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6-羟基四羟黄酮 | 18003-33-3

中文名称
6-羟基四羟黄酮
中文别名
——
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
6-羟基四羟黄酮化学式
CAS
18003-33-3
化学式
C15H10O7
mdl
——
分子量
302.24
InChiKey
VYAKIUWQLHRZGK-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

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。

SDS

SDS:cbc4c9cecdf5179515c9154779f16d86
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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。

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量
    • 1
    • 2
    • 3
  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量
    • 1
    • 2

反应信息

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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%甘甜菜碱6,约总9%的氨基酸用脯酸为主要化合物酸,以及约61%单-和低聚碳水化合物蔗糖为主要化合物。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-n-4-1 3a,5,6,7-三羟基-8-(吡咯烷基甲基)-2-苯基-4H-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,
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