methyl 2-hydroxydocosanoate | 641637-47-0

• 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-hydroxydocosanoate
• 英文别名: Methyl (2R)-2-Hydroxydocosanoate；2R-hydroxydocosanoic acid methyl ester
• CAS: 641637-47-0
• 化学式: C₂₃H₄₆O₃
• 分子量: 370.616
• InChiKey: KUHHQOLYDNMSJW-JOCHJYFZSA-N

物化性质

• 沸点：
  401.6±13.0 °C(Predicted)
• 密度：
  0.904±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10
• 重原子数：
  26
• 可旋转键数：
  21
• 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 2-hydroxydocosanoate 、 N-三甲硅基吡咯 生成 methyl (2R)-2-trimethylsilyloxydocosanoate
  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]docosanamide 生成 methyl 2-hydroxydocosanoate
  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

• Separation and Identification of Four New Compounds with Antibacterial Activity from Portulaca oleracea L.
  作者：Xia Lei、Jianmin Li、Bin Liu、Ning Zhang、Haiyang Liu

  DOI：10.3390/molecules200916375

  日期：——

  The Portulaca oleracea L. (P. oleracea) has been used to treat bacillary dysentery for thousands of years in China. Pharmacology studies on P. oleracea have also showed its significant antibacterial effects on the enteropathogenic bacteria, which might reveal the treatment of P. oleracea in cases of bacillary dysentery to some extent. To date, however, the therapeutic basis of P. oleracea treating on bacillary dysentery remains unknown. We determined the antibacterial effective fraction of P. oleracea in a previous study. The current study, which is based on our previous study, was first designed to isolate, identify and screen antibacterial active constituents from P. oleracea. As a result, four new compounds (1–4), portulacerebroside B (1), portulacerebroside C (2), portulacerebroside D (3) and portulaceramide A (4) along with five known compounds (5–9) were isolated, and structures were established by their physico-chemical constants and spectroscopic analysis. The antibacterial activities against common enteropathogenic bacteria were evaluated for all compounds and the new compounds 1–4 showed significant antibacterial effect on enteropathogenic bacteria in vitro, which might contribute to revealing the treatment of P. oleracea in cases of bacillary dysentery.

  马齿苋(Portulaca oleracea L.)在中国数千年以来一直被用作治疗细菌性痢疾。关于马齿苋的药理研究表明它对肠道致病菌有显著的抗菌作用,在一定程度上揭示了马齿苋治疗细菌性痢疾的作用。然而,迄今为止,马齿苋治疗细菌性痢疾的药理基础尚未明确。我们前期研究已确定马齿苋的抗菌有效部位。本研究是在前期研究的基础上,通过分离、鉴定和筛选抗菌活性成分,首次从马齿苋中分离得到4个新的化合物,即马齿苋脑苷脂B(1),马齿苋脑苷脂C(2),马齿苋脑苷脂D(3)和马齿苋酰胺A(4),同时分离得到5个已知化合物(5-9),并通过理化常数和光谱分析确定了它们的结构。并对这些化合物进行抗肠道致病菌活性评价,结果显示,新化合物1-4在体外对肠道致病菌有显著抗菌活性,可能揭示了马齿苋治疗细菌性痢疾的作用机制。
• Cerebrosides from the Roots of Serratula chinensis
  作者：Tiejun Ling、Tao Xia、Xiaochun Wan、Daxiang Li、Xiaoyi Wei

  DOI：10.3390/11090677

  日期：——

  A new cerebroside, 1-O-β-D-glucopyranosyl-(2S,3R,8E)-2-[(2’R)-2-hydroxy- palmitoylamino]-8-octadecene-1,3-diol, along with aralia cerebroside and 1-O-β-D- glucopyranosyl-(2S,3S,4R,8E)-2-[(2’R)-2-hydroxybehenoylamino]-8-octadecene-1,3,4-triol were isolated from the roots of Serratula chinensis S. Moore. The structure of the new cerebroside was established by spectroscopic and chemical means. Occurrence of cerebrosides in Serratula is reported here for the first time.

  从黄花蒿（Serratula chinensis S. Moore）的根部分离得到一种新的脑苷脂，1-O-β-D-吡喃葡糖基-(2S,3R,8E)-2-[(2'R)-2-羟基棕榈酰氨基]-8-十八碳烯-1,3-二醇，以及人参脑苷脂和1-O-β-D-吡喃葡糖基-(2S,3S,4R,8E)-2-[(2'R)-2-羟基山萮酰氨基]-8-十八碳烯-1,3,4-三醇。通过光谱和化学方法确定了新型脑苷脂的结构。在这里首次报道了蒿属植物中存在脑苷脂。
• Ceramides Isolated from<i>Helianthus annuus</i>L.
  作者：Maorong Suo、Junshan Yang

  DOI：10.1002/hlca.201300194

  日期：2014.3

  3‐dihydroxy‐N‐[(2S,3S,4R,10E)‐1,3,4‐trihydroxyicos‐10‐en‐2‐yl]docosanamide (2), N‐(2‐phenylethyl)tetracosanamide (3), together with a known ceramide, (2R)‐N‐[(2S,3S,4R,8E)‐1‐(β‐D‐Glucopyranosyloxy)‐3,4‐dihydroxyoctadec‐8‐en‐2‐yl]‐2‐hydroxyhexadecanamide (4), were isolated from acetone extract of flower disc of Helianthus annuus L. The structures were identified on the basis of chemical and spectroscopic

  三个新化合物（2 R）-2-羟基‐ N -[（2 S，3 S，4 R，10 E）-1,3,4-三羟基icos-10-en-2-基]二十二碳酰胺（1）， （2 R，3 R）‐2,3‐二羟基‐N ‐（（2 S，3 S，4 R，10 E）‐1,3,4‐三羟基icos‐10‐en‐2‐yl】二十二碳酰胺（2），N-（2-苯基乙基）四乙酰胺（3）与已知的神经酰胺，（2 R）-N -[（2 S，3 S，4 R从向日葵花盘的丙酮提取物中分离出，8 E）-1（β - D-葡糖基葡糖氧基）-3,4-二羟基十八烷基-8-en-2-基] -2-羟基六癸酰胺（4）。结构是根据化学和光谱学方法鉴定的。
• A new cerebrogalactoside from Juglans mandshurica
  作者：Jiaming Sun、Renlong Chang、Hui Zhang

  DOI：10.1007/s10600-011-9895-3

  日期：2011.5

  A new cerebrogalactoside, Juglans cerebroside A (1), together with five known compounds, quercetin-3-O-β-D-galactopyranoside (2), myricetin-3-O-β-D-galactopyranoside (3), 2″E-quercetin-3-O-β-D-(6″″-O-[3″(4′″-hydroxyphenyl) propylene acyl]) glucopyranoside (4), gallic acid (5), and 2-methyl-1-hexadecanol (6) were isolated from the leaves of Juglans mandshurica Maxim. The structures of these compounds were determined by 1D, 2D NMR, and MS techniques.

  一种新的脑半乳糖苷，核桃脑苷 A (1)，以及五种已知化合物，槲皮素-3-O-β-D-吡喃半乳糖苷 (2)、杨梅素-3-O-β-D-吡喃半乳糖苷 (3)，2″E -槲皮素-3-O-β-D-(6″″-O-[3″(4″″-羟基苯基)丙烯酰基])吡喃葡萄糖苷(4)、没食子酸(5)和2-甲基-1-从胡桃木 (Juglans mandshurica Maxim) 的叶子中分离出十六烷醇 (6)。这些化合物的结构通过 1D、2D NMR 和 MS 技术确定。
• 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）。