cincholic acid | 5948-32-3

• 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: cincholic acid
• 英文别名: Cincholsaeure；(4aS,6aR,6aR,6bR,8aR,10S,12aR,14bS)-10-hydroxy-2,2,6b,9,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a,6a-dicarboxylic acid
• CAS: 5948-32-3
• 化学式: C₃₀H₄₆O₅
• 分子量: 486.692
• InChiKey: NGAUATZUWHZXEK-NLCQKWKWSA-N

物化性质

• 熔点：
  246-248 °C
• 沸点：
  618.3±55.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  35
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  94.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  cincholic acid 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 Erythrodiol-27-saeuremethylester
  参考文献：
  名称：

  Tschesche,R. et al., Justus Liebigs Annalen der Chemie, 1963, vol. 667, p. 151 - 163

  摘要：

  DOI：
• 作为产物：
  描述：

  尚含鸡纳甙 在 Nocardia sp. NRRL 5646 作用下， 以 乙醇 为溶剂， 反应 120.0h， 以40%的产率得到鸡纳酸
  参考文献：
  名称：

  Biotransformation of Quinovic Acid Glycosides by Microbes:  Direct Conversion of the Ursane to the Oleanane Triterpene Skeleton by Nocardia sp. NRRL 5646

  摘要：

  Quinovic acid glycosides were microbially deglycosylated by a Nocardia sp. to their aglycon quinovic acid and its biogenetic counterpart, cincholic acid (3), via an unprecedented carbon skeleton rearrangement involving a methyl group migration. The structures of the metabolites were established by ESI-LC/MS and 2D-NMR techniques.

  DOI：

  10.1021/ol048787b

文献信息

• Triterpenoid glycosides from Ladenbergia hexandra Klotzsch
  作者：Megumi Furukawa、Satoshi Kamo、Mitsuko Makino、Masahiro Kurita、Keiichi Tabata、Keiichi Matsuzaki、Takashi Suzuki、Taketo Uchiyama

  DOI：10.1016/j.phytochem.2017.01.014

  日期：2017.4

  From the bark of Ladenbergia hexandra Klotzsch, ten triterpenoid glycosides were isolated along with five known compounds, and their structures were determined based on extensive NMR and mass spectroscopic, GC and HPLC analyses. Some triterpenoid glycosides contained 6-deoxy-D-allose or D-allose as a sugar moiety. The absolute stereochemical assignment of the sugars was determined by comparison with

  从 Ladenbergia hexandra Klotzsch 的树皮中分离出 10 种三萜糖苷和 5 种已知化合物，并基于广泛的 NMR 和质谱、GC 和 HPLC 分析确定了它们的结构。一些三萜糖苷含有 6-脱氧-D-阿洛糖或 D-阿洛糖作为糖部分。糖的绝对立体化学归属是通过与合成样品的比较以及 GC 和 HPLC 分析来确定的。
• Nagai,M. et al., Chemical and pharmaceutical bulletin, 1969, vol. 17, p. 1438 - 1443
  作者：Nagai,M. et al.

  DOI：——

  日期：——
• ARRIAGA, F. JAVIER;, RUMBERO ANGEL;VAZQUEZ, PURIFICACION, PHYTOCHEMISTRY, 29,(1990) N, C. 209-213
  作者：ARRIAGA, F. JAVIER、, RUMBERO ANGEL、VAZQUEZ, PURIFICACION

  DOI：——

  日期：——
• RUMBERO-SANCHEZ, A.;VAZQUEZ, P., PHYTOCHEMICTRY, 30,(1991) N, C. 623-626
  作者：RUMBERO-SANCHEZ, A.、VAZQUEZ, P.

  DOI：——

  日期：——
• Biotransformation of Quinovic Acid Glycosides by Microbes:  Direct Conversion of the Ursane to the Oleanane Triterpene Skeleton by <i>Nocardia </i>sp. NRRL 5646
  作者：Zhi-Hong Cheng、Bo-Yang Yu、Geoffrey A. Cordell、Sheng-Xiang Qiu

  DOI：10.1021/ol048787b

  日期：2004.9.1

  Quinovic acid glycosides were microbially deglycosylated by a Nocardia sp. to their aglycon quinovic acid and its biogenetic counterpart, cincholic acid (3), via an unprecedented carbon skeleton rearrangement involving a methyl group migration. The structures of the metabolites were established by ESI-LC/MS and 2D-NMR techniques.