CAS: 70110-59-7; 5-Henicosylbenzene-1,3-Diol

该化合物是一种长链替代的代谢残留物衍生物,其特点是其氢恐惧性烷尾和苯基氢氧基基组,这种结构具有两栖特性,在要求有机基质中的溶解性和二氧基苯典型的反活性的应用中有用.扩展的烷基链会增强热稳定性和与非极系统兼容性,而芳香二醇功能允许参与氢联结,氧化减低反应和聚合过程.其平衡的脂性与苯基再活性使得它可以选择用于特殊聚合物,表面修改和抗氧化剂配方.该化合物的固定结构确保了研究和工业应用的一贯性能.

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1-heneicosyl-3,5-dimethoxybenzene 1,3-dimethoxyphenol-5-nonadecylbenzene 3,5-dimethoxybenzyl alcohol 3,5-dimethoxybenzyl bromide 5-Heneicosyl-resorcin-diacetat 3]-5-heneicosylresorcinol[2,4,6-2H3]-5-heneicosylresorcinol

合成工艺路线路线简述

    📜3,5-二甲氧基苄醇置于dilithium Tetrachlorocuprate,三溴化硼,三溴化磷体系中,用 四氢呋喃,乙醚 作为反应溶剂,化学反应生成 5-二十一烷基间苯二酚
    参考文献:Properties Of Mixed Monolayers And Bilayers Of Long-Chain 5-N-Alkylresorcinols And Dipalmitoylphosphatidylcholine
    标题:Properties Of Mixed Monolayers And Bilayers Of Long-Chain 5-N-Alkylresorcinols And Dipalmitoylphosphatidylcholine
    摘要:5-N-Alkylresorcinols With Different Chain Length Are Known To occur In Different Plants And Procaryonts,For Example In The Cysts Of The Azotobacter Genus. To Study The Monolayer And Bilayer Behaviour Of These Amphiphilic Compounds,We Synthesized Three Analogues With Different Chain Length,Namely 5-N-octadecylresorcinol (18Ar),5-N-Nonadecylresorcinol(19Ar) And 5-N-Heneicosylresorcinol (21Ar). The Pure Alkylresorcinols Form Stable Monolayers,18Ar And 19Ar,Show A Phase Transition From A Liquid-Condensed To A Liquid-Expanded State At Temperatures Between 20 And 40 Degrees C And At Lateral Pressures Below 15 Dyn/cm. In Mixtures With Dipalmitoylphosphatidylcholine (Dppc),Monolayer Isobars At Higher Lateral Pressures (20-30 Dyn/cm) Show An Increase In The Transition Temperature To Values Greater Than 50 Degrees C For The Liquid-Condensed To Liquid-Expanded State Of Dppc When The Alkylresorcinol Content Is Increased. Particularly In The Liquid-Expanded State,Alkylresorcinols Show A Strong Condensing Effect On Dppc Monolayers. 18Ar/dppc Monolayers At A Pressure Of 5 Dyn/cm Show Indications Of An Azeotropic Behaviour. A Similar Increase In Transition Temperature Is Observed By Differential Scanning Calorimetry (Dsc) And Differential Scanning Densitometry (Dsd) In Dppc/alkylresorcinol Bilayers. The Transition Enthalpy Decreases With Increasing Alkylresorcinol Content. All Alkylresorcinols Seem To Be Completely Miscible With Dppc Up To At Least 50 Mol%. The Dsd Data Indicate A Slight Condensing Effect Of The Alkylresorcinols On The Liquid-Crystalline Phase Of Dppc.
    DOI:10.1016/0009-3084(94)90074-4

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    主要参考文献

    参考标题:An Expedient Synthesis Of 5-N-Alkylresorcinols And Novel 5-N-Alkylresorcinol Haptens
    作者:Kirsti Parikka,Kristiina Wähälä
    摘要:The First Synthesis Of Bioactive Long Alkyl Chain 5-N-Alkylresorcinols, Present In Whole Grain Products, By A Novel Modification Of The Wittig Reaction Is Described. All The Main Long Chain 5-N-Alkylresorcinols Present In Rye And Wheat, Including C23 And C25 Analogues And Haptens, Which Have Not Been Previously Prepared, Were Synthesised. Microwave-Promoted Reactions Of A Semi-Stabilized Ylid And Alkanals In Water Gave Good Yields In Both Pressurized And Open Systems. An Alternative Microwave-Promoted Synthesis Starting From Non-Stabilized Alkyltriphenylphosphonium Salts And 3,5-Dimethoxybenzaldehyde Worked As Well. Aqueous Media Were Suitable For The Reactions Even If The Starting Materials Were Not Soluble In Water. The 5-N-Alkylresorcinols Are Potential Biomarkers Of Whole Grain Intake, And The New Hapten Derivatives Of 5-N-Alkylresorcinols Will Open The Way For The Immunochemical Detection Techniques Of Alkylresorcinols.

    合成参考文献


    参考文献:10.1021/jf034745a
    摘要:Rejman J, Kozubek A. Inhibitory effect of natural phenolic lipids upon NAD-dependent dehydrogenases and on triglyceride accumulation in 3T3-L1 cells in culture. J Agric Food Chem. 2004 Jan 28;52(2):246–50. doi: 10.1021/jf034745a.
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