CAS: 491-80-5; 5,7-Dihydroxy-3-(4-Methoxyphenyl)-4H-Chromen-4-One

该化合物是一种自然产生的叶索夫酮,主要存在于红三叶草(TRIATIONE)和其他豆类中,它作为一种植物质,表现出雌激素受体,特别是ERET的选择性亲近性.该化合物具有潜在的抗氧化剂,抗炎和化疗预防特性,因此引起人们的兴趣.Biochanin A也是通过脱甲基化而产生的另一个生物活性异己素甘斯坦氏的先兆.它的中度亲脂允许合理的细胞吸收,使其适合热温调和氧化应激研究.该化合物通常用于生物化学和药理研究,以调查其对代谢途径,细胞扩散和与雌激素有关的机制的影响.

结构式图片

上下游产品

CAS号487-70-7 2,4,6-三羟基苯甲醛 | CAS号2632-13-5 4-甲氧基-α-溴代苯乙酮 | CAS号15485-66-2 2-(4-甲氧基苯基)-1-(... | CAS号68-12-2 N,N-二甲基甲酰胺 | CAS号1393533-64-6 5,7-bis(benzylo... | CAS号108-73-6 间苯三酚 | CAS号122-51-0 原甲酸三乙酯 | CAS号290-87-9 1,3,5-三嗪 | CAS号124-63-0 甲基磺酰氯 | CAS号2258-42-6 甲乙酐 | CAS号34086-51-6 7-O-甲基鹰嘴豆芽素A | CAS号446-72-0 染料木素 | CAS号5928-26-7 鸡豆黄素配糖物; 印度黄檀苷 | CAS号15485-66-2 2-(4-甲氧基苯基)-1-(... | CAS号83920-62-1 2,3-dihydrobi°C... | CAS号68939-22-0 7-hydroxy-5-met... | CAS号54443-59-3 [5-acetyloxy-3-...

合成工艺路线路线简述

  • 合成目标产物 5,7-Dihydrox -4'-Methoxyisoflavone 主要起始原料 2,4,6-Trihydroxybenzaldehyde And 2-Bromo-4'-Methoxyacetophenone
  • (文献来源)合成步骤主要原料 2,4,6-Trihydroxybenzaldehyde 和 2-Bromo-4'-Methoxyacetophenone
2-(4-甲氧基苯基)-1-(2,4,6-三羟基苯基)乙酮置于吡啶体系中,化学反应生成 鹰嘴豆芽素a
参考文献:Yoder Et Al.,Proceedings Of The Iowa Academy Of Science,1954,Vol. 61,P. 271,275
标题:Yoder Et Al.,Proceedings Of The Iowa Academy Of Science,1954,Vol. 61,P. 271,275

海关参考信息

专利信息


专利号:WO-2020032913-A1
优先权日:2018-08-04
标题:Process for synthesis of oroxylin a
发明人:MAJEED MUHAMMED; NAGABHUSHANAM KALYANAM; RAMANUJAM RAJENDRAN; HEMANTHA HOSAHALLI
权利人:MAJEED MUHAMMED; NAGABHUSHANAM KALYANAM; RAMANUJAM RAJENDRAN; HEMANTHA HOSAHALLI PRABHAKARA
摘要: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.

专利号:US-10407401-B1
优先权日:2018-08-04
标题 :Process for synthesis of Oroxylin A
发明人:MAJEED MUHAMMED; NAGABHUSHANAM KALYANAM; RAMANUJAM RAJENDRAN; HEMANTHA HOSAHALLI PRABHAKARA
权利人:MAJEED MUHAMMED; NAGABHUSHANAM KALYANAM; RAMANUJAM RAJENDRAN; HEMANTHA HOSAHALLI PRABHAKARA; SAMI LABS LTD
摘要: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.

专利号:US-2009062555-A1
优先权日:2007-08-28
标 题 :Synthesis of Isoflavone
发明人:HARMS ARTHUR E
权利人:HARMS ARTHUR E
摘要:The invention provides a process of manufacturing an isoflavone of the general formula 7 n n n n n n n n n n wherein R 1 , R 2 , R 3 , and R 4 each independently are H, OH, or an alkoxy, provided at least one of R 1 , R 2 , R 3 , and R 4 being OH, and one being alkoxy, or at least 2 groups being OH, comprising providing ketone (3) n n n n n n n n n n wherein R 1 , R 2 , R 3 , and R 4 are as stated above, combining (3) with trialkylortho formate, and a Lewis or Bronsted acid to produce the isoflavone, precipitating the isoflavone.

专利号:US-5639785-A
优先权日:1995-06-07
标 题 :Methods for the treatment of baldness and gray hair using isoflavonoid derivatives
发明人:KUNG PATRICK C
权利人:GLOBAL PHARMA LTD
摘要:The present invention relates to novel pharmaceutical compositions of isoflavanoid derivatives useful for the treatment of male pattern baldness and alopecia areata, and their use in promoting the conversion of gray hair to the original pigment in hair follicles. Also described herein are methods for the synthesis of isoflavanoid derivatives.

专利号:US-10030003-B2
优先权日:2014-09-10
标 题:Synthesis of isoflavanes and intermediates thereof
发明人:BELIAEV NIKOLAI; SHAFRAN YURI
权利人:SYSTEM BIOLOGIE AG
摘要:Subject of the invention is a method for enantioselective production of an isoflavane from an isoflavone, comprising the steps: (a) selectively reducing the isoflavone, such that the 4-keto group of the isoflavone is converted to a 4-hydroxy group, and the 2,3-double bond of the isoflavone is converted to a 2,3-single bond, thereby obtaining a 4-hydroxy intermediate, and (b) reacting the 4-hydroxy intermediate with a chiral reagent, such that a chiral group is covalently attached to the C4-position of the 4-hydroxy intermediate, thereby obtaining a chiral intermediate. The invention also relates to intermediates of formulae (IV), (V), (VI) and (VII) obtainable in the inventive process.

专利号:US-8969596-B2
优先权日:2008-08-14
标题:Synthesis of equol
发明人:STEFFAN BERT
权利人:STEFFAN BERT
摘要:Subject of the invention is a method for the production of isoflavanes from isoflavones, whereby in a first reaction step (a) the 4-keto group of the isoflavone is reduced in a enantioselective manner, whilst the 2,3-double bond is maintained, to the 4-hydroxy compound.
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主要参考文献


1: Jain A, Lai JC, Bhushan A. Biochanin A inhibits endothelial cell functions and proangiogenic pathways: implications in glioma therapy. Anticancer Drugs. 2015 Mar;26(3):323-30. doi: 10.1097/CAD.0000000000000189. doi: 10.3892/ijmm.2014.2020. Epub 2014 Dec 2. doi: 10.1097/CAD.0000000000000044. doi: 10.1007/s11064-014-1480-2. Epub 2014 Nov 29. doi: 10.1371/journal.pone.0121529. eCollection 2015.
7: Wang W, Tang L, Li Y, Wang Y. Biochanin A protects against focal cerebral ischemia/reperfusion in rats via inhibition of p38-mediated inflammatory responses. J Neurol Sci. 2015 Jan 15;348(1-2):121-5. doi: 10.1016/j.jns.2014.11.018. Epub 2014 Nov 18. doi: 10.1371/journal.pone.0115115. eCollection 2014.
9: Chen J, Ge B, Wang Y, Ye Y, Zeng S, Huang Z. Biochanin A promotes proliferation that involves a feedback loop of microRNA-375 and estrogen receptor alpha in breast cancer cells. Cell Physiol Biochem. 2015;35(2):639-46. doi: 10.1159/000369725. Epub 2015 Jan 28. doi: 10.1016/j.lfs.2015.06.015. Epub 2015 Jul 2. doi: 10.1186/1472-6882-14-444.

合成参考文献


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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