vitexin 2"-O-sulfate | 1173925-24-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: vitexin 2"-O-sulfate
• 英文别名: vitexin 2"-sulfate；perchafuroside B；[(2S,3R,4S,5S,6R)-2-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] hydrogen sulfate
• CAS: 1173925-24-0
• 化学式: C₂₁H₂₀O₁₃S
• 分子量: 512.448
• InChiKey: OSALNYNYADJXIW-BOCLWZTGSA-N

物化性质

• 密度：
  1.90±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  35
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  229
• 氢给体数：
  7
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  vitexin 2"-O-sulfate 在 吡啶 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.0h， 生成 牡荆素
  参考文献：
  名称：

  Quantitation of Chafurosides A and B in Tea Leaves and Isolation of Prechafurosides A and B from Oolong Tea Leaves

  摘要：

  A procedure was developed for the quantitative determination of chafuroside A, a flavone C glycoside with potent anti-inflammatory activity, and its regioisomer chafuroside B, as well as isovitexin and vitexin, by selected reaction monitoring liquid chromatography-tandem mass spectrometry (SRM LC-MS/MS) analysis. This method was successfully applied to commercial leaves of green tea, houji tea, oolong tea, and black tea. High levels of chafurosides A and B were found in oolong tea leaves that had been heated at >140 degrees C. Next, their precursors, prechafurosides A and B, were isolated from methanol extract of oolong tea leaves prepared from Shizu 7132, Camellia sinensis (L.) O. Kuntze, by partition with n-butanol and H2O and chromatography on Diaion SP-825, Sephadex LH-20, and ODS C-18, guided by assay of chafuroside formation. Prechafurosides A and B gave chafurosides A and B, respectively, in good yields when heated at 160 degrees C for 0.5 h. Solvolysis of prechafurosides A and B with pyridine and dioxane quantitatively afforded isovitexin and vitexin, respectively. On the basis of these results and physicochemical data (MS, UV, and NMR), prechafurosides A and B were concluded to be new flavone C-glycoside sulfates, isovitexin-2 ''-sulfate and vitexin-2 ''-sulfate, respectively.

  DOI：

  10.1021/jf900032z
• 作为产物：
  描述：

  牡荆素 在 4-甲基苯磺酸吡啶 三氧化硫吡啶 作用下， 以 吡啶 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 vitexin 2"-O-sulfate
  参考文献：
  名称：

  EP2385049

  摘要：

  公开号：

文献信息

• SULFATED C-GLYCOSIDE, METHOD FOR ISOLATING SAME AND METHOD FOR SYNTHESIZING SAME
  申请人：Ishida Hitoshi

  公开号：US20120029183A1

  公开（公告）日：2012-02-02

  Provided are a sulfated C-glycoside which is a novel compound serving as a precursor of chafuroside and chafuroside analogs; a method for efficiently producing the sulfated C-glycoside; and a method for efficiently producing chafuroside and chafuroside analogs using said sulfated C-glycoside. A sulfated C-glycoside represented by general formula (A1) or (B1) [wherein R 1 , R 2 and R 3 independently represent each a hydrogen atom or an OH group] is obtained by extracting tea leaves or tea tannins with water, a lower alcohol solvent having 1 to 3 carbon atoms or a liquid mixture comprising the same. Alternatively, the sulfated C-glycoside is produced by reacting a flavone C-glycoside such as isovitexin or vitexin with a sulfate group-introducing agent to thereby sulfate the flavone C-glycoside. By heating the sulfated C-glycoside thus obtained, chafuroside and chafuroside analogs are efficiently produced.
• US8367622B2
  申请人：——

  公开号：US8367622B2

  公开（公告）日：2013-02-05
• JP2016/222581
  申请人：——

  公开号：——

  公开（公告）日：——
• Quantitation of Chafurosides A and B in Tea Leaves and Isolation of Prechafurosides A and B from Oolong Tea Leaves
  作者：Hitoshi Ishida、Toshiyuki Wakimoto、Yukiko Kitao、Shimako Tanaka、Toshio Miyase、Haruo Nukaya

  DOI：10.1021/jf900032z

  日期：2009.8.12

  A procedure was developed for the quantitative determination of chafuroside A, a flavone C glycoside with potent anti-inflammatory activity, and its regioisomer chafuroside B, as well as isovitexin and vitexin, by selected reaction monitoring liquid chromatography-tandem mass spectrometry (SRM LC-MS/MS) analysis. This method was successfully applied to commercial leaves of green tea, houji tea, oolong tea, and black tea. High levels of chafurosides A and B were found in oolong tea leaves that had been heated at >140 degrees C. Next, their precursors, prechafurosides A and B, were isolated from methanol extract of oolong tea leaves prepared from Shizu 7132, Camellia sinensis (L.) O. Kuntze, by partition with n-butanol and H2O and chromatography on Diaion SP-825, Sephadex LH-20, and ODS C-18, guided by assay of chafuroside formation. Prechafurosides A and B gave chafurosides A and B, respectively, in good yields when heated at 160 degrees C for 0.5 h. Solvolysis of prechafurosides A and B with pyridine and dioxane quantitatively afforded isovitexin and vitexin, respectively. On the basis of these results and physicochemical data (MS, UV, and NMR), prechafurosides A and B were concluded to be new flavone C-glycoside sulfates, isovitexin-2 ''-sulfate and vitexin-2 ''-sulfate, respectively.
• EP2385049
  申请人：——

  公开号：——

  公开（公告）日：——