车轴草醇 | 487-24-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 车轴草醇
• 中文别名: 7-羟基-4'-甲氧基黄酮(普拉托尔)
• 英文名称: pratol
• 英文别名: 7-hydroxy-4'-methoxyflavone；7-hydroxy-2-(4-methoxyphenyl)-4H-chromen-4-one；7-hydroxy-4′-methoxyflavone；7-hydroxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one；4'-Methoxy-7-hydroxyflavone；7-hydroxy-2-(4-methoxyphenyl)chromen-4-one
• CAS: 487-24-1
• 化学式: C₁₆H₁₂O₄
• 分子量: 268.269
• InChiKey: SQVXWIUVAILQRH-UHFFFAOYSA-N

物化性质

• 熔点：
  263-264°C
• 沸点：
  479.4±45.0 °C(Predicted)
• 密度：
  1.329±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）
• LogP：
  3.590 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

ADMET

代谢

7-羟基-4'-甲氧基黄酮已知的人类代谢物包括(2S,3S,4S,5R)-3,4,5-三羟基-6-[2-(4-甲氧基苯基)-4-氧代色原-7-基]氧杂环己烷-2-羧酸。

7-Hydroxy-4p-methoxyflavone has known human metabolites that include (2S,3S,4S,5R)-3,4,5-trihydroxy-6-[2-(4-methoxyphenyl)-4-oxochromen-7-yl]oxyoxane-2-carboxylic acid.

来源:NORMAN Suspect List Exchange

安全信息

• 储存条件：
  存储条件：2-8°C，干燥，密封。

制备方法与用途

Pratol 是一种有效的 NF-κB 抑制剂，显著降低了 LPS 刺激的 RAW 264.7 细胞中 NO 和前列腺素 PGE2 的产生，并且没有细胞毒性。此外，Pratol 还能减少促炎细胞因子的表达。因此，Pratol 可用于炎性疾病和癌症的研究。

反应信息

• 作为反应物：
  描述：

  车轴草醇 在 氢碘酸 作用下， 生成 大豆甙元
  参考文献：
  名称：

  761.地下三叶草的化学性质。第一部分。formononetin和染料木黄酮的分离

  摘要：

  DOI：

  10.1039/jr9510003447
• 作为产物：
  描述：

  2'-hydroxy-4'-(methoxymethoxy)-4-methoxychalcone 在 碘 作用下， 以 二甲基亚砜 为溶剂， 反应 0.33h， 以81.5%的产率得到车轴草醇
  参考文献：
  名称：

  Synthesis and biological evaluations of chalcones, flavones and chromenes as farnesoid x receptor (FXR) antagonists

  摘要：

  Farnesoid X receptor (FXR), a nuclear receptor mainly distributed in liver and intestine, has been regarded as a potential target for the treatment of various metabolic diseases, cancer and infectious diseases related to liver. Starting from two previously identified chalcone-based FXR antagonists, we tried to increase the activity through the design and synthesis of a library containing chalcones, flavones and chromenes, based on substitution manipulation and conformation (ring closure) restriction strategy. Many chalcones and four chromenes were identified as microM potent FXR antagonists, among which chromene 11c significantly decreased the plasma and hepatic triglyceride level in KKay mice. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.02.037

文献信息

• Accurate Prediction of Glucuronidation of Structurally Diverse Phenolics by Human UGT1A9 Using Combined Experimental and In Silico Approaches
  作者：Baojian Wu、Xiaoqiang Wang、Shuxing Zhang、Ming Hu

  DOI：10.1007/s11095-012-0666-z

  日期：2012.6

  Catalytic selectivity of human UGT1A9, an important membrane-bound enzyme catalyzing glucuronidation of xenobiotics, was determined experimentally using 145 phenolics and analyzed by 3D-QSAR methods. Catalytic efficiency of UGT1A9 was determined by kinetic profiling. Quantitative structure activity relationships were analyzed using CoMFA and CoMSIA techniques. Molecular alignment of substrate structures was made by superimposing the glucuronidation site and its adjacent aromatic ring to achieve maximal steric overlap. For a substrate with multiple active glucuronidation sites, each site was considered a separate substrate. 3D-QSAR analyses produced statistically reliable models with good predictive power (CoMFA: q2 = 0.548, r2 = 0.949, r pred 2  = 0.775; CoMSIA: q2 = 0.579, r2 = 0.876, r pred 2  = 0.700). Contour coefficient maps were applied to elucidate structural features among substrates that are responsible for selectivity differences. Contour coefficient maps were overlaid in the catalytic pocket of a homology model of UGT1A9, enabling identification of the UGT1A9 catalytic pocket with a high degree of confidence. CoMFA/CoMSIA models can predict substrate selectivity and in vitro clearance of UGT1A9. Our findings also provide a possible molecular basis for understanding UGT1A9 functions and substrate selectivity.

  通过实验使用145种酚类化合物，并通过3D-QSAR方法分析，确定了人UGT1A9的催化选择性。UGT1A9是一种重要的膜结合酶，催化外源性物质的葡糖醛酸化反应。通过动力学分析确定了UGT1A9的催化效率。使用CoMFA和CoMSIA技术分析了定量结构活性关系。通过将葡糖醛酸化位点及其相邻的芳香环重叠，实现了底物结构的最大立体重叠。对于具有多个活性葡糖醛酸化位点的底物，每个位点被视为单独的底物。3D-QSAR分析产生了统计上可靠的模型，具有良好的预测能力（CoMFA：q2=0.548，r2=0.949，r pred 2=0.775；CoMSIA：q2=0.579，r2=0.876，r pred 2=0.700）。通过轮廓系数图阐明了底物中负责选择性差异的结构特征。将轮廓系数图叠加在UGT1A9的同源模型的催化口袋中，能够高度自信地识别UGT1A9的催化口袋。CoMFA/CoMSIA模型可以预测底物的选择性和UGT1A9的体外清除率。我们的发现还提供了理解UGT1A9功能和底物选择性的可能分子基础。
• 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。
• An Efficient Approach to Dihydrofuroflavonoids<i>via</i>Palladium-Catalyzed Annulation of 1,3-Dienes by<i>o</i>-Iodoacetoxyflavonoids
  作者：Roman V. Rozhkov、Richard C. Larock

  DOI：10.1002/adsc.200404226

  日期：2004.12

  The palladium-catalyzed annulation of 1,3-dienes by o-iodoacetoxyflavonoids provides an efficient approach to biologically interesting dihydrofuroflavonoids. This reaction is very general, stereo- and regioselective, and a wide variety of terminal, cyclic and internal 1,3-dienes can be utilized.

  邻碘乙酰氧基类黄酮在钯催化的1,3-二烯上的环化反应提供了一种有效的方法，用于制备生物学上令人关注的二氢呋喃类黄酮。该反应是非常普遍的，立体和区域选择性的，并且可以使用各种各样的末端，环状和内部的1，3-二烯。
• GLUCOSYRINGIC ACID ANALOGS AS SWEETNESS PROFILE MODIFIERS
  申请人：PepsiCo, Inc.

  公开号：US20180020708A1

  公开（公告）日：2018-01-25

  The present disclosure provides novel sweetener compositions comprising a compound having a structure according to Formula I: wherein R 1 , R 2 , R 3 , and R 4 are described herein. Also provided are methods of modulating sweetness profile of a product by adding a compound of Formula I to the product, such as a beverage product or a food product. For example, the compound described herein can be added to increase the overall sweetness of a nutritive sweetener sweetened beverages; decrease the sweetness time-of-onset for high potency sweeteners such as rebaudioside A; decreasing bitter, metallic and licorice off-notes of high potency sweeteners; and improve the sweet quality of sweetened products.

  本公开提供了包含具有如下式I的结构的化合物的新型甜味剂组合物： 其中R1、R2、R3和R4如本文所述。还提供了通过向产品添加式I的化合物来调节产品的甜味特性的方法，例如饮料产品或食品产品。例如，本文描述的化合物可添加以增加富含甜味剂的饮料的整体甜度；减少高效甜味剂（如甜菊糖A）的甜味起始时间；减少高效甜味剂的苦味、金属味和甘草味等异味；并改善甜味产品的甜味质量。
• COLORING AGENTS AND METHODS OF USE THEREOF
  申请人：Living Proof, Inc.

  公开号：US20160106648A1

  公开（公告）日：2016-04-21

  Dyes, compositions comprising dyes and methods for using the same are provided.

  染料、包含染料的组合物以及使用这些染料的方法。