(2S)-4-(3,4-dihydroxyphenyl)-2-butanol | 259727-11-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (2S)-4-(3,4-dihydroxyphenyl)-2-butanol
• 英文别名: 4-(3',4'-Dihydroxyphenyl)-2R-butanol；(-)-rhodolatouchol；4-[(3S)-3-hydroxybutyl]benzene-1,2-diol
• CAS: 259727-11-2
• 化学式: C₁₀H₁₄O₃
• 分子量: 182.219
• InChiKey: BCSAQTFHGURJII-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-hydroxy-4-[(3S)-3-hydroxybutyl]phenyl-β-D-glucopyranoside 在 almond β-glucosidase 作用下， 生成 (2S)-4-(3,4-dihydroxyphenyl)-2-butanol
  参考文献：
  名称：

  Biotransformation of raspberry ketone and zingerone by cultured cells of Phytolacca americana

  摘要：

  The biotransformation of raspberry ketone and zingerone were individually investigated using cultured cells of Phytolacca americana. In addition to (2S)-4-(4-hydroxyphenyl)-2-butanol (2%), (2S)-4-(3,4-dihydroxyphenyl)-2-butanol (5%), 4-[4-beta-D-glucopyranosyloxy)phenyl]-2-butanone (19%), 4-[(3S)-3-hydroxybutyl]phenyl-beta-D-glucopyranoside (23%), and (2S)-4-(4-hydroxyphenyl)but-2-yl-beta-D-glucopyrdnoside (20%), two biotransformation products, i.e., 2-hydroxy-4-[(3S)-3-hydroxybutyl]phenyl-beta-D-glucopyranoside(12%) and 2-hydroxy-5-[(3S)-3-hydroxybutyl]phenyl-beta-D-glucopyranoside (11%), were isolated from suspension cells after incubation with raspberry ketone Or three days. On the other hand, two compounds, i.e., (2S)-4-(4-hydroxy-3-methoxyphenyl)but-2-yl-beta-D-glucopyranoside (17%) and (2S)-2-(beta-D-glucopyranosyloxy)-4-[4-(beta-D-glucopyranosyloxy)-3-methoxyphenyl]butane (16%), together with (2S)-4-(4-hydroxy-3-methoxyphenyl)-2-butanol (15%), 4-[4-(beta-D-glucopyranosyloxy)-3-methoxyphenyt]-2-butanone (21%), and 4-[(3S)-3-hydroxybutyl]-2-methoxyphenyl-beta-D-glucopyranoside (24%) were obtained upon addition of zingerone. Cultured cells of P. americana can reduce, and regioselectively hydroxylate and glucosylate, these food ingredients to their beta-glycosides. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2006.11.030

文献信息

• Biotransformation of raspberry ketone and zingerone by cultured cells of Phytolacca americana
  作者：Kei Shimoda、Toshio Harada、Hatsuyuki Hamada、Nobuyoshi Nakajima、Hiroki Hamada

  DOI：10.1016/j.phytochem.2006.11.030

  日期：2007.2

  The biotransformation of raspberry ketone and zingerone were individually investigated using cultured cells of Phytolacca americana. In addition to (2S)-4-(4-hydroxyphenyl)-2-butanol (2%), (2S)-4-(3,4-dihydroxyphenyl)-2-butanol (5%), 4-[4-beta-D-glucopyranosyloxy)phenyl]-2-butanone (19%), 4-[(3S)-3-hydroxybutyl]phenyl-beta-D-glucopyranoside (23%), and (2S)-4-(4-hydroxyphenyl)but-2-yl-beta-D-glucopyrdnoside (20%), two biotransformation products, i.e., 2-hydroxy-4-[(3S)-3-hydroxybutyl]phenyl-beta-D-glucopyranoside(12%) and 2-hydroxy-5-[(3S)-3-hydroxybutyl]phenyl-beta-D-glucopyranoside (11%), were isolated from suspension cells after incubation with raspberry ketone Or three days. On the other hand, two compounds, i.e., (2S)-4-(4-hydroxy-3-methoxyphenyl)but-2-yl-beta-D-glucopyranoside (17%) and (2S)-2-(beta-D-glucopyranosyloxy)-4-[4-(beta-D-glucopyranosyloxy)-3-methoxyphenyl]butane (16%), together with (2S)-4-(4-hydroxy-3-methoxyphenyl)-2-butanol (15%), 4-[4-(beta-D-glucopyranosyloxy)-3-methoxyphenyt]-2-butanone (21%), and 4-[(3S)-3-hydroxybutyl]-2-methoxyphenyl-beta-D-glucopyranoside (24%) were obtained upon addition of zingerone. Cultured cells of P. americana can reduce, and regioselectively hydroxylate and glucosylate, these food ingredients to their beta-glycosides. (c) 2006 Elsevier Ltd. All rights reserved.