CAS: 80366-15-0; 2',3,5,6',7-Pentahydroxyflavanone

该化合物是一种氟甲类化合物,其特点是与法原龙骨相连的多种羟基(-OH)组,这种结构有助于其潜在的抗氧化性特性,因为氢氧组可以蒸发自由基.该化合物通常出现在各种植物中,并可能在植物防御机制和颜料中发挥作用.其溶解性受这些氢氧基组的存在影响,使其在极地溶剂中更易溶解.此外,2,3,5,6,6,6,7欧元-丙氧基氟丙酮可能展示出各种生物活动,包括抗氟化和抗微生物效应,这在药理学研究中具有意义.多种氢氧基组的存在还表明,它可能与生物巨蛋白质和核酸等生物巨蛋白素发生相互作用,从而影响其生物活动.

英文名称2',3,5,6',7-Pentahydroxyflavanone
中文名称甘肃黄芩素; 2',5,6',7-四羟基二氢黄烷酮
IUPAC名称2-(2,6-dihydroxyphenyl)-3,5,7-trihydroxychroman-4-one
其它别名4H-1-Benzopyran-4-One, 2-(2,6-Dihydroxyphenyl)-2,3-Dihydro-3,5,7-Trihy Droxy-, (2R,3R)-; 2',3,5,6',7-Pentahydroxyflavane; 2',3,5,6',7-Pentahydroxyflavanone; (2R,3R)-2',3,5,6',7-Pentahydroxyflavanone; 2',6'-Dihydroxypinobanksin; 3,5,7,2',6'-Pentahydroxyflavanone; Ganhuangemin; Trans-5,7,2',6'-Tetrahydroxyflavanonol
CAS编号80366-15-0
MFCD编号:MFCD21333525
分子式:C15H12O7分子量:304.25
产品CID: 1798984
产品分类天然产物 → 黄酮类化合物

相似结构搜索
产品信息参考;
InChIKey: NBQYBZYBTNQEQG-LSDHHAIUSA-N
InChI=1S/C15H12O7/c16-6-4-9(19)12-10(5-6)22-15(14(21)13(12)20)11-7(17)2-1-3-8(11)18/h1-5,14-19,21H
计算化学: 氢键受体数7.0氢键供体数5.0可旋转键数1.0

物理性质

沸点713.4±60.0 °C(预测)
闪点273.8 °C
密度1.702±0.06 g/cm3(预测)
pKa:7.37±0.60(预测)
PSA:127.45
LogP:1.1863
蒸汽压2.33E-21 mmHg at 25 °C
溶解性Soluble In Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,Etc.
外观形态粉末
储存条件2-8°C

上下游产品

2,4,6-trihydroxyacetophenone 2,6-dihydroxybenzaldehyde 2,6-bis((2-methoxyethoxy)methoxy)benzaldehyde 5,7,3,2′,6′-pentahydroxy flavanone

合成工艺路线路线简述

1402054-86-7 = 80366-15-0 [标题:Reaction Conditions
标题:Stereospecific Inhibition Of Nitric Oxide Production In Macrophage Cells By Flavanonols: Synthesis And The Structure-Activity Relationship
作者:Jiang,Wen-Jun; Et Al
参考文献:Bioorganic & Medicinal Chemistry 日期:2015 卷标:23(21) 页码:6922-6929]

= 80366-15-0
反应条件:1.1 Reagents: Sodium Hydroxide,Hydrogen Peroxide Solvents: Methanol,Water; 3 H,Rt2.1 Reagents: Hydrochloric Acid Solvents: Methanol; 25 Min,55 °C3.1 -
标题:Stereospecific Inhibition Of Nitric Oxide Production In Macrophage Cells By Flavanonols: Synthesis And The Structure-Activity Relationship
作者:Jiang,Wen-Jun; Et Al
参考文献:Bioorganic & Medicinal Chemistry 日期:2015 卷标:23(21) 页码:6922-6929]

480-66-0 = 80366-15-0
反应条件:1.1 Reagents: Sodium Hydride Solvents: Dimethylformamide; 0 - 5 °C1.2 15 Min,< 5 °C; 30 Min,Rt1.3 Reagents: Water; Cooled2.1 Reagents: Potassium Hydroxide Solvents: Ethanol; 3 H,Rt3.1 Reagents: Sodium Hydroxide,Hydrogen Peroxide Solvents: Methanol,Water; 3 H,Rt4.1 Reagents: Hydrochloric Acid Solvents: Methanol; 25 Min,55 °C5.1 -
标题:Stereospecific Inhibition Of Nitric Oxide Production In Macrophage Cells By Flavanonols: Synthesis And The Structure-Activity Relationship
作者:Jiang,Wen-Jun; Et Al
参考文献:Bioorganic & Medicinal Chemistry 日期:2015 卷标:23(21) 页码:6922-6929]

= 80366-15-0
反应条件:1.1 Reagents: Hydrochloric Acid Solvents: Methanol; 25 Min,55 °C2.1 -
标题:Stereospecific Inhibition Of Nitric Oxide Production In Macrophage Cells By Flavanonols: Synthesis And The Structure-Activity Relationship
作者:Jiang,Wen-Jun; Et Al
参考文献:Bioorganic & Medicinal Chemistry 日期:2015 卷标:23(21) 页码:6922-6929]

36804-11-2 + 79834-12-1 = 80366-15-0
反应条件:1.1 Reagents: Potassium Hydroxide Solvents: Ethanol; 3 H,Rt2.1 Reagents: Sodium Hydroxide,Hydrogen Peroxide Solvents: Methanol,Water; 3 H,Rt3.1 Reagents: Hydrochloric Acid Solvents: Methanol; 25 Min,55 °C4.1 -
标题:Stereospecific Inhibition Of Nitric Oxide Production In Macrophage Cells By Flavanonols: Synthesis And The Structure-Activity Relationship
作者:Jiang,Wen-Jun; Et Al
参考文献:Bioorganic & Medicinal Chemistry 日期:2015 卷标:23(21) 页码:6922-6929]

387-46-2 = 80366-15-0
反应条件:1.1 Reagents: Potassium Carbonate Solvents: Acetone; Rt -> 5 °C1.2 15 Min,< 5 °C; 30 Min,Rt1.3 Reagents: Water; Cooled2.1 Reagents: Potassium Hydroxide Solvents: Ethanol; 3 H,Rt3.1 Reagents: Sodium Hydroxide,Hydrogen Peroxide Solvents: Methanol,Water; 3 H,Rt4.1 Reagents: Hydrochloric Acid Solvents: Methanol; 25 Min,55 °C5.1 -
标题:Stereospecific Inhibition Of Nitric Oxide Production In Macrophage Cells By Flavanonols: Synthesis And The Structure-Activity Relationship
作者:Jiang,Wen-Jun; Et Al
参考文献:Bioorganic & Medicinal Chemistry 日期:2015 卷标:23(21) 页码:6922-6929

📜2,6-Bis(Methoxymethoxy)Benzaldehyde置于盐酸,双氧水,Potassium Hydroxide,Sodium Hydroxide体系中,用甲醇,乙醇,正己烷,水作为反应溶剂,化学反应 6.42H,反应生成 Trans-5,7,2',6'-Tetrahydroxyflavanonol,甘肃黄芩素; 2',5,6',7-四羟基二氢黄烷酮
参考文献:Stereospecific Inhibition Of Nitric Oxide Production In Macrophage Cells By Flavanonols: Synthesis And The Structure-activity Relationship
标题:Stereospecific Inhibition Of Nitric Oxide Production In Macrophage Cells By Flavanonols: Synthesis And The Structure-activity Relationship
摘要:To Explore The Structure-Activity Relationships On The Inhibitory Activity Of Flavanonols Against Nitric Oxide (No) Production In Inflammatory Cells,We Synthesized 19 Flavanonols Which Shared A Common 3,5,7-Trihydroxychroman Scaffold. A Range Of Substitutions Was Included In The B Ring In Order To Investigate The Structure-Activity Relationship. We Also Succeeded In Isolating Stereoisomers From 16 Of The Flavanonols Using Chiral Column Chromatography. The Inhibitory Effects Of These Compounds On No Production Were Examined In Raw 264.7 Cells (A Murine Macrophage-Like Cell Line),Which Were Activated By Lipopolysaccharide (Lps). We Only Observed Inhibitory Activity Against No Production In (2R,3R) Stereoisomers,While The Inhibitory Activities Of (2S,3S) Stereoisomers Were Significantly Weaker. We Also Evaluated The Free Radical Scavenging Potential Of The Flavanonols Using 1,1-Diphenyl-2-Picrylhydrazyl (Dpph). Each Stereoisomer Indicated The Equivalent Dpph Scavenging Potential As Expected. The Radical Scavenging Activity Was Not Correlated With The Inhibitory Activity Against No. The Inhibition Of No Production By Flavanonols Is Stereospecific And Cannot Simply Be Explained By Their Radical Scavenging Activity. We Propose The Possible Existence Of A 'Target' Molecule For Flavanonols Which Is Involved In The Production And/or Regulation Of No In Raw 264.7 Cells. (C) 2015 Elsevier Ltd. All Rights Reserved.
DOI:10.1016/j.Bmc.2015.09.042