6-羟基十八烷酸甲酯 | 2379-94-4

• 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: 6-羟基十八烷酸甲酯
• 英文名称: methyl-6-hydroxy octadecanoate
• 英文别名: methyl 6-hydroxyoctadecanoate；6-hydroxy-octadecanoic acid methyl ester；6-Hydroxy-octadecansaeure-methylester；d,l-6-Hydroxy-octadecansaeure-methylester；6-Hydroxy-octadecansaeuremethylester；6-Hydroxystearinsaeuremethylester
• CAS: 2379-94-4
• 化学式: C₁₉H₃₈O₃
• 分子量: 314.509
• InChiKey: LCFAELUIVWCIJF-UHFFFAOYSA-N

物化性质

• 熔点：
  56-57 °C
• 沸点：
  399.7±25.0 °C(Predicted)
• 密度：
  0.915±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  22
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2918199090

反应信息

• 作为反应物：
  描述：

  6-羟基十八烷酸甲酯 在 吡啶 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 244.5h， 生成 Methyl 6-(3-methoxy-3-oxopropyl)sulfanyloctadecanoate
  参考文献：
  名称：

  Synthesis and biological properties of hydroxythioether fatty acids related to leukotrienes: Antagonists and agonists of slow-reacting substance of anaphylaxis (SRS-A)

  摘要：

  A series of 6-hydroxy-7-thioether and 6-thioether-7-hydroxy derivatives of commercially available petroselinic acid and 5-hydroxy-6-thioether derivatives of fatty acids containing an aromatic moiety were synthesized. Several of the compounds have exhibited SRS-A antagonist (eg, 5, 10)/agonist (eg, 34, 35) activity. Compound 5 antagonized SRS-A-induced contractions of the isolated guinea pig ileum with IC50 = 0.09 muM.

  DOI：

  10.1016/0223-5234(93)90073-n
• 作为产物：
  描述：

  6-羟基己酸甲酯 在 aluminum oxide 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 6-羟基十八烷酸甲酯
  参考文献：
  名称：

  A New Family of Polymerizable Lyotropic Liquid Crystals:  Control of Feature Size in Cross-Linked Inverted Hexagonal Assemblies via Monomer Structure

  摘要：

  An efficient and versatile synthesis of a series of polymerizable amphiphilic mesogens that affords control over tail length and position of the :polymerizable group is described. The synthesis employs a novel and facile method of preparing styrene ethers. The monomers are sadium salts of styrene ether-modified fatty acids that can be used to form cross-linkable inverted hexagonal (H-II) lyotropic liquid crystal (LLC) phases at ambient temperature with controllable nanometer-scale dimensions. Examination of a series of regioisomers with the same alkyl chain length but with the styrene: ether group at different locations along the chain revealed that the position of the styrene ether has a profound effect on the dimensions of the resulting HII phase at a fixed temperature and composition. Increasing overall monomer tail length also has a significant, although smaller, effect on the unit cell dimensions of the LLC phase. By controlling the structure of the LLC monomer in this manner, cross-linked HII phases with interchannel distances (ICD) ranging from 29 to 54 Angstrom can be obtained. Furthermore, changing the counterion from Na+ to tetraalkylammonium ions leads to further expansion of the H-II unit cell to a maximum ICD of 65 Angstrom, as well as to the production of a lamellar phase. Use of these monomers affords a new and unparalleled degree of control over phase structure and dimensions for the production of nanostructured organic materials.

  DOI：

  10.1021/ja002462i

文献信息

• Mitochondria-Targeted Inhibitors of Cytochrome C Peroxidase for Protection from Apoptosis
  申请人：Atkinson Jeffrey

  公开号：US20130203829A1

  公开（公告）日：2013-08-08

  The present application is directed to novel imidazole-substituted fatty acids that have been functionalized with an alkyl triphenylphosphonium group, compositions comprising these compounds and their use as inhibitors of cytochrome c peroxidase, in particular for the treatment and prevention of apoptosis.

  本申请涉及一种新型咪唑基取代脂肪酸，其已被烷基三苯基膦基团官能化，包括这些化合物的组合物以及它们作为细胞色素c过氧化物酶抑制剂的用途，特别用于治疗和预防凋亡。
• Locating intercalants within lipid bilayers using fluorescence quenching by bromophospholipids and iodophospholipids
  作者：Carmit Alexenberg、Michal Afri、Shlomi Eliyahu、Hani Porat、Ayala Ranz、Aryeh A. Frimer

  DOI：10.1016/j.chemphyslip.2019.03.018

  日期：2019.7

  fluorescent moiety. We have synthesized various phospholipids with bromine (or iodine) atoms substituted at various locations along the lipid chain. The latter halolipids were intercalated in turn with various fluorophores into DMPC liposomes, biomembranes and erythrocyte ghosts. The most effective fluorescence quenching occurs when the heavy atom location corresponds to that of the fluorophore. The

  在以前的工作中，我们已经可以使用三种光谱技术的溶剂极性敏感性来确定脂质双层中插入分子的深度：13 C NMR化学位移（δ）；荧光发射波长（λem）和ESRβ-H分裂常数（aβ-H）。在本文中，我们使用位于磷脂链已知位置的重原子（Br或I）淬灭作为荧光部分位置的探针。我们已经合成了在脂质链的各个位置上都被溴（或碘）原子取代的各种磷脂。后面的类脂与各种荧光基团依次插入DMPC脂质体，生物膜和红细胞鬼影。当重原子的位置与荧光团的位置相对应时，会发生最有效的荧光猝灭。结果表明，一般而言，荧光团插入相同的深度，而与所使用的脂质双层无关。当荧光团位于水相中或水相中时，KBr（或KI）是最有效的淬灭剂。据推测，由于碘的半径较大和自旋耦合常数较大，因此碘类似物在其淬灭的深度范围内的分辨力要小得多。
• Mitochondria-targeted inhibitors of cytochrome c peroxidase for protection from apoptosis
  申请人：Brock University

  公开号：US09365597B2

  公开（公告）日：2016-06-14

  The present application is directed to novel imidazole-substituted fatty acids that have been functionalized with an alkyl triphenylphosphonium group, compositions comprising these compounds and their use as inhibitors of cytochrome c peroxidase, in particular for the treatment and prevention of apoptosis.

  本申请涉及新型咪唑基取代脂肪酸，该脂肪酸已经被烷基三苯基膦基团官能化，包括这些化合物的组合物以及它们作为细胞色素c过氧化物酶抑制剂的用途，特别是用于治疗和预防细胞凋亡。
• Bergstroem et al., Acta Chemica Scandinavica (1947), 1952, vol. 6, p. 1157,1160, 1169
  作者：Bergstroem et al.

  DOI：——

  日期：——
• Tanchuk,Yu.V. et al., Soviet progress in chemistry, 1978, vol. 44, # 1, p. 77 - 81
  作者：Tanchuk,Yu.V. et al.

  DOI：——

  日期：——