machaerinic acid | 25763-71-7

• 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: machaerinic acid
• 英文别名: 21β-hydroxy-oleanolic acid；3β,21β-dihydroxy-olean-12-en-28-oic acid；Machaerinsaeure；3β,21β-Dihydroxy-olean-12-en-28-saeure；Olean-12-en-28-oic acid, 3,21-dihydroxy-, (3beta,21beta)-；(3S,4aR,6aR,6aS,6bR,8aR,10S,12aR,14bS)-3,10-dihydroxy-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: 25763-71-7
• 化学式: C₃₀H₄₈O₄
• 分子量: 472.709
• InChiKey: AMHZZVCMERHTFM-FMMUPTMQSA-N

物化性质

• 沸点：
  585.0±50.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)
• 熔点：
  268-270 °C

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 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

• 作为反应物：
  描述：

  重氮甲烷 、 machaerinic acid 在 乙醚 作用下， 生成 methyl machaerinate
  参考文献：
  名称：

  Reaktionsmechanismen. Erste Folge von Dr. rer. nat.Volker Franzen, Privatdozent an der Universität Heidelberg. Dr. Alfred Hüthig-Verlag GMBH. Heidelberg. Ganzleinen mit Schutzumschlag DM 18,—

  摘要：

  DOI：

  10.1002/ardp.19592920111
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 硫酸 作用下， 生成 machaerinic acid
  参考文献：
  名称：

  Farooq et al., Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1958, vol. 246, p. 3261

  摘要：

  DOI：

文献信息

• Biotransformation of oleanolic acid by<i>Alternaria longipes</i>and<i>Penicillium adametzi</i>
  作者：Dai-Lin Liu、Ying Liu、Feng Qiu、Ying Gao、Jing-Ze Zhang

  DOI：10.1080/10286020.2010.547028

  日期：2011.2

  Microbial transformation of oleanolic acid (1) was carried out. Six transformed products (2-7) from 1 by Alternaria longipes and three transformed products (8-10) from 1 by Penicillium adametzi were isolated. Their structures were elucidated as 2,3,19-trihydroxy-ursolic acid-28-O--d-glucopyranoside (2), 2,3,19-trihydroxy-ursolic acid-28-O--d-glucopyranoside (3), oleanolic acid 28-O--d-glucopyranosyl ester (4), oleanolic acid-3-O--d-glucopyranoside (5), 3-O-(-d-glucopyranosyl)-oleanolic acid-28-O--d-glucopyranoside (6), 2,3,19a-trihydroxy-oleanolic acid-28-O--d-glucopyranoside (7), 21-hydroxyl oleanolic acid-28-O--d-glucopyranoside (8), 21-hydroxyl oleanolic acid (9), and 7,21-dihydroxyl oleanolic acid (10) based on the extensive NMR studies. Among them, 10 was a new compound and compounds 5 and 8-10 had stronger cytotoxic activities against Hela cell lines than the substrate. At the same time, it was reported for the first time in this paper that the skeletons of compounds 2 and 3 were changed from oleanane to uranane and seven glycosidation products were obtained by biotransformation.
• Reaktionsmechanismen. Erste Folge von Dr. rer. nat.Volker Franzen, Privatdozent an der Universität Heidelberg. Dr. Alfred Hüthig-Verlag GMBH. Heidelberg. Ganzleinen mit Schutzumschlag DM 18,—
  作者：Awe

  DOI：10.1002/ardp.19592920111

  日期：——
• Farooq et al., Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1958, vol. 246, p. 3261
  作者：Farooq et al.

  DOI：——

  日期：——
• Anjaneyulu,A.S.R. et al., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1977, vol. 15B, p. 1 - 6
  作者：Anjaneyulu,A.S.R. et al.

  DOI：——

  日期：——