4-hydroxyphenyl-(6'-O-benzoyl)-O-β-D-glucopyranoside | 71202-99-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-hydroxyphenyl-(6'-O-benzoyl)-O-β-D-glucopyranoside
• 英文别名: 6'-O-benzoyl-arbutin；flacourtoside A；eximine；eximin；6-O-benzoyl arbutin；[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(4-hydroxyphenoxy)oxan-2-yl]methyl benzoate
• CAS: 71202-99-8
• 化学式: C₁₉H₂₀O₈
• 分子量: 376.363
• InChiKey: ZNWJKOJJZQDPSW-OGJJZOIMSA-N

物化性质

• 沸点：
  616.9±55.0 °C(Predicted)
• 密度：
  1.449±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  126
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  苯甲酸乙烯酯 、 熊果苷 在 immobilized lipase from Penicillium expansum 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 以86%的产率得到4-hydroxyphenyl-(6'-O-benzoyl)-O-β-D-glucopyranoside
  参考文献：
  名称：

  Highly regioselective synthesis of novel aromatic esters of arbutin catalyzed by immobilized lipase from Penicillium expansum

  摘要：

  Ester derivatives of phenolic glycosides have attracted more attention in food, cosmetic and pharmaceutical industries, due to their potent biological activities. In the present study, a group of novel aromatic esters of arbutin were successfully synthesized by using immobilized lipase from Penicillium expansum with excellent 6'-regioselectivities (>99%) and moderate to excellent isolated yields (68-93%), except for 6'-O-vanilloyl-arbutin and 6'-O-(p-hydroxycinnamoyl)-arbutin with 28% and 34% yields, respectively. Among all the acyl donors tested, the lipase was most active towards vinyl 3-phenylpropionate, while remarkable decrease in the activity was recorded when the phenyl of acyl donors carried the hydroxyl and/or methoxyl. (C) 2010 Published by Elsevier B.V.

  DOI：

  10.1016/j.molcatb.2010.07.003

文献信息

• VEGETATIVE STIGMATA THERAPEUTIC AGENT
  申请人：SNOWDEN CO., LTD.

  公开号：EP0012774A1

  公开（公告）日：1980-07-09

  A vegetative stigmata therapeutic agent contains as an effective ingredient a human umbilical cord extract which is obtained by the steps of subjecting a human umbilical cord to a physically-destructive treatment such as crushing treatment, ultrasonic treament, repetitive freezing and melting treatment and the like, or to a proteolytic decomposing treatment by the use of acids or enzymes, or to both treatments and then extracting the umbilical cord extract from the destroyed and/or decomposed umbilical cord by a solvent.

  一种植物性瘢痕治疗剂含有人类脐带提取物作为有效成分，该提取物是通过以下步骤获得的：将人类脐带进行物理破坏处理，如粉碎处理、超声波处理、重复冷冻和熔化处理等，或使用酸或酶进行蛋白分解处理，或同时进行这两种处理，然后用溶剂从破坏和/或分解的脐带中提取脐带提取物。
• Polyphenolic Glycosides from African Proteaceae
  作者：L. Verotta、F. Orsini、F. Pelizzoni、G. Torri、C. B. Rogers

  DOI：10.1021/np9902237

  日期：1999.11.1

  The phytochemical investigation of members of the genus Protea afforded a series of polyphenolic compounds (1-5) that were identified by 1D and 2D NMR experiments. Of these, 2-5 are new compounds. Chemical syntheses of 1-3 were performed in order to confirm the structures and to prepare additional material for biological evaluation.
• Highly regioselective synthesis of novel aromatic esters of arbutin catalyzed by immobilized lipase from Penicillium expansum
  作者：Rong-Ling Yang、Ning Li、Min Ye、Min-Hua Zong

  DOI：10.1016/j.molcatb.2010.07.003

  日期：2010.11

  Ester derivatives of phenolic glycosides have attracted more attention in food, cosmetic and pharmaceutical industries, due to their potent biological activities. In the present study, a group of novel aromatic esters of arbutin were successfully synthesized by using immobilized lipase from Penicillium expansum with excellent 6'-regioselectivities (>99%) and moderate to excellent isolated yields (68-93%), except for 6'-O-vanilloyl-arbutin and 6'-O-(p-hydroxycinnamoyl)-arbutin with 28% and 34% yields, respectively. Among all the acyl donors tested, the lipase was most active towards vinyl 3-phenylpropionate, while remarkable decrease in the activity was recorded when the phenyl of acyl donors carried the hydroxyl and/or methoxyl. (C) 2010 Published by Elsevier B.V.