17990-42-0

• 常用中文名：3-氧代-12-烯-28-齐墩果酸
• 常用英文名：3-oxo-Olean-12-en-28-oic acid
• CAS号：17990-42-0
• 分子式：C₃₀H₄₆O₃
• 分子量：454.684
• 相关类别： 天然产物 萜类
• 发布时间：2018-12-25 11:57:11
• 更新时间：2024-01-02 16:24:19
• Oleanonic acid是一种三萜,可以抑制HIV-1对细胞的感染。起抑制HIV-1体外感染PBMC,自然感染PBMC和单核细胞/巨噬细胞的EC50分别为22.7mM,24.6mM和57.4mM。除此之外,它可以抑制鼠腹腔白细胞产生白三烯B4,IC50为17μm。

名称

• 中文名: 3-氧代-12-烯-28-齐墩果酸
• 英文名: (4aS,6aR,6aS,6bR,8aR,12aR,14bS)-2,2,6a,6b,9,9,12a-heptamethyl-10-oxo-3,4,5,6,6a,7,8,8a,11,12,13,14b-dodecahydro-1H-picene-4a-carboxylic acid
• 中文别名: 3-氧代-12-齐墩果烯-28-羧酸; 齐墩果酮酸
• 英文别名: oleanoic acid; 3-oxooleana-12-en-28-oic acid; Olean-12-en-28-oic acid,3-oxo; oleanonic acid; 3-oxo-oleanolic acid; 3-Oxoolean-12-en-28-oic acid; Olean-12-en-28-oic acid, 3-oxo-; 3-keto oleanolic acid; 3-oxo-olean-12-en-28-oic acid

物化性质

• 密度: 1.1±0.1 g/cm3
• 沸点: 551.7±50.0 °C at 760 mmHg
• 分子式: C₃₀H₄₆O₃
• 分子量: 454.684
• 闪点: 301.5±26.6 °C
• 精确质量: 454.344696
• PSA: 54.37000
• LogP: 8.48
• 蒸汽压: 0.0±3.2 mmHg at 25°C
• 折射率: 1.552
• 储存条件: -20°C

生物活性

• 描述: Oleanonic acid是一种三萜,可以抑制HIV-1对细胞的感染。起抑制HIV-1体外感染PBMC,自然感染PBMC和单核细胞/巨噬细胞的EC50分别为22.7mM,24.6mM和57.4mM。除此之外,它可以抑制鼠腹腔白细胞产生白三烯B4,IC50为17μm。
• 相关类别:
  信号通路 >> 抗感染 >> HIV
  天然产物 >> 萜类化合物和糖苷
  研究领域 >> 癌症
• 参考文献:

  [1]. Giner-Larza EM et al.Oleanonic acid, a 3-oxotriterpene from Pistacia, inhibits leukotriene synthesis and has anti-inflammatory activity.Eur J Pharmacol.Sep 28;428(1):137-43.doi:10.1016/S0014-2999(01)01290-0(2001)

  [2]. Fabio Mengoni.Anti-HIV Activity of Oleanolic Acid on Infected Human Mononuclear Cells.Planta Med 68(2): 111-114.DOI: 10.1055/s-2002-20256(2002)

合成路线

508-02-1 ~10% 17990-42-0

文献：Organic and Biomolecular Chemistry, , vol. 11, # 10 p. 1726 - 1738

25499-90-5 ~93% 17990-42-0

文献：Molecules, , vol. 18, # 3 p. 3615 - 3629

33608-08-1 ~% 17990-42-0

文献：Gazzetta Chimica Italiana, , vol. 104, p. 1269 - 1278

508-02-1 ~% 17990-42-0 113306-85-7 1721-60-4

文献：Pharmazie, , vol. 42, # 1 p. 67

508-02-1 1066-30-4 ~% 17990-42-0

文献：Journal of the Chemical Society, , vol. 103, p. 2050,2057 Justus Liebigs Annalen der Chemie, , vol. 517, p. 211,222 Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, , vol. 215, p. 199,202 Berichte der Deutschen Pharmazeutischen Gesellschaft, , vol. 15, p. 121 Chem. Zentralbl., , vol. 76, # II p. 533 Yakugaku Zasshi, , vol. 54, p. 67 Chem. Zentralbl., , vol. 105, # II p. 2536 Acta Phytochimica, , vol. 6, p. 211 Chem. Zentralbl., , vol. 103, # II p. 1790 Collection of Czechoslovak Chemical Communications, vol. 5, p. 165 Chem. Zentralbl., , vol. 104, # II p. 1035 Collection of Czechoslovak Chemical Communications, vol. 2, p. 414 Chem. Zentralbl., , vol. 101, # II p. 3292 Acta Phytochimica, , vol. 7, p. 180 Chem. Zentralbl., , vol. 105, # I p. 2766 Chemicke Listy, , vol. 25, p. 393,396 Chem. Zentralbl., , vol. 103, # I p. 1247

64-19-7 89503-61-7 ~% 17990-42-0

文献：Helvetica Chimica Acta, , vol. 21, p. 1371,1382 Acta Phytochimica, , vol. 7, p. 180 Chem. Zentralbl., , vol. 105, # I p. 2766

545-48-2 64-19-7 ~% 17990-42-0

文献：Helvetica Chimica Acta, , vol. 19, p. 247,249 Recueil des Travaux Chimiques des Pays-Bas, , vol. 51, p. 1200,1202