trimethyl octa-O-methyltergallate | 131959-69-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: trimethyl octa-O-methyltergallate
• 英文别名: methyl 2-[2,4-dimethoxy-6-methoxycarbonyl-3-(2,3,4-trimethoxy-6-methoxycarbonylphenoxy)phenyl]-3,4,5-trimethoxybenzoate
• CAS: 131959-69-8
• 化学式: C₃₂H₃₆O₁₅
• 分子量: 660.629
• InChiKey: FYKZAVRGSSMIAG-UHFFFAOYSA-N

物化性质

• 沸点：
  714.9±60.0 °C(Predicted)
• 密度：
  1.244±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.57
• 重原子数：
  47.0
• 可旋转键数：
  14.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  161.97
• 氢给体数：
  0.0
• 氢受体数：
  15.0

反应信息

• 作为产物：
  描述：

  C₂₅H₂₀O₁₅ 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 反应 2.5h， 生成 trimethyl octa-O-methyltergallate
  参考文献：
  名称：

  邻醌介子效应的邻醌合成鞣花单宁的二芳基醚成分

  摘要：

  描述了合成CO-0没食子酸酯结构的方法，该化合物是天然鞣花单宁的二芳基醚成分的基本单元。在从没食子酸衍生的设计构件中，介观重叠的介观效应增强了其亲电子性。该结构单元显示出显着的反应活性，可改善脱氢二氢二氢酰基，三氢酰基和瓦龙酰基的合成。

  DOI：

  10.1039/d0cc00889c

文献信息

• 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 and Related Compounds. CXXIV. Five New Ellagitannins, Platycaryanins A, B, C, and D, and Platycariin, and a New Complex Tannin, Strobilanin, from the Fruits and Bark of Platycarya strobilacea SIEB et ZUCC., and Biomimetic Synthesis of C-Glycosidic Ellagitannins from Glucopyranose-Based Ellagitannins.
  作者：Takashi TANAKA、Shinji KIRIHARA、Gen-ichiro NONAKA、Itsuo NISHIOKA

  DOI：10.1248/cpb.41.1708

  日期：——

  Five new ellagitannins, platycaryanins A (27), B (26), C (30), and D (25), and platycariin (31), and a new complex tannin, strobilanin (32), have been isolated from the fruits and bark of Platycarya strobilacea SIEB. et ZUCC. (Juglandaceae), together with twenty-six known compounds. On the basis of spectroscopic and chemical evidence, platycaryanins A, B and C, and platycariin have been characterized as the ellagitannins having a tergalloyl ester group, while platycaryanin D was found to be an unusual ellagitannin possessing (R)-hexahydroxydiphenoyl esters at the glucopyranose 2, 3- and 4, 6-positions. During these chemical studies, re-examination of the similar ellagitannins, alnusnins A and B, which were previously reported from Alnus sieboldiana, led us to revise their structures to 29 and 28, respectively, in which the tergalloyl group forms a lactone ring. Furthermore, biomimetic conversion of ellagitannins having a glucopyranose core into C-glycosidic ellagitannins was successfully achieved for the first time, and the reaction was applied to the structure elucidation of platycariin (31).

  从Platycarya strobilacea SIEB. et ZUCC.（胡桃科）的果实和树皮中分离出了五种新的鞣花酸类化合物，分别是platycaryanins A（27）、B（26）、C（30）和D（25），以及platycariin（31），同时还分离出了二十六种已知化合物。根据光谱学和化学证据，platycaryanins A、B和C以及platycariin被鉴定为具有军团酸酯基团的鞣花酸类化合物，而platycaryanin D则被发现是一种不寻常的鞣花酸，具有在葡萄糖吡喃糖2、3位和4、6位的(R)-六羟基二苯酸酯。在这些化学研究过程中，对以前从Alnus sieboldiana分离出的相似鞣花酸alnusnins A和B进行了重新审查，导致我们修正了它们的结构，分别为29和28，其中军团酸基团形成了内酯环。此外，首次成功实现了将具有葡萄糖吡喃核的鞣花酸转化为C-糖苷鞣花酸的生物仿生转化，该反应被应用于platycariin（31）的结构阐明。
• Alnusnins A and B from the leaves of Alnus sieboldiana
  作者：Makoto Ishimatsu、Takashi Tanaka、Gen-ichiro Nonaka、Itsuo Nishioka

  DOI：10.1016/0031-9422(89)80302-4

  日期：1989.1

  Abstract Two new ellagitannins, alnusnins A and B, have been isolated from the leaves of Alnus sieboldiana (Betulaceae) and characterized as 1- O -galloyl-2,3-( S )-hexahydroxydiphenoyl-4,6-( S )-tergalloyl-β- d -glucose and 2,3-( S )-hexahydroxydiphenoyl-4,6-( S )-tergalloyl- d -glucose, respectively, by chemical and spectral evidence. The occurrence of eight known tannins, 1,2,6-tri- O -galloyl-β-

  摘要 从桦木科 (Alnus sieboldiana) 的叶子中分离出两种新的鞣花单宁, alnusnins A 和 B, 并表征为 1-O-galloyl-2,3-( S )-hexahydroxydiphenoyl-4,6-( S )-tergalloyl -β- d -葡萄糖和 2,3-( S )-六羟基二苯甲酰基-4,6-( S )-tergalloyl-d -葡萄糖，分别通过化学和光谱证据。八种已知单宁、1,2,6-三-O-没食子酰-β-d-葡萄糖、严格素、木麻黄素、水苏素、花梗素、1(β)-O-没食子酰花梗素和藤黄素 A，以及两种黄酮类化合物松树素的出现和槲皮素 3-O-β-d-葡糖苷酸，也已被证实。
• Eucalbanins A,B and C, Monomeric and Dimeric Hydrolyzable Tannins from Eucalyptus alba REINW.
  作者：Takashi YOSHIDA、Tetsuhiro MARUYAMA、Aya NITTA、Takuo OKUDA

  DOI：10.1248/cpb.40.1750

  日期：——

  Three new hydrolyzable tannins, eucalbanins A (5), B (8) and C (11), have been isolated from the fruit extract of Eucalyptus alba REINW., and their structures were elucidated on the basis of spectral data and chemical correlation with known tannins. Quercetin-3-O-α-L-arabinopyranoside, (+)-catechin, procyanidin b-7, and nine known hydrolyzable tannins [casuarinin, casuariin, pedunculagin, tellimagrandin I (1), gemin D (2), cornusiin B (3), 2, 3-(S)-hexa-hydroxydiphenoyl-D-glucose, penta-O-galloyl-β-D-glucose and oenothein B (4)] have also been isolated.

  从白桉 REINW. 的果实提取物中分离出三种新的可水解单宁，尤卡班宁 A (5)、B (8) 和 C (11)，并根据光谱数据和与已知单宁的化学相关性阐明了它们的结构。单宁酸。槲皮素-3-O-α-L-阿拉伯吡喃糖苷、(+)-儿茶素、原花青素 b-7 和九种已知的可水解单宁 [木麻黄苷、木麻黄苷、pedunculagin、tellimagrandin I (1)、gemin D (2)、cornusiin B ( 3), 2, 3-(S)-六-羟基二苯酰-D-葡萄糖、五-O-没食子酰-β-D-葡萄糖和月见草苷 B (4)] 也已被分离。
• Isolation of Ellagitannin Monomer and Macrocyclic Dimer from Castanopsis carlesii Leaves
  作者：Takashi Tanaka、Yong-Lin Huang、Yosuke Matsuo、Isao Kouno、Dian-Peng Li、Gen-ichiro Nonaka

  DOI：10.3987/com-12-s(n)29

  日期：——

  (Fagaceae), new monomeric and dimeric ellagitannins, named carlesiins A (1) and B (2), were isolated from fresh leaves of Castanopsis carlesii along with 55 known compounds. Carlesiin A was identified as 1-O-galloyl-4,6-(S)-tergalloyl-β-D-glucose. Carlesiin B is a macrocyclic ellagitannin dimer with a symmetrical structure composed of two tergalloyl and two glucopyranose moieties. Their structures were elucidated

  在对 Castanopsis 物种（Fagaceae）的植物化学和化学分类学研究中，新的单体和二聚鞣花单宁，命名为 carlesiins A (1) 和 B (2)，与 55 种已知化合物一起从 Castanopsis carlesii 的新鲜叶子中分离出来。Carlesiin A 被鉴定为 1-O-galloyl-4,6-(S)-tergaloyl-β-D-葡萄糖。Carlesiin B 是一种具有对称结构的大环鞣花单宁二聚体，由两个三萜酰和两个吡喃葡萄糖部分组成。基于光谱和化学证据阐明了它们的结构。简介 栲（Fagaceae）属的物种是在东亚发现的常绿乔木，有时是森林中的优势物种。这些树木常被用作林业或观赏树木，木材是重要的建筑材料。该属约有120种，但只研究了少数物种的化学成分。中国和日本栲树的叶子。是多酚的丰富来源，每个物种都有独特的酚类成分。我们对 Castanopsis sp