间双没食子酸 | 536-08-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 中文名称: 间双没食子酸
• 中文别名: 2,3-二羟基-间-二没食子酸；間貳五倍子酸
• 英文名称: digallic acid
• 英文别名: gallic acid 3-O-gallate；m-digallic acid；m-galloylgallic acid；3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyl)oxybenzoic acid
• CAS: 536-08-3
• 化学式: C₁₄H₁₀O₉
• 分子量: 322.228
• InChiKey: COVFEVWNJUOYRL-UHFFFAOYSA-N

物化性质

• 熔点：
  267-269°C
• 沸点：
  420.86°C (rough estimate)
• 密度：
  1.5467 (rough estimate)
• 溶解度：
  DMSO：可溶；甲醇：可溶
• LogP：
  1.970 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  23
• 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：
  165
• 氢给体数：
  6
• 氢受体数：
  9

安全信息

• 海关编码：
  2918990090
• 储存条件：
  -20°C，密封保存，干燥环境中

制备方法与用途

digallic acid 是一种天然的多酚类物质，可以通过水解没食子单宁得到。

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	4-hydroxy-3,5-bis-methoxycarbonyloxy-benzoic acid	861570-63-0	C11H10O9	286.195
  ——	3,4,5-tris[(methoxycarbonyl)oxy]benzoic acid	222320-76-5	C13H12O11	344.232
  没食子酸	3,4,5-trihydroxybenzoic acid	149-91-7	C7H6O5	170.122

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  3,5-二羟基-4-[(3,4,5-三羟基苯甲酰基)氧基]苯甲酸	para digallic acid	47307-06-2	C14H10O9	322.228
  没食子酸	3,4,5-trihydroxybenzoic acid	149-91-7	C7H6O5	170.122

反应信息

• 作为反应物：
  描述：

  间双没食子酸 在 protonating media 作用下， 生成 3,5-二羟基-4-[(3,4,5-三羟基苯甲酰基)氧基]苯甲酸
  参考文献：
  名称：

  Verzele, M.; Delahaye, P.; Dijck, J. Van, Bulletin des Societes Chimiques Belges, 1983, vol. 92, # 2, p. 181 - 186

  摘要：

  DOI：
• 作为产物：
  描述：

  3,4,5-tris[(methoxycarbonyl)oxy]benzoic acid 在 sodium hydroxide 、 乙醚 作用下， 生成 间双没食子酸
  参考文献：
  名称：

  Fischer,E., Chemische Berichte, 1908, vol. 41, p. 2872

  摘要：

  DOI：

文献信息

• COMBINATION OF COMPOUNDS DERIVED FROM GALLIC ACID FOR THE TREATMENT OF CANCER
  申请人：FIORENTINO Susana

  公开号：US20150313925A1

  公开（公告）日：2015-11-05

  The invention relates to a combination of compounds derived from gallic acid, with an antitumoral and antimetastatic activity via a mechanism that involves the induction of apoptosis and the immunogenic death of the tumour cells and the subsequent activation of the specific immune response. The invention also relates to a composition containing a combination of derivatives of gallic acid and pharmaceutically acceptable excipients for the production of useful medicaments in the treatment of cancer. The invention further relates to the use of said composition in a coadjuvant in conventional chemotherapy, reducing the doses of chemptherapeutic agents used in the treatment of cancer.

  该发明涉及一种由没食子酸衍生的化合物组合，具有抗肿瘤和抗转移活性，通过诱导细胞凋亡和肿瘤细胞的免疫原性死亡以及后续激活特异性免疫应答的机制。该发明还涉及一种含有没食子酸衍生物组合和药用可接受的赋形剂的组合物，用于生产用于治疗癌症的有用药物。该发明进一步涉及在常规化疗中使用该组合物作为辅助剂，减少用于癌症治疗的化疗药物的剂量。
• Cost Effectiveness of Treatment Options in Advanced Breast Cancer in the UK
  作者：Ruth E. Brown、John Hutton、Anita Burrell

  DOI：10.2165/00019053-200119110-00003

  日期：——

  Objective: To compare clinical and economic study data for docetaxel, paclitaxel and vinorelbine in the treatment of anthracycline-resistant advanced breast cancer. Study design and methods: A Markov decision-analysis model to simulate the clinical course of a ‘typical’ patient with advanced breast cancer during salvage chemotherapy was updated with response rates and adverse effect rates from phase III clinical trial data for docetaxel, paclitaxel and vinorelbine. Costs were taken from UK national databases and hospitals. Utilities were estimated from 30 oncology nurses in the UK using the standard gamble method. Perspective: National Health Service. Results: When compared with other chemotherapeutic agents, docetaxel has been shown to increase response rate, time to progression and survival in patients with advanced breast cancer. In the base-case analysis, the incremental cost-utility ratio for docetaxel versus paclitaxel was £1995 per quality-adjusted life year (QALY) gained (1998 values). The incremental cost-utility ratio for docetaxel versus vinorelbine was £14 055 per QALY gained. In the comparison with vinorelbine, docetaxel provided the equivalent of an additional 92 days of perfect health. Sensitivity analyses confirmed the robustness of the model and the validity of the base-case analysis results. Even in the worst case scenarios, docetaxel remained cost effective compared with paclitaxel and vinorelbine. Conclusions: These findings support the use of the taxoids, notably docetaxel, in the management of advanced breast cancer.

  目标：比较多柔比星、紫杉醇和长春瑞滨在治疗抗蒽环类药物耐药晚期 breast cancer 中的临床和经济研究数据。研究设计和方法：更新了一个马尔可夫决策分析模型，用于模拟“典型”晚期乳腺癌患者在救治化疗期间的临床过程，该模型根据多柔比星、紫杉醇和长春瑞滨的三期临床试验数据更新了响应率和不良反应的发生率。成本数据来源于英国的国家数据库和医院。效用通过标准赌注法由30名英国肿瘤护士估算。视角：国家卫生服务。结果：与其他化疗药物比较，多柔比星在晚期乳腺癌患者中已显示出提高响应率、进展时间和生存率。在基线分析中，多柔比星与紫杉醇相比的增量成本效用比为每增加一个质量调整生命年（QALY）1995英镑（1998年数据）。多柔比星与长春瑞滨相比的增量成本效用比为每增加一个QALY 14055英镑。在与长春瑞滨的比较中，多柔比星提供了相当于额外92天完美健康的效益。敏感性分析确认了模型的稳健性和基线分析结果的有效性。即使在最坏的情况下，多柔比星与紫杉醇和长春瑞滨相比仍然具有成本效益。结论：这些发现支持在晚期乳腺癌管理中使用紫杉类药物，特别是多柔比星。
• Plasminogen Activator Inhibitor-1 Inhibitors And Methods Of Use Thereof To Modulate Lipid Metabolism
  申请人：Lawrence Daniel A.

  公开号：US20090011055A1

  公开（公告）日：2009-01-08

  The invention relates to plasminogen activator-1 (PAI-1) inhibitor compounds and uses thereof in the treatment of any disease or condition associated with elevated PAI-1. The invention includes, but is not limited to, the use of such compounds to modulate lipid metabolism and treat conditions associated with elevated PAI-1, cholesterol, or lipid levels.

  该发明涉及纤溶酶原激活物-1（PAI-1）抑制剂化合物及其在治疗与升高的PAI-1相关的任何疾病或状况中的应用。该发明包括但不限于利用这些化合物来调节脂质代谢并治疗与升高的PAI-1、胆固醇或脂质水平相关的疾病。
• Compositions and methods for prevention and treatment of chronic diseases and disorders including the complications of diabetes mellitus
  申请人：——

  公开号：US20010031744A1

  公开（公告）日：2001-10-18

  This invention relates to nutrient and therapeutic compositions for treatment and prevention of symptoms and disease conditions associated with microangiopathy and macroangiopathy and to methods using the compositions. In particular, the invention relates to compositions useful in the treatment of diabetic retinopathy and nephropathy, to compositions useful in the treatment of other retinal disorders including macular degeneration and cataracts, to compositions useful in wound healing, to compositions useful for treatment and prevention of neuropathy, to compositions useful for treatment and prevention of cardiovascular disease and to compositions useful for the treatment and prevention of dental and periodontal disorders.

  这项发明涉及用于治疗和预防与微血管病和大血管病相关的症状和疾病状况的营养和治疗组合物，以及使用这些组合物的方法。具体来说，该发明涉及用于治疗糖尿病视网膜病和肾病的组合物，用于治疗其他视网膜疾病包括黄斑变性和白内障的组合物，用于伤口愈合的组合物，用于治疗和预防神经病变的组合物，用于治疗和预防心血管疾病的组合物，以及用于治疗和预防口腔和牙周疾病的组合物。
• Processes for the preparation of protected-(+)-catechin and (-)-epicatechin monomers, for coupling the protected monomers with an activated, protected epicatechin monomer, and for the preparation of epicatechin-(4B,8)-epicatechin or -catechin dimers and their digallates
  申请人：Romanczyk Leo

  公开号：US20070004796A1

  公开（公告）日：2007-01-04

  Improved processes for the preparation of tetra-O-benzyl protected catechin, for the coupling of the tetra-O-benzyl protected catechin or epicatechin with a C-4 activated, tetra-O-benzyl protected epicatechin for the galloylation of the epicatechin-(4β,8)-catechin or -epicatechin dimer-the dimer digallates, and for the deprotection (i.e., debenzylation) of the protected epicatechin dimers and protected epicatechin dimer digallates are disclosed.

  揭示了用于制备四重O-苄基保护的儿茶素的改进工艺，用于将四重O-苄基保护的儿茶素或表儿茶素与C-4活化的四重O-苄基保护的表儿茶素偶联以进行表儿茶素-(4β,8)-儿茶素或-表儿茶素二聚体的没食子酸化，以及用于去保护（即去苄基化）保护的表儿茶素二聚体和保护的表儿茶素二聚体二没食子酸酯的工艺。