(2R)-2-hydroxynonadecanoic methyl ester

• 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: (2R)-2-hydroxynonadecanoic methyl ester
• 英文别名: Methyl (2R)-2-Hydroxynonadecanoate
• 化学式: C₂₀H₄₀O₃
• 分子量: 328.536
• InChiKey: JUVFFSOMSJFLGJ-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  23
• 可旋转键数：
  18
• 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

反应信息

• 作为产物：
  描述：

  甲醇 、 1-O-β-D-glucopyranosyl-(2S,3S,4R)-2-[(2'R)-2'-hydroxynonadecanoylamino]-16-methyl-heptadeca-1,3,4-triol 在 盐酸 作用下， 以0.13 mg的产率得到(2R)-2-hydroxynonadecanoic methyl ester
  参考文献：
  名称：

  海洋海绵Haliclona（Reniera）sp。的新脑苷。

  摘要：

  对从韩国Ulleung岛海岸收集的海洋海绵Haliclona（Reniera）sp。的MeOH提取物进行的化学研究导致分离出13种新的脑苷（1--3、5--14），以及已知的类似物（4）。在1D和2D NMR光谱，MS光谱和化学方法的基础上阐明了它们的结构。这些葡糖脑苷脂的主要新特征是C15和C19酰基链，长（C24-C28）酰基链或酰基链的S-构型。值得注意的是，在同一样品中观察到酰基链的R-和S-构型。

  DOI：

  10.1248/cpb.57.106

文献信息

• Cerebrosides and 2-Pyridone Alkaloids from the Halotolerant Fungus <i>Penicillium chrysogenum</i> Grown in a Hypersaline Medium
  作者：Xiaoping Peng、Yi Wang、Kunlai Sun、Peipei Liu、Xia Yin、Weiming Zhu

  DOI：10.1021/np1008976

  日期：2011.5.27

  Five new cerebrosides, chrysogesides A-E (1-5), and two new 2-pyridone alkaloids, chrysogedones A and B (6 and 7), were isolated from the fermentation broth of Penicillium chrysogenum PXP-55, a halotolerant fungus grown in a hypersaline medium. Among them, chrysogesides B-D (2-4) are the first cerebrosides that contain an unsaturated C-19-fatty acid. Their structures were identified by spectroscopic and chemical methods, including CD spectroscopy as well as the modified Mosher's method. Compound 2 showed antimicrobial activity against Enterobacter aerogenes with an MIC value of 1.72 mu M.
• Two new cerebrosides from the pollen of Typha angustifolia
  作者：Wei-Wei Tao、Nian-Yun Yang、Li Liu、Jin-Ao Duan、De-Kang Wu、Da-Wei Qian、Yu-Ping Tang

  DOI：10.1016/j.fitote.2009.08.026

  日期：2010.4

  Two new cerebrosides, 1-O-(beta-D-glucopyranosyloxy)-(2S,3S,4R,8Z)-2-[(2'R)-2'-hydroxytricosanoylamino]-8-nonadecene-3,4-diol (1) and 1-O-(beta-D-glucopyranosyloxy)-(2S,3R,4E,8Z)-2-[(2'R)-2'-hydroxynonadecanoylamino]-4,13-nonadecene-3-diol (2), were isolated from the pollen of Typha angusitfolia Their structures were elucidated by chemical and spectral means. This is the first report on the occurrence of cerebroside in Typha (Typhaceae) Compounds 1 and 2 exhibited effect on the proliferation of cultured vascular smooth Muscle cell (VSMCs) induced by fatal bovine serum (FBS) (C) 2009 Elsevier B V All rights reserved.
• New Sphingosines from a Gorgonian, <i>Pseudopterogorgia </i><i>a</i><i>ustraliensis</i> Ridley, of the Indian Ocean
  作者：N. Krishna、P. Muralidhar、M. Muralikrishna Kumar、D. Venkata Rao、Ch. Bheemasankara Rao

  DOI：10.1021/np040022p

  日期：2004.8.1

  Two new sphingosines, (2S,3R)-2-(docosanoyl amino)nonadecane-1,3-diol (1) and (2S,3S,4R)-2-[(2'R)-2'-hydroxynonadecanoylamino]nonadecane-1,3,4-triol (3), along with the known (2S,3R,4E)-2-(heptadecanoylamino)octadec-4-ene-1,3-diol, have been isolated from Pseudopterogorgia australiensis, of the Indian Ocean. The structures were deduced from spectral and chemical methods. Compounds 1-3 showed moderate antibacterial activity.
• New Cerebrosides from a Marine Sponge Haliclona (Reniera) sp.
  作者：Taeseong Park、Tayyab Ahmad Mansoor、Pramod Bapurao Shinde、Baoquan Bao、Jongki Hong、Jee Hyung Jung

  DOI：10.1248/cpb.57.106

  日期：——

  A chemical investigation of the MeOH extract of a marine sponge Haliclona (Reniera) sp., collected off the coast of Ulleung Island, Korea, led to the isolation of thirteen new cerebrosides (1--3, 5--14), along with a known analogue (4). Their structures were elucidated on the basis of 1D and 2D NMR spectroscopy, MS spectrometry, and chemical method. The major new features of these glucocerebrosides

  对从韩国Ulleung岛海岸收集的海洋海绵Haliclona（Reniera）sp。的MeOH提取物进行的化学研究导致分离出13种新的脑苷（1--3、5--14），以及已知的类似物（4）。在1D和2D NMR光谱，MS光谱和化学方法的基础上阐明了它们的结构。这些葡糖脑苷脂的主要新特征是C15和C19酰基链，长（C24-C28）酰基链或酰基链的S-构型。值得注意的是，在同一样品中观察到酰基链的R-和S-构型。