(S)-7-acetoxy-2-(4-acetoxy-phenyl)-5-hydroxy-chroman-4-one | 18196-13-9

• 物质功能分类: 天然产物 - 黄酮类化合物
• 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: (S)-7-acetoxy-2-(4-acetoxy-phenyl)-5-hydroxy-chroman-4-one
• 英文别名: (S)-7-Acetoxy-2-(4-acetoxy-phenyl)-5-hydroxy-chroman-4-on；Naringenin-4',7-diacetate；[4-[(2S)-7-acetyloxy-5-hydroxy-4-oxo-2,3-dihydrochromen-2-yl]phenyl] acetate
• CAS: 18196-13-9
• 化学式: C₁₉H₁₆O₇
• 分子量: 356.332
• InChiKey: PPTNIBIWQQIJJN-KRWDZBQOSA-N

物化性质

• 熔点：
  140-142 °C
• 沸点：
  578.9±50.0 °C(Predicted)
• 密度：
  1.361±0.06 g/cm3(Predicted)
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  99.1
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S)-7-acetoxy-2-(4-acetoxy-phenyl)-5-hydroxy-chroman-4-one 在 乙醇 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 potassium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 蜡菊亭; 4,2',4'-三羟基-6'-甲氧基查耳酮
  参考文献：
  名称：

  [EN] A METHOD FOR SYNTHESIZING XANTHOHUMOL
  [FR] PROCÉDÉ DE SYNTHÈSE DE XANTHOHUMOL

  摘要：

  A method for synthesizing xanthohumol (XN) from naringenin comprising steps of acylating hydroxyl groups of a naringenin flavone moiety to obtain an acylation product, a reaction of conversion of the flavone moiety into a chalcone moiety, and subjecting the chalcone compound to a reaction of hydrolysis of its ester groups, and next to a reaction of substitution of a prenyl moiety of the chalcone moiety to obtain xanthohumol. The xanthohumol produced by this method can be purified using crystallisation.

  公开号：

  WO2022233428A1
• 作为产物：
  描述：

  (2S)-(-)-naringenin-5-O-β-D-glucopyranoside 在 吡啶 、 甲酸 、 乙二醇 作用下， 生成 (S)-7-acetoxy-2-(4-acetoxy-phenyl)-5-hydroxy-chroman-4-one
  参考文献：
  名称：

  Zwei diastereomere Naringenin-β-D-glukoside aus Flores Stoechados

  摘要：

  DOI：

  10.1002/ardp.19592920803

文献信息

• A Practical Access to Highly Enantiomerically Pure Flavanones by Catalytic Asymmetric Transfer Hydrogenation
  作者：Marie-Kristin Lemke、Pia Schwab、Petra Fischer、Sandra Tischer、Morris Witt、Laurence Noehringer、Victor Rogachev、Anne Jäger、Olga Kataeva、Roland Fröhlich、Peter Metz

  DOI：10.1002/anie.201306500

  日期：2013.10.25

  A surprisingly selective, non‐enzymatic kinetic resolution of readily available, racemic β‐chiral ketones enabled the title process, which was applied to a rapid synthesis of several bioactive flavanones in virtually enantiopure form (see scheme; MOM=methoxymethyl, Ts=p‐toluenesulfonyl).

  令人惊讶的选择性容易获得的，外消旋的β-手性酮的，非酶动力学拆分启用标题处理，（见方案将其应用于多个生物活性黄烷酮的快速合成在几乎对映体纯形式; MOM =甲氧基甲基，在Ts = p -甲苯磺酰基）。
• BIOREACHABLE CHIRAL DOPANTS FOR LIQUID CRYSTAL APPLICATIONS
  申请人：Zymergen Inc.

  公开号：US20220025267A1

  公开（公告）日：2022-01-27

  The disclosure discusses chiral dopants for liquid-crystalline materials. Chiral dopants can be bioreachable compounds, i.e. compounds produced from microbes through fermentation. Chiral dopants can also include bioreachable materials that are further modified by chemical synthetic steps. Chiral dopants as discussed herein can include biomolecules such as glycyrrhetinic acid (1), S-narigenin (2), shikimic acid (3), alpha-phellandrene (4), betulin (5), malic acid (6), valencene (7), or nootkatone (8), and any stereoisomers or chemically modified derivatives thereof. The disclosure further shows optical properties of such compounds in a liquid-crystalline material.
• [EN] BIOREACHABLE CHIRAL DOPANTS FOR LIQUID CRYSTAL APPLICATIONS<br/>[FR] DOPANTS CHIRAUX "BIOATTEIGNABLES" POUR DES APPLICATIONS DE CRISTAUX LIQUIDES
  申请人：ZYMERGEN INC

  公开号：WO2020159620A9

  公开（公告）日：2020-10-22

  [EN] The disclosure discusses chiral dopants for liquid-crystalline materials. Chiral dopants can be bioreachable compounds, i.e., compounds produced from microbes through fermentation. Chiral dopants can also include bioreachable materials that are further modified by chemical synthetic steps. Chiral dopants as discussed herein can include biomolecules such as glycyrrhetinic acid (1), S-narigenin (2), shikimic acid (3), alpha-phellandrene (4), betulin (5), malic acid (6), valencene (7), or nootkatone (8), and any stereoisomers or chemically modified derivatives thereof. The disclosure further shows optical properties of such compounds in a liquid-crystalline material.
  [FR] La divulgation présente des dopants chiraux pour des matières cristallines liquides. Les dopants chiraux peuvent être des composés "bioatteignables", c'est-à-dire des composés produits à partir de microbes par fermentation. Les dopants chiraux peuvent également comprendre des matières "bioatteignables" qui sont encore modifiées par des étapes synthétiques chimiques. Les dopants chiraux selon l'invention peuvent comprendre des biomolécules telles que l'acide glycyrrhétinique (1), la S-narigénine (2), l'acide shikimique (3), l'alpha-phellandrène (4), la bétuline (5), l'acide malique (6), le valencène (7), ou le nootkatone (8), et tout stéréo-isomère ou ses dérivés chimiquement modifiés. La divulgation présente en outre les propriétés optiques de tels composés dans une matière cristalline liquide.
• Zwei diastereomere Naringenin-β-D-glukoside aus Flores Stoechados
  作者：R. Hänsel、D. Heise

  DOI：10.1002/ardp.19592920803

  日期：——
• [EN] A METHOD FOR SYNTHESIZING XANTHOHUMOL<br/>[FR] PROCÉDÉ DE SYNTHÈSE DE XANTHOHUMOL
  申请人：[en]DERMOTECH BEAUTY SP. Z O.O.

  公开号：WO2022233428A1

  公开（公告）日：2022-11-10

  A method for synthesizing xanthohumol (XN) from naringenin comprising steps of acylating hydroxyl groups of a naringenin flavone moiety to obtain an acylation product, a reaction of conversion of the flavone moiety into a chalcone moiety, and subjecting the chalcone compound to a reaction of hydrolysis of its ester groups, and next to a reaction of substitution of a prenyl moiety of the chalcone moiety to obtain xanthohumol. The xanthohumol produced by this method can be purified using crystallisation.