6-羟基四羟黄酮 | 18003-33-3

• 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: 6-羟基四羟黄酮
• 英文名称: 3',4',5,6,7-pentahydroxyflavone
• 英文别名: 5,6,7,3′,4′-pentahydroxyflavone；5,6,7,3',4'-pentahydroxy flavone；5,6,7,3',4'-pentahydroxyflavone；6-hydroxyluteolin；6-hydroxylutelin；uteolin；2-(3,4-dihydroxyphenyl)-5,6,7-trihydroxychromen-4-one
• CAS: 18003-33-3
• 化学式: C₁₅H₁₀O₇
• 分子量: 302.24
• InChiKey: VYAKIUWQLHRZGK-UHFFFAOYSA-N

物化性质

• 熔点：
  275 °C
• 沸点：
  706.4±60.0 °C(Predicted)
• 密度：
  1.763±0.06 g/cm3(Predicted)
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  127
• 氢给体数：
  5
• 氢受体数：
  7

安全信息

• 海关编码：
  2914501900
• 储存条件：
  存储条件：2-8°C，密封保存，并保持干燥。

制备方法与用途

6-羟基木犀草素（化合物17）是一种类黄酮化合物，具有抑制醛糖还原酶（AR）的作用。

反应信息

• 作为反应物：
  描述：

  6-羟基四羟黄酮 在 吡啶 、 sodium hydroxide 、 dipotassium peroxodisulfate 、 potassium carbonate 、 丙酮 作用下， 生成 川陈皮素
  参考文献：
  名称：

  Murti; Seshadri, Proceedings - Indian Academy of Sciences, Section A, 1948, # 27, p. 217,220

  摘要：

  DOI：
• 作为产物：
  描述：

  羟基木犀草素 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 4.0h， 生成 6-羟基四羟黄酮
  参考文献：
  名称：

  Tlc, uv and acidic treatment in the differentiation of 5,6- and 5,8-dihydroxyflavones, 3-methoxyflavones and flavonols

  摘要：

  DOI：

  10.1016/s0040-4020(01)91379-1

文献信息

• [EN] PROCESS FOR SYNTHESIS OF OROXYLIN A<br/>[FR] PROCÉDÉ DE SYNTHÈSE D'OROXYLINE A
  申请人：MAJEED MUHAMMED

  公开号：WO2020032913A1

  公开（公告）日：2020-02-13

  Disclosed is a novel, simple, scalable and environment friendly process for the synthesis of Oroxylin A from Baicalin. Baicalm is esterified to obtain a methyl ester which is further selectively methylated to provide Oroxylin A gluciironide methyl ester which on de- glycosylation results in the formation of Oroxylin A.

  揭示了一种新颖、简单、可扩展且环境友好的过程，用于从黄芩苷合成黄芩素A。将黄芩苷酯化以获得甲酯，进一步选择性地甲基化以提供黄芩素A葡糖苷甲酯，脱糖后形成黄芩素A。
• Process for synthesis of Oroxylin A
  申请人：Majeed Muhammed

  公开号：US10407401B1

  公开（公告）日：2019-09-10

  Disclosed is a novel, simple, scalable and environment friendly process for the synthesis of Oroxylin A from Baicalin. Baicalin is esterified to obtain a methyl ester which is further selectively methylated to provide Oroxylin A glucuronide methyl ester which on de-glycosylation results in the formation of Oroxylin A.

  揭示了一种新颖、简单、可扩展且环境友好的过程，用于从黄芩苷合成黄芩素A。将黄芩苷酯化以获得甲酯，进一步选择性地进行甲基化以提供甲酯化的黄芩素A葡萄糖苷，脱糖后形成黄芩素A。
• Phytochemical Characterization of Low Molecular Weight Constituents from Marshmallow Roots (<i>Althaea officinalis</i>) and Inhibiting Effects of the Aqueous Extract on Human Hyaluronidase-1
  作者：Jandirk Sendker、Ines Böker、Isabelle Lengers、Simone Brandt、Joachim Jose、Timo Stark、Thomas Hofmann、Careen Fink、Heba Abdel-Aziz、Andreas Hensel

  DOI：10.1021/acs.jnatprod.6b00670

  日期：2017.2.24

  Extract RE was obtained from the roots of Althaea officinalis in a yield of 8.1%, related to the dried plant material, by extraction with MeOH–H2O (1:1), followed by precipitation with EtOH to remove high molecular weight constituents. Phytochemical investigation of RE revealed the presence of N-phenylpropenoyl-l-amino acid amides 1–5, 8% glycine betaine 6, about 9% total amino acids with proline as

  提取物RE是从山茱的根中提取的，相对于干燥的植物材料，其提取率为8.1％，方法是用MeOH-H 2 O（1：1）提取，然后用EtOH沉淀以除去高分子量成分。的植物化学物质调查RE揭示的存在Ñ -phenylpropenoyl-升-氨基酸酰胺1 - 5，8％甘氨酸甜菜碱6，约总9％的氨基酸用脯氨酸为主要化合物酸，以及约61％单-和低聚碳水化合物与蔗糖为主要化合物。进一步分馏显示存在次黄素二糖苷（12）和四个带有O-磺基碳水化合物部分的次黄素苷（7 – 9和11）；另外，4'- ö -methylisoscutellarein -8- ö -β- d - （3“ -直径：磺基）glucuronopyranoside（10）和所述diglycosylated香豆素haploperoside d（13）进行了鉴定。该hypolaetin- Ø -sulfoglycosides 7 - 10是新的天然产品。RE通过IC
• Importance of the B Ring and Its Substitution on the α-Glucosidase Inhibitory Activity of Baicalein, 5,6,7-Trihydroxyflavone
  作者：Hong GAO、Jun KAWABATA

  DOI：10.1271/bbb.68.1858

  日期：2004.1

  Hydroxychromones and B-ring-substituted 5,6,7-trihydroxyflavones were prepared to evaluate the contribution of the B ring of baicalein (5,6,7-trihydroxyflavone, 1) to its potent α-glucosidase inhibitory activity. Hydroxychromones, which lack 6-hydroxyl substitution, did not show any inhibitory activity, while 5,6,7-trihydroxy-2-methylchromone (5) showed high activity. Among the tested B-ring-substituted 5,6,7-trihydroxyflavones, the 4′-hydroxy-, 3′,4′-dihydroxy-, and 3′,4′,5′-trihydroxy-substituted derivatives were found to give more activity than that of 1. The methoxy-substituted derivatives, however, showed less activity than 1. The results suggest that the B ring of 1 was not essential, although advantageous to the activity; hydroxyl substitution on the B ring of 5,6,7-trihydroxyflavones was favorable to the activity, whereas methoxyl substitution was unfavorable; at least 4′-hydroxyl substitution of 5,6,7-trihydroxyflavones was required for enhanced activity, in which the number of hydroxyl groups did not take part.

  为了评估黄芩素（5,6,7-三羟基黄酮，1）的 B 环对其强效α-葡萄糖苷酶抑制活性的贡献，我们制备了羟基色酮和 B 环取代的 5,6,7- 三羟基黄酮。缺乏 6-羟基取代的羟基色酮没有显示出任何抑制活性，而 5,6,7-三羟基-2-甲基色酮（5）则显示出较高的活性。在测试的 B 环取代的 5,6,7-三羟基黄酮中，4′-羟基、3′,4′-二羟基和 3′,4′,5′-三羟基取代的衍生物的活性高于 1。结果表明，1 的 B 环虽然对活性有利，但并不是必需的；5,6,7-三羟基黄酮 B 环上的羟基取代对活性有利，而甲氧基取代则不利；5,6,7-三羟基黄酮至少需要 4′-羟基取代才能提高活性，羟基的数量与活性无关。
• Nitrogen-containing flavonoid analogues as CDK1/cyclin B inhibitors: Synthesis, SAR analysis, and biological activity
  作者：Shixuan Zhang、Jigang Ma、Yongming Bao、Puwen Yang、Liang Zou、Kangjian Li、Xiaodan Sun

  DOI：10.1016/j.bmc.2008.06.055

  日期：2008.8

  A series of nitrogen-containing flavonoid analogues were designed and synthesized by Mannich reaction, and screened for the inhibitory activities of cyclin-dependent kinases using a FRET-based biochemical assay method. The results showed that C-8 nitrogen-containing baicalein analogues 3a-3f exhibited potent CDK1/Cyclin B inhibitory activities. 5,6,7-Trihydroxy-8-(dimethylaminomethyl)-2-phenyl-4H-chromen-4-one

  通过曼尼希反应设计和合成了一系列含氮类黄酮类似物，并使用基于FRET的生化分析方法筛选了细胞周期蛋白依赖性激酶的抑制活性。结果表明，C-8含氮黄ical素类似物3a-3f表现出有效的CDK1 / Cyclin B抑制活性。5,6,7-三羟基-8-（二甲基氨基甲基）-2-苯基-4H-铬n-4-1 3a，5,6,7-三羟基-8-（吡咯烷基甲基）-2-苯基-4H-铬n- 4-one 3b和5,6,7-三羟基-8-（哌啶基甲基）-2-苯基-4H-chromen-4-one 3c（IC（50）1.05-1.28 microM）的效力是黄ical素2的约六倍（IC（50）6.53 microM）。5,6,7-三羟基-8-（吗啉代甲基）-2-苯基-4H-chromen-4-one 3d，5,6,7-三羟基-8-（硫代吗啉代）-2-苯基-4H-chrom en- 4个3e和5,6，