8-羟基十八烷酸 | 6807-91-6

• 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: 8-羟基十八烷酸
• 中文别名: 8-羟基十八酸
• 英文名称: 8-hydroxyoctadecanoic acid
• 英文别名: 8-hydroxystearic acid；8HSA；(+/-)-8-hydroxy-octadecanoic acid；8-hydroxy-octadecanoic acid；(+/-)-8-Hydroxy-octadecansaeure；7-Hydroxy-heptadecan-carbonsaeure-(1)
• CAS: 6807-91-6
• 化学式: C₁₈H₃₆O₃
• 分子量: 300.482
• InChiKey: YYWHSFVJGXJTKD-UHFFFAOYSA-N

物化性质

• 熔点：
  84 °C
• 沸点：
  433.9±28.0 °C(Predicted)
• 密度：
  0.944±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  21
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8-羟基十八烷酸 在 Novozym 435 作用下， 以 乙醚 为溶剂， 反应 168.0h， 生成 methyl (8R)-8-{[(2R)-2-(acetyloxy)-2-phenylacetyl]oxy}octadecanoate
  参考文献：
  名称：

  Enzymatic kinetic resolution of hydroxystearic acids: A combined experimental and molecular modelling investigation

  摘要：

  Enantioenriched 7-, 8-, 9-, and 10-hydroxystearic acids (HSA) were obtained, for the first time, by kinetic resolution of their racemates with lipases CALB and PS, in the presence of vinyl acetate. Among them, the best results were obtained for 7-HSA and 9-HSA, whose enantiomeric excess was around 55%. The same resolutions carried out on the hydroxy esters completely failed. For the acid substrates neither the Kazlauskas' rule nor the 3D-QSAR model could be applied, since both models are focused on the CALB alcohol-pocket evaluation and not on the acyl-pocket one. Therefore, a semiquantitative approach was used, whose results were in accordance with our findings, as far as the absolute configuration of the product is concerned. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2012.06.017
• 作为产物：
  描述：

  辛二酸 在 sodium tetrahydroborate 、 氯化亚砜 、 乙醇 、 硫酸 、 potassium hydroxide 作用下， 以 乙醇 、 环己烷 、 水 、 苯 为溶剂， 反应 33.0h， 生成 8-羟基十八烷酸
  参考文献：
  名称：

  位置异构体对其分子凝胶，分散体和固态中外消旋羟基十八烷酸聚集体的宏观和纳米结构的影响

  摘要：

  研究了一系列羟基硬脂酸（HSA）的分子间/分子间氢键。由这些具有异构羟基的脂肪酸获得的分子凝胶的自组装受到仲羟基位置的影响。如FT-IR所示，2-羟基硬脂酸（2HSA）不会形成分子二聚体，并且由于仲羟基无法形成分子间的H键，因此沿仲轴的生长受到抑制。同样，XRD长间隔短于羟基硬脂酸的二聚体长度。3-羟基硬脂酸（3HSA）形成无环二聚体，并且羟基无法氢键结合，从而阻止了晶体结构沿副轴生长。最后，异构体6HSA，8HSA，10HSA，12HSA和14HSA具有相似的XRD和FT-IR模式，这表明这些分子都以相似的方式自组装。单体形成羧基环状二聚体，并且仲羟基促进沿仲轴的生长。

  DOI：

  10.1021/la204412t

文献信息

• THE FERMENTATION OF LONG-CHAIN COMPOUNDS BY TORULOPSIS MAGNOLIAE: I. STRUCTURES OF THE HYDROXY FATTY ACIDS OBTAINED BY THE FERMENTATION OF FATTY ACIDS AND HYDROCARBONS
  作者：A. P. Tulloch、J. F. T. Spencer、P. A. J. Gorin

  DOI：10.1139/v62-203

  日期：1962.7.1

  The yield of extracellular glycolipid produced by Torulopsis magnoliae is increased three-to five-fold by the addition of suitable compounds to the growing culture. The supplement, which can be a long-chain acid, ester, hydrocarbon, or glyceride, is hydroxylated and converted to hydroxy fatty acid sophorosides. Fatty esters of all chain lengths from C₁₆to C₂₂, including several unsaturated esters, and even-numbered hydrocarbons from C₁₆to C₂₄are readily fermented. Shorter-chain compounds are used poorly or not at all. With compounds of 16 to 18 carbon atoms, hydroxylation occurs at the terminal or penultimate carbon atom, depending on degree of unsaturation and chain length. Substrates of more than 18 carbon atoms are mainly reduced in chain length by one or more two-carbon units and hydroxylated, giving C₁₇or C₁₈acids with the hydroxyl group on the penultimate carbon atom. The various enzymic reactions which occur during the fermentation are discussed.

  扩大培养基中添加适当化合物可将Magnoliae酵母产生的细胞外糖脂产量提高三到五倍。这种添加剂可以是长链酸、酯、碳氢化合物或甘油酯，经过羟基化后转化为羟基脂肪酸索非酮苷。从C16到C22的所有链长的脂肪酯，包括几种不饱和酯，以及从C16到C24的偶数碳氢化合物都容易发酵。较短链的化合物使用效果不佳或根本不使用。对于含有16到18个碳原子的化合物，羟基化发生在末端或次末端碳原子上，取决于不饱和度和链长。含有超过18个碳原子的底物主要通过一个或多个二碳单位减少链长并进行羟基化，从而在次末端碳原子上带有羟基的C17或C18酸。讨论了发酵过程中发生的各种酶反应。
• [EN] DRUG CONJUGATES<br/>[FR] CONJUGUÉS DE MÉDICAMENT
  申请人：UNIV MISSOURI

  公开号：WO2009158633A1

  公开（公告）日：2009-12-30

  Conjugated compounds comprising a therapeutic or diagnostic agent linked to a substrate for a cell membrane transporter or receptor by lipophilic linker are provided.

  提供了包含治疗或诊断药物与细胞膜转运体或受体的底物通过亲脂性连接剂连接的共轭化合物。
• Effects of Regioisomerism on the Antiproliferative Activity of Hydroxystearic Acids on Human Cancer Cell Lines
  作者：Natalia Calonghi、Carla Boga、Patrizia Nitti、Dario Telese、Silvia Bordoni、Giovanna Farruggia、Fioretta Asaro、Martina Grandi、Chiara Zalambani、Gabriele Micheletti

  DOI：10.3390/molecules27082396

  日期：——

  A series of regioisomers of the hydroxystearic acid (HSA) was prepared, and the effect of the position of the hydroxyl group along the chain on a panel of human cancer cell lines was investigated. Among the various regioisomers, those carrying the hydroxyl at positions 5, 7, and 9 had growth inhibitor activity against various human tumor cell lines, including CaCo-2, HT29, HeLa, MCF7, PC3, and NLF

  制备了一系列羟基硬脂酸 (HSA) 的区域异构体，并研究了羟基沿链的位置对一组人类癌细胞系的影响。在各种区域异构体中，5、7 和 9 位带有羟基的那些对各种人类肿瘤细胞系（包括 CaCo-2、HT29、HeLa、MCF7、PC3 和 NLF 细胞）具有生长抑制剂活性。10-HSA 和 11-HSA 显示出非常微弱的效果。8-HSA 未在所有细胞系中显示抑制活性。7-HSA 和 9-HSA 的生物学作用得到广泛认可，而对 5-HSA 的作用知之甚少。因此，使用 Livecyte 的 ptychography 技术研究了 5-HSA 在 HeLa、HT29、MCF7 和 NLF 细胞系中的生物学效应，该技术可以关联增殖、运动、和形态同时作为治疗的功能。5-HSA 不仅可以减少细胞增殖，还可以诱导细胞位移、方向性和速度的变化。表征 5-HSA 的生物学效应很重要，该分子是羟基脂肪酸脂肪酰基酯 (FAHFA)
• (Polyurethane) Elastomer and process for producing it (with a specific releasing agent)
  申请人：MITSUI TOATSU CHEMICALS, Inc.

  公开号：EP0513964A2

  公开（公告）日：1992-11-19

  An elastomer is molded by a reaction injection molding of polyurethane resins, polyurea resins, polyurethane/urea resins and polyurea/amide resins in the presence of an internal release agent which is a polyester condensate of a saturated or unsaturated fatty acid having a hydroxy group produced by transesterification or a molecular end-aminated or iminated polyester condensate. The elastomer has a good mold releasing property and a good coating property.

  通过聚氨酯树脂、聚脲树脂、聚氨酯/聚脲树脂和聚脲/酰胺树脂在内含脱模剂的情况下进行反应注塑成型，内含脱模剂是具有羟基的饱和或不饱和脂肪酸通过酯交换反应生成的聚酯缩合物或分子末端酰胺化或亚胺化聚酯缩合物。这种弹性体具有良好的脱模性能和涂层性能。
• Refrigerator oil composition
  申请人：IDEMITSU KOSAN COMPANY LIMITED

  公开号：EP0802254A1

  公开（公告）日：1997-10-22

  Disclosed is a refrigerator oil composition comprising at least one base oil selected from mineral oils and synthetic oils, and at least one hydroxy-fatty acid derivative selected from (A) hydroxy-fatty acids or their condensates, (B) metal salts or amine salts of hydroxy-fatty acids or their condensates, and (C) esters of hydroxy-fatty acids. The composition has an excellent lubricating property, while specifically improving the lubricity between aluminium materials and steel materials. This is effective for preventing such materials from being seized and worn, and is suitable as a lubricating oil in refrigerators using hydrogen-containing Flon refrigerants, such as R134a, that do not cause environmental pollution.

  本发明公开了一种冷冻机油组合物，该组合物包含至少一种选自矿物油和合成油的基础油，以及至少一种选自 (A) 羟基脂肪酸或其缩合物、(B) 羟基脂肪酸或其缩合物的金属盐或胺盐，以及 (C) 羟基脂肪酸酯的羟基脂肪酸衍生物。该组合物具有极佳的润滑性能，尤其能改善铝材料和钢材料之间的润滑性。这可有效防止此类材料卡死和磨损，适用于使用不会造成环境污染的含氢氟隆制冷剂（如 R134a）的冰箱的润滑油。