or one or more polymer intermediates.

  本申请涉及从一种或多种不饱和脂质分子生产一种或多种脂肪醇和/或一种或多种脂肪醛的方法，方法是将从生物来源获得或生产一种或多种不饱和脂质分子与通过非生物手段将一种或多种不饱和脂质分子转化为一种或多种脂肪醇和/或一种或多种脂肪醛结合起来。本申请还涉及具有生产一种或多种不饱和脂质分子的生物合成途径的重组微生物。一种或多种脂肪醇可进一步化学转化为一种或多种相应的脂肪乙酸酯。本文所述方法生产的一种或多种脂肪醇、一种或多种脂肪醛和/或一种或多种脂肪乙酸酯可以是一种或多种昆虫信息素、一种或多种香料、一种或多种调味剂或一种或多种聚合物中间体。
• PERIE, JACQUES;MONSAN, PIERRE FREDERIC;WILLSON, MICHELE JEANNE;KISEBE, AL+
  作者：PERIE, JACQUES、MONSAN, PIERRE FREDERIC、WILLSON, MICHELE JEANNE、KISEBE, AL+

  DOI：——

  日期：——
• MICROORGANISMS FOR THE PRODUCTION OF INSECT PHEROMONES AND RELATED COMPOUNDS
  申请人：Provivi, Inc.

  公开号：EP3635124A1

  公开（公告）日：2020-04-15
• SEMI-BIOSYNTHETIC PRODUCTION OF FATTY ALCOHOLS AND FATTY ALDEHYDES
  申请人：Provivi, Inc.

  公开号：US20190136272A1

  公开（公告）日：2019-05-09

  The present application relates to methods of producing one or more fatty alcohols and/or one or more fatty aldehydes from one or more unsaturated lipid moieties by combining the obtainment or production of the one or more unsaturated lipid moieties from a biological source with conversion by non-biological means of the one or more unsaturated lipid moieties to one or more fatty alcohols and/or one or more fatty aldehydes. The present application also relates to recombinant microorganisms having a biosynthesis pathway for the production of one or more unsaturated lipid moieties. The one or more fatty alcohols can further be chemically converted to one or more corresponding fatty acetates. The one or more fatty alcohols, one or more fatty aldehydes and/or one or more fatty acetates produced by the methods described herein may be one or more insect pheromones, one or more fragrances, one or more flavoring agents, or one or more polymer intermediates.