quinic acid bisacetonide | 209965-31-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: quinic acid bisacetonide
• 英文别名: quinic acid bis-acetonide；Tetrahydro-7-hydroxy-tetramethylspiro[1,3-benzodioxole-[1,3]dioxolan]-5'-one；(3'aS,4'R,5R,7'aR)-4'-hydroxy-2,2,2',2'-tetramethylspiro[1,3-dioxolane-5,6'-4,5,7,7a-tetrahydro-3aH-1,3-benzodioxole]-4-one
• CAS: 209965-31-1
• 化学式: C₁₃H₂₀O₆
• 分子量: 272.298
• InChiKey: XDUHCBIXCVVZDA-RVBSWOSCSA-N

物化性质

• 沸点：
  424.3±45.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿；甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  quinic acid bisacetonide 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 (-)-5-咖啡酰奎宁酸
  参考文献：
  名称：

  First Efficient Synthesis of Chlorogenic Acid

  摘要：

  The first efficient synthesis of chlorogenic acid (1) was achieved in four steps (three purifications) from quinic acid (2). The overall yield was 65%. The key intermediate was quinic acid bisacetonide (6), selectively prepared by a modified kinetic acetalization protocol. Esterification of 6 with caffeic acid chloride (3) afforded ester 12. Cleavage of all the protecting groups of 12 was accomplished in one step under acidic conditions. The progress of the hydrolysis was monitored by MALDI-MS.

  DOI：

  10.1002/1099-0690(200103)2001:6<1137::aid-ejoc1137>3.0.co;2-2
• 作为产物：
  描述：

  右旋奎宁酸 、 alkaline earth salt of/the/ methylsulfuric acid 在 三氟甲磺酸三甲基硅酯 、 三乙胺 、 2,2-二甲氧基丙烷 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 生成 quinic acid bisacetonide
  参考文献：
  名称：

  First Efficient Synthesis of Chlorogenic Acid

  摘要：

  The first efficient synthesis of chlorogenic acid (1) was achieved in four steps (three purifications) from quinic acid (2). The overall yield was 65%. The key intermediate was quinic acid bisacetonide (6), selectively prepared by a modified kinetic acetalization protocol. Esterification of 6 with caffeic acid chloride (3) afforded ester 12. Cleavage of all the protecting groups of 12 was accomplished in one step under acidic conditions. The progress of the hydrolysis was monitored by MALDI-MS.

  DOI：

  10.1002/1099-0690(200103)2001:6<1137::aid-ejoc1137>3.0.co;2-2

文献信息

• Structure-Activity Relationship of Caffeoylquinic Acids on the Accelerating Activity on ATP Production
  作者：Yusaku Miyamae、Manami Kurisu、Junkyu Han、Hiroko Isoda、Hideyuki Shigemori

  DOI：10.1248/cpb.59.502

  日期：——

  Caffeoylquinic acid (CQA) is one of the phenylpropanoids which have various bioactivities such as antioxidant, antibacterial, anticancer, antihistamic, and other biological effects. We previously reported that 3,5-di-O-caffeoylquinic acid inhibited amyloid β1—42-induced cellular toxicity on human neuroblastoma SH-SY5Y cells and increased the mRNA expression level of glycolytic enzymes and the intracellular ATP level. To investigate structure–activity relationship on the accelerating activity on ATP production, we synthesized 1,4,5-tri-O-caffeoylquinic acid, 4,5-di-O-caffeoylquinic acid, 3,4,5-tri-O-caffeoylquinic acid, and other derivatives. Additionally, we evaluated intracellular ATP level in SH-SY5Y treated with each CQA derivative. As a result, 3,4,5-tri-O-caffeoylquinic acid showed the highest accelerating activity on ATP production among tested compounds. It was suggested that caffeoyl groups bound to quinic acid are important for activity and the more caffeoyl groups are bound to quinic acid, the higher accelerating activity on ATP production exhibits.

  咖啡酰奎宁酸（CQA）是一种酚丙烷类化合物，具有多种生物活性，如抗氧化、抗菌、抗癌、抗组胺和其他生物效应。我们之前报道过，3,5-二-O-咖啡酰奎宁酸抑制了淀粉样蛋白β1—42引起的人类神经母细胞瘤SH-SY5Y细胞的细胞毒性，并提高了糖酵解酶的mRNA表达水平和细胞内ATP水平。为了研究结构—活性关系对ATP生产加速活性的影响，我们合成了1,4,5-三-O-咖啡酰奎宁酸、4,5-二-O-咖啡酰奎宁酸、3,4,5-三-O-咖啡酰奎宁酸及其他衍生物。此外，我们评估了用每种CQA衍生物处理的SH-SY5Y细胞的细胞内ATP水平。结果显示，3,4,5-三-O-咖啡酰奎宁酸在测试化合物中对于ATP生产的加速活性最高。研究表明，结合在奎宁酸上的咖啡酰基团对活性至关重要，结合到奎宁酸上的咖啡酰基团越多，ATP生产的加速活性就越高。
• Differentiation of prototropic ions in regioisomeric caffeoyl quinic acids by electrospray ion mobility mass spectrometry
  作者：Nikolai Kuhnert、Ghada H. Yassin、Rakesh Jaiswal、Marius F. Matei、Christian H. Grün

  DOI：10.1002/rcm.7151

  日期：2015.4.15

  A series of dietary important regioisomeric chlorogenic acids were investigated by ion mobility mass spectrometry (IM‐MS). The existence of prototropic isomers separated in the drift dimension was observed and investigated further using tandem mass spectrometry (MS/MS) and compared with suitable synthetic analogues.

  通过离子迁移质谱（IM-MS）研究了一系列饮食中重要的区域异构绿原酸。观察到了在漂移方向上分离的质子异构体的存在，并使用串联质谱（MS / MS）进行了进一步研究，并与合适的合成类似物进行了比较。
• Synthesis, Anti-HCV, Antioxidant and Reduction of Intracellular Reactive Oxygen Species Generation of a Chlorogenic Acid Analogue with an Amide Bond Replacing the Ester Bond
  作者：Ling-Na Wang、Wei Wang、Masao Hattori、Mohsen Daneshtalab、Chao-Mei Ma

  DOI：10.3390/molecules21060737

  日期：——

  acid is a well known natural product with important bioactivities. It contains an ester bond formed between the COOH of caffeic acid and the 3-OH of quinic acid. We synthesized a chlorogenic acid analogue, 3α-caffeoylquinic acid amide, using caffeic and quinic acids as starting materials. The caffeoylquinc acid amide was found to be much more stable than chlorogenic acid and showed anti-Hepatitis C virus

  绿原酸是众所周知的具有重要生物活性的天然产物。它包含在咖啡酸的 COOH 和奎尼酸的 3-OH 之间形成的酯键。我们以咖啡酸和奎宁酸为原料合成了绿原酸类似物 3α-咖啡酰奎尼酸酰胺。发现咖啡酰奎宁酸酰胺比绿原酸稳定得多，并显示出抗丙型肝炎病毒 (anti-HCV) 活性，其效力类似于绿原酸。咖啡酰奎宁酸酰胺有效保护 HepG2 细胞免受叔丁基氢过氧化物诱导的氧化应激。
• WO2008/9138
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis, anti-HIV and anti-oxidant activities of caffeoyl 5,6-anhydroquinic acid derivatives
  作者：Chao-Mei Ma、Takuya Kawahata、Masao Hattori、Toru Otake、Lili Wang、Mohsen Daneshtalab

  DOI：10.1016/j.bmc.2009.11.043

  日期：2010.1

  In our continued research on chlorogenic acid analogues and derivatives with improved bioactivity, we have synthesized some caffeoyl 5,6-anhydroquinic acid derivatives. The 1,7 acetonides of chlorogenic acid ( 15), and of the mono-caffeoyl 5,6-anhydroquinic acids (7-8) showed appreciable anti-HIV activity. The 3,4-dicaffeoyl 5,6-anhydroquinic acid ( 12) exhibited an anti-HIV activity twice as that of 3,5-dicaffeoylquinic acid ( 22). The caffeoyl 5,6-anhydroquinic acid derivatives displayed potent anti-oxidant activities. The mono-caffeoyl 5,6-anhydroquinic acids (10-11) were more than twice stronger than chlorogenic acid ( 21) on SOD-like activity. (C) 2009 Elsevier Ltd. All rights reserved.