(2beta,3alpha)-2,3-二羟基乌苏-12-烯-28-酸 | 856012-03-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: (2beta,3alpha)-2,3-二羟基乌苏-12-烯-28-酸
• 英文名称: 2α,3β-dihydroxylurs-12-en-28-oic acid
• 英文别名: 2β,3α-dihydroxyurs-12-en-28-oic acid；corosolic acid；corsolic acid；(2beta,3alpha)-2,3-Dihydroxy-urs-12-en-28-oic acid；(1S,2R,4aS,6aR,6aS,6bR,8aR,10S,11S,12aR,14bS)-10,11-dihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid
• CAS: 856012-03-8
• 化学式: C₃₀H₄₈O₄
• 分子量: 472.709
• InChiKey: HFGSQOYIOKBQOW-FEZPFBHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  34
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  熊果酸 在 吡啶 、 4-二甲氨基吡啶 、 高氯酸 、 palladium 10% on activated carbon 、 水 、 氢气 、 碳酸氢钠 、 甲基磺酰氯 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2beta,3alpha)-2,3-二羟基乌苏-12-烯-28-酸
  参考文献：
  名称：

  方便的合成2β，3α-二羟基urs-12-en-28-油酸作为天然的硬脂酸的非对映异构体

  摘要：

  摘要2β，3α-Dihydroxyurs-12-en-28-oic acid（6）是天然存在的硬脂酸的非对映异构体，具有糖原磷酸化酶抑制活性。开发了半合成6的新策略。使用市售的熊果酸（1）作为起始原料，通过五个容易的反应以高立体选择性和47.3％的总产率合成了6。通过旋光，ESI-MS，1 H NMR和13 C NMR数据确认6的结构。

  DOI：

  10.1016/j.cclet.2013.04.022

文献信息

• Practical Synthesis of Bredemolic Acid, a Natural Inhibitor of Glycogen Phosphorylase
  作者：Keguang Cheng、Pu Zhang、Jun Liu、Juan Xie、Hongbin Sun

  DOI：10.1021/np8003886

  日期：2008.12.1

  Bredemolic acid (3) is a naturally occurring 2beta,3alpha-isomer of maslinic acid (1) that is an allosteric site inhibitor of glycogen phosphorylase (GP). A practical synthesis of 3 was accomplished (18% yield) in five steps starting from the readily available 2beta,3beta-diol 6a. In a similar fashion, 2beta,3alpha-dihydroxyurs-12-en-28-oic acid (4) was synthesized as a natural 2beta,3alpha-isomer

  布雷地摩尔酸（3）是山梨酸（1）的天然2beta，3alpha异构体，是糖原磷酸化酶（GP）的变构位点抑制剂。从容易获得的2beta，3beta-二醇6a开始，分5个步骤完成了3的实际合成（产率为18％）。以类似的方式，合成了2β，3α-二羟基urs-12-en-28-oic酸（4），作为天然的β2，3α-椰油酸（2）。化合物3和4对兔肌肉GPa表现出显着的抑制活性，IC（50）值分别为6.25和1.1μM。
• Tecoma plant based compositions for treating skin lesions
  申请人：National Guard Health Affairs

  公开号：US11090347B2

  公开（公告）日：2021-08-17

  A plant-based composition containing an alcohol extract of Tecoma species (e.g. Tecoma stans) and an exogenous carrier and/or excipient. Also provided is a composition including a mixture of three acids, namely corosolic acid, oleanolic acid, and ursolic acid, which can be found in the Tecoma species. Methods of treating skin lesions (e.g. warts, corns, calluses, and umbilical granulomas) and reducing symptoms associated with the skin lesions using such compositions are specified.

  一种以植物为基础的组合物，含有 Tecoma 物种（如 Tecoma stans）的醇提取物和外源载体和/或赋形剂。还提供了一种组合物，其中包括三种酸的混合物，即科罗索酸、齐墩果酸和熊果酸，这三种酸可在 Tecoma 树种中找到。具体说明了使用此类组合物治疗皮肤病变（如疣、鸡眼、胼胝和脐肉芽肿）和减轻与皮肤病变有关的症状的方法。
• Componds, Composition and Method for Controlling Biofolms and Bacterail Infections
  申请人：Eldridge Gary R.

  公开号：US20080145322A1

  公开（公告）日：2008-06-19

  The present invention provides compounds and compositions useful for controlling bacterial biofilms as well as for controlling and/or preventing bacterial infections. The compounds of the invention are pentacyclic acid triterpenes. Methods for controlling biofilms and for controlling and/or preventing bacterial infections are also disclosed.
• TECOMA PLANT BASED COMPOSITIONS FOR TREATING SKIN LESIONS
  申请人：National Guard Health Affairs

  公开号：US20200085894A1

  公开（公告）日：2020-03-19

  A plant-based composition containing an alcohol extract of Tecoma species (e.g. Tecoma stans ) and an exogenous carrier and/or excipient. Also provided is a composition including a mixture of three acids, namely corosolic acid, oleanolic acid, and ursolic acid, which can be found in the Tecoma species. Methods of treating skin lesions (e.g. warts, corns, calluses, and umbilical granulomas) and reducing symptoms associated with the skin lesions using such compositions are specified.
• COMPOSITION AND METHOD FOR TREATING SKIN DISORDERS
  申请人：National Guard Health Affairs

  公开号：US20210290714A1

  公开（公告）日：2021-09-23

  A plant-based composition containing an alcohol extract of Tecoma species (e.g. Tecoma stans ) and an exogenous carrier and/or excipient. Also provided is a composition including a mixture of three acids, namely corosolic acid, oleanolic acid, and ursolic acid, which can be found in the Tecoma species. Methods of treating skin lesions (e.g. warts, corns, calluses, and umbilical granulomas) and reducing symptoms associated with the skin lesions using such compositions are specified.