4,6-O-(S)-hexahydroxydiphenoyl-D-gluconic acid | 103488-44-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: 4,6-O-(S)-hexahydroxydiphenoyl-D-gluconic acid
• 英文别名: 4,6-(S)-hexahydroxydiphenoylgluconic acid；ponigluconin；(2R,3R)-3-[(10R,11R)-3,4,5,11,17,18,19-heptahydroxy-8,14-dioxo-9,13-dioxatricyclo[13.4.0.02,7]nonadeca-1(19),2,4,6,15,17-hexaen-10-yl]-2,3-dihydroxypropanoic acid
• CAS: 103488-44-4
• 化学式: C₂₀H₁₈O₁₅
• 分子量: 498.354
• InChiKey: KRIFOBHDCNXTNN-WLWOSTOTSA-N

物化性质

• 沸点：
  1223.9±65.0 °C(Predicted)
• 密度：
  1.920±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  35
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  272
• 氢给体数：
  10
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  lagerstannic C 以 水 为溶剂， 反应 3.0h， 以2 mg的产率得到没食子酸
  参考文献：
  名称：

  Tannins and Related Compounds. CXVII. Isolation and Characterization of Three New Ellagitannins, Lagerstannins A,B and C, Having a Gluconic Acid Core, from Lagerstroemia speciosa (L.) PERS.

  摘要：

  从紫薇（Lagerstroemia speciosa (L.) PERS.）的果实和叶子中分离出了Lagerstannins A (6)、B (11)和C (8)，这些埃拉吉单宁以葡萄糖醛酸为核心。根据化学和光谱证据，它们的结构分别确定为2, 3;4, 6-双-O-(S)-六羟基二苯酰-D-葡萄糖醛酸 (6)、2, 3, 5-O-(S, R)-黄酮甘露糖苷-4, 6-O-(S)-六羟基二苯酰-D-葡萄糖醛酸 (11)，以及5-O-没食子酸-4, 6-O-(S)-六羟基二苯酰-D-葡萄糖醛酸 (8)。此外，之前从石榴树皮（Punica granatum L.）中分离出的埃拉吉单宁punigluconin，其结构经过光谱重新审查后修订为2, 5-双-O-没食子酸-4, 6-O-(S)-六羟基二苯酰-D-葡萄糖醛酸 (10)。

  DOI：

  10.1248/cpb.40.2975

文献信息

• Tannins and related compounds. XLI. Isolation and characterization of novel ellagitannins, punicacorteins A, B, C and D, and punigluconin from the bark of Punica granatum L.
  作者：TAKASHI TANAKA、GEN-ICHIRO NONAKA、ITSUO NISHIOKA

  DOI：10.1248/cpb.34.656

  日期：——

  A chemical examination of the bark of Punica granatum L. (Punicaceae) has led to the isolation of five new ellagitannins, punicacorteins A, B, C and D, and punigluconin, together with the known ellagitannins, casuariin (6) and casuarinin (7). Based on chemical and spectroscopic evidence, the structures of punicacorteins A, B, C and D were established as novel C-glycosideic ellagitannins, the former two possessing a unique tetraphenyl (gallagyl) ester group (1 and 2), and the latter two containing a galloyl group in place of the gallagyl group (3 and 4), while punigluconin was characterized as 2, 3-di-O-galloyl-4, 6-(S)-hexahydroxydiphenoylgluconic acid (5).

  对石榴（Punica granatum L.）树皮的化学分析导致分离出五种新的椰子单宁，分别是punicacorteins A、B、C和D，以及punigluconin，同时还发现了已知的椰子单宁，casuariin（6）和casuarinin（7）。基于化学和光谱证据，确定了punicacorteins A、B、C和D的结构为新型C-糖苷类型的椰子单宁，其中前两种具有独特的四苯基（gallagyl）酯基团（1和2），而后两种则在其位置替换为没食子酰基（3和4）。同时，punigluconin被表征为2, 3-二-O-没食子酰-4, 6-(S)-六羟基二苯酰葡萄糖酸（5）。
• Tannins and Related Compounds. CXVII. Isolation and Characterization of Three New Ellagitannins, Lagerstannins A,B and C, Having a Gluconic Acid Core, from Lagerstroemia speciosa (L.) PERS.
  作者：Takashi TANAKA、Hui-Hong TONG、Ya-Ming XU、Kanji ISHIMARU、Gen-ichiro NONAKA、Itsuo NISHIOKA

  DOI：10.1248/cpb.40.2975

  日期：——

  Lagerstannins A (6), B (11) and C (8), ellagitannins having a gluconic acid core, have been isolated from the fruits and leaves of Lagerstroemia speciosa (L.) PERS. (=L. flos-reginae RETZ.)(Lythraceae). On the basis of chemical and spectroscopic evidence, their structures were established as 2, 3;4, 6-bis-O-(S)-hexahydroxydiphenoyl-D-gluconic acid (6), 2, 3, 5-O-(S, R)-flavogallonyl-4, 6-O-(S)-hexahydroxydiphenoyl-D-gluconic acid (11), and 5-O-galloyl-4, 6-O-(S)-hexahydroxydiphenoyl-D-gluconic acid (8), respectively. Furthermore, the structure of an ellagitannin, punigluconin, previously isolated from the bark of Punica granatum L., was revised as 2, 5-di-O-galloyl-4, 6-O-(S)-hexahydroxy-diphenoyl-D-gluconic acid (10), based on spectral re-examination.

  从紫薇（Lagerstroemia speciosa (L.) PERS.）的果实和叶子中分离出了Lagerstannins A (6)、B (11)和C (8)，这些埃拉吉单宁以葡萄糖醛酸为核心。根据化学和光谱证据，它们的结构分别确定为2, 3;4, 6-双-O-(S)-六羟基二苯酰-D-葡萄糖醛酸 (6)、2, 3, 5-O-(S, R)-黄酮甘露糖苷-4, 6-O-(S)-六羟基二苯酰-D-葡萄糖醛酸 (11)，以及5-O-没食子酸-4, 6-O-(S)-六羟基二苯酰-D-葡萄糖醛酸 (8)。此外，之前从石榴树皮（Punica granatum L.）中分离出的埃拉吉单宁punigluconin，其结构经过光谱重新审查后修订为2, 5-双-O-没食子酸-4, 6-O-(S)-六羟基二苯酰-D-葡萄糖醛酸 (10)。