cleomiscosin A | 76948-72-6

• 物质功能分类: 天然产物 - 木脂素
• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 香豆素木脂素
• 英文名称: cleomiscosin A
• 英文别名: (2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-5-methoxy-2,3-dihydropyrano[3,2-h][1,4]benzodioxin-9-one；3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-5-methoxy-2,3-dihydropyrano[3,2-h][1,4]benzodioxin-9-one
• CAS: 76948-72-6
• 化学式: C₂₀H₁₈O₈
• 分子量: 386.358
• InChiKey: OCBGWPJNUZMLCA-UHFFFAOYSA-N

物化性质

• 熔点：
  245-247℃
• 沸点：
  632.7±55.0 °C(Predicted)
• 密度：
  1.403
• 溶解度：
  乙腈（微溶，加热）、甲醇（微溶）、吡啶（微溶）
• LogP：
  2.161 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  8

安全信息

• 储存条件：
  存储条件：2-8℃，干燥，密闭。

制备方法与用途

Cleomiscosin A 是一种香豆素类木质素，源自澳洲坚果的枝条。研究显示，Cleomiscosin A 能够激活小鼠腹腔巨噬细胞并促进其分泌 TNF-α。

反应信息

• 作为反应物：
  描述：

  cleomiscosin A 在 potassium permanganate 作用下， 以 乙醚 、 水 、 丙酮 为溶剂， 反应 48.5h， 生成 藜芦酸
  参考文献：
  名称：

  cleomiscosins的结构的香豆素黄花草种子1

  摘要：

  cleomiscosins A，B和C的结构中，从种子中分离三个新coumarino-lignoids黄花草Linné酒店，已被确定为1A，2A和1F无关，的光谱和化学证据的基础上。该化合物显示出肝脏保护特性。

  DOI：

  10.1016/s0040-4020(01)83488-8

文献信息

• NOVEL USE FOR SCOPOLIN AND DERIVATIVES THEREOF
  申请人：Park Tae Sun

  公开号：US20120322754A1

  公开（公告）日：2012-12-20

  The present invention relates to a novel use for the compound of Chemical formula 1 in order to produce drugs or foods for the prevention or treatment of obesity, fatty liver, diabetes, metabolic syndrome or the like, and to a composition for the prevention or treatment of obesity, fatty liver, diabetes, metabolic syndrome or the like which contains the compound of Chemical formula 1 as an active ingredient, and also to a method for the prevention or treatment of obesity, fatty liver, diabetes, metabolic syndrome or the like comprising the administration of the compound of Chemical formula 1 to a mammal in a therapeutically effective dose. According to the present invention, the compound of Chemical formula 1 has been confirmed to suppress the differentiation of adipocytes, to reduce body weight and the amount of visceral fat, to reduce concentrations of cholesterol, triglycerides, free fatty acids and glucose which are associated with fatty liver and diabetes and the like and to reduce the fatty component in liver tissue, to suppress gene expression associated with obesity in visceral fatty tissue, and to increase the amount of expression of UCP1 and UCP3 which are UCP (uncoupling protein) genes involved in thermogenesis. The compound of Chemical formula 1 can be used to advantage in order to prevent or treat obesity, fatty liver, diabetes, metabolic syndrome and the like since, unlike the obesity treating agents based on synthetic drugs currently in use, it is based on a natural substance and hence entails a very low risk of adverse effects and, additionally, it exhibits its pharmacological effects by regulating the expression of genes associated with obesity rather than exhibiting pharmacological effects by acting on enzymes or the nervous system.
• US8828954B2
  申请人：——

  公开号：US8828954B2

  公开（公告）日：2014-09-09