methyl (2R)-2-hydroxytricosanoate | 118745-41-8

• 物质功能分类: 分析化学 - 食品安全 - 脂肪酸、脂肪酸甲酯
• 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)-2-hydroxytricosanoate
• 英文别名: methyl (R)-2-hydroxytricosanoate；methyl 2-hydroxytricosanoate；FAM-2
• CAS: 118745-41-8
• 化学式: C₂₄H₄₈O₃
• 分子量: 384.643
• InChiKey: CVDOLGNPMWRXBI-HSZRJFAPSA-N

物化性质

• 沸点：
  412.9±13.0 °C(Predicted)
• 密度：
  0.902±0.06 g/cm3(Predicted)
• 溶解度：
  溶于二甲基亚砜

计算性质

• 辛醇/水分配系数(LogP)：
  10.5
• 重原子数：
  27
• 可旋转键数：
  22
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.96
• 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 (2R)-2-hydroxytricosanoate 、 N-三甲硅基吡咯 生成 methyl (2R)-2-trimethylsilyloxytricosanoate
  参考文献：
  名称：

  KAWANO, YASUHIRO;HIGUCHI, RYUICHI;ISOBE, RYUICHI;KOMORI, TETSUYA, LIEBIGS ANN. CHEM.,(1988) N 1, 19-24

  摘要：

  DOI：
• 作为产物：
  描述：

  (2R)-2-hydroxy-N-[(2S,3R,4E,10E)-3-hydroxy-1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoctadeca-4,10-dien-2-yl]tricosanamide 生成 methyl (2R)-2-hydroxytricosanoate
  参考文献：
  名称：

  KAWANO, YASUHIRO;HIGUCHI, RYUICHI;ISOBE, RYUICHI;KOMORI, TETSUYA, LIEBIGS ANN. CHEM.,(1988) N 1, 19-24

  摘要：

  DOI：

文献信息

• Isolation of Protein Tyrosine Phosphatase 1B Inhibitory Constituents from the Sclerotia of Polyporus umbellatus Fries
  作者：Hee-Sang Lee、In-Hyun Hwang、Jeong-Ah Kim、Ji-Young Choi、Tae-Su Jang、Hiruyuki Osada、Jong-Seog Ahn、Min-Kyun Na、Seung-Ho Lee

  DOI：10.5012/bkcs.2011.32.2.697

  日期：2011.2.20

  spectrometer and a Varian 600 MHZ (VNS 600), respectively, using Bruker's and Varian's standard pulse pro-gram, with chemical shifts reported in ppm downfield from TMS. Column chromatography was carried out on Merck silica gel (70 - 230 mesh, Merck). TLC was performed on aluminum plates precoated with Kieselgel 60 F

  使用 JASCO DIP-1000 (Tokyo, Japan) 自动数字旋光仪测量旋光度。FT-IR 光谱在 JASCO FT-IR 300E 分光光度计上记录，UV 光谱在 JASCO V-550 分光光度计上记录。NMR 光谱分别使用 Bruker 和 Varian 的标准脉冲程序在 Bruker 250 MHz (DMX 250) 光谱仪和 Varian 600 MHZ (VNS 600) 上记录，化学位移从 TMS 以 ppm 低场报告。在默克硅胶(70-230目，默克)上进行柱层析。TLC 在预涂有 Kieselgel 60 F 的铝板上进行
• Regulosides A–C: Glycosphingolipids from the StarfishPentaceraster regulus
  作者：Uddagiri Venkannababu、Shanker Pratap Singh Bhandari、Hari Shanker Garg

  DOI：10.1002/jlac.199719970629

  日期：1997.6

  The glycosphingolipid (GSL) composition of the starfish Pentaceraster regulus has been studied. The structure of the major component, a new cerebroside named Reguloside A (1) and two minor homologues, Regulosides B (1a) and C (1b), are described.

  已经研究了海星五爪的糖鞘脂（GSL）组成。描述了主要成分的结构，即新的脑苷，名为瑞古洛糖苷A（1）和两个较小的同系物，瑞古洛糖苷B（1a）和C（1b）。
• Cytotoxic ceramides and glycerides from the roots of Livistona chinensis
  作者：Xiaobin Zeng、Limin Xiang、Chen-Yang Li、Yihai Wang、Guofu Qiu、Zhen-xue Zhang、Xiangjiu He

  DOI：10.1016/j.fitote.2012.01.008

  日期：2012.4

  A 70% ethanol extract of the roots of Livistona chinensis has been investigated, led to the isolation of 13 compounds, including a new ceramide, (2S,35,4R,9Z)-2-[(2R)-2-hydroxytricosanoylamino]-9-octadecene-1,3,4-triol (2), a new glycosyl ceramide, 1-O-beta-D-glucopyranosyl-(2S,3S,4R,9Z)-2-[(2R)-2-hydroxydocosanoylamino]-9-octadecene-1,3,4-triol (3), three new monoacylglycerols, 1-(34-hydroxytetratriacontanoyl)-sn-glycerol (9), 1-[nonadeca-(9Z,12Z)-dienoyl]-sn-glycerol (10), and 1-[12-hydroxypentatriaconta-(13E,15Z)-dienoyl]-sn-glycerol (11), a new diacylglycerol, 1-(heptadeca-6Z,9Z-dienoyl)-3-(octadeca-6Z,9Z,12Z-trienoyl)-sn-glycerol (12), as well as a new diacylglycerol aminoglycoside, 1-octadecanoyl-2-nonadecanoyl-3-O-(6-amino-6-deoxy)-beta-D-glucopyranosyl-sn-glycerol (13). The structures of new compounds were elucidated. based on spectroscopic, zymologic and chemical methods. Among the compounds tested, compounds 3, 4 and 13 showed significantly antiproliferative effects against the human tumor cell lines (K562, HL-60, HepG2, and CNE-1) with the IC50 of 10-65 mu M. To our knowledge, this is first report of the occurrence of ceramides and acylglycerols in the genus Livistona. (C) 2012 Elsevier B.V. All rights reserved.
• A new cerebroside from Gynura divaricata
  作者：Lei Chen、Houquan Li、Hongtao Song、Guogang Zhang

  DOI：10.1016/j.fitote.2009.06.010

  日期：2009.12

  A new cerebroside, 1-O-beta-D-glucopyranosyl-(2S,3S,4R,10E)-2-[(2'R)-2'-hydroxyltricosanoyl-amino]-10-octadecene-1,3,4-triol was isolated from the aerial parts of Gynura divaricata DC. Crown Copyright (C) 2009 Published by Elsevier B.V. All rights reserved.
• 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.