methyl (2R,17Z)-2-hydroxyhexacos-17-enoic acid | 700367-48-2

• 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 (2R,17Z)-2-hydroxyhexacos-17-enoic acid
• 英文别名: methyl (2R)-2-hydroxy-(17Z)-hexacosenoate；(17Z)-methyl (2R)-hydroxyhexacosenoate；Methyl 2-hydroxy-(17Z)-hexacosenoate；methyl 2-hydroxyhexacosenoate
• CAS: 700367-48-2
• 化学式: C₂₇H₅₂O₃
• 分子量: 424.708
• InChiKey: IJLWBOCHMQCOED-ZXAYODBVSA-N

物化性质

• 沸点：
  507.2±23.0 °C(Predicted)
• 密度：
  0.905±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.29
• 重原子数：
  30.0
• 可旋转键数：
  23.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  二甲基二硫 、 methyl (2R,17Z)-2-hydroxyhexacos-17-enoic acid 在 碘 作用下， 以 二硫化碳 为溶剂， 反应 40.0h， 生成
  参考文献：
  名称：

  Falsone, G.; Cateni, F.; Katusian, F., Zeitschrift fur Naturforschung, B: Chemical Sciences, 1993, vol. 48, # 8, p. 1121 - 1126

  摘要：

  DOI：
• 作为产物：
  描述：

  (2R,17Z)-N-{(1S,2S,3R,7Z)-1-[(β-D-glucopyranosyloxy)methyl]-2,3-dihydroxyheptadec-7-en-1-yl}-2-hydroxyhexacos-17-enamide 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 18.0h， 生成 methyl (2R,17Z)-2-hydroxyhexacos-17-enoic acid 、 (2R,3R,4S,5S,6R)-2-((Z)-(2S,3S,4R)-2-Amino-3,4-dihydroxy-octadec-8-enyloxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol
  参考文献：
  名称：

  Falsone, G.; Cateni, F.; Baumgartner, M., Zeitschrift fur Naturforschung, B: Chemical Sciences, 1994, vol. 49, # 1, p. 135 - 140

  摘要：

  DOI：

文献信息

• Renierosides, Cerebrosides from a Marine Sponge <i>Haliclona</i> (<i>Reniera</i>) sp.
  作者：Tayyab A. Mansoor、Pramod B. Shinde、Xuan Luo、Jongki Hong、Chong-O. Lee、Chung Ja Sim、Byeng Wha Son、Jee H. Jung

  DOI：10.1021/np070078u

  日期：2007.9.1

  Guided by the brine shrimp lethality assay, eight new cerebrosides (1-8) have been isolated from an extract of the marine sponge Haliclona (Reniera) sp. A novel feature of these cerebrosides was the presence of unprecedented amide-linked long-chain fatty acid moieties. The planar structures of the cerebrosides (1-8) were established by 1D and 2D NMR spectroscopic techniques, mass spectrometric analyses

  在盐水虾致死率测定的指导下，从海洋海绵Haliclona（Reniera）sp。的提取物中分离出八种新的脑苷（1-8）。这些脑苷的新颖特征是空前的酰胺连接的长链脂肪酸部分的存在。脑苷（1-8）的平面结构是通过1D和2D NMR光谱技术，质谱分析和化学降解方法建立的。分离出的化合物对一组五种人类实体瘤细胞系没有细胞毒性。
• Preliminary biological assay on cerebroside mixture from Euphorbia nicaeensis All. Isolation and structure determination of five glucocerebrosides
  作者：F. Cateni、J. Zilic、G. Falsone、F. Hollan、F. Frausin、V. Scarcia

  DOI：10.1016/s0014-827x(03)00137-x

  日期：2003.9

  Preliminary studies of in vitro cytostatic activity on less polar fraction of the MeOH extract of the plant Euphorbia nicaeensis All., carried out on KB cells, have evinced a relatively low ability of extract to inhibit cell growth. Successive, five glucocerebrosides were isolated from the cerebroside molecular species obtained from this extract using normal and reversed phase column 'flash-chromatography'. The structures of these cerebrosides were determined on the basis of chemical and spectroscopic evidences. Mass spectrometry of dimethyl disulfide derivatives was useful for the determination of the double-bond positions in the long-chain bases.
• Lipid metabolites with free-radical scavenging activity from Euphorbia helioscopia L.
  作者：F. Cateni、J. Zilic、T. Altieri、M. Zacchigna、G. Procida、R. Gaggeri、D. Rossi、S. Collina

  DOI：10.1016/j.chemphyslip.2014.03.001

  日期：2014.7

  The methanolic extract of the plant Euphorbia helioscopia L. exhibited an interesting free-radical scavenging activity. From the aerial parts of Euphorbia helioscopia L. (Euphorbiaceae), a complex mixture of seven cerebrosides together with glucoclionasterol, a digalactosyldiacylglycerol and a diacylmonogalactosylglycerol were identified. The structures of the cerebrosides were characterized as 1-O-β-D-glucosides of phytosphingosines, which comprised (2S, 3S, 4E, 8E)-2-amino-4(E),8(E)-octadecadiene-1,3-diol, (2S, 3S, 4E, 8Z)-2-amino-4(E),8(Z)-octadecadiene-1,3-diol, (2S, 3S, 4R, 8Z)-2-amino-8(Z)-octadecene-1,3,4-triol as long chain bases with seven 2-hydroxy fatty acids of varying chain lengths (C16, C24:1, C26:1, C24, C26, C28:1) linked to the amino group. The glycosylglycerides were characterized as (2S)-2,3-O-di-(9,12,15-octadecatrienoyl)-glyceryl-6-O-(α-D-galactopyranosyl)-β-D-galactopyranoside and (2S)-2,3-O-di-(9,12,15-octadecatrienoyl)-glyceryl-1-O-β-D-galactopyranoside. The structures were established on the basis of spectroscopic data and chemical reactions.
• Falsone; Cateni; Jurman, Il Farmaco, 1993, vol. 48, # 12, p. 1617 - 1629
  作者：Falsone、Cateni、Jurman、Wagner、Seligmann

  DOI：——

  日期：——