(R)-4'-methoxy-3',5,7-trihydroxyflavanone | 24604-97-5

• 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: (R)-4'-methoxy-3',5,7-trihydroxyflavanone
• 英文别名: (R)-hesperetin；R-hesperetin；hespertin；(+)-(R)-hesperetin；R-HST；5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one；(2R)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydrochromen-4-one
• CAS: 24604-97-5
• 化学式: C₁₆H₁₄O₆
• 分子量: 302.284
• InChiKey: AIONOLUJZLIMTK-CQSZACIVSA-N

物化性质

• 熔点：
  223-225 °C
• 沸点：
  586.2±50.0 °C(Predicted)
• 密度：
  1.458±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  96.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (R)-4'-methoxy-3',5,7-trihydroxyflavanone 在 6-氨基-9-[3-羟基-5-[(羟基-磺基氧基-磷酰)氧基甲基]-4-膦酰氧基-四氢呋喃-2-基]-嘌呤 、 magnesium chloride 作用下， 以 二甲基亚砜 为溶剂， 反应 0.08h， 生成 (R)-hesperetin 7-O-sulfate 、 (R)-hesperetin 3-O-sulfate
  参考文献：
  名称：

  Stereoselective Conjugation, Transport and Bioactivity ofS- andR-Hesperetin Enantiomers in Vitro

  摘要：

  The flavanone hesperetin ((+/-)-4'-methoxy-3',5,7-trihydroxyflavanone) is the aglycone of hesperidin, which is the major flavonoid present in sweet oranges. Hesperetin contains a chiral C-atom and so can exist as an S- and R-enantiomer, however, in nature 2S-hesperidin and its S-hesperetin aglycone are predominant. The present study reports a chiral HPLC method to separate S- and R-hesperetin on an analytical and semipreparative scale. This allowed characterization of the stereoselective differences in metabolism and transport in the intestine and activity in a selected bioassay of the separated hesperetin enantiomers in in vitro model systems: (1) with human small intestinal fractions containing UDP-glucuronosyl transferases (UGTs) or sulfotransferases (SULTs); (2) with Caco-2 cell monolayers as a model for the intestinal transport barrier; (3) with mouse Hepa-1c1c7 cells transfected with human EpRE-controlled luciferase to test induction of EpRE-mediated gene expression. The results obtained indicate some significant differences in the metabolism and transport characteristics and bioactivity between S- and R-hesperetin, however, these differences are relatively small. This indicates that for these end points, including intestinal metabolism and transport and EpRE-mediated gene induction, experiments performed with racemic hesperetin may adequately reflect what can be expected for the naturally occurring S-enantiomer. This is an important finding since at present hesperetin is only commercially available as a racemic mixture, while it exists in nature mainly as an S-enantiomer.

  DOI：

  10.1021/jf1008617
• 作为产物：
  描述：

  (S)-2,3-dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-benzopyrone 在 per(4-chloro-3-methyl)phenylcarbamate β-cyclodextrin clicked onto an alkynyl surface modified silica support 作用下， 以 乙醇 、 正己烷 为溶剂， 生成 (R)-4'-methoxy-3',5,7-trihydroxyflavanone 、 橙皮素
  参考文献：
  名称：

  在HPLC中，功能性调节了氨基甲酸苯酯环糊精点击的手性固定相的对映选择性。

  摘要：

  混合的氯官能团和甲基官能团可以极大地调节苯基氨基甲酸酯环糊精（CD）咔哒手性固定相（CSP）的对映选择性。本文报道了对（4-氯-3-甲基）苯基氨基甲酸酯和（2-氯-5-甲基）苯基氨基甲酸酯β-CD裂解的CSP（即CCC4M3-CSP和CCC2M5-CSP）的比较研究。在正相和反相模式高效液相色谱（HPLC）中均研究了对映选择性对柱温的依赖性。热力学研究表明，CCC4M3-CSP与手性溶质之间可形成更强的分子间相互作用，以驱动手性分离。通过在HPLC中对17种模型外消旋物进行对映分离，进一步证明了CCC4M3-CSP的对映选择性更高。

  DOI：

  10.1002/chir.22732

文献信息

• [EN] PREPARATION METHOD FOR HESPERETIN, PREPARATION METHOD FOR HESPERETIN INTERMEDIATE, AND BIOLOGICAL ENZYME USED FOR PREPARING HESPERETIN<br/>[FR] PROCÉDÉ DE PRÉPARATION D'HESPÉRÉTINE, PROCÉDÉ DE PRÉPARATION D'UN INTERMÉDIAIRE D'HESPÉRÉTINE, ET ENZYME BIOLOGIQUE UTILISÉE POUR PRÉPARER L'HESPÉRÉTINE<br/>[ZH] 一种橙皮素的制备方法、橙皮素中间体的制备方法和用于制备橙皮素的生物酶
  申请人：BONTAC BIO ENG SHENZHEN CO LTD

  公开号：WO2019076021A1

  公开（公告）日：2019-04-25

  本发明提供了一种橙皮素的制备方法，包括：将橙皮苷或新橙皮苷悬浮于水中，并加入氢氧化钠溶液至所述橙皮苷或所述新橙皮苷完全溶解后得到底物配制液；采用底物流加法将所述底物配制液以0.1-1mL/min的速度加入至含有α-L-鼠李糖苷酶和β-葡萄糖苷酶的缓冲液中进行搅拌反应并得到反应液，流加完成后继续反应0.5-1h，所述反应液的pH为6.0-7.0，反应温度维持在45-65℃，所述α-L-鼠李糖苷酶来源于链霉菌属，所述β-葡萄糖苷酶来源于海栖热袍菌属；调节所述反应液的pH至3.0-5.0使固体产物完全析出，收集所述固体产物，制得橙皮素。该方法高效简便，绿色环保，可以适用于工业化大规模生产。
• Functionalities tuned enantioselectivity of phenylcarbamate cyclodextrin clicked chiral stationary phases in HPLC
  作者：Jian Tang、Yuzhou Lin、Bo Yang、Jie Zhou、Weihua Tang

  DOI：10.1002/chir.22732

  日期：2017.9

  phenylcarbamate cyclodextrin (CD) clicked chiral stationary phases (CSPs). A comparison study is herein reported for per(4‐chloro‐3‐methyl)phenylcarbamate and per(2‐chloro‐5‐methyl)phenylcarbamate β‐CD clicked CSPs (i.e., CCC4M3‐CSP and CCC2M5‐CSP). The enantioselectivity dependence on column temperature was studied in both normal‐phase and reversed‐phase mode high performance liquid chromatography

  混合的氯官能团和甲基官能团可以极大地调节苯基氨基甲酸酯环糊精（CD）咔哒手性固定相（CSP）的对映选择性。本文报道了对（4-氯-3-甲基）苯基氨基甲酸酯和（2-氯-5-甲基）苯基氨基甲酸酯β-CD裂解的CSP（即CCC4M3-CSP和CCC2M5-CSP）的比较研究。在正相和反相模式高效液相色谱（HPLC）中均研究了对映选择性对柱温的依赖性。热力学研究表明，CCC4M3-CSP与手性溶质之间可形成更强的分子间相互作用，以驱动手性分离。通过在HPLC中对17种模型外消旋物进行对映分离，进一步证明了CCC4M3-CSP的对映选择性更高。
• Stereoselective Conjugation, Transport and Bioactivity of<i>S</i>- and<i>R</i>-Hesperetin Enantiomers in Vitro
  作者：Walter Brand、Jia Shao、Elisabeth F. Hoek-van den Hil、Kathelijn N. van Elk、Bert Spenkelink、Laura H. J. de Haan、Maarit J. Rein、Fabiola Dionisi、Gary Williamson、Peter J. van Bladeren、Ivonne M. C. M. Rietjens

  DOI：10.1021/jf1008617

  日期：2010.5.26

  The flavanone hesperetin ((+/-)-4'-methoxy-3',5,7-trihydroxyflavanone) is the aglycone of hesperidin, which is the major flavonoid present in sweet oranges. Hesperetin contains a chiral C-atom and so can exist as an S- and R-enantiomer, however, in nature 2S-hesperidin and its S-hesperetin aglycone are predominant. The present study reports a chiral HPLC method to separate S- and R-hesperetin on an analytical and semipreparative scale. This allowed characterization of the stereoselective differences in metabolism and transport in the intestine and activity in a selected bioassay of the separated hesperetin enantiomers in in vitro model systems: (1) with human small intestinal fractions containing UDP-glucuronosyl transferases (UGTs) or sulfotransferases (SULTs); (2) with Caco-2 cell monolayers as a model for the intestinal transport barrier; (3) with mouse Hepa-1c1c7 cells transfected with human EpRE-controlled luciferase to test induction of EpRE-mediated gene expression. The results obtained indicate some significant differences in the metabolism and transport characteristics and bioactivity between S- and R-hesperetin, however, these differences are relatively small. This indicates that for these end points, including intestinal metabolism and transport and EpRE-mediated gene induction, experiments performed with racemic hesperetin may adequately reflect what can be expected for the naturally occurring S-enantiomer. This is an important finding since at present hesperetin is only commercially available as a racemic mixture, while it exists in nature mainly as an S-enantiomer.