furosin | 148077-26-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: furosin
• 英文别名: [(1S,8R,9R,18R,19S,21R,22S)-7,7,8,12,13,22-hexahydroxy-21-(hydroxymethyl)-3,6,16-trioxo-2,17,20,23-tetraoxapentacyclo[16.3.1.18,11.04,9.010,15]tricosa-4,10,12,14-tetraen-19-yl] 3,4,5-trihydroxybenzoate
• CAS: 148077-26-3
• 化学式: C₂₇H₂₂O₁₉
• 分子量: 650.46
• InChiKey: CXTMLIMZRPKULL-DDKHUQCISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.6
• 重原子数：
  46
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  317
• 氢给体数：
  10
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  furosin 在 5percent Pd/C 氢气 作用下， 以 乙醇 为溶剂， 反应 1.5h， 以13.6 mg的产率得到phyllanemblinin B
  参考文献：
  名称：

  Phyllanemblinins A−F, New Ellagitannins from Phyllanthus emblica

  摘要：

  Six new ellagitannins, phyllanemblinins A-F (1-6), were isolated from Phyllanthus emblica, along with 30 known tannins and related compounds. Their structures were determined by spectral and chemical methods. Phyllanemblinins A (1) and B (2) were confirmed to be ellagitannins having a tetrahydroxybenzofuran dicarboxyl group and a hexahydroxydiphenoyl group, respectively, by chemical synthesis from furosin (8). Phyllanemblinin C (3) has a new acyl group at the glucose 2,4-positions and is structurally related to chebulagic acid. Phyllanemblinins D (4), E (5), and F 6) were found to be positional isomers of neochebuloyl 1(beta)-O-galloylglucose.

  DOI：

  10.1021/np010370g

文献信息

• Tannins and Related Compounds. CXVIII. Structures, Preparation, High-Performance Liquid Chromatography and Some Reactions of Dehydroellagitannin-Acetone Condensates.
  作者：Takashi TANAKA、Hiroshi FUJISAKI、Gen-ichiro NONAKA、Itsuo NISHIOKA

  DOI：10.1248/cpb.40.2937

  日期：——

  The dehydroellagitannins having a dehydrohexahydroxydiphenoyl ester group in the molecule were found to undergo highly regio- and stereospecific condensation with acetone in the presence of ammonium ion under almost neutral conditions. This reaction was successfully applied to high-performance liquid chromatographic analysis to detect the dehydroellagitannins in the plant extract. Furthermore, the reactions of the acetone condensates with L-cysteine methyl ester were examined, and appear to be applicable to structural studies of dehydroellagitannins.

  含有脱氢六羟基二苯酰酯基的脱氢椴树单宁在几乎中性的条件下，与氨离子存在时与丙酮发生高度区域选择性和立体选择性的缩合反应。该反应成功应用于高效液相色谱分析，以检测植物提取物中的脱氢椴树单宁。此外，还研究了丙酮缩合物与L-半胱氨酸甲酯的反应，似乎适用于脱氢椴树单宁的结构研究。
• Amariinic acid and related ellagitannins from Phyllanthus amarus
  作者：L. Yeap Foo

  DOI：10.1016/0031-9422(94)00836-i

  日期：1995.5
• Phyllanemblinins A−F, New Ellagitannins from <i>Phyllanthus </i><i>e</i><i>mblica</i>
  作者：Ying-Jun Zhang、Tomomi Abe、Takashi Tanaka、Chong-Ren Yang、Isao Kouno

  DOI：10.1021/np010370g

  日期：2001.12.1

  Six new ellagitannins, phyllanemblinins A-F (1-6), were isolated from Phyllanthus emblica, along with 30 known tannins and related compounds. Their structures were determined by spectral and chemical methods. Phyllanemblinins A (1) and B (2) were confirmed to be ellagitannins having a tetrahydroxybenzofuran dicarboxyl group and a hexahydroxydiphenoyl group, respectively, by chemical synthesis from furosin (8). Phyllanemblinin C (3) has a new acyl group at the glucose 2,4-positions and is structurally related to chebulagic acid. Phyllanemblinins D (4), E (5), and F 6) were found to be positional isomers of neochebuloyl 1(beta)-O-galloylglucose.