2-((6-O-(β-D-apiofuranosyl)-β-D-glucopyranosyl)oxy)-2-methylbutanenitrile | 170033-25-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-((6-O-(β-D-apiofuranosyl)-β-D-glucopyranosyl)oxy)-2-methylbutanenitrile
• 英文别名: 2-[(6-O-D-Apio-I(2)-D-furanosyl-I(2)-D-glucopyranosyl)oxy]-2-methylbutanenitrile；2-[(2S,3R,4S,5S,6R)-6-[[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-2-methylbutanenitrile
• CAS: 170033-25-7
• 化学式: C₁₆H₂₇NO₁₀
• 分子量: 393.391
• InChiKey: MTXHSRQBZHUBTP-COJGIXICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.9
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  182
• 氢给体数：
  6
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 2-((6-O-(β-D-apiofuranosyl)-β-D-glucopyranosyl)oxy)-2-methylbutanenitrile 在 吡啶 作用下， 反应 48.0h， 生成 Acetic acid (3S,4R,5R)-4-acetoxy-3-acetoxymethyl-5-[(2R,3R,4S,5R,6S)-3,4,5-triacetoxy-6-(1-cyano-1-methyl-propoxy)-tetrahydro-pyran-2-ylmethoxy]-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  Cyanogenic and non-cyanogenic glycosides from Manihot esculenta

  摘要：

  In addition to lotaustralin and linamarin, a novel cyanogenic glycoside, 2-((6-O-(beta-D-apiofuranosyl)-beta-D-glucopyranosyl)oxy)-2-methylbutanenitrile two novel non-cyanogenic glycosides, (2S)-((6-O-(beta-D-apiofuranosyl)-beta-D-glucopyranosyl)oxy)butane and 2-((6-O-(beta-D-apiofuranosyl)-beta-D-glucopyranosyl)oxy)propane, and a simple non-cyanogenic glycoside, ethyl beta-D-glucopyranoside, were isolated from an ethanolic extract of the fresh root cortex of Manihot esculenta. From a methanolic extract of the fresh leaves of this species lotaustralin and linamarin, and two flavonoid glycosides, kaempferol-3-O-rutinoside and quercetin-3-O-rutinoside were isolated.

  DOI：

  10.1016/0031-9422(95)00398-q

文献信息

• Cyanogenic and non-cyanogenic glycosides from Manihot esculenta
  作者：Hunsa Prawat、Chulabhorn Mahidol、Somsak Ruchirawat、Uma Prawat、Pittaya Tuntiwachwuttikul、Uncharee Tooptakong、Waltor C. Taylor、Chaveng Pakawatchai、Brian W. Skelton、Allen H. White

  DOI：10.1016/0031-9422(95)00398-q

  日期：1995.11

  In addition to lotaustralin and linamarin, a novel cyanogenic glycoside, 2-((6-O-(beta-D-apiofuranosyl)-beta-D-glucopyranosyl)oxy)-2-methylbutanenitrile two novel non-cyanogenic glycosides, (2S)-((6-O-(beta-D-apiofuranosyl)-beta-D-glucopyranosyl)oxy)butane and 2-((6-O-(beta-D-apiofuranosyl)-beta-D-glucopyranosyl)oxy)propane, and a simple non-cyanogenic glycoside, ethyl beta-D-glucopyranoside, were isolated from an ethanolic extract of the fresh root cortex of Manihot esculenta. From a methanolic extract of the fresh leaves of this species lotaustralin and linamarin, and two flavonoid glycosides, kaempferol-3-O-rutinoside and quercetin-3-O-rutinoside were isolated.