isoflav-3-ene-4',5,7-triol | 81267-63-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: isoflav-3-ene-4',5,7-triol
• 英文别名: 5-hyroxy-dehydroequol；3-(4-hydroxyphenyl)-2H-chromene-5,7-diol
• CAS: 81267-63-2
• 化学式: C₁₅H₁₂O₄
• 分子量: 256.258
• InChiKey: MXSBGPUCTKSXHL-UHFFFAOYSA-N

物化性质

• 沸点：
  551.1±49.0 °C(Predicted)
• 密度：
  1.439±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  69.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,O-双(三甲基硅烷基)三氟乙酰胺 、 isoflav-3-ene-4',5,7-triol 反应 0.08h， 生成
  参考文献：
  名称：

  Biosynthesis of (−)-5-Hydroxy-equol and 5-Hydroxy-dehydroequol from Soy Isoflavone, Genistein Using Microbial Whole Cell Bioconversion

  摘要：

  Equols are isoflavandiols formed by reduction of soy isoflavones such as daidzein and genistein by gut microorganisms. These phytoestrogens are of interest for their various biological effects. We report biosynthesis from genistein to (-)-5-hydroxy-equol in recombinant E. coli expressing three reductases (daidzein reductase DZNR, dihidroclaidzein reductaier DHDR, tetrahydrodaidzein reductase THDR) and a racemase (dihydrodaidzein racemase, DDRC) originating from the Or, bacterium, Slackia isoflavoniconvertens. The biosynthesized 5-hydroxy4equol proved as an optically negative enantioiner,, none-theless it displayed an inverse Circular dichroism spectrum to (S)-equol. Compartmentalized expression of DZNR and DDRC in one E. coli strain and DHDR and THDR in another increased the yield, to 230 mg/L and the productivity to 38 mg/L/h. If the last reductase was Missing, the intermediate spontaneously dehydrated to 5-hydroxy-dehydroequol in up to 99 mg/L This novel isoflavene, previously not known to be synthesized in nature, was also detected in this biotransformation system:, Although (S)-equol favors binding to human estrogen receptor (hER) beta over,hER alpha, (-)-5-hydroxy-equol showed the opposite preference. This study provides elucidation of the biosynthetic route of (-)-5-hydroxy-equol and measurement of its potent antagonistic character as a phytoestrogen for the first time.

  DOI：

  10.1021/acschembio.7b00624
• 作为产物：
  描述：

  染料木素 在 葡萄糖 作用下， 以 aq. phosphate buffer 、 二甲基亚砜 、 甘油 为溶剂， 生成 isoflav-3-ene-4',5,7-triol
  参考文献：
  名称：

  Biosynthesis of (−)-5-Hydroxy-equol and 5-Hydroxy-dehydroequol from Soy Isoflavone, Genistein Using Microbial Whole Cell Bioconversion

  摘要：

  Equols are isoflavandiols formed by reduction of soy isoflavones such as daidzein and genistein by gut microorganisms. These phytoestrogens are of interest for their various biological effects. We report biosynthesis from genistein to (-)-5-hydroxy-equol in recombinant E. coli expressing three reductases (daidzein reductase DZNR, dihidroclaidzein reductaier DHDR, tetrahydrodaidzein reductase THDR) and a racemase (dihydrodaidzein racemase, DDRC) originating from the Or, bacterium, Slackia isoflavoniconvertens. The biosynthesized 5-hydroxy4equol proved as an optically negative enantioiner,, none-theless it displayed an inverse Circular dichroism spectrum to (S)-equol. Compartmentalized expression of DZNR and DDRC in one E. coli strain and DHDR and THDR in another increased the yield, to 230 mg/L and the productivity to 38 mg/L/h. If the last reductase was Missing, the intermediate spontaneously dehydrated to 5-hydroxy-dehydroequol in up to 99 mg/L This novel isoflavene, previously not known to be synthesized in nature, was also detected in this biotransformation system:, Although (S)-equol favors binding to human estrogen receptor (hER) beta over,hER alpha, (-)-5-hydroxy-equol showed the opposite preference. This study provides elucidation of the biosynthetic route of (-)-5-hydroxy-equol and measurement of its potent antagonistic character as a phytoestrogen for the first time.

  DOI：

  10.1021/acschembio.7b00624

文献信息

• Production of isoflavone derivatives
  申请人：Heaton Andrew

  公开号：US20050143588A1

  公开（公告）日：2005-06-30

  Methods for the hydrogenation of isoflavones are described which provide access to workable quantities of isoflavan-4-ols, isoflav-3-enes, and isoflavans. The isoflavone derivatives can be obtained in high purity and in near quantitative yields whilst employing pharmaceutically acceptable reagents and solvents.

  描述了异黄酮氢化的方法，可以获得可操作数量的异黄烷-4-醇、异黄烯和异黄烷。在使用药用可接受的试剂和溶剂时，可以高纯度地获得异黄酮衍生物，并且产率接近定量。
• [EN] PRODUCTION OF ISOFLAVONE DERIVATIVES<br/>[FR] DERIVES D'ISOFLAVONE
  申请人：NOVOGEN RES PTY LTD

  公开号：WO2000049009A1

  公开（公告）日：2000-08-24

  Methods for the hydrogenation of isoflavones are described which provide access to workable quantities of isoflavan-4-ols, isoflav-3-enes, and isoflavans. The isoflavone derivatives can be obtained in high purity and in near quantitative yields whilst employing pharmaceutically acceptable reagents and solvents.

  本文描述了一些对异黄酮进行氢化的方法，可以获得可用量的异黄酮-4-醇、异黄酮-3-烯和异黄酮。在使用药用可接受试剂和溶剂的同时，可以高纯度地获得异黄酮衍生物，并且接近定量收率。
• Liepa, Andris J., Australian Journal of Chemistry, 1981, vol. 34, # 12, p. 2647 - 2655
  作者：Liepa, Andris J.

  DOI：——

  日期：——
• PRODUCTION OF ISOFLAVONE DERIVATIVES
  申请人：Novogen Research Pty. Ltd.

  公开号：EP1153020A1

  公开（公告）日：2001-11-14
• EP1153020A4
  申请人：——

  公开号：EP1153020A4

  公开（公告）日：2002-08-21