dehydrodigallic acid | 5693-34-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: dehydrodigallic acid
• 英文别名: Dehydro-digallussaeure；2-(5-carboxy-2,3-dihydroxyphenoxy)-3,4,5-trihydroxybenzoic acid
• CAS: 5693-34-5
• 化学式: C₁₄H₁₀O₁₀
• 分子量: 338.227
• InChiKey: UFTJIVPLVDDULX-UHFFFAOYSA-N

物化性质

• 沸点：
  660.6±55.0 °C(Predicted)
• 密度：
  1.908±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  185
• 氢给体数：
  7
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  dehydrodigallic acid 在 硫酸 作用下， 生成 3,4,5,6,7-pentahydroxyxanthone-1-carboxylic acid
  参考文献：
  名称：

  Tamarixellagic acid, an ellagitannin from the galls of Tamarix aphylla

  摘要：

  DOI：

  10.1016/s0031-9422(06)80123-8
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 aluminum tri-bromide 、 苯 作用下， 生成 dehydrodigallic acid
  参考文献：
  名称：

  Mayer; Fikentscher, Chemische Berichte, 1958, vol. 91, p. 1536,1540

  摘要：

  DOI：

文献信息

• Facile Preparation of Dehydrodigallic Acid and Its Derivative for the Synthesis of Ellagitannins
  作者：Kazuma Shioe、Shingo Ishikura、Yoshikazu Horino、Hitoshi Abe

  DOI：10.1248/cpb.c13-00458

  日期：——

  A facile method for the synthesis of dehydrodigallic acid, which is a fundamental structure of ellagitannins, was developed. A classical Ullmann condition was effective for the formation of the highly hindered biaryl ether structure, and we clarified that the suitable protection of the phenolic hydroxy groups was crucial in this reaction. In this way, the synthesis of dehydrodigallic acid and its derivative

  开发了一种简便的合成去氢二氢戊二酸的方法，这是一种鞣花单宁的基本结构。经典的乌尔曼条件对于形成高度受阻的联芳醚结构是有效的，并且我们阐明了酚羟基的适当保护在该反应中至关重要。以这种方式，成功地进行了脱氢二没食子酸及其衍生物的合成。所描述的方法将提供针对鞣花单宁的合成用途。
• Aphyllin, the first isoferulic acid glycoside and other phenolics from Tamarix aphylla flowers
  作者：Nawwar, Mahmoud A. M.、Hussein、Ayoub、Hofmann、Linscheid、Harms、Wende、Lindequist

  DOI：10.1691/ph.2009.8822

  日期：——

  The first glycosylated isoferulic acid, isoferulic acid 3-O-β-glucopyranoside, together with the new phenolics, tamarixetin 3,3′-di-sodium sulphate and dehydrodigallic acid dimetyl ester have been characterized from a flower extract of Tamarix aphylla. The structures were established on the basis of spectral data. The extract exhibited a distinct radical scavenging effect and to improve the viability of human keratinocytes (HaCaT cells). Also, the known isoferulic acid and ferulic acid which have been determined to be the major components of the investigated extract by HPLC/ESI mass spectrometric screening have been separated, characterized and evaluated as active antioxidants and as cell activity stimulating agents as well.

  从 Tamarix aphylla 的花提取物中鉴定出了第一种糖基化的异阿魏酸（异阿魏酸 3-O-β-吡喃葡萄糖苷），以及新的酚类物质--柽柳黄素 3,3′-二硫酸钠和脱氢双胍酸二甲酯。根据光谱数据确定了它们的结构。该提取物具有明显的自由基清除作用，并能提高人类角质细胞（HaCaT 细胞）的活力。此外，通过 HPLC/ESI 质谱筛选确定的已知异阿魏酸和阿魏酸是所研究提取物的主要成分，它们作为活性抗氧化剂和细胞活性刺激剂已被分离、表征和评估。
• Ishimatsu, Makoto; Tanaka, Takashi; Nonaka, Gen-ichiro, Chemical and pharmaceutical bulletin, 1989, vol. 37, # 7, p. 1735 - 1743
  作者：Ishimatsu, Makoto、Tanaka, Takashi、Nonaka, Gen-ichiro、Nishioka, Itsuo、Nishizawa, Makoto、Yamagishi, Takashi

  DOI：——

  日期：——
• Cytotoxic ellagitannins from Reaumuria vermiculata
  作者：Mahmoud A. Nawwar、Nahla A. Ayoub、Mohamed A. El-Rai、Fatma Bassyouny、Eman S. Mostafa、Ahmed M. Al-Abd、Manuela Harms、Kristian Wende、Ulrike Lindequist、Michael W. Linscheid

  DOI：10.1016/j.fitote.2012.06.007

  日期：2012.10

  Three ellagitannins and one disulfated flavonol were isolated from the aerial parts of Reaumuria vermiculata L. Besides that, 16 known compounds were characterized as well. The structures of all compounds were elucidated on the basis of spectroscopic data including 1D and 2D NMR and ESI HR-FTMS. The in vivo antioxidant activity using the oxygen radical absorbance capacity (ORAC) method, of the extract, its column fractions and two of the isolated ellagitannins was accomplished. In addition, a possible cytotoxicity of the extract and two of the new ellagitannins on HaCaT human keratinocytes and the activity of both compounds against the prostate cancer cell line (PC-3) were also assessed, whereby a potent cytotoxicity with IC50 less than 1 mu g/ml was determined for both compounds. Besides, the extract exhibited a potential cytotoxic effect against four different solid tumor cell lines, namely liver (Huh-7), colorectal (HCT-116), breast (MCF-7) and prostate (PC-3). The IC(50)s were found to be substantially low (ranged from 1.3 +/- 0.15 to 2.4 +/- 0.22 mu g/ml) with relatively low resistance possibility reaching to 0% in the case of Huh-7 cell. (c) 2012 Elsevier B.V. All rights reserved.
• ISHIMATSU, MAKOTO;TANAKA, TAKASHI;NONAKA, GEN-ICHIRO;NISHIOKA, ITSUO;NISH+, CHEM. AND PHARM. BULL., 37,(1989) N, C. 1735-1743
  作者：ISHIMATSU, MAKOTO、TANAKA, TAKASHI、NONAKA, GEN-ICHIRO、NISHIOKA, ITSUO、NISH+

  DOI：——

  日期：——