1-[(2-methylpropanoyl)phloroglucinyl]-β-D-glucopyranoside | 17004-75-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[(2-methylpropanoyl)phloroglucinyl]-β-D-glucopyranoside
• 英文别名: 2-(2-methylpropanoyl)phloroglucinol 1-O-β-D-glucopyranoside；2-isobutyrylphloroglucinol-1-O-β-glucopyranoside；2-(2-methylbutyryl)phloroglucinol-1-O-β-glucopyranside；1-O-((2-methylpropanoyl)phloroglucinol) β-D-glucopyranoside；1-[(2-methylpropanoyl)-5-hydroxyphloroglucinyl]-β-D-glucopyranoside；1-O-[2-(2'-methylpropanoyl)phloroglucinyl]-β-D-glucopyranoside；1-O-[(2-methylpropanoyl)phloroglucinyl]-β-D-glucopyranoside；1-O-β-D-(2-methylpropanoyl)-phloroglucinol-glucopyranoside；co-multifidolglucoside；2-isobutyrylphloroglucinol-1-O-β-D-glucopyranoside；1-Propanone, 1-[2-(beta-D-glucopyranosyloxy)-4,6-dihydroxyphenyl]-2-methyl-；1-[2,4-dihydroxy-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-2-methylpropan-1-one
• CAS: 17004-75-0
• 化学式: C₁₆H₂₂O₉
• 分子量: 358.345
• InChiKey: PSBKCHXAPMSDFN-LMXXTMHSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  157
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-[(2-methylpropanoyl)phloroglucinyl]-β-D-glucopyranoside 在 盐酸 作用下， 反应 0.5h， 以28 mg的产率得到phlorisobutyrophenone
  参考文献：
  名称：

  Anti-inflammatory Acylphloroglucinol Derivatives from Hops (Humulus lupulus)

  摘要：

  The polyphenol-enriched fraction of an ethanolic hops extract (Humulus lupulus) was separated to provide four acylphloroglucinol-glucopyranosides (1-4). 1-(2-Methylpropanoyl)phloroglucinol-glucopyranoside 1 has been isolated from hops before, whereas 1-(2-methylbutyryl)phloroglucinol-glucopyranoside 2, known as multifidol glucoside, and 1-(3-methylbutyryl)phloroglucinol-glucopyranoside 3 were found in hops for the first time. 5-(2-Methylpropanoyl)phloroglucinol-glueopyranoside 4 was identified as a new natural product. The compounds were tested for inhibition of COX-1 activity. The aglycon 5, obtained by acid hydrolysis of 1, was equally effective as phloroglucinol, with an IC50 of 3.8 mu M. The inhibitory potential of the glucosides was 1 > 2 > 3 and decreased with increasing length of the acyl side chain. Compound 4 was about 2.5-fold less active than 1 (IC50: 23.7 and 58.7 mu M, respectively).

  DOI：

  10.1021/np050164z