(S)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)decan-3-one | 41743-69-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (S)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)decan-3-one
• 英文别名: 6-gingerol；(5S)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)nonan-3-one
• CAS: 41743-69-5
• 化学式: C₁₆H₂₄O₄
• 分子量: 280.364
• InChiKey: JZLXEKNVCWMYHI-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)decan-3-one 、 D-(+)-纤维二糖 在 ammonium sulfate 、 recombinant α-glucosidase from Halomonas sp. H11 作用下， 反应 6.0h， 以60%的产率得到(S)-5-(O-α-D-glucopyranosyl)-1-(4-hydroxy-3-methoxyphenyl)decan-3-one
  参考文献：
  名称：

  α-Glucosylated 6-gingerol: chemoenzymatic synthesis using α-glucosidase from Halomonas sp. H11, and its physical properties

  摘要：

  6-Gingerol [(S)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)decan-3-one] is a biologically active compound and is abundant in the rhizomes of ginger (Zingiber officinale). It has some beneficial functions in healthcare, but its use is limited because of its insolubility in water and its heat-instability. To improve these physical properties, the glucosylation of 6-gingerol was investigated using alpha-glucosidases (EC. 3.2.1.20) from Aspergillus niger, Aspergillus nidulans ABPU1, Acremonium strictum, Halomonas sp. H11, and Saccharomyces cerevisiae, and cyclodextrin glucanotransferases (CGTase, EC. 2.4.1.19) from Bacillus coagulans, Bacillus sp. No. 38-2, Bacillus clarkii 7364, and Geobacillus stearothermophilus. Among these, only alpha-glucosidase from Halomonas sp. H11 (HaG) transferred a glucosyl moiety to 6-gingerol, and produced glucosylated compounds. The chemical structure of the reaction product, determined by nuclear magnetic resonance spectroscopy and mass spectrometry, was (S)-5-(O-alpha-D-glucopyranosyl)-1-(4-hydroxy-3-methoxyphenyl) decan-3-one (5-alpha-Glc-gingerol). Notably, the regioisomer formed by glucosylation of the phenolic OH was not observed at all, indicating that HaG specifically transferred the glucose moiety to the 5-OH of the beta-hydroxy keto group in 6-gingerol. Almost 60% of the original 6-gingerol was converted into 5-alpha-Glc-gingerol by the reaction. In contrast to 6-gingerol, 5-alpha-Glc-gingerol, in the form of an orange powder prepared by freeze-drying, was water-soluble and stable at room temperature. It was also more stable than 6-gingerol under acidic conditions and to heat. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.03.012

文献信息

• TREATMENT OF PAIN
  申请人：INNOVATIVE HERBAL PRODUCTS (AUST) PTY LTD

  公开号：US20160317599A1

  公开（公告）日：2016-11-03

  The invention relates to a method of treating or preventing pain, or a condition associated with pain, in a subject in need thereof comprising applying topically an effective amount of an extract of Zingiber Officinale (ginger), and to topical compositions and articles of manufacture comprising an extract of Zingiber Officinale.
• α-Glucosylated 6-gingerol: chemoenzymatic synthesis using α-glucosidase from Halomonas sp. H11, and its physical properties
  作者：Teruyo Ojima、Kenta Aizawa、Wataru Saburi、Takeshi Yamamoto

  DOI：10.1016/j.carres.2012.03.012

  日期：2012.6

  6-Gingerol [(S)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)decan-3-one] is a biologically active compound and is abundant in the rhizomes of ginger (Zingiber officinale). It has some beneficial functions in healthcare, but its use is limited because of its insolubility in water and its heat-instability. To improve these physical properties, the glucosylation of 6-gingerol was investigated using alpha-glucosidases (EC. 3.2.1.20) from Aspergillus niger, Aspergillus nidulans ABPU1, Acremonium strictum, Halomonas sp. H11, and Saccharomyces cerevisiae, and cyclodextrin glucanotransferases (CGTase, EC. 2.4.1.19) from Bacillus coagulans, Bacillus sp. No. 38-2, Bacillus clarkii 7364, and Geobacillus stearothermophilus. Among these, only alpha-glucosidase from Halomonas sp. H11 (HaG) transferred a glucosyl moiety to 6-gingerol, and produced glucosylated compounds. The chemical structure of the reaction product, determined by nuclear magnetic resonance spectroscopy and mass spectrometry, was (S)-5-(O-alpha-D-glucopyranosyl)-1-(4-hydroxy-3-methoxyphenyl) decan-3-one (5-alpha-Glc-gingerol). Notably, the regioisomer formed by glucosylation of the phenolic OH was not observed at all, indicating that HaG specifically transferred the glucose moiety to the 5-OH of the beta-hydroxy keto group in 6-gingerol. Almost 60% of the original 6-gingerol was converted into 5-alpha-Glc-gingerol by the reaction. In contrast to 6-gingerol, 5-alpha-Glc-gingerol, in the form of an orange powder prepared by freeze-drying, was water-soluble and stable at room temperature. It was also more stable than 6-gingerol under acidic conditions and to heat. (C) 2012 Elsevier Ltd. All rights reserved.