3-O-咖啡酰基奎宁酸甲酯 | 123483-19-2

• 物质功能分类: 分析化学 - 标准品
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-O-咖啡酰基奎宁酸甲酯
• 英文名称: 5-caffeoylquinic acid methyl ester
• 英文别名: methyl chlorogenate；chlorogenic acid methyl ester；5-O-caffeoylquinic acid methyl ester；3-caffeoylquinic acid methyl ester；methyl 3-O-caffeoylquinate；5-O-trans-caffeoylquinic acid methyl ester；trans-chlorogenic acid methyl ester；methyl 5-O-caffeoylquinate；methyl (1S,3R,4R,5R)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,4,5-trihydroxycyclohexane-1-carboxylate
• CAS: 123483-19-2
• 化学式: C₁₇H₂₀O₉
• 分子量: 368.34
• InChiKey: MZNIJRAPCCELQX-AWOKGZDASA-N

物化性质

• 沸点：
  577.0±50.0 °C(Predicted)
• 密度：
  1.53±0.1 g/cm3(Predicted)
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。
• LogP：
  0.310 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  154
• 氢给体数：
  5
• 氢受体数：
  9

安全信息

• 储存条件：
  存放在2-8°C环境中，应密封并保持干燥。

制备方法与用途

概述

咖啡酰奎尼酸甲酯是一种苯丙烯酸类化合物，研究证实这类化合物普遍存在于顺式双键和反式双键两种异构体中。一般而言，反式异构体的含量较高，而顺式异构体的含量较低。

用途

咖啡酰奎尼酸甲酯可以应用于有机合成中。

生物活性

3-O-咖啡酰奎尼酸甲酯是铁芒萁（Pyrrosia calvata）的一种成分。

反应信息

• 作为反应物：
  描述：

  3-O-咖啡酰基奎宁酸甲酯 、 乙酸酐 以 吡啶 为溶剂， 生成 (1S,3R,4R,5R)-1,3,4-Triacetoxy-5-[(E)-3-(3,4-diacetoxy-phenyl)-acryloyloxy]-cyclohexanecarboxylic acid methyl ester
  参考文献：
  名称：

  Deyama, Takeshi; Ikawa, Takeko; Kitagawa, Shizuka, Chemical and pharmaceutical bulletin, 1987, vol. 35, # 5, p. 1785 - 1789

  摘要：

  DOI：
• 作为产物：
  描述：

  (-)-5-咖啡酰奎宁酸 、 三甲基硅烷化重氮甲烷 以 甲醇 为溶剂， 反应 15.0h， 以51.9%的产率得到3-O-咖啡酰基奎宁酸甲酯
  参考文献：
  名称：

  신규 클로로겐산 유도체 및 이를 유효성분으로 포함하는 염증성 질환 치료용 조성물

  摘要：

  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。

  公开号：

  KR101693033B1

文献信息

• Synthesis and biological evaluation of caffeic acid derivatives as potent inhibitors of α-MSH-stimulated melanogenesis
  作者：Hyeju Jo、Minho Choi、Jaeuk Sim、Mayavan Viji、Siyuan Li、Young Hee Lee、Youngsoo Kim、Seung-Yong Seo、Yuanyuan Zhou、Kiho Lee、Wun-Jae Kim、Jin Tae Hong、Heesoon Lee、Jae-Kyung Jung

  DOI：10.1016/j.bmcl.2017.06.011

  日期：2017.8

  We have disclosed our effort to develop caffeic acid derivatives as potent and non-toxic inhibitors of α-MSH-stimulated melanogenesis to treat pigmentation disorders and skin medication including a cosmetic skin-whitening agent. The SAR studies revealed that cyclohexyl ester and secondary amide derivatives of caffeic acid showed significant inhibitory activities.

  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。
• 5-Lipoxygenase inhibitors isolated from Gardeniae Fructus.
  作者：MAKOTO NISHIZAWA、RURIKO IZUHARA、KO KANEKO、YASUKO KOSHIHARA、YASUO FUJIMOTO

  DOI：10.1248/cpb.36.87

  日期：——

  Five 5-lipoxygenase inhibitors, chlorogenic acid (1), 6''-p-coumaroyl genipin gentiobioside (2), 3, 4-di-O-caffeoylquinic acid (3), 3-O-caffeoyl-4-O-sinapoylquinic acid (4) and 3, 5-di-O-caffeoyl-4-O-(3-hydroxy-3-methyl)glutaroylquinic acid (5), were isolated from Gardeniae Fructus. The structures of the new compounds (2, 4 and 5) were elucidated on the basis of spectral data and chemical evidence. These hydroxycinnamic acid derivatives inhibit 5-lipoxygenase activity, and 3 was the most potent inhibitor. The inhibitory effects were enhanced on methylation of the carboxyl group(s) of 1, 3, 4 and 5, and the ID<50> values of the methyl esters of 3, 4 and 5 were of the order of 10<-8>M.

  从栀子果实中分离出五种5-脂氧合酶抑制剂，分别为绿原酸（1）、6''-对香豆酰基京尼平龙胆二糖苷（2）、3,4-二-O-咖啡酰基奎宁酸（3）、3-O-咖啡酰基-4-O-芥子酰基奎宁酸（4）和3,5-二-O-咖啡酰基-4-O-（3-羟基-3-甲基）戊二酰基奎宁酸（5）。根据光谱数据和化学证据，新化合物（2、4和5）的结构得到阐明。这些羟基肉桂酸衍生物能抑制5-脂氧合酶活性，其中3是最强的抑制剂。对1、3、4和5的羧基进行甲基化增强了抑制效果，3、4和5的甲酯的ID<50>值约为10<−8>M。
• Synthesis of 1-<i>O</i>-Methylchlorogenic Acid: Reassignment of Structure for MCGA3 Isolated from Bamboo (<i>Phyllostachys edulis</i>) Leaves
  作者：Wayne E. Zeller

  DOI：10.1021/jf4042112

  日期：2014.2.26

  coincide with those reported for the original isolation from bamboo (Phyllostachys edulis) leaves of the compound designated MCGA3. Comparison of the published spectroscopic data reported for MCGA3, with both reported literature values and spectroscopic data obtained from an authentic sample, leads to the conclusion that the compound isolated from bamboo (Phyllostachys edulis) leaves is instead methyl

  描述了1- O-甲基绿原酸的第一次合成。这种化合物的短而有效的合成提供了实验室规模的材料以研究其生物学特性。合成包括将已知的（-）-4,5-环己叉基奎宁内酯进行C-1烷基化，然后将甲醇盐打开至羟基酯。将C-5羟基酰化，随后依次除去保护基，得到1- O-甲基绿原酸。该化合物的NMR光谱特征与最初从竹子（毛竹（Phyllostachys edulis））称为MCGA3的化合物的叶子。将报告的MCGA3光谱数据与已报道的文献数据和从真实样品中获得的光谱数据进行比较，得出的结论是，从竹叶（Phyllostachys edulis）叶中分离出的化合物是氯代甲烷。
• In Vitro Evaluation of Caffeoyl and Cinnamoyl Derivatives as Potential Prolyl Oligopeptidase Inhibitors
  作者：Luciana Adolpho、Daniele Marin、Albert Puigpinos、Laura Mendieta、Teresa Tarragó、Ademir Morel、Ernest Giralt、Ionara Dalcol

  DOI：10.1055/s-0033-1350897

  日期：——

  A screening of the natural product chlorogenic acid, isolated from the Brazilian medicinal plant Hypericum brasiliense, caffeic acid, cinnamic acid, and p-methoxycinnamic acid, and derivatives of caffeoylquinic, caffeoyl, and cinnamoyl against the enzymes prolyl oligopeptidase and dipeptidyl peptidase IV was carried out. Caffeoylquinic, caffeoyl, and cinnamoyl derivatives were prepared using simple derivatization procedures and through coupling reactions with the amino acid proline. The dipeptidyl peptidase IV assay showed inhibitory activity of the tested compounds at a high concentration (500 mu M) in the range of 81.5-7.2%. In contrast, the derivatives methyl ester and 1,7-acetonide obtained from chlorogenic acid, and caffeic acid and its methyl ester derivative showed selectivity and activity as prolyl oligopeptidase inhibitors, with IC50 values of 3 to 14mM.
• Chlorogenic Acid and Synthetic Chlorogenic Acid Derivatives:  Novel Inhibitors of Hepatic Glucose-6-phosphate Translocase
  作者：Horst Hemmerle、Hans-Joerg Burger、Peter Below、Gerrit Schubert、Robert Rippel、Peter W. Schindler、Erich Paulus、Andreas W. Herling

  DOI：10.1021/jm9607360

  日期：1997.1.1

  The enzyme system glucose-6-phosphatase (EC 3.1.3.9) plays a major role in the homeostatic regulation of blood glucose. It is responsible for the formation of endogenous glucose originating from gluconeogenesis and glycogenolysis. Recently, chlorogenic acid was identified as a specific inhibitor of the glucose-6-phosphate translocase component (G1-6-P translocase) of this enzyme system in microsomes of rat liver. Glucose B-phosphate hydrolysis was determined in the presence of chlorogenic acid or of new synthesized derivatives in intact rat liver microsomes in order to assess the inhibitory potency of the compounds on the translocase component. Variation in the 3-position of chlorogenic acid had only poor effects on inhibitory potency. Introduction of lipohilic side chain in the 1-position led to 100-fold more potent inhibitors. Functional assays on isolated perfused rat liver with compound 29i, a representative of the more potent derivatives, showed a dose-dependent inhibition of gluconeogenesis and glycogenolyosis, suggesting glucose-6-phosphatase as the locus of interference of the compound for inhibition of hepatic glucose production also in the isolated organ model. G1-6-P translocase inhibitors may be useful for the reduction of inappropriately high rates of hepatic glucose output often found in non-insulin-dependent diabetes.