CAS: 90-19-7; 2-(3,4-Dihydroxyphenyl)-3,5-Dihydroxy-7-Methoxy-4H-Chromen-4-One

该化合物是一种该化合物是一种自制的甲酸衍生物,这种改变增强了其代谢稳定性和生物利用率,使其与母体化合物相比,成为生化和药理研究的宝贵工具.7位置上的甲基化改善了亲脂性,有利于更好的细胞吸收和膜渗透性.它显示出强效抗氧化剂,抗炎和潜在的抗癌特性,研究表明,NF-B和MAPK等调制信号路径的功效有所提高.它在生理条件下的稳定使其适合进行体外和活体内研究,为研究人员提供了调查浮质代生物影响的可靠化合物.

结构式图片

欧盟法规

ECHA物质C&L通报REACH预注册

上下游产品

CAS号143631-95-2 3,3',4',5-tetra... | CAS号74-88-4 碘甲烷 | CAS号117-39-5 槲皮素 | CAS号77-78-1 硫酸二甲酯 | CAS号357194-03-7 2-(2,2-diphenyl... | CAS号186581-53-3 重氮甲烷 | CAS号857617-58-4 2-benzoyloxy-1-... | CAS号108-73-6 间苯三酚 | CAS号99-50-3 原儿茶酸 | CAS号117-39-5 槲皮素 | CAS号2174-64-3 5-甲氧基间苯二酚 | CAS号1245-15-4 栎精-3,7,3',4'-四甲醚 | CAS号552-54-5 3,7-二甲氧基-3',4',...

合成工艺路线路线简述

  • 合成目标产物 Rhamnetin 主要起始原料 Quercetin And Iodomethane
  • 498548-16-6 = 90-19-7
    反应条件:1.1 Reagents: Hydrochloric Acid Solvents: Acetic Acid,Water; 4 H,Reflux
    标题:A Planar Conformation And The Hydroxyl Groups In The B And C Rings Play A Pivotal Role In The Antioxidant Capacity Of Quercetin And Quercetin Derivatives
    作者:Moalin,Mohamed; Van Strijdonck,Gino P. F.; Beckers,Maud; Hagemen,Geja J.; Borm,Paul J.; Et Al
    参考文献:Molecules 日期:2011 卷标:16 页码:9636-9650]

    498548-19-9 = 90-19-7
    反应条件:1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol,Tetrahydrofuran; 12 H,1 Atm,Rt
    标题:Metabolism-Based Synthesis,Biologic Evaluation And Sars Analysis Of O-Methylated Analogs Of Quercetin As Thrombin Inhibitors
    作者:Shi,Zhi-Hao; Li,Nian-Guang; Tang,Yu-Ping; Li,Wei; Yin,Lian; Et Al
    参考文献:European Journal Of Medicinal Chemistry 日期:2012 卷标:54 页码:210-222]

    498548-19-9 = 90-19-7
    反应条件:1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol,Tetrahydrofuran; 12 H
    标题:Synthetic Studies On The Construction Of 7-O-Methylquercetin Through Regioselective Protection And Alkylation Of Quercetin
    作者:Li,Nian Guang; Shi,Zhi Hao; Tang,Yu Ping; Yang,Jian Ping; Lu,Tu Lin; Et Al
    参考文献:Chinese Chemical Letters 日期:2011 卷标:22(1) 页码:5-8]

    1247-97-8 = 90-19-7
    反应条件:1.1 Reagents: Boron Tribromide Solvents: Dichloromethane; 0 °C; 3 H,0 °C
    标题:Efficient Preparation Of Various O-Methylquercetins By Selective Demethylation
    作者:Kimura,Yuki; Kato,Ryo; Oyama,Kin-Ichi; Kondo,Tadao; Yoshida,Kumi
    参考文献:Natural Product Communications 日期:2016 卷标:11(7)]

    29908-03-0 + 117-39-5 = 90-19-7
    反应条件:1.1 Catalysts: Methionine S-Adenosyltransferase Solvents: Water; 36 H,25 °C
    标题:Optimization Of Rhamnetin Production In Escherichia Coli
    作者:Sung,Su Hyun; Kim,Bong-Gyu; Ahn,Joong-Hoon
    参考文献:Journal Of Microbiology And Biotechnology 日期:2011 卷标:21(8) 页码:854-857]

    16280-26-5 = 90-19-7
    反应条件:1.1 Reagents: Hydrochloric Acid Solvents: Acetonitrile,Water; 1.5 H,Rt
    标题:Regioselective O-Derivatization Of Quercetin Via Formation Of Ester Intermediates. An Improved Synthesis Of Rhamnetin And Development Of A New Mitochondriotropic Derivative
    作者:Mattarei,Andrea; Biasutto,Lucia; Rastrelli,Federico; Garbisa,Spiridione; Marotta,Ester; Et Al
    参考文献:Molecules 日期:2010 卷标:15 页码:4722-4736]

    117-39-5 = 90-19-7
    反应条件:1.1 Reagents: Ampicillin Catalysts: Flavonoid 7-O-Methyltransferase Solvents: Water; 12 H,30 °C
    标题:Regiospecific Flavonoid 7-O-Methylation With Streptomyces Avermitilis O-Methyltransferase Expressed In Escherichia Coli
    作者:Kim,Bong-Gyu; Jung,Bo-Ra; Lee,Youngshim; Hur,Hor-Gil; Lim,Yoongho; Et Al
    参考文献:Journal Of Agricultural And Food Chemistry 日期:2006 卷标:54(3) 页码:823-828]

    498548-19-9 = 90-19-7
    反应条件:1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol,Tetrahydrofuran; 25 °C
    标题:Biological Evaluation And Sar Analysis Of O-Methylated Analogs Of Quercetin As Inhibitors Of Cancer Cell Proliferation
    作者:Shi,Zhi-Hao; Li,Nian-Guang; Tang,Yu-Ping; Shi,Qian-Ping; Tang,Hao; Et Al
    参考文献:Drug Development Research 日期:2014 卷标:75(7) 页码:455-462]

    498548-19-9 = 90-19-7
    反应条件:1.1 Reagents: Hydrogen Catalysts: Palladium Dihydroxide Solvents: Ethanol,Tetrahydrofuran; Overnight,Rt1.2 Reagents: Acetic Acid Solvents: Water; Overnight,Reflux
    标题:Chemical Synthesis Of Flavonoid Conjugates
    作者:Barron,Denis; Cren-Olive,Cecile; Needs,Paul W.
    参考文献:Methods In Polyphenol Analysis 日期:2003 卷标:187 页码:187-213]

    498548-19-9 = 90-19-7
    反应条件:1.1 Reagents: Hydrogen Catalysts: Palladium Dihydroxide Solvents: Ethanol,Tetrahydrofuran; Overnight,Rt1.2 Reagents: Acetic Acid Solvents: Water; Overnight,Reflux1.3 Solvents: Ethyl Acetate,Water
    标题:Hemisynthesis Of All The O-Monomethylated Analogues Of Quercetin Including The Major Metabolites,Through Selective Protection Of Phenolic Functions
    作者:Bouktaib,Mohamed; Lebrun,Stephane; Atmani,Aziz; Rolando,Christian
    参考文献:Tetrahedron 日期:2002 卷标:58(50) 页码:10001-10009]

    117-39-5 = 90-19-7
    反应条件:1.1 Reagents: Sodium Bicarbonate,Borax (B4Na2O7.10H2O) Solvents: Acetone,Water; 30 Min,70 °C1.2 Reagents: Sodium Bicarbonate Solvents: Acetone; 6 H,50 °C1.3 Reagents: Hydrochloric Acid Solvents: Water; Ph 3 - 4
    标题:Selective Monomethylation Of Quercetin
    作者:Zhou,Zhong-Hua; Fang,Zhuan; Jin,Hui; Chen,Yue; He,Ling
    参考文献:Synthesis 日期:2010 卷标:(23) 页码:3980-3986]

    117-39-5 = 90-19-7
    反应条件:1.1 Catalysts: Flavonoid 7-O-Methyltransferase Solvents: Water; 12 H,30 °C
    标题:Regioselectivity Of 7-O-Methyltransferase Of Poplar To Flavones
    作者:Kim,Bong-Gyu; Kim,Hojung; Hur,Hor-Gil; Lim,Yoongho; Ahn,Joong-Hoon
    参考文献:Journal Of Biotechnology 日期:2006 卷标:126(2) 页码:241-247]

    153-18-4 = 90-19-7 + 603-61-2 + 529-40-8
    反应条件:1.1 Reagents: Potassium Carbonate Solvents: Dimethylformamide; 6 H,65 °C1.2 Reagents: Hydrochloric Acid Solvents: Water; 2 H,80 °C
    标题:Synthesized Quercetin Derivatives Stimulate Melanogenesis In B16 Melanoma Cells By Influencing The Expression Of Melanin Biosynthesis Proteins Mitf And P38 Mapk
    作者:Yamauchi,Kosei; Mitsunaga,Tohru; Inagaki,Mizuho; Suzuki,Tohru
    参考文献:Bioorganic & Medicinal Chemistry 日期:2014 卷标:22(13) 页码:3331-3340]

    117-39-5 = 90-19-7 + 2068-02-2 + 529-40-8 + 1486-70-0
    反应条件:1.1 Reagents: Potassium Carbonate Solvents: Acetone; Rt; 3 H,Rt
    标题:Quercetin Analogs With High Fetal Hemoglobin-Inducing Activity
    作者:Pabuprapap,Wachirachai; Wassanatip,Yanisa; Khetkam,Pichit; Chaichompoo,Waraluck; Kunkaewom,Sukanya; Et Al
    参考文献:Medicinal Chemistry Research 日期:2019 卷标:28(10) 页码:1755-1765]

    117-39-5 = 90-19-7 + 603-61-2 + 2068-02-2 + 1245-15-4 + 529-40-8 + 572-32-7
    反应条件:1.1 Solvents: Methanol; 1 H,Rt
    标题:Structural Requirements Of Flavonoids And Related Compounds For Aldose Reductase Inhibitory Activity
    作者:Matsuda,Hisashi; Morikawa,Toshio; Toguchida,Iwao; Yoshikawa,Masayuki
    参考文献:Chemical & Pharmaceutical Bulletin 日期:2002 卷标:50(6) 页码:788-795
3,5-Dihydroxy-7-Methoxy-3',4'-Diphenylmethylendioxy-Flavon置于溶剂黄146体系中,用 水 作为反应溶剂,化学反应生成 鼠李素
参考文献:Synthesis Of Quercetin And Luteolin Derivatives With Cell Proliferation Inhibitory Activity And Toxicity In B16 Melanoma Cells
标题:Synthesis Of Quercetin And Luteolin Derivatives With Cell Proliferation Inhibitory Activity And Toxicity In B16 Melanoma Cells
摘要:黑色素瘤是一种由黑色素细胞损伤引起的恶性皮肤肿瘤,可扩散到其他器官.因此,人们对防止黑色素瘤扩散进行了各种研究.芹菜素和高良姜素等黄酮类结构物质是抑制黑色素瘤增殖和转移的有效治疗药物.本研究合成了木犀草素,槲皮素及其各自的衍生物.这些化合物抑制了 B16 黑色素瘤细胞的增殖.这些结果证实,槲皮素和木犀草素的衍生物可作为防止黑色素瘤转移的治疗药物.
DOI:10.5012/jkcs.2023.67.3.181

海关参考信息

专利信息


专利号:US-2002165207-A1
优先权日:2001-05-02
标题 :Compositions and methods for the treatment of diabetic neuropathy
发明人:ROSENBLOOM RICHARD
摘要:Compositions and a method for the treatment of diabetic neuropathy is disclosed. The compositions comprise a mixture of a compound that promotes synthesis of nerve growth factor, an aldose reductase inhibitor and an antioxidant, optionally formulated in a pharmaceutically acceptable carrier. This combination of active agents provides significant, effective relief of the symptoms of diabetic neuropathy, as well as at least partial recovery of lost neurological function in some cases. In addition, the compositions of the present invention, when used in effective amounts to treat diabetic neuropathy, do not exhibit the severe side effects of many prior art compositions proposed for treatment of this ailment. n In a second aspect, a method for the administration of a composition in accordance with the present invention for the treatment of diabetic neuropathy is disclosed. In the method, an effective amount of the composition of the invention is administered on a regular basis over a period of time sufficient to provide the beneficial effects of relief from the symptoms of diabetic neuropathy, as well as at least some recovery of the damaged nerve tissues.

专利号:US-7914823-B2
优先权日:2000-12-21
标题 :Method and composition for the topical treatment of diabetic neuropathy
发明人:ROSENBLOOM RICHARD ALLEN
权利人:PROPHASE LABS INC
摘要:A method and composition for the treatment of diabetic neuropathy is disclosed. The composition comprises a cold compounded mixture of a compound that promotes synthesis of nerve growth factor, an aldose reductase inhibitor and an antioxidant formulated in a pharmaceutically acceptable carrier. It has been found that this combination of active agents provides significant, effective relief of the symptoms of diabetic neuropathy, as well as at least partial recovery of lost neurological function in some cases. In view of the consensus in the art that effective combinations of various active agents have not been demonstrated to be effective for the treatment of diabetic neuropathy, the present invention provides a surprising and unexpected effect. In addition, the topical compositions of the present invention, when used in effective amounts to treat diabetic neuropathy, do not exhibit the severe side effects of many prior art compositions proposed for treatment of this ailment. n In a second aspect, a method for the topical administration of a composition in accordance with the present invention for the treatment of diabetic neuropathy is disclosed. In the method, an effective amount of the composition of the invention is topically administered to the areas of the body that have been adversely affected by the diabetic neuropathy on a regular basis over a period of time sufficient to provide the beneficial effects of relief from the symptoms and at least some recovery of the damaged nerve tissues.

专利号:US-2007232495-A1
优先权日:2006-03-24
标题:Compositions and methods to add value to plant products, increasing the commercial quality, resistance to external factors and polyphenol content thereof
发明人:NAPPA ALVARO O; LORENZINI FELIPE C; SANHUEZA ANDRES L
权利人:NAPPA ALVARO O; LORENZINI FELIPE C; SANHUEZA ANDRES L
摘要:The invention is related to compositions and methods that naturally protect plant tissues against ultraviolet radiation and temperature, thus giving protection against sunburn to plants, plant parts, fruits and/or flowers during their development. The invention is also related to compositions and methods to naturally improve the color of plants, plant parts, fruits and/or flowers by inducing the natural synthesis of flavonoids and anthocyanins present in plants. Likewise, the present invention is directed to improving the nutritional value of plants, plant parts, fruits and/or flowers by increasing the normal levels of polyphenolic compounds, especially flavonoids, present therein. Additionally, the present invention is related to compositions and methods that give more resistance to plants, plant parts, fruits and/or flowers against pathogens as bacteria and fungi. Finally, the present invention is related to plants, plant parts, fruits, flowers and/or propagating material treated with the compositions described in the present document.

专利号:US-12036300-B2
优先权日:2021-03-31
标题:Methods and compositions for improving skin
发明人:LIAO I-CHIEN; BRIEVA PATRICIA; JUCHAUX FRANCK; BOUEZ CHARBEL; ZHENG QIAN; QIAN KUN
权利人:OREAL
摘要:A method for managing skin tone comprising reducing the synthesis of melanin by applying a skin treatment composition to skin. The skin treatment composition may include about 0.1 to about 25 wt. % of acetyl trifluoromethylphenyl valylglycine; about 0.5 to about 30 wt. % of a polyol; about 0.1 to about 30 wt. % of a silicone, fatty compound, or a mixtures thereof, wherein the skin treatment composition is an emulsion, and all weight percentages are based on the total weight of the skin treatment composition.

专利号:US-2727890-A
优先权日:1953-03-02
标 题 :Synthesis of an aldohexoside of a flavonol
发明人:WENDER SIMON H; ICE CLARK H
权利人:WENDER SIMON H; ICE CLARK H

专利号:CN-118291418-A
优先权日:2024-04-24
标 题 :Fusion protein containing flavone methyltransferase, preparation method and application thereof in efficient synthesis of rhamnoides
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合成参考文献


参考文献:10.1186/1475-2891-10-73
摘要:Bojić M, Debeljak Ž, Tomičić M, Medić-Šarić M, Tomić S. Evaluation of antiaggregatory activity of flavonoid aglycone series. Nutrition Journal. 2011 Jul 11;10(1):73. doi: 10.1186/1475-2891-10-73.
参考文献:10.1021/np50001a002
摘要:Edwards JM, Raffauf RF, Le Quesne PW. Antineoplastic activity and cytotoxicity of flavones, isoflavones, and flavanones. J Nat Prod. 1979 Jan;42(1):85–91. doi: 10.1021/np50001a002.
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