2,5,7,8-tetramethyl-2-(4,8-dimethylnonyl)chroman-6-yl 6-O-β-D-glucopyranosyl-β-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,5,7,8-tetramethyl-2-(4,8-dimethylnonyl)chroman-6-yl 6-O-β-D-glucopyranosyl-β-D-glucopyranoside
• 英文别名: (2R,3R,4S,5S,6R)-2-[[(2R,3S,4S,5R,6S)-6-[[2-(4,8-dimethylnonyl)-2,5,7,8-tetramethyl-3,4-dihydrochromen-6-yl]oxy]-3,4,5-trihydroxyoxan-2-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• 化学式: C₃₆H₆₀O₁₂
• 分子量: 684.865
• InChiKey: FMAPJNGYWTXCOG-ZZVRITPYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  48
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  188
• 氢给体数：
  7
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  3-methenyl-7,11-dimethyldodeca-1,6-diene 在 Catharanthus roseus cells 作用下， 以 various solvent(s) 为溶剂， 反应 168.0h， 生成 2,5,7,8-tetramethyl-2-(4,8-dimethylnonyl)chroman-6-yl 6-O-β-D-glucopyranosyl-β-D-glucopyranoside
  参考文献：
  名称：

  Formation of water-soluble vitamin derivatives from lipophilic vitamins by cultured plant cells

  摘要：

  Glycosylation of vitamin E, its homologues, and vitamin A by Cultured plant cells of Phytolacca americana and Catharanthus roseus was investigated to produce water-soluble vitamin derivatives. Two new compounds, that is, 2,5,7,8-tetramethyl-2-(4-methylpentyl)chroman-6-yl beta-D-glucopyranoside and 2,5,7,8-tetramethyl-2-(4,8-dimethynonyl)chroman-6-yl beta-D-glucopyranoside, together with 2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)chroman-6-yl beta-D-glucopyranoside were isolated from the cultured cells of P. americana following administration of vitamin E and its homologues, that is, 2,5,7,8-tetramethyl-2-(4-methylpentyl)-6-chromanol, 2,5,7,8-tetramethyl-2-(4,8-dmethylnonyl)-6-chromanol and 2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-6-chromanol (vitamin E). On the other hand, glycosylation by C roseus gave two new compounds, that is, 2,5,7,8-tetramethyl-2-(4-methylpentyl)chrornan-6-yl 6-O-beta-D-glucopyranosyl-beta-D-glucopyranoside and 2,5,7,8-tetramethyl-2-(4,8-dimethylnonyl)chroman-6-yl 6-O-beta-D-glucopyranosyl-beta-D-glucopyranoside, as well. Furthermore, conversion of vitamin A (retinol) by these cultured cells afforded retinyl beta-13-glucopyranoside. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.02.082

文献信息

• Formation of water-soluble vitamin derivatives from lipophilic vitamins by cultured plant cells
  作者：Kei Shimoda、Yoko Kondo、Koichi Abe、Hatsuyuki Hamada、Hiroki Hamada

  DOI：10.1016/j.tetlet.2006.02.082

  日期：2006.4

  Glycosylation of vitamin E, its homologues, and vitamin A by Cultured plant cells of Phytolacca americana and Catharanthus roseus was investigated to produce water-soluble vitamin derivatives. Two new compounds, that is, 2,5,7,8-tetramethyl-2-(4-methylpentyl)chroman-6-yl beta-D-glucopyranoside and 2,5,7,8-tetramethyl-2-(4,8-dimethynonyl)chroman-6-yl beta-D-glucopyranoside, together with 2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)chroman-6-yl beta-D-glucopyranoside were isolated from the cultured cells of P. americana following administration of vitamin E and its homologues, that is, 2,5,7,8-tetramethyl-2-(4-methylpentyl)-6-chromanol, 2,5,7,8-tetramethyl-2-(4,8-dmethylnonyl)-6-chromanol and 2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-6-chromanol (vitamin E). On the other hand, glycosylation by C roseus gave two new compounds, that is, 2,5,7,8-tetramethyl-2-(4-methylpentyl)chrornan-6-yl 6-O-beta-D-glucopyranosyl-beta-D-glucopyranoside and 2,5,7,8-tetramethyl-2-(4,8-dimethylnonyl)chroman-6-yl 6-O-beta-D-glucopyranosyl-beta-D-glucopyranoside, as well. Furthermore, conversion of vitamin A (retinol) by these cultured cells afforded retinyl beta-13-glucopyranoside. (c) 2006 Elsevier Ltd. All rights reserved.