CAS: 5975-78-0; (S)-Zearalanone

Zearalanone,化学组织包括一个苯球环和乳腺杂物,有助于其生物活动.该化合物主要以其致癌性能而闻名,可导致牲畜的生殖和发育问题,并有可能通过食物链影响人类健康.Zearalanone经常在食品安全和毒理学方面进行研究,因为它污染谷物和饲料.它存在于农产品中,因此有必要监测和监管其健康风险.此外,Zearalanone在环境中的稳定性和持久性引起了人们对其对生态系统和动物健康的长期影响的关注.

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zearalenone

合成工艺路线路线简述

    📜玉米烯酮置于palladium On Activated Charcoal 氢气体系中,20.0 °C,100.0 Kpa 条件下,反应生成 玉米赤霉酮
    参考文献:Pochonins Af,来自pochonia Chlamydosporia Var的新型抗病毒和抗寄生虫间苯二酸内酯.悬链线.
    标题:Pochonins Af,来自pochonia Chlamydosporia Var的新型抗病毒和抗寄生虫间苯二酸内酯.悬链线.
    摘要:Monorden(1)和新颖的间苯二酸内酯蛋白软骨素a(2),B(4),C(6),D(7)和e(8)以及四氢monorden(5)和假神经素a(22)分别为分离自锁骨次霉菌pochonia Chlamydosporia Var的培养物.catenulata菌株p0297.在含溴的培养基中发酵p 0297导致次生代谢产物的转移,并产生了monocillins Iii(3)和ii(9)作为除monorden(1)以及新型化合物软骨素的主要代谢产物f(10)和monocillin Ii糖苷(11)作为次要代谢物.这些化合物中的大多数在针对单纯疱疹病毒1(hsv1)和寄生虫原生动物艾美球虫的细胞复制试验中显示中等活性.与结构相关的玉米赤霉烯酮衍生物相反,菌株p 0297的代谢产物在荧光偏振测定中没有活性,可以测定对人雌激素受体erbeta的调节活性.β-玉米赤霉烯醇(17),但没有玉米赤霉烯酮(1
    DOI:10.1021/np020556V

    海关参考信息

    专利信息


    专利号:US-3901922-A
    优先权日:1972-04-25
    标题 :Synthesis of zearalanone and related compounds and intermediates useful in their synthesis
    发明人:URRY WILBERT HERBERT; MULLENBACH GUY TOWNS
    权利人:COMMERCIAL SOLVENTS CORP
    摘要:WHEREIN X is an integer having a value from 2 to 6 inclusive and Y is an integer having a value from 2 to 8 inclusive. It also provides for new methods of making compounds useful in the synthesis of zearalanone and related compounds. The new compounds useful as intermediates are 2,7-octadienoic acid; methyl 2,7-octadienoate; sodium ethyl 6-(4-pentenyl)- Beta -dihydroesorcylate; ethyl 6-(4-pentenyl)- Beta dihydroresorcylate; sodium methyl 6-(4-pentenyl)- Beta dihydroresorcylate; methyl 6-(4-pentenyl)- Beta dihydroresorcylate; methyl 3-bromo-6-(4-pentenyl)- Beta dihydroresorcylate; methyl 6-(4-pentenyl)- Beta -resorcylate; ethyl 6-(4-pentenyl)- Beta -resorcylate; ethyl 6-(4-pentenyl)Beta -resorcylate dibenzyl ether; tetrahydropyran-2-yl 4-penten2-yl ether; ethyl 6-(6-oxo-10-tetrahydropyran-2-xyloxyundecyl)Beta -resorcylate dibenzyl ether; and 6-(10-hydroxy-6oxounderyl)- Beta -resorcylic acid dibenzyl ether. Methods for preparing these intermediates are also disclosed. This invention provides a new synthesis for zearalanone and for related compounds having more or fewer carbon atoms in the nonaromatic ring than does zearalanone, which related compounds and zearalanone are represented by the formula

    专利号:US-3852307-A
    优先权日:1972-04-25
    标 题 :Synthesis of zearalanone and related compounds
    发明人:URRY W; MULLENBACH G
    权利人:COMMERCIAL SOLVENTS CORP
    摘要:WHEREIN X is an integer having a value from 0 to 6 inclusive and Y is an integer having a value from 3 to 8 inclusive. It also provides for new methods of making compounds useful in the synthesis of zearalanone and related compounds. The compounds 6-acetoxyhexanoic acid; 2-(5-hexenoyl)cyclohexanone; 7-keto-11-dodecenoic acid; 2-hydroxyethyl 7-keto11-dodecenoate ethylene ketal; N,N-dimethyl 7-keto-11dodecenamide ethylene ketal; 7-keto-11-dodecenal ethylene ketal; 9-keto-2,13-tetradecadienic acid ethylene ketal; 2-hydroxyethyl 9-keto-2,13-tetradecadienoate ethylene ketal; the sodium salt of ethyl 6-(6-keto-10-undecenyl)- Beta -dihydroresorcylate ethylene ketal; ethyl 3-bromo-6-(6-keto-10-undecenyl)- Beta dihydroresorcylate ethylene ketal; ethyl 6-(6-keto-10-undecenyl)Beta -resorcylate ehtylene ketal; ethyl 6-(6-keto-10-undecenyl)Beta -resorcylate ethylene ketal dibenzyl ether; ethyl 6-(6keto-10-hydroxyundecyl)- Beta -resorcylate ethylene ketal dibenzyl ether; and 6-(10-hydroxy-6-keto-undecyl)- Beta resorcylic acid dibenzyl ether are disclosed. Methods for preparing these compounds are also disclosed. This invention provides a new synthesis for zearalanone and for related compounds having more or fewer carbon atoms in the nonaromatic ring than does zearalanone, which related compounds and zearalanone are represented by the formula

    专利号:US-3810918-A
    优先权日:1972-04-25
    标题:Synthesis of zearalanone
    发明人:URRY W; MULLENBACH G
    权利人:COMMERCIAL SOLVENT CORP
    摘要:4,5-(-COO-CH(-CH3)-(CH2)X-CO-(CH2)Y-)RESORCINOL THIS INVENTION PROVIDES A NEW SYNTHESIS FOR ZEARALANONE AND FOR RELATED COMPOUNDS HAVING MORE OR FEWER CARBON ATOMS IN THE NON-AROMATIC RING THAN DOES ZEARLANONE, WHICH RELATED COMPOUNDS AND ZEARALANONE ARE REPRESENTED BY THE FORMULA WHEREIN X IS AN INTEGER HAVING A VALUE FROM 2 TO 6 INCLUSIVE AND Y IS AN INTEGER HAVING A VALUE FROM 2 TO 8 INCLUSIVE. IT ALSO PROVIDES FOR NEW METHODS FOR MAKING COMPOUNDS USEFUL IN THE SYNTHESIS OF ZEARALANONE AND RELATED COMPOUNDS. THE NEW COMPOUNDS USEFUL AS INTERMEDIATES ARE 2,7-OCTADIENOIC ACID; METHYL 2,7-OCTADIENOATE; SODIUM ETHYL 6-(4-PENTENYL-B-DIHYDRORESORCYLATE; ETHYL 6-(4-PENTENYL)-B-DIHYDRORESORCYLATE; SODIUM METHYL 6-(4-PENTENYL)-B-DIHYDRORESORCYLATE; METHYL 6-(4-PENTENYL)-B-DIHYDRORESORCYLATE; METHYL 3-BROMO-6(4-PENTENYL)-B-DIHYDRORESORCYLATE; METHYL6-(4-PENTENYL9-B-RESORCYLATE; ETHYL 6-(4-PENTENYL)-B-RESORCYLATE; ETHYL 6-(4-PENTENYL)-B-R-RESORCYLATE DIBENZYL ESTER; TETRAHYDROJPYRAN-2-YL 4-YL 4-PENTEN-2-YL ETHER; ETHYL 6-(6-OXO-10-TETRAHYDROPYRAN-2-XYLOXYUNDECYL)-BRESORCYLATE DIBENZYL ETHER; AND 6-(10-HYDROXY-6-OXOUNDECYL)-B-RESORCYLIC ACID DIBENZYL ETHER. METHODS FOR PREPARING THESE INTERMEDIATES ARE ALSO DISCLOSED.

    专利号:US-3839363-A
    优先权日:1972-04-25
    标 题:Synthesis of zearalanone and related compounds and intermediates useful in the synthesis thereof
    发明人:SHAH D; HURD R
    权利人:COMMERCIAL SOLVENTS CORP
    摘要:1. A COMPOUND OF THE FORMULA 1-(O=),3-(C6H5-CH2-O-(CH2)N0-),4-(CH3-OOC-),- 6,8-DI(R''-O-)ISOCHROMAN WHEREIN NO IS AN INTEGER HAVING THE VALUE 1,2,3,4,5 OR 6 AND R'' IS SELECTED FROM THE GROUP CONSISTING OF BENZYL, METHYL, ETHYL, BUTYL, CYCLOPENTYL, AND CYCLOHEXYL.

    专利号:US-3704249-A
    优先权日:1969-05-01
    标题:Synthesis of the biologically active diastereoisomer of (-) zearalanol
    发明人:CZAJA ROBERT F; GRENDA VICTOR J; CHAMBERLIN EARL M
    权利人:MERCK & CO INC
    摘要:THE ACTIVE GROWTH FACTOR DIASTEREOISOMER OF 6-(6,10DIHYDROXY - UNDECYL) - B - RESORCYLIC ACID - U - LACTONE OR (-) ZEARALANOL IS PREPARED BY STEREOSPECIFIC REDUCTION OF THE CARBONYL MOIETY OF ZEARALANONE, ZEARALENONE, AND DIETHER DERIVATIVES THEREOF.

    专利号:US-3957825-A
    优先权日:1972-04-25
    标 题 :Process for synthesizing zearalanone and related compounds
    发明人:URRY WILBERT HERBERT; MULLENBACH GUY TOWNS
    权利人:COMMERCIAL SOLVENTS CORP
    摘要:This invention provides a new synthesis for zearalanone and for related compounds having more or fewer carbon atoms in the non-aromatic ring than does zearalanone, which related compounds and zearalanone are represented by the formula ##SPC1## n Wherein X is an integer having a value from 2 to 6 inclusive and Y is an integer having a value from 2 to 8 inclusive. It also provides for new methods of making compounds useful in the synthesis of zearalanone and related compounds. n The new compounds useful as intermediates are 2,7-octadienoic acid; methyl 2,7-octadienoate; sodium ethyl 6-(4-pentenyl)-β-dihydroresorcylate; ethyl 6-(4-pentenyl)-β-dihydroresorcylate; sodium methyl 6-(4-pentenyl)-β-dihydroresorcylate; methyl 6-(4-pentenyl)-β-dihydroresorcylate; methyl 3-bromo-6-(4-pentenyl)-β-dihydroresorcylate; methyl 6-(4-pentenyl)-β-resorcylate; ethyl 6-(4-pentenyl)-β-resorcylate; ethyl 6-(4-pentenyl)-β-resorcylate dibenzyl ether; and 4-penten-2-yl 6-(4-pentenyl)-β-resorcylate dibenzyl ether.

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    ✅ COA系统入驻 | 共享模式

    主要参考文献


    1: Faisal Z, Vörös V, Fliszár-Nyúl E, Lemli B, Kunsági-Máté S, Poór M. Interactions of zearalanone, α-zearalanol, β-zearalanol, zearalenone-14-sulfate, and zearalenone-14-glucoside with serum albumin. Mycotoxin Res. 2020 Nov;36(4):389-397. doi: 10.1007/s12550-020-00404-w. Epub 2020 Aug 1.
    2: Wu Z, Jiang X, Yang Y, Shi R, Ruan G, Huang Y. Amphiphilic polymers facilitated solid-phase extraction coupled with ultra-performance liquid chromatography-tandem mass spectrometry for direct extraction and analysis of zearalenone and zearalanone in corn juice samples. J Sep Sci. 2023 Jul;46(14):e2300112. doi: 10.1002/jssc.202300112. Epub 2023 May 9. 89(18):13800-13805. doi: 10.1021/acs.joc.4c01793. Epub 2024 Sep 10.
    7:583-595. doi: 10.1016/j.toxrep.2020.04.010.

    合成参考文献


    摘要:S109 | PARCEDC | List of 7074 potential endocrine disrupting compounds (EDCs) by PARC T4.2 | DOI:10.5281/zenodo.10944198
    参考文献:10.1007/s00216-008-1943-x
    摘要:Schmidt K, Stachel C, Gowik P. Development and in-house validation of an LC-MS/MS method for the determination of stilbenes and resorcylic acid lactones in bovine urine. Analytical and Bioanalytical Chemistry. 2008 Mar 25;391(4):1199–210. doi: 10.1007/s00216-008-1943-x.
    参考文献:10.1007/s12550-018-0318-1
    摘要:Chilaka CA, De Boevre M, Atanda OO, De Saeger S. Stability of fumonisin B1, deoxynivalenol, zearalenone, and T-2 toxin during processing of traditional Nigerian beer and spices. Mycotoxin Res. 2018 Nov;34(4):229–39. doi: 10.1007/s12550-018-0318-1.
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