5-hydroxy-4'-methoxy-7-[(2-O-α-L-rhamnopyranosyl-β-D-glucopyranosyl)oxy]flavone | 20633-93-6

• 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: 5-hydroxy-4'-methoxy-7-[(2-O-α-L-rhamnopyranosyl-β-D-glucopyranosyl)oxy]flavone
• 英文别名: acacetin 7-O-neohesperidoside；acacetin-7-O-neohesperidoside；fortunellin；linarin；5-hydroxy-2-(4-methoxy-phenyl)-7-(O²-α-L-rhamnopyranosyl-β-D-glucopyranosyloxy)-chromen-4-one；5-Hydroxy-2-(4-methoxy-phenyl)-7-(O²-α-L-rhamnopyranosyl-β-D-glucopyranosyloxy)-chromen-4-on；7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-methoxyphenyl)chromen-4-one
• CAS: 20633-93-6
• 化学式: C₂₈H₃₂O₁₄
• 分子量: 592.554
• InChiKey: MLWDGPFGTFOLRJ-CUVHLRMHSA-N

物化性质

• 熔点：
  193-198°C
• 沸点：
  888.7±65.0 °C(Predicted)
• 密度：
  1.62±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  42
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.464
• 拓扑面积：
  214
• 氢给体数：
  7
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  5-hydroxy-4'-methoxy-7-[(2-O-α-L-rhamnopyranosyl-β-D-glucopyranosyl)oxy]flavone 在 乙醇 、 硫酸 作用下， 反应 2.0h， 以87%的产率得到金合欢素
  参考文献：
  名称：

  Synthesis of acacetin and resveratrol 3,5-di-O-β-glucopyranoside using lipase-catalyzed regioselective deacetylation of polyphenol glycoside peracetates as the key step

  摘要：

  Acacetin and re sveratrol 3,5-di-O-beta-glucopyranoside were synthesized from naturally abundant naringin and piceid in 65% and 62% overall yield, respectively. The key steps were the regioselective deacetylation of the peracetates of the glycosylated forms with Candida antarctica lipase B (Novozym 435) and Burkholderia cepacia lipase (Amano PS-IM). Deacetylation occurred exclusively at the least hindered position of the aromatic moieties and all acetyl groups in the sugar side chain remained intact. This excellent selectivity enabled regiospecific transformation of the liberated phenolic hydroxy groups, resulting in efficient synthesis of the target molecules. (C) 2016 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2016.03.001
• 作为产物：
  描述：

  5-acetoxy-7-[hexa-O-acetyl-(2-O-α-L-rhamnopyranosyl-β-D-glucopyranosyl)oxy]-4'-methoxyflavone 在 甲醇 、 sodium methylate 作用下， 反应 1.0h， 以88%的产率得到5-hydroxy-4'-methoxy-7-[(2-O-α-L-rhamnopyranosyl-β-D-glucopyranosyl)oxy]flavone
  参考文献：
  名称：

  Synthesis of acacetin and resveratrol 3,5-di-O-β-glucopyranoside using lipase-catalyzed regioselective deacetylation of polyphenol glycoside peracetates as the key step

  摘要：

  Acacetin and re sveratrol 3,5-di-O-beta-glucopyranoside were synthesized from naturally abundant naringin and piceid in 65% and 62% overall yield, respectively. The key steps were the regioselective deacetylation of the peracetates of the glycosylated forms with Candida antarctica lipase B (Novozym 435) and Burkholderia cepacia lipase (Amano PS-IM). Deacetylation occurred exclusively at the least hindered position of the aromatic moieties and all acetyl groups in the sugar side chain remained intact. This excellent selectivity enabled regiospecific transformation of the liberated phenolic hydroxy groups, resulting in efficient synthesis of the target molecules. (C) 2016 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2016.03.001

文献信息

• Schwer lösliche Salze von Aminoglykosidantibiotika
  申请人：MERCK PATENT GmbH

  公开号：EP0065123A1

  公开（公告）日：1982-11-24

  Neue schwer lösliche Flavanoidphosphate von Aminoglykosidantibiotika, insbesondere Hesperidinphosphate wie Gentamycin-hesperidinphosphat, bewirken eine langsame Freisetzung dieser Antibiotika.

  氨基糖苷类抗生素的新型难溶性黄酮类磷酸盐，特别是橙皮甙磷酸盐（如庆大霉素橙皮甙磷酸盐），可使这些抗生素缓慢释放。
• Tire with rubber containing flavone
  申请人：THE GOODYEAR TIRE & RUBBER COMPANY

  公开号：EP1391327A1

  公开（公告）日：2004-02-25

  The invention relates to a rubber composition and a pneumatic tire having a component comprising a rubber containing the reaction product of a flavone and a methylene donor.

  本发明涉及一种橡胶组合物和充气轮胎，其成分包括含有黄酮和亚甲基供体反应产物的橡胶。
• Rubber composition and tire with rubber containing flavone
  申请人：The Goodyear Tire & Rubber Company

  公开号：EP2730431A1

  公开（公告）日：2014-05-14

  A rubber composition comprising a diene based elastomer and an adhesion promoter derived from a flavone, a methylene donor and a methylene acceptor is disclosed. The rubber composition is essentially free of cobalt. Also, a pneumatic tire comprising such a rubber composition is disclosed.

  本发明公开了一种橡胶组合物，该组合物包含一种二烯基弹性体和一种由黄酮、亚甲基供体和亚甲基受体衍生的附着力促进剂。该橡胶组合物基本上不含钴。此外，还公开了一种包含这种橡胶组合物的充气轮胎。
• 感染症の治療を目的としたフラボン類、クマリン類および関連化合物の使用
  申请人：プレンダーガスト、パトリック、ティ.

  公开号：JP2003504327A

  公开（公告）日：2003-02-04

  \n (57)【要約】\n本発明は感染症、特にウイルス（例えばHCV、HIV、ピコルナウイルスあるいは呼吸器ウイルス）あるいは寄生虫（例えばトキソプラズマ症）感染症の治療におけるシルシリオール、3'4'-ジアセトキシ-5,6,7-トリメトキシフラボンあるいはナリンギンなどのフラビン類の使用を提供する。また前記方法で使用するための組成物群も提供する。\n

  \(57) [Abstract] The invention provides for the use of silsiliol, 3'4'-diacetoxy-5,6,7-trimethoxyflavone or柚皮苷等黄素的用途。还提供了一组用于上述方法的组合物。\n
• Concentrated fruit juice powder and method for preparing the same using a non-linear screw press juicer and convection current freeze drying apparatus
  申请人：VINAMIT USA LLC

  公开号：US10966439B2

  公开（公告）日：2021-04-06

  A concentrated fruit juice powder obtained by a convection current vacuum freeze drying process that includes: selecting and preparing fruits by predetermined quality guideline; extracting fruit juice by inserting the fruits into a screw press juicing apparatus having a precutter and a screw press whose body surface varies non-linearly, which is configured to achieve a maximum extraction efficiency; adding probiotics into the extracted fruit juice; freezing the fruit juice mixed with the probiotics in molds using an individual quick freezer (IQF) to obtain frozen fruit juice blocks; and vacuum freezing the frozen fruit juice blocks using a convection current vacuum freeze drying apparatus.

  一种通过对流真空冷冻干燥工艺获得的浓缩果汁粉，该工艺包括根据预定的质量准则选择和制备水果；将水果放入螺旋压榨榨汁机中榨取果汁，该榨汁机具有一个预切割器和一个螺旋压榨机，其机身表面非线性变化，可实现最高的榨汁效率；在榨取的果汁中加入益生菌；使用独立快速冷冻机（IQF）将与益生菌混合的果汁装入模具中冷冻，以获得冷冻果汁块；使用对流真空冷冻干燥设备对冷冻果汁块进行真空冷冻。