methyl 2-hydroxy-heptadecanoate | 58054-78-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 2-hydroxy-heptadecanoate
• 英文别名: methyl 2-hydroxyheptadecanoate
• CAS: 58054-78-7
• 化学式: C₁₈H₃₆O₃
• 分子量: 300.482
• InChiKey: OGSBNYHFFMLFJI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 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：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 2-hydroxy-heptadecanoate 在 lithium aluminium tetrahydride 、 silver(l) oxide 作用下， 以 乙醚 、 苯 为溶剂， 反应 18.5h， 生成 2-Allyloxy-heptadecan-1-ol
  参考文献：
  名称：

  Darmstoff analogs. 2. Ring and side chain effects on smooth muscle contraction

  摘要：

  2-cis-delta 8-Heptadecenyl-4-(hydroxymethyl)-1,3-dioxolane monosodium phosphate (1b) has been shown to be present as a major component of Darmstoff in mammalian intestine and to be a potent inducer for contraction of intestinal smooth muscle. The analogous 2-pentadecyl material 1a, also found abundantly in the intestine, is inactive. In this study, synthesis of phosphorylated hydroxymethyl-1,4-dioxanes, -tetrahydrofurans, -cyclopentanes, and -oxathiolanes bearing both oleyl and palmityl side chains is reported. Of these, 2-(hydroxymethyl)-5-cis-delta 8-heptadecenyl-1,4-dioxane monosodium phosphate (2b) exhibits about 12% of the activity of 1b. Its pentadecyl analogue 2a, like 1a, is totally inactive, as are all other compounds prepared. The results indicate that Darmstoff-like compounds exhibit specific chemical requirements for activity and that where activity is encountered, the side-chain specificity noted in 1a and 1b can be preserved.

  DOI：

  10.1021/jm00344a006
• 作为产物：
  描述：

  甲醇 、 2-hydroxyheptadecanoic acid 在 乙酰氯 作用下， 生成 methyl 2-hydroxy-heptadecanoate
  参考文献：
  名称：

  Darmstoff analogs. 2. Ring and side chain effects on smooth muscle contraction

  摘要：

  2-cis-delta 8-Heptadecenyl-4-(hydroxymethyl)-1,3-dioxolane monosodium phosphate (1b) has been shown to be present as a major component of Darmstoff in mammalian intestine and to be a potent inducer for contraction of intestinal smooth muscle. The analogous 2-pentadecyl material 1a, also found abundantly in the intestine, is inactive. In this study, synthesis of phosphorylated hydroxymethyl-1,4-dioxanes, -tetrahydrofurans, -cyclopentanes, and -oxathiolanes bearing both oleyl and palmityl side chains is reported. Of these, 2-(hydroxymethyl)-5-cis-delta 8-heptadecenyl-1,4-dioxane monosodium phosphate (2b) exhibits about 12% of the activity of 1b. Its pentadecyl analogue 2a, like 1a, is totally inactive, as are all other compounds prepared. The results indicate that Darmstoff-like compounds exhibit specific chemical requirements for activity and that where activity is encountered, the side-chain specificity noted in 1a and 1b can be preserved.

  DOI：

  10.1021/jm00344a006

文献信息

• A new cerebroside from the entomopathogenic fungus Ophiocordyceps longiissima: Structural-electronic and antioxidant relations. Experimental and DFT calculated studies
  作者：Abdelsamed I. Elshamy、Tatsuro Yoneyama、Nguyen Van Trang、Ninh The Son、Yasuko Okamoto、Sayaka Ban、Masaaki Noji、Akemi Umeyama

  DOI：10.1016/j.molstruc.2019.127061

  日期：2020.1

  The chemical characterization of n-butanol soluble extract of the fungus Ophiocordyceps longiissima NBRC 106965 afforded a new cerebroside, 1-O-(beta-D-glucopyranosyl)-(2S,3R,4E,8E)-2-[(20R)-2'-hydroxyheptadecanoylamino]-9-methylheptadeca-4,8-diene-1,3-diol, trivially named ophiocordylongiiside A (1), in addition to 22E,24R-24-methylcholest-5,22-diene-3-O-beta-D-O-glucopyranoside (2). The chemical structure of 1 was established based upon the by modern spectroscopic and chemical techniques. Compound 1 exhibited strong DPPH-free radical scavenging with the IC50 value of 55.72 mg/mL. The biological result can be explained by density functional theoretical (DFT) calculation, in which antioxidant activity is mostly controlled by the O-H bond dissociation enthalpy (BDE) following hydrogen atom transfer (HAT) mechanism. In all studied environments, the lowest BDE values are found in 2'-OH. (C) 2019 Elsevier B.V. All rights reserved.
• Ubik,K. et al., Collection of Czechoslovak Chemical Communications, 1975, vol. 40, p. 2826 - 2837
  作者：Ubik,K. et al.

  DOI：——

  日期：——
• A method of preparing primary amide derivatives
  申请人：Takasago International Corporation

  公开号：EP0835864B1

  公开（公告）日：2002-02-13
• US5831125A
  申请人：——

  公开号：US5831125A

  公开（公告）日：1998-11-03
• Darmstoff analogs. 2. Ring and side chain effects on smooth muscle contraction
  作者：Robert A. Wiley、Wayne T. Harris、Catherine Brungardt、Michael Marx

  DOI：10.1021/jm00344a006

  日期：1982.2

  2-cis-delta 8-Heptadecenyl-4-(hydroxymethyl)-1,3-dioxolane monosodium phosphate (1b) has been shown to be present as a major component of Darmstoff in mammalian intestine and to be a potent inducer for contraction of intestinal smooth muscle. The analogous 2-pentadecyl material 1a, also found abundantly in the intestine, is inactive. In this study, synthesis of phosphorylated hydroxymethyl-1,4-dioxanes, -tetrahydrofurans, -cyclopentanes, and -oxathiolanes bearing both oleyl and palmityl side chains is reported. Of these, 2-(hydroxymethyl)-5-cis-delta 8-heptadecenyl-1,4-dioxane monosodium phosphate (2b) exhibits about 12% of the activity of 1b. Its pentadecyl analogue 2a, like 1a, is totally inactive, as are all other compounds prepared. The results indicate that Darmstoff-like compounds exhibit specific chemical requirements for activity and that where activity is encountered, the side-chain specificity noted in 1a and 1b can be preserved.