3-O-对香豆酰基奎宁酸 | 1899-30-5

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-O-对香豆酰基奎宁酸
• 英文名称: trans-3-p-coumaroylquinic acid
• 英文别名: 5-O-(trans-p-coumaroyl)quinic acid；5'-O-(E-4-coumaroyl)-quinic acid；5-O-trans-p-coumaroylquinic acid；trans-3-O-p-coumaroylquinic acid；3-O-(E)-p-coumaroylquinic acid；3-O-trans-Coumaroylquinic acid；trans-5-O-(4-coumaroyl)-D-quinic acid；(1S,3R,4R,5R)-1,3,4-trihydroxy-5-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxycyclohexane-1-carboxylic acid
• CAS: 1899-30-5；5746-55-4；32451-86-8；32719-13-4；82659-64-1；82659-65-2；82889-89-2；87099-71-6；87099-74-9
• 化学式: C₁₆H₁₈O₈
• 分子量: 338.314
• InChiKey: BMRSEYFENKXDIS-OTCYKTEZSA-N

物化性质

• 沸点：
  613.2±55.0 °C(Predicted)
• 密度：
  1.55±0.1 g/cm3(Predicted)
• 稳定性/保质期：

  存在于烟叶中。

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  24
• 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：
  145
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-O-对香豆酰基奎宁酸 在 硫酸 1-环已基-2-吗啉乙基碳二亚胺对甲苯磺酸盐 、 1-羟基苯并三唑 作用下， 生成
  参考文献：
  名称：

  WO2008/9138

  摘要：

  公开号：
• 作为产物：
  描述：

  右旋奎宁酸 在 盐酸 、 sodium hydroxide 、 硫酸 、 sodium hydride 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 33.0h， 生成 3-O-对香豆酰基奎宁酸
  参考文献：
  名称：

  Chlorogenic Acid and Synthetic Chlorogenic Acid Derivatives:  Novel Inhibitors of Hepatic Glucose-6-phosphate Translocase

  摘要：

  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.

  DOI：

  10.1021/jm9607360

文献信息

• CHEMOSENSORY RECEPTOR LIGAND-BASED THERAPIES
  申请人：Anji Pharma (US) LLC

  公开号：EP3763419A1

  公开（公告）日：2021-01-13

  Provided herein are methods for treating conditions associated with a chemosensory receptor, including diabetes, obesity, and other metabolic diseases, disorders or conditions by administrating a composition comprising a chemosensory receptor ligand, such as a bitter receptor ligand. Also provided herein are chemosensory receptor ligand compositions, including bitter receptor ligand compositions, and methods for the preparation thereof for use in the methods of the present invention. Also provided herein are compositions comprising metformin and salts thereof and methods of use.

  本文提供了通过施用包含化感受体配体（如苦味受体配体）的组合物来治疗与化感受体相关的病症（包括糖尿病、肥胖症和其他代谢性疾病、失调或病症）的方法。本文还提供了化学感觉受体配体组合物，包括苦味受体配体组合物，及其用于本发明方法的制备方法。本文还提供了包含二甲双胍及其盐类的组合物和使用方法。
• Chemosensory receptor ligand-based therapies
  申请人：Anji Pharma (US) LLC

  公开号：US10610500B2

  公开（公告）日：2020-04-07

  Provided herein are methods for treating conditions associated with a chemosensory receptor, including diabetes, obesity, and other metabolic diseases, disorders or conditions by administrating a composition comprising a chemosensory receptor ligand, such as a bitter receptor ligand. Also provided herein are chemosensory receptor ligand compositions, including bitter receptor ligand compositions, and methods for the preparation thereof for use in the methods of the present invention. Also provided herein are compositions comprising metformin and salts thereof and methods of use.

  本文提供了通过施用包含化感受体配体（如苦味受体配体）的组合物来治疗与化感受体相关的病症（包括糖尿病、肥胖症和其他代谢性疾病、失调或病症）的方法。本文还提供了化学感觉受体配体组合物，包括苦味受体配体组合物，及其用于本发明方法的制备方法。本文还提供了包含二甲双胍及其盐类的组合物和使用方法。
• Whole green coffee bean products and methods of production and use for preventing or treating obesity and diabetes
  申请人：GOBEAN GREEN COFFEE PRODUCTS, LLC

  公开号：US11083769B2

  公开（公告）日：2021-08-10

  Disclosed are novel processing methods for green coffee beans that result in novel green coffee bean products, including products that incorporate whole green coffee beans. Methods include selecting whole coffee beans in their fresh green unroasted state with naturally-occurring levels of phytonutrients, sterilizing and drying them, applying iterative grinding processes and stabilization techniques, all while avoiding high temperatures. Whole green coffee bean products created and defined by these methods are used to treat or prevent diabetes and obesity.

  本发明公开了新颖的绿咖啡豆加工方法，可加工出新颖的绿咖啡豆产品，包括含有整粒绿咖啡豆的产品。这些方法包括挑选新鲜绿色、未经烘焙、含有天然植物营养素的整粒咖啡豆，对其进行灭菌和干燥处理，采用迭代研磨工艺和稳定技术，同时避免高温。通过这些方法制作和定义的全绿色咖啡豆产品可用于治疗或预防糖尿病和肥胖症。
• Identification and Quantification of Phenolic Compounds from the Forage Legume Sainfoin (Onobrychis viciifolia)
  作者：Ionela Regos、Andrea Urbanella、Dieter Treutter

  DOI：10.1021/jf900625r

  日期：2009.7.8

  Phenolic compounds of sainfoin (Onobrychis viciifolia) variety Cotswold Common are assumed to contribute to its nutritive value and bioactive properties. A purified acetone/water extract was separated by Sephadex LH-20 gel chromatography. Sixty-three phenolic and other aromatic compounds were identified by means of chemical, chromatographic, and spectroscopic methods. Reverse phase HPLC with diode array and chemical reaction detection was used to investigate the phenolic composition of different plant organs. All plant parts showed specific phenolic profiles. Moreover, there were considerable variations in the phenolic content among individual plants of the same variety. The three most abundant phenolic compounds were found to be arbutin [predominant in petiols, 17.7 mg/g of dry weight (DW)], rutin (predominant in leaves, 19.9 mg/g of DW), and catechin (predominant flavanol in petiols, 3.5 mg/g of DW). The present study reveals that the phenolic profile of sainfoin is even more complex than hitherto assumed.
• Synthesis of chlorogenic acid derivatives with promising antifungal activity
  作者：Chao-Mei Ma、Maureen Kully、Jehangir K. Khan、Masao Hattori、Mohsen Daneshtalab

  DOI：10.1016/j.bmc.2007.07.038

  日期：2007.11

  Derivatives of chlorogenic acid or its analogues were synthesized by coupling protected chlorogenic acid or its analogues with p-octyloxyaniline and selected amino acids. Most of the compounds exhibited significant potency against Cryptococcus neoformans and Candida species with low toxicity to brine shrimps. The 4,5-dihydroxyl groups in the quinic acid moiety were necessary for the activity and introduction of a free amino group increased the inhibitory activity against Aspergillus fumigatus. (C) 2007 Elsevier Ltd. All rights reserved.