dimethyl penta-O-methyl-m-dehydrodigallate | 82220-66-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: dimethyl penta-O-methyl-m-dehydrodigallate
• 英文别名: dimethyl penta-O-methyl-dehydrodigallate；dimethyl penta-O-methyldehydrodigallate；Dimethyl pentamethoxydehydrodigallate；3,4,5,4',5'-pentamethoxy-2,3'-oxy-di-benzoic acid dimethyl ester；3,4,5,4',5'-Pentamethoxy-2,3'-oxy-di-benzoesaeure-dimethylester；Pentamethyl-dehydrodigallussaeure-dimethylester；Methyl 2-(2,3-dimethoxy-5-methoxycarbonylphenoxy)-3,4,5-trimethoxybenzoate
• CAS: 82220-66-4
• 化学式: C₂₁H₂₄O₁₀
• 分子量: 436.416
• InChiKey: ZPESEMZCGKYTGM-UHFFFAOYSA-N

物化性质

• 熔点：
  118 °C
• 沸点：
  543.0±50.0 °C(Predicted)
• 密度：
  1.226±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  dimethyl penta-O-methyl-m-dehydrodigallate 在 硫酸 作用下， 生成 3,4,5,6,7-pentamethoxy-9-oxo-xanthene-1-carboxylic acid methyl ester
  参考文献：
  名称：

  Drop model for formation of the polyacenequinone domain structure

  摘要：

  DOI：

  10.1134/1.171753
• 作为产物：
  描述：

  生成 dimethyl penta-O-methyl-m-dehydrodigallate
  参考文献：
  名称：

  ISHIMATSU, MAKOTO;TANAKA, TAKASHI;NONAKA, GEN-ICHIRO;NISHIOKA, ITSUO;NISH+, CHEM. AND PHARM. BULL., 37,(1989) N, C. 1735-1743

  摘要：

  DOI：

文献信息

• Tannins and related compounds. CV. Monomeric and dimeric hydrolyzable tannins having a dehydrohexahydroxydiphenoyl group, supinanin, euphorscopin, euphorhelin and jolkianin, from euphorbia species.
  作者：Seung-Ho LEE、Takashi TANAKA、Gen-ichiro NONAKA、Itsuo NISHIOKA

  DOI：10.1248/cpb.39.630

  日期：——

  A chemical investigation of tannins in three Euphorbia species (E. helioscopia, E. jolkini and E. supina) has led to the isolation and characterization of four new hydrolyzable tannins, named supinanin (15), euphorscopin (16), euphorhelin (17) and jolkianin (18), together with fourteen known compounds (1-14). On the basis of chemical and spectroscopic evidence, the structures of supinanin and euphorscopin were established as 1, 3, 6-tri-O-galloyl-2, 4-(S)-dehydrohexahydroxydiphenoyl-β-D-glucose (15) and 1, 3-(S)-dehydrohexahydroxydiphenoyl-2-O-galloyl-4, 6-(S)-hexahydroxydiphenoyl-β-D-glucose (16), respectively. Euphorhelin and jolkianin were characterized as dimeric hydrolyzable tannins (17 and 18, respectively), in which two glucopyranose units are linked via valoneoyl and dehydrodigalloyl groups, respectively, and each molecule possesses a dehydrohexahydroxydiphenoyl group.

  对三种大戟属植物（E. helioscopia, E. jolkini 和 E. supina）中的单宁进行的化学研究导致了四种新可水解单宁的分离和表征，分别命名为supinanin (15)、euphorscopin (16)、euphorhelin (17) 和 jolkianin (18)，以及十四种已知化合物 (1-14)。根据化学和光谱学证据，supinanin 和 euphorscopin 的结构被确立为1, 3, 6-三-O-鞣酸基-2, 4-(S)-脱氢六羟基二苯酰-β-D-葡萄糖 (15) 和1, 3-(S)-脱氢六羟基二苯酰-2-O-鞣酸基-4, 6-(S)-六羟基二苯酰-β-D-葡萄糖 (16)。euphorhelin 和 jolkianin 被特征化为二聚体可水解单宁 (17 和 18)，其中两个葡萄糖单位分别通过瓦碧酸和脱氢二鞣酸基连接，并且每个分子都具有一个脱氢六羟基二苯酰基。
• Tannins and related compounds. XCVI. Structures of macaranins and macarinins, new hydrolyzable tannins possessing macaranoyl and tergalloyl ester groups, from the leaves of Macaranga sinensis (Baill.) Muell.-Arg.
  作者：Jer-Huei LIN、Makoto ISHIMATSU、Takashi TANAKA、Gen-ichiro NONAKA、Itsuo NISHIOKA

  DOI：10.1248/cpb.38.1844

  日期：——

  Together with eleven known compounds (1-11), seven new tannins, 3-desgalloylterchebin (12), macaranins A, B and C, and macarinins A, B and C, have been isolated from the leaves of Macaranga sinensis (BAILL.) MUELL.-ARG. (Euphorbiaceae). Macaranins A (14), B (13) and C (17) have been determined on the basis of chemical and spectroscopic evidence to be hydrolyzable tannins possessing a novel acyl group (macaranoly group) at the 3, 6-positions of the 1C4 (or skew boat) β-D-glucopyranose ring, while macarinins A (18), B (15) and (16) were characterized as those having a tergalloyl group at the same positions.

  与已知的十一种化合物（1-11）一起，从Macaranga sinensis (BAILL.) MUELL.-ARG.（大戟科）的叶子中分离出了七种新单宁，分别为3-desgalloylterchebin（12）、macaranins A、B和C。根据化学和光谱证据，确定macaranins A（14）、B（13）和C（17）为可水解的单宁，具有在1C4（或倾斜船型）β-D-葡萄糖环的3、6位上的新型酰基（macaranoly基团），而macarinins A（18）、B（15）和C（16）被鉴定为在相同位置具有tergalloyl基团的化合物。
• Tannins of rosaceous medicinal plants. I. Structures of potentillin, agrimonic acids A and B, and agrimoniin, a dimeric ellagitannin.
  作者：TAKUO OKUDA、TAKASHI YOSHIDA、MASAAKI KUWAHARA、M.USMAN MEMON、TETSURO SHINGU

  DOI：10.1248/cpb.32.2165

  日期：——

  Four new ellagitannins, potentillin (1), agrimoniin (2), and agrimonic acids A (3) and B (4), have been isolated from the roots of Agrimonia japonica (MIQ.) KOIDZ., and their structures, with an α-glucosidic linkage, were elucidated on the basis of spectral and chemical evidence. Potentillin (1) and agrimoniin (2) have also been isolated from Potentilla kleiniana WIGHT et ARNOTT.

  从日本茯苓（Agrimonia japonica (MIQ.) KOIDZ.）的根部分离出了四种新的鞣酸酯，分别是强鞣酸（potentillin, 1）、苦荨麻素（agrimoniin, 2）以及苦荨麻酸A（agrimonic acid A, 3）和B（agrimonic acid B, 4），它们的结构具有α-葡萄糖苷键，基于光谱和化学证据进行了阐明。强鞣酸（potentillin, 1）和苦荨麻素（agrimoniin, 2）也从小草莓（Potentilla kleiniana WIGHT et ARNOTT）中分离出来。
• Euscaphinin, a New Ellagitannin Dimer from Euscaphis japonica (THUNB.) KANITZ
  作者：Hajime Maeda、Yosuke Matsuo、Takashi Tanaka、Isao Kouno

  DOI：10.1248/cpb.57.421

  日期：——

  A new ellagitannin dimer named euscaphinin was isolated from the leaves of Euscaphis japonica (THUNB.) KANITZ. The structure of this dimer was determined on the basis of spectroscopic and chemical evidence. The resulting structure indicated that it was produced by intermolecular C-O oxidative coupling between the galloyl groups of molecules of 1(beta)-O-galloyl pedunculagin, the major ellagitannin of

  从Euscaphis japonica（THUNB。）KANITZ的叶子中分离出一种新的鞣花单宁二聚体，名为euscaphinin。该二聚体的结构是根据光谱和化学证据确定的。所得结构表明，它是由叶的主要鞣花单宁的1β-O-galloylpedunculagin分子的没食子酰基之间的分子间CO氧化偶联产生的。在植物的树皮和木质部分未检出鞣花单宁。这是从葡萄球菌植物中分离鞣花单宁的第一个例子。
• Agrimoniin and potentillin, an ellagitannin dimer and monomer having an α-glucose core
  作者：Takuo Okuda、Takashi Yoshida、Masaaki Kuwahara、M. Usman Memon、Tetsuro Shingu

  DOI：10.1039/c39820000163

  日期：——

  Potentillin (3), which has an α-glucosyl linkage, and its dimer, agrimoniin (1) have been isolated from Agrimonia pilosa ledeb. and Potentilla kleiniana Wight et Arnott., and their structures elucidated.

  Potentillin（3），其具有α葡糖基键，和其二聚体，agrimoniin（1）已经被分离自仙鹤草草木樨。和委陵菜（Potentilla kleiniana Wight et Arnott。），并阐明了它们的结构。