(3β)-3-((3-carboxypropanoyl)oxy)-olean-12-en-28-oic acid | 4847-30-7

• 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
• 英文名称: (3β)-3-((3-carboxypropanoyl)oxy)-olean-12-en-28-oic acid
• 英文别名: (4As,6as,6br,10s,12ar)-10-(4-hydroxy-4-oxo-butanoyl)oxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid；(4aS,6aS,6bR,10S,12aR)-10-(3-carboxypropanoyloxy)-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
• CAS: 4847-30-7
• 化学式: C₃₄H₅₂O₆
• 分子量: 556.783
• InChiKey: ZLVQQEYNCCJVLQ-FNOYKFJWSA-N

物化性质

• 熔点：
  261-263 °C
• 沸点：
  653.9±55.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  40
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  丁二酸酐 、 oleanolic acid 在 4-二甲氨基吡啶 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 以92%的产率得到(3β)-3-((3-carboxypropanoyl)oxy)-olean-12-en-28-oic acid
  参考文献：
  名称：

  Semi-synthesis of new antimicrobial esters from the natural oleanolic and maslinic acids

  摘要：

  In this article, we report an effective procedure for the selective isolation of oleanolic acid 1 and maslinic acid 2 (3.4 and 8.5mg/g DW, respectively) from pomace olive (Olea europaea L.) using an ultrasonic bath, and the synthesis of a series of new triterpenic acid esters. The compounds were characterized by their spectral data and were evaluated for their antimicrobial activity. Among the compounds tested, those having sulfur and chlorine atoms were found to be antibacterial. They showed activity against two Gram-positive bacteria Staphylococcus aureus and Enterococcus faecalis and two Gram-negative bacteria Escherichia coli and Pseudomonas aeruginosa (MICs within a range of 5-25μg/mL). The fungus Penicillium italicum was found to be the most sensitive to both sulfur derivatives: (3β)-3-((thiophene-2-carbonyl)oxy)-olean-12-en-28-oic acid (1a) (IZ=22mm) and (2α,3β-2,3-bis((thiophene-2-carbonyl)oxy)olean-12-en-28-oic acid (2a) (IZ=24mm).

  DOI：

  10.1016/j.foodchem.2015.03.018

文献信息

• Semi-synthesis of new antimicrobial esters from the natural oleanolic and maslinic acids
  作者：Karim Chouaïb、Fayçal Hichri、Asma Nguir、Majda Daami-Remadi、Nicolas Elie、David Touboul、Hichem Ben Jannet、M’hamed Ali Hamza

  DOI：10.1016/j.foodchem.2015.03.018

  日期：2015.9

  In this article, we report an effective procedure for the selective isolation of oleanolic acid 1 and maslinic acid 2 (3.4 and 8.5mg/g DW, respectively) from pomace olive (Olea europaea L.) using an ultrasonic bath, and the synthesis of a series of new triterpenic acid esters. The compounds were characterized by their spectral data and were evaluated for their antimicrobial activity. Among the compounds tested, those having sulfur and chlorine atoms were found to be antibacterial. They showed activity against two Gram-positive bacteria Staphylococcus aureus and Enterococcus faecalis and two Gram-negative bacteria Escherichia coli and Pseudomonas aeruginosa (MICs within a range of 5-25μg/mL). The fungus Penicillium italicum was found to be the most sensitive to both sulfur derivatives: (3β)-3-((thiophene-2-carbonyl)oxy)-olean-12-en-28-oic acid (1a) (IZ=22mm) and (2α,3β-2,3-bis((thiophene-2-carbonyl)oxy)olean-12-en-28-oic acid (2a) (IZ=24mm).