(-)-5-咖啡酰奎宁酸 | 202650-88-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (-)-5-咖啡酰奎宁酸
• 英文名称: 3-caffeoylquinic acid
• 英文别名: chlorogenic acid；3-O-caffeoylquinic acid；5-caffeoylquinic acid；5-O-caffeoylquinic acid；neochlorogenic acid；3-(3,4-dihydroxycinnamoyl)quinic acid；5‐O‐caffeoylquinic acid；trans-5-O-caffeoylquinic acid；caffeoylquinic acid；5-CQA；(1S,3R,4R,5R)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,4,5-trihydroxycyclohexane-1-carboxylic acid
• CAS: 202650-88-2
• 化学式: C₁₆H₁₈O₉
• 分子量: 354.314
• InChiKey: CWVRJTMFETXNAD-JUHZACGLSA-N

物化性质

• 沸点：
  665.0±55.0 °C(Predicted)
• 密度：
  1.65±0.1 g/cm3(Predicted)
• 物理描述：
  Solid
• 熔点：
  205-209°C
• 溶解度：
  40 mg/mL at 25 °C
• 碰撞截面：
  185.1 Ų [M+H]+ [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  165
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (-)-5-咖啡酰奎宁酸 在 palladium on activated charcoal 、 氢气 作用下， 以 乙醇 为溶剂， 反应 16.0h， 以67%的产率得到(1S,3S,4R,5R)-3-((3-(3,4-dihydroxyphenyl)propanoyl)oxy)-1,4,5-trihydroxycyclohexane-1-carboxylic acid
  参考文献：
  名称：

  咖啡酸衍生物作为α-MSH刺激的黑色素生成的有效抑制剂的合成和生物学评估

  摘要：

  我们已经公开了开发咖啡酸衍生物作为α-MSH刺激的黑色素生成的有效和无毒抑制剂的努力，以治疗色素沉着症和包括美容性皮肤增白剂的皮肤药物。SAR研究表明，咖啡酸的环己酯和仲酰胺衍生物表现出显着的抑制活性。

  DOI：

  10.1016/j.bmcl.2017.06.011
• 作为产物：
  描述：

  Trimethylsilyltetra-O-trimethylsilylchinat 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 三氟甲磺酸三甲基硅酯 、 2,2-二甲氧基丙烷 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
• 作为试剂：
  描述：

  矢车菊素-3-O-半乳糖苷 、 乙醛 、 表儿茶素 在 苹果酸 、 (-)-5-咖啡酰奎宁酸 、 phloridizin 作用下， 以 乙醇 、 水 为溶剂， 反应 1440.0h， 生成 2-(3,4-Dihydroxy-phenyl)-8-{1-[(2R,3R)-2-(3,4-dihydroxy-phenyl)-3,6,7-trihydroxy-chroman-8-yl]-ethyl}-5,7-dihydroxy-3-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-chromenylium
  参考文献：
  名称：

  Characterization and structures of anthocyanin pigments generated in rosé cider during vinification

  摘要：

  Anthocyanin pigments, which are trot found in apple juice, were detected in rose cider. We confirmed by HPLC/DAD and LC/ESI-MS analyses that some of these anthocyanin pigments generated in rose cider during vinification corresponded to those formed in model cider containing anthocyanin and flavan-3-ol in the presence of acetaldehyde. To confirm their structures, two anthocyanin pigments formed in a model cider containing cyanidin-3-galactoside and (-)-epicatechin in the presence of acetaldehyde were isolated and purified, and their structures were elucidated by high resolution FAB-MS and H-1 and C-13 NMR analyses. These two pigments were found to consist of cyanidin-3-galactoside and (-)-epicatechin linked by a CH3-CH bridge at the 8-position. They were diastereomers that differed in the configuration of the asymmetric methine carbon. (C) 2002 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(01)00427-7

文献信息

• Flavonoid derivative
  申请人：Buchholz Herwig

  公开号：US20070134172A1

  公开（公告）日：2007-06-14

  The invention relates to a novel flavonoid derivative, to an extract comprising the flavonoid derivative, to the cosmetic and pharmaceutical use thereof, to preparations comprising the flavonoid derivative or extract, and to a process for the preparation of the flavonoid derivative or extract.

  这项发明涉及一种新型黄酮衍生物，一种包含该黄酮衍生物的提取物，以及其在化妆品和药用方面的使用，包括含有该黄酮衍生物或提取物的制剂，以及一种制备该黄酮衍生物或提取物的方法。
• Kinetic Study on the Free Radical-Scavenging and Vitamin E-Regenerating Actions of Caffeic Acid and Its Related Compounds
  作者：Keishi Ohara、Yoko Ichimura、Kumi Tsukamoto、Mayumi Ogata、Shin-ichi Nagaoka、Kazuo Mukai

  DOI：10.1246/bcsj.79.1501

  日期：2006.10

  A kinetic study involving 4-hydroxycinnamic acid derivatives (HCAs) was performed in order to clarify the mechanism for free radical-scavenging and vitamin E-regenerating. The second-order rate con...

  为了阐明自由基清除和维生素 E 再生的机制，进行了涉及 4-羟基肉桂酸衍生物 (HCA) 的动力学研究。二阶速率控制...
• MYOCARDIAL REGENERATION PROMOTING COMPOUNDS, PREPARATION METHOD THEREOF, PHARMACEUTICAL COMPOSITION, AND THEIR USE
  申请人：GENHEALTH PHARMA CO., LTD.

  公开号：US20200317602A1

  公开（公告）日：2020-10-08

  The present invention discloses a novel 3-aryl-2-propen-1-one series derivative and the synthesis processes thereof. Besides, the present invention also discloses the series derivative as a pharmaceutical composition and their use for promoting myocardial regeneration.

  本发明公开了一种新型的3-芳基-2-丙烯-1-酮系列衍生物及其合成方法。此外，本发明还公开了该系列衍生物作为一种药物组合物，以及它们用于促进心肌再生的用途。
• METHOD OF IMPROVING STABILITY OF SWEET ENHANCER AND COMPOSITION CONTAINING STABILIZED SWEET ENHANCER
  申请人：TACHDJIAN Catherine

  公开号：US20120041078A1

  公开（公告）日：2012-02-16

  The present invention includes methods of stabilizing one or more sweet enhancers when they are exposed to a light source as well as liquid compositions containing one or more sweet enhancers and one or more photostabilizers.

  本发明包括在甜味增强剂暴露于光源时稳定一个或多个甜味增强剂的方法，以及包含一个或多个甜味增强剂和一个或多个光稳定剂的液体组合物。
• 신규 클로로겐산 유도체 및 이를 유효성분으로 포함하는 염증성 질환 치료용 조성물
  申请人：Chungbuk National University Industry-Academic Cooperation Foundation 충북대학교 산학협력단(220040168226) BRN ▼301-82-16304

  公开号：KR101693033B1

  公开（公告）日：2017-01-09

  본 발명은 항염증 활성을 갖는 신규 클로로겐산 유도체 화합물 및 이를 유효성분으로 포함하는 항염증 조성물에 관한 것이다. 본 발명의 클로로겐산 유도체 화합물은 대식세포에서 LPS에 처리에 의해 유도되는 산화질소(NO)의 과생성을 억제한다. 본 발명의 클로로겐산 유도체 화합물은 산화적 스트레스 및 염증 촉진 경로에서 중요한 신호전달 매개 전사인자인 NF-κB의 활성화를 저해한다. 본 발명의 클로로겐산 유도체 화합물은 산화질소 과생성과 NF-κB의 활성화를 저해함으로써 다양한 염증성질환의 치료제로 개발될 가능성이 높다.

  本发明涉及具有抗炎活性的新型克罗洛糖酸衍生物化合物及其作为有效成分包含的抗炎组合物。本发明的克罗洛糖酸衍生物化合物可以抑制由大食细胞对LPS处理引起的氧化氮(NO)的过度产生。本发明的克罗洛糖酸衍生物化合物还可以抑制在氧化应激和炎症促进途径中重要的信号传导介质转录因子NF-κB的活化。通过抑制氧化氮的过度产生和NF-κB的活化，本发明的克罗洛糖酸衍生物化合物有望被开发为治疗各种炎症性疾病的治疗剂。

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