CAS: 906-33-2; 5-O-(Trans-3,4-Dihydroxycinnamoyl)-D-Quinic Acid

该化合物是一种天然的,可水溶的,可氯化的酸类似物,具有强效抗氧化性特性.它能加强保护皮肤,防止氧化性压力,促进科林合成,提高皮肤弹性和坚固性,同时提供紫外线辐射吸收,并清除自由基,以保护细胞不受损害.

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

ne°Chlorogenic acid 3-caffeoylquinic acid (E)-3,4-di-O-acetylcaffeoyl chloride (2S,3S,4aR,6S,8R,8aR)-6,8-Dihydroxy-2,3-dimethoxy-2,3-dimethyl-°Ctahydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester3-O-caffeoylquinic acid methyl ester ortoquinone 3-O-(cis-caffeoyl)quinic acid (1S,3R,4R,5R)-5-[3-(3,4-dihydroxyphenyl)-2-hydroxypropanoyl]-1,4,5-trihydroxycyclohexanecarboxylic acid

合成工艺路线路线简述

    (E)-Methyl 3-(3,4-Bis(Methoxymethoxy)Phenyl)Acrylate置于五甲基苯,三氯化硼,N,N-二异丙基乙胺,对甲苯磺酰氯,Potassium Hydroxide体系中,用 四氢呋喃,二氯甲烷,1,2-二氯乙烷 作为反应溶剂,化学反应 30.5H,反应生成 新绿原酸
    参考文献:以对甲氧基苄基奎宁酸酯为关键中间体,通过直接酯化反应高效合成5-O-酰基奎宁酸
    标题:以对甲氧基苄基奎宁酸酯为关键中间体,通过直接酯化反应高效合成5-O-酰基奎宁酸
    摘要:从市售(-)-奎宁酸完成了5-O-酰基奎宁酸的有效和通用合成.我们设计了对甲氧基苄基奎宁酸酯作为关键中间体,并解决了两个问题,即空间位阻的5-Oh基团的酯化,以实现简洁的发散合成和最终脱保护步骤的收率低.对于第一个问题,我们通过添加i-Pr 2 Net改进了田边的方法,即使用游离羧酸的tscl / Nmi介导的酯化反应.对于第二个问题,我们为最终的脱保护步骤建立了tfa或bcl 3 / C 6 Hme 5催化的脱保护反应.5 ø-酰基奎尼酸通过七个步骤合成,总收率为45-60%.
    DOI:10.1016/j.Tet.2014.08.064

    海关参考信息

    专利信息


    专利号:US-2025268860-A1
    优先权日:2021-10-22
    标 题 :Composition for use in the cutaneous synthesis of hyaluronic acid, in an immuno-cutaneous response and to improve skin
    发明人:BERNARD PHILIPPE
    权利人:JR
    摘要:A composition comprising baicalin or a derivative thereof, more particularly in combination with chlorogenic acid or a derivative thereof, as well as the cosmetic use of such a composition and its medical applications.

    专利号:WO-0063152-A1
    优先权日:1999-02-22
    标题:Acetylated and related analogues of chicoric acid as hiv integrase inhibitors
    发明人:BURKE TERRENCE R; ZHAIWEI LIN; ZHAO HE; NEAMATI NOURI; POMMIER YVES
    权利人:US HEALTH; BURKE TERRENCE R; ZHAIWEI LIN; ZHAO HE; NEAMATI NOURI; POMMIER YVES
    摘要:Chicoric acid analogues and derivatives have activity against HIV-1 integrase. The structural features that are required for this activity are elucidated by assaying these analogues and derivatives against HIV-1 integrase. Furthermore, methods of synthesis of the enantiomers of chicoric acid itself, as well as its analogues and derivatives, are disclosed. Additionally, methods of use of chicoric acid analogues and derivatives to inhibit HIV-1 integrase are disclosed, as are compositions comprising chicoric acid analogues and derivatives.

    专利号:WO-2023067251-A1
    优先权日:2021-10-22
    标 题:Composition for use in the cutaneous synthesis of hyaluronic acid, in an immuno-cutaneous response and to improve skin

    专利号:US-6495147-B1
    优先权日:1997-11-07
    标题 :Uses of D-xylose, the esters thereof and oligosaccharides containing xylose for improving the functionality of epidermal cells
    发明人:DUMAS MARC; BONTE FREDERIC
    权利人:LVMH RECH
    摘要:A method for stimulating the synthesis and/or secretion of proteoglycans and/or glycosaminoglycans by keratinocytes of a human in need thereof, by applying to an external body area of the human a composition containing an effective amount of D-xylose, an ester thereof or an oligosaccharide containing D-xylose, in a combination with a cosmetically or pharmaceutically acceptable excipient.

    专利号:CN-102796746-A
    优先权日:2012-08-07
    标题:A gene segment regulating the synthesis of Solanaceae flavonoids and caffeoylquinic acid and its application

    专利号:CN-102796746-B
    优先权日:2012-08-07
    标题 :Gene segment for regulating synthesis of solanaceae flavonoids and caffeoyl quinic acid, and uses thereof
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    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:10.1016/j.phytochem.2008.02.003
    摘要:Nakamura S, Hongo M, Sugimoto S, Matsuda H, Yoshikawa M. Steroidal saponins and pseudoalkaloid oligoglycoside from Brazilian natural medicine, "fruta do lobo" (fruit of Solanum lycocarpum). Phytochemistry. 2008 May;69(7):1565–72. doi: 10.1016/j.phytochem.2008.02.003.
    参考文献:10.1021/acs.jmedchem.9b00270
    摘要:Pativada T, Kim MH, Lee JH, Hong SS, Choi CW, Choi YH, Kim WJ, Song DW, Park SI, Lee EJ, Seo BY, Kim H, Kim HK, Lee KH, Ahn SK, Ku JM, Park GH. Benzylideneacetone Derivatives Inhibit Osteoclastogenesis and Activate Osteoblastogenesis Independently Based on Specific Structure-Activity Relationship. J Med Chem. 2019 Jul 11;62(13):6063–82. doi: 10.1021/acs.jmedchem.9b00270.
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