(S)-zingerol | 932042-60-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (S)-zingerol
• 英文别名: Zingerol, (S)-；4-[(3S)-3-hydroxybutyl]-2-methoxyphenol
• CAS: 932042-60-9
• 化学式: C₁₁H₁₆O₃
• 分子量: 196.246
• InChiKey: GTLGHKNKLRZSMO-QMMMGPOBSA-N

物化性质

• 沸点：
  344.4±27.0 °C(Predicted)
• 密度：
  1.117±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (S)-zingerol 在 吡啶 作用下， 反应 0.33h， 以99%的产率得到(S)-4-(4'-acetyloxy-3'-methoxyphenyl)-2-butyl acetate
  参考文献：
  名称：

  对映体纯姜油醇经脂肪酶催化酯交换反应的不对称合成及其类似物的有效合成

  摘要：

  容易从姜中获得的非手性姜油酮1可以容易地转化为手性衍生物。姜油酮1的还原产物Zingerol 2被认为是重要的新药用铅化合物。我们已经通过脂肪酶催化的消旋体2的立体选择性酯交换反应实现了光学活性姜油醇（R）-2和（S）-2的简明合成。在优化的条件下，来自Alcaligenes sp。的脂肪酶。（Meito QLM）和乙酸乙烯酯在i -Pr 2 O或己烷中于35°C在1小时内得到醇（S）-2和具有高对映选择性的乙酸盐（R）-9而不会产生乙酰化的副产物。由于通过脂肪酶催化的酯交换反应获得了旋光性（S）-2和（R）-9，因此可以合成其他对映体纯的新型化合物。

  DOI：

  10.1016/j.tetasy.2013.04.013
• 作为产物：
  描述：

  姜酮 在 glucose dehydrogenase 、 葡萄糖 、 alcohol dehydrogenase from Rhodococcus ruber 、 烟酰胺腺嘌呤双核苷酸磷酸盐 作用下， 以 aq. phosphate buffer 、 二甲基亚砜 为溶剂， 反应 24.0h， 以90.3%的产率得到(S)-zingerol
  参考文献：
  名称：

  立体选择性生物催化还原工业废物中回收的生姜活性成分

  摘要：

  生姜活性成分已成功从发酵生姜的工业废生物质中回收，并通过立体选择性生物催化还原转化为相应的二醇和醇。

  DOI：

  10.1002/cbic.202200105

文献信息

• Bumaldosides A, B and C from the Leaves of Staphylea bumalda
  作者：Hideaki Otsuka、Qian Yu、Katsuyoshi Matsunami

  DOI：10.3987/com-09-s(s)22

  日期：——

  Two new aliphatic diglycosides and a phenolic glucoside (4, 5 and 7) have been isolated from leaves of Staphylea bumalda DC., together with three known compounds, benzyl and phenethyl alcohol glycosides (1 and 2), and zingerone beta-D-glucopyranoside (6). 2-Ethyl-3-methylmaleimide N-glucopyranoside (3) was first isolated as a free form. Their structures were determined on the basis of spectroscopic analysis.
• 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.
• Asymmetric synthesis of enantiomerically pure zingerols by lipase-catalyzed transesterification and efficient synthesis of their analogues
  作者：Takashi Kitayama、Sachiko Isomori、Kaoru Nakamura

  DOI：10.1016/j.tetasy.2013.04.013

  日期：2013.6

  readily available from ginger, can be easily transformed into chiral derivatives. Zingerol 2, a reduced product of zingerone 1 is expected to be an important new medicinal lead compound. We have achieved a concise synthesis of optically active zingerol (R)-2 and (S)-2 by the lipase-catalyzed stereoselective transesterification of racemic 2. Under the optimized conditions, a lipase from Alcaligenes sp

  容易从姜中获得的非手性姜油酮1可以容易地转化为手性衍生物。姜油酮1的还原产物Zingerol 2被认为是重要的新药用铅化合物。我们已经通过脂肪酶催化的消旋体2的立体选择性酯交换反应实现了光学活性姜油醇（R）-2和（S）-2的简明合成。在优化的条件下，来自Alcaligenes sp。的脂肪酶。（Meito QLM）和乙酸乙烯酯在i -Pr 2 O或己烷中于35°C在1小时内得到醇（S）-2和具有高对映选择性的乙酸盐（R）-9而不会产生乙酰化的副产物。由于通过脂肪酶催化的酯交换反应获得了旋光性（S）-2和（R）-9，因此可以合成其他对映体纯的新型化合物。
• Stereoselective Biocatalyzed Reductions of Ginger Active Components Recovered from Industrial Wastes
  作者：Rita Nasti、Ivan Bassanini、Erica Elisa Ferrandi、Federica Linguardo、Susanna Bertuletti、Marta Vanoni、Sergio Riva、Luisella Verotta、Daniela Monti

  DOI：10.1002/cbic.202200105

  日期：2022.4.20

  Ginger active constituents have been successfully recovered from industrial waste biomasses of fermented ginger and converted into the corresponding diols and alcohols by stereoselective biocatalyzed reductions.

  生姜活性成分已成功从发酵生姜的工业废生物质中回收，并通过立体选择性生物催化还原转化为相应的二醇和醇。