CAS: 70872-29-6; (S)-7-Hydroxy-2-(4-Hydroxyphenyl)-5-Methoxy-8-(3-Methylbut-2-En-1-yl)Chroman-4-One

该化合物是主要在跳中(Humululs lupulus)找到的,源自前硝酸铬(Humulus lupulus)的手性氟芳烃,作为生物活性化合物,它表现出显著的抗氧化剂和潜在的化学预防特性.它的立体特性(2S)配置增强了它与某些细胞目标的结合性,改善了生物利用率和代谢稳定性,与种族对应体相比.研究表明它可能调节致癌途径并抑制细胞色素P450酶,使之与与激素相关条件和药物新陈代谢有关的研究相关.它的高度纯度和定义明确的结构使得它对于药理学和生物化学研究很有价值,特别是在探索前红花类的结构-活动关系方面.

结构式图片

上下游产品

xanthoarnol xanthohumol desmethylxanthohumol 2-(4-acetoxyphenyl)-5-hydroxy-4-ox°Chroman-7-yl acetate2'',3''-dihydroisoxanthohumol

合成工艺路线路线简述

    📜黄腐酚置于sodium Hydroxide体系中,用 水 作为反应溶剂,以90 %的收率获得产物异黄腐醇
    参考文献:异黄腐醇胺类共聚物及其制备方法和抗菌应用
    标题:异黄腐醇胺类共聚物及其制备方法和抗菌应用
    摘要:本发明公开了一系列异黄腐醇胺类共聚物及其制备方法和抗菌应用.该系列化合物以黄腐醇为母体,将黄腐醇转化成为异黄腐醇,之后将异黄腐醇作为亲脂性部分,通过不同长度的烷基连接物与各种不同的脂肪胺和杂环胺相连,合成了一系异黄腐醇胺型共聚物,在此基础上可以继续进行结构优化,在其氮原子部位引入甲基形成氮正离子.本发明制得的异黄腐醇胺类共聚物对金黄色葡萄球菌atcc 29213和各种耐甲氧西林金黄色葡萄球菌(Mrsa)具有较好的抑菌效果,并且具有水溶性好,生物毒性低,产率较高等优点,有望进一步发展为临床上的半合成抗菌药物.

    海关参考信息

    专利信息


    专利号:US-2008221377-A1
    优先权日:2006-06-16
    标题 :Methods for synthesis of carotenoids, including analogs, derivatives, and synthetic and biological intermediates
    发明人:LOCKWOOD SAMUEL F; TANG PENG CHO; NADOLSKI GEOFF; JACKSON HENRY L; FANG ZHIQIANG; DU YISHU; YANG MIN; GEISS WILLIAM; WILLIAMS RICHARD; BURDICK DAVID; BRAUN CRISTI L
    权利人:LOCKWOOD SAMUEL F; TANG PENG CHO; NADOLSKI GEOFF; JACKSON HENRY L; FANG ZHIQIANG; DU YISHU; YANG MIN; GEISS WILLIAM; WILLIAMS RICHARD; BURDICK DAVID; BRAUN CRISTI L
    摘要:A method for synthesizing intermediates for use in the synthesis of carotenoid synthetic intermediates, carotenoid analogs, and/or carotenoid derivatives. The carotenoid analog, derivative, or intermediate may be administered to a subject for the inhibition and/or amelioration of any disease that involves production of reactive oxygen species, reactive nitrogen species, radicals and/or non-radicals. In some embodiments, the invention may include methods for synthesizing chemical compounds including an analog or derivative of a carotenoid. Carotenoid analogs or derivatives may include acyclic end groups. In some embodiments, a carotenoid analog or derivative may include at least one substituent. The substituent may enhance the solubility of the carotenoid analog or derivative such that the carotenoid analog or derivative at least partially dissolves in water.

    专利号:US-2009099061-A1
    优先权日:2006-01-27
    标 题:Synthesis of carotenoid analogs or derivatives with improved antioxidant characteristics
    发明人:FOSS BENTE J; NADOLSKI GEOFFRY T; LOCKWOOD SAMUEL F
    权利人:FOSS BENTE J; NADOLSKI GEOFFRY T; LOCKWOOD SAMUEL F
    摘要:A method is described for synthesizing and administering carotenoid compounds with improved antioxidant characteristics. In some embodiments, extension or improvement of conjugation may be employed in structural modification of carotenoids. In other embodiments, reduction of ring/chain steric hindrance may improve the lambda max, and hence, the overall antioxidant capability, of particular compounds. In other embodiments, introduction and/or increase in synthetic handles for conjugation may improve the stoichiometric ratios of conjugating moieties to the polyene backbone. The methods may be used to improve natural and/or synthetic compounds for medicinal application in the treatment of disease.

    专利号:US-2007015735-A1
    优先权日:2005-03-23
    标 题 :Water-dispersible carotenoids, including analogs and derivatives
    发明人:LOCKWOOD SAMUEL F; NADOLSKI GEOFF
    权利人:LOCKWOOD SAMUEL F; NADOLSKI GEOFF
    摘要:A method used for synthesizing intermediates for use in the synthesis of carotenoid synthetic intermediates, carotenoid analogs, and/or carotenoid derivatives. The analog, derivative, or intermediate may be administered such that a subject's risk of experiencing diseases associated with reactive oxygen species, reactive nitrogen species, radicals and/or non-radicals may be thereby reduced. The analog or analog combination may be administered to a subject for the inhibition and/or amelioration of any disease that involves production of reactive oxygen species, reactive nitrogen species, radicals and/or non-radicals. In some embodiments, the invention may include methods for synthesizing chemical compounds including an analog or derivative of a carotenoid. The carotenoid analog or derivative may be synthetic. In some embodiments, a carotenoid analog or derivative may include at least one substituent. The substituent may enhance the solubility of the carotenoid analog or derivative such that the carotenoid analog or derivative at least partially dissolves in water.

    专利号:WO-2007090095-A2
    优先权日:2006-01-27
    标 题:Synthesis of carotenoid analogs or derivatives with improved antioxidant characteristics

    专利号:ES-2955412-T3
    优先权日:2021-05-07
    标题:A method of xanthohumol synthesis

    供应商参考报价(招募中)

    品牌试剂参考报价(招募中)

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    ✅ COA系统入驻 | 共享模式

    主要参考文献


    1: Żołnierczyk AK, Mączka WK, Grabarczyk M, Wińska K, Woźniak E, Anioł M. Isoxanthohumol--Biologically active hop flavonoid. Fitoterapia. 2015 Jun;103:71-82. doi: 10.1016/j.fitote.2015.03.007. Epub 2015 Mar 12. doi: 10.1021/acs.jafc.5b02025. Epub 2015 Jul 27. doi: 10.1002/mnfr.201500118. Epub 2015 Jul 1. doi: 10.1007/s00232-015-9782-0. Epub 2015 Feb 17.
    5: Quifer-Rada P, Martínez-Huélamo M, Chiva-Blanch G, Jáuregui O, Estruch R, Lamuela-Raventós RM. Urinary isoxanthohumol is a specific and accurate biomarker of beer consumption. J Nutr. 2014 Apr;144(4):484-8. doi: 10.3945/jn.113.185199. Epub 2014 Jan 29. doi: 10.1002/jat.1602. Epub 2010 Nov 9. doi: 10.1007/s10637-011-9643-3. Epub 2011 Feb 22. doi: 10.1002/biof.1122. Epub 2013 Aug 1. doi: 10.1002/biof.1084. Epub 2013 Jan 30. doi: 10.1021/jf2011722. Epub 2011 Jun 10. doi: 10.1007/s00394-015-0843-z. Epub 2015 Feb 3. doi: 10.1016/j.phrs.2016.01.011. Epub 2016 Jan 16. doi: 10.1016/j.talanta.2010.09.041. Epub 2010 Oct 1. doi: 10.1016/j.cbi.2008.06.005. Epub 2008 Jun 20.
    15: Magalhães PJ, Guido LF, Cruz JM, Barros AA. Analysis of xanthohumol and isoxanthohumol in different hop products by liquid chromatography-diode array detection-electrospray ionization tandem mass spectrometry. J Chromatogr A. 2007 May 25;1150(1-2):295-301. Epub 2006 Sep 7. Epub 2006 Apr 12. Epub 2007 Jul 13. pii: E208. doi: 10.3390/toxins9070208.

    合成参考文献


    参考文献:10.1016/s0278-6915(99)00019-8
    摘要:Miranda CL, Stevens JF, Helmrich A, Henderson MC, Rodriguez RJ, Yang YH, Deinzer ML, Barnes DW, Buhler DR. Antiproliferative and cytotoxic effects of prenylated flavonoids from hops (Humulus lupulus) in human cancer cell lines. Food Chem Toxicol. 1999 Apr;37(4):271–85. doi: 10.1016/s0278-6915(99)00019-8.
    参考文献:10.1248/cpb.34.2094
    摘要:Ohmoto T, Aikawa R, Nikaido T, Sankawa U, Wu LJ, Ueno A, Fukushima S. Inhibition of adenosine 3',5'-cyclic monophosphate phosphodiesterase by components of Sophora flavescens Aiton. Chem Pharm Bull (Tokyo). 1986 May;34(5):2094–9. doi: 10.1248/cpb.34.2094.
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