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mw-ui-icon-wikimedia-userAdd"></span> <span>创建账号</span></a></li><li id="pt-login" class="user-links-collapsible-item mw-list-item"><a href="/w/index.php?title=Special:%E7%94%A8%E6%88%B7%E7%99%BB%E5%BD%95&returnto=%E5%92%96%E5%95%A1%E9%85%B8" title="建议你登录，尽管并非必须。[o]" accesskey="o"><span class="vector-icon mw-ui-icon-logIn mw-ui-icon-wikimedia-logIn"></span> <span>登录</span></a></li> </ul> </div> </div> <div id="p-user-menu-anon-editor" class="vector-menu mw-portlet mw-portlet-user-menu-anon-editor" > <div class="vector-menu-heading"> 未登录编辑者的页面 <a href="/wiki/Help:%E6%96%B0%E6%89%8B%E5%85%A5%E9%97%A8" aria-label="了解有关编辑的更多信息"><span>了解详情</span></a> </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="pt-anoncontribs" class="mw-list-item"><a href="/wiki/Special:%E6%88%91%E7%9A%84%E8%B4%A1%E7%8C%AE" title="来自此IP地址的编辑列表[y]" accesskey="y"><span>贡献</span></a></li><li id="pt-anontalk" class="mw-list-item"><a href="/wiki/Special:%E6%88%91%E7%9A%84%E8%AE%A8%E8%AE%BA%E9%A1%B5" title="对于来自此IP地址编辑的讨论[n]" accesskey="n"><span>讨论</span></a></li> </ul> </div> </div> </div> </div> </nav> </div> </header> </div> <div class="mw-page-container"> <div class="mw-page-container-inner"> <div class="vector-sitenotice-container"> <div id="siteNotice"></div> </div> <div class="vector-column-start"> <div class="vector-main-menu-container"> <div id="mw-navigation"> <nav id="mw-panel" class="vector-main-menu-landmark" aria-label="站点"> <div id="vector-main-menu-pinned-container" class="vector-pinned-container"> </div> </nav> </div> </div> <div class="vector-sticky-pinned-container"> <nav id="mw-panel-toc" aria-label="目录" data-event-name="ui.sidebar-toc" class="mw-table-of-contents-container vector-toc-landmark"> <div id="vector-toc-pinned-container" class="vector-pinned-container"> <div id="vector-toc" class="vector-toc vector-pinnable-element"> <div class="vector-pinnable-header vector-toc-pinnable-header vector-pinnable-header-pinned" data-feature-name="toc-pinned" data-pinnable-element-id="vector-toc" > <h2 class="vector-pinnable-header-label">目录</h2> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-toc.pin">移至侧栏</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-toc.unpin">隐藏</button> </div> <ul class="vector-toc-contents" id="mw-panel-toc-list"> <li id="toc-mw-content-text" class="vector-toc-list-item vector-toc-level-1"> <a href="#" class="vector-toc-link"> <div class="vector-toc-text">序言</div> </a> </li> <li id="toc-自然中的含量" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#自然中的含量"> <div class="vector-toc-text"> <span class="vector-toc-numb">1</span> <span>自然中的含量</span> </div> </a> <button aria-controls="toc-自然中的含量-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>开关自然中的含量子章节</span> </button> <ul id="toc-自然中的含量-sublist" class="vector-toc-list"> <li id="toc-食物中的含量" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#食物中的含量"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.1</span> <span>食物中的含量</span> </div> </a> <ul id="toc-食物中的含量-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-代谢途径" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#代谢途径"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>代谢途径</span> </div> </a> <button aria-controls="toc-代谢途径-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>开关代谢途径子章节</span> </button> <ul id="toc-代谢途径-sublist" class="vector-toc-list"> <li id="toc-生源合成" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#生源合成"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1</span> <span>生源合成</span> </div> </a> <ul id="toc-生源合成-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-生物转化" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#生物转化"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.2</span> <span>生物转化</span> </div> </a> <ul id="toc-生物转化-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-药理作用" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#药理作用"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>药理作用</span> </div> </a> <ul id="toc-药理作用-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-化学性质" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#化学性质"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>化学性质</span> </div> </a> <ul id="toc-化学性质-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-其他用途" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#其他用途"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>其他用途</span> </div> </a> <ul id="toc-其他用途-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-同分异构体" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#同分异构体"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>同分异构体</span> </div> </a> <ul id="toc-同分异构体-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-参考文献" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#参考文献"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>参考文献</span> </div> </a> <ul id="toc-参考文献-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="目录" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="开关目录" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">开关目录</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">咖啡酸</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="前往另一种语言写成的文章。27种语言可用" > <label id="p-lang-btn-label" for="p-lang-btn-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive mw-portlet-lang-heading-27" aria-hidden="true" ><span class="vector-icon mw-ui-icon-language-progressive mw-ui-icon-wikimedia-language-progressive"></span> <span class="vector-dropdown-label-text">27种语言</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%AD%D9%85%D8%B6_%D8%A7%D9%84%D9%83%D8%A7%D9%81%D8%A6%D9%8A%D9%83" title="حمض الكافئيك – 阿拉伯语" lang="ar" hreflang="ar" data-title="حمض الكافئيك" data-language-autonym="العربية" data-language-local-name="阿拉伯语" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%DA%A9%D8%A7%D9%81%D8%A6%DB%8C%DA%A9_%D8%A7%D8%B3%DB%8C%D8%AF" title="کافئیک اسید – South Azerbaijani" lang="azb" hreflang="azb" data-title="کافئیک اسید" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%9A%D0%B0%D1%84%D0%B5%D0%B5%D0%BD%D0%B0_%D0%BA%D0%B8%D1%81%D0%B5%D0%BB%D0%B8%D0%BD%D0%B0" title="Кафеена киселина – 保加利亚语" lang="bg" hreflang="bg" data-title="Кафеена киселина" data-language-autonym="Български" data-language-local-name="保加利亚语" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Kofeinska_kiselina" title="Kofeinska kiselina – 波斯尼亚语" lang="bs" hreflang="bs" data-title="Kofeinska kiselina" data-language-autonym="Bosanski" data-language-local-name="波斯尼亚语" class="interlanguage-link-target"><span>Bosanski</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/%C3%80cid_cafeic" title="Àcid cafeic – 加泰罗尼亚语" lang="ca" hreflang="ca" data-title="Àcid cafeic" data-language-autonym="Català" data-language-local-name="加泰罗尼亚语" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Kyselina_k%C3%A1vov%C3%A1" title="Kyselina kávová – 捷克语" lang="cs" hreflang="cs" data-title="Kyselina kávová" data-language-autonym="Čeština" data-language-local-name="捷克语" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Kaffees%C3%A4ure" title="Kaffeesäure – 德语" lang="de" hreflang="de" data-title="Kaffeesäure" data-language-autonym="Deutsch" data-language-local-name="德语" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-en mw-list-item"><a href="https://en.wikipedia.org/wiki/Caffeic_acid" title="Caffeic acid – 英语" lang="en" hreflang="en" data-title="Caffeic acid" data-language-autonym="English" data-language-local-name="英语" class="interlanguage-link-target"><span>English</span></a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Kafeata_acido" title="Kafeata acido – 世界语" lang="eo" hreflang="eo" data-title="Kafeata acido" data-language-autonym="Esperanto" data-language-local-name="世界语" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/%C3%81cido_cafeico" title="Ácido cafeico – 西班牙语" lang="es" hreflang="es" data-title="Ácido cafeico" data-language-autonym="Español" data-language-local-name="西班牙语" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Azido_kafeiko" title="Azido kafeiko – 巴斯克语" lang="eu" hreflang="eu" data-title="Azido kafeiko" data-language-autonym="Euskara" data-language-local-name="巴斯克语" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%DA%A9%D8%A7%D9%81%D8%A6%DB%8C%DA%A9_%D8%A7%D8%B3%DB%8C%D8%AF" title="کافئیک اسید – 波斯语" lang="fa" hreflang="fa" data-title="کافئیک اسید" data-language-autonym="فارسی" data-language-local-name="波斯语" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Kahvihappo" title="Kahvihappo – 芬兰语" lang="fi" hreflang="fi" data-title="Kahvihappo" data-language-autonym="Suomi" data-language-local-name="芬兰语" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Acide_caf%C3%A9ique" title="Acide caféique – 法语" lang="fr" hreflang="fr" data-title="Acide caféique" data-language-autonym="Français" data-language-local-name="法语" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/K%C3%A1v%C3%A9sav" title="Kávésav – 匈牙利语" lang="hu" hreflang="hu" data-title="Kávésav" data-language-autonym="Magyar" data-language-local-name="匈牙利语" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Acido_caffeico" title="Acido caffeico – 意大利语" lang="it" hreflang="it" data-title="Acido caffeico" data-language-autonym="Italiano" data-language-local-name="意大利语" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%B3%E3%83%BC%E3%83%92%E3%83%BC%E9%85%B8" title="コーヒー酸 – 日语" lang="ja" hreflang="ja" data-title="コーヒー酸" data-language-autonym="日本語" data-language-local-name="日语" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%BB%A4%ED%94%BC%EC%82%B0" title="커피산 – 韩语" lang="ko" hreflang="ko" data-title="커피산" data-language-autonym="한국어" data-language-local-name="韩语" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Koffiezuur" title="Koffiezuur – 荷兰语" lang="nl" hreflang="nl" data-title="Koffiezuur" data-language-autonym="Nederlands" data-language-local-name="荷兰语" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Kwas_kawowy" title="Kwas kawowy – 波兰语" lang="pl" hreflang="pl" data-title="Kwas kawowy" data-language-autonym="Polski" data-language-local-name="波兰语" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/%C3%81cido_cafeico" title="Ácido cafeico – 葡萄牙语" lang="pt" hreflang="pt" data-title="Ácido cafeico" data-language-autonym="Português" data-language-local-name="葡萄牙语" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Acid_cafeic" title="Acid cafeic – 罗马尼亚语" lang="ro" hreflang="ro" data-title="Acid cafeic" data-language-autonym="Română" data-language-local-name="罗马尼亚语" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%9A%D0%BE%D1%84%D0%B5%D0%B9%D0%BD%D0%B0%D1%8F_%D0%BA%D0%B8%D1%81%D0%BB%D0%BE%D1%82%D0%B0" title="Кофейная кислота – 俄语" lang="ru" hreflang="ru" data-title="Кофейная кислота" data-language-autonym="Русский" data-language-local-name="俄语" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Kofeinska_kiselina" title="Kofeinska kiselina – 塞尔维亚-克罗地亚语" lang="sh" hreflang="sh" data-title="Kofeinska kiselina" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="塞尔维亚-克罗地亚语" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Kyselina_k%C3%A1vov%C3%A1" title="Kyselina kávová – 斯洛伐克语" lang="sk" hreflang="sk" data-title="Kyselina kávová" data-language-autonym="Slovenčina" data-language-local-name="斯洛伐克语" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Kofeinska_kiselina" title="Kofeinska kiselina – 塞尔维亚语" lang="sr" hreflang="sr" data-title="Kofeinska 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data-mw-deduplicate="TemplateStyles:r84833064">.mw-parser-output .hatnote{font-size:small}.mw-parser-output div.hatnote{padding-left:2em;margin-bottom:0.8em;margin-top:0.8em}.mw-parser-output .hatnote-notice-img::after{content:"\202f \202f \202f \202f "}.mw-parser-output .hatnote-notice-img-small::after{content:"\202f \202f "}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}body.skin-minerva .mw-parser-output .hatnote-notice-img,body.skin-minerva .mw-parser-output .hatnote-notice-img-small{display:none}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable selfref"><span typeof="mw:File"><a href="/wiki/File:Star_of_life_caution.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d5/Star_of_life_caution.svg/20px-Star_of_life_caution.svg.png" decoding="async" width="20" height="18" class="mw-file-element" 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border-style:solid; border:1px; border-collapse:collapse; empty-cells:show; width:305px; font-size:90%;"> <tbody><tr> <th colspan="2" style="font-size:120%; text-align:center; background:#d6e0dc;">咖啡酸 </th></tr> <tr> <td colspan="2" style="background:#ffffff; text-align:center;"><span typeof="mw:File"><a href="/wiki/File:Caffeic_acid.svg" class="mw-file-description" title="Caffeic acid"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4a/Caffeic_acid.svg/200px-Caffeic_acid.svg.png" decoding="async" width="200" height="107" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4a/Caffeic_acid.svg/300px-Caffeic_acid.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/4a/Caffeic_acid.svg/400px-Caffeic_acid.svg.png 2x" data-file-width="248" data-file-height="133" /></a></span> </td></tr> <tr> <td colspan="2" style="background:#ffffff; text-align:center;"><span typeof="mw:File"><a href="/wiki/File:CaffeicAcid3d.png" class="mw-file-description" title="Caffeic acid"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/ef/CaffeicAcid3d.png/200px-CaffeicAcid3d.png" decoding="async" width="200" height="139" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/ef/CaffeicAcid3d.png/300px-CaffeicAcid3d.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/ef/CaffeicAcid3d.png/400px-CaffeicAcid3d.png 2x" data-file-width="736" data-file-height="510" /></a></span> </td></tr> <tr> <td colspan="2" style="max-width:305px; word-wrap: break-word; text-align: center;"><a href="/wiki/IUPAC%E5%91%BD%E5%90%8D%E6%B3%95" title="IUPAC命名法">IUPAC名</a><br />3-(3,4-Dihydroxyphenyl 2-propenoic acid<br />3,4-Dihydroxy-cinnamic acid<br />trans-Caffeate<br />3,4-Dihydroxy-trans-cinnamate)<br /> <p>(E)-3-(3,4-dihydroxyphenyl)-2-propenoic acid<br />3,4-Dihydroxybenzeneacrylicacid<br />3-(3,4-Dihydroxyphenyl)-2-propenoic acid<br />3-(3,4-二羟苯基)-2-<a href="/wiki/%E4%B8%99%E7%83%AF%E9%85%B8" title="丙烯酸">丙烯酸</a><br />3,4-二<a href="/wiki/%E7%BE%9F%E5%9F%BA" title="羟基">羟基</a>苯丙烯酸<br />β-(3,4-二羟苯基)丙烯酸<br />3,4-二羟基肉桂酸<br />3,4-二羟基肉桂酸<br />3,4-二羥基<a href="/wiki/%E6%A1%82%E7%9A%AE%E9%85%B8" class="mw-redirect" title="桂皮酸">桂皮酸</a> </p> </td></tr> <tr> <th style="background:#D6E0DC; text-align:center;" colspan="2">识别 </th></tr> <tr> <td><a href="/wiki/CAS%E5%8F%B7" title="CAS号">CAS号</a> </td> <td><span class="reflink plainlinks nourlexpansion"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=331-39-5">331-39-5</a></span> <sup>?</sup> </td></tr> <tr> <td><a href="/wiki/PubChem" title="PubChem">PubChem</a> </td> <td><span class="reflink plainlinks nourlexpansion"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/689043">689043</a></span> </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><span class="reflink plainlinks nourlexpansion"><a rel="nofollow" class="external text" href="http://www.chemspider.com/600426">600426</a></span> </td></tr> <tr> <td><a href="/wiki/SMILES" class="mw-redirect" title="SMILES">SMILES</a> </td> <td><div style="word-break:break-all;"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div> </div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0;"><li style="line-height: inherit; margin: 0"><span lang="en">O=C(O)\C=C\c1cc(O)c(O)cc1</span></li></ul> </div></div> </td></tr> <tr> <td><a href="/wiki/%E5%9B%BD%E9%99%85%E5%8C%96%E5%90%88%E7%89%A9%E6%A0%87%E8%AF%86" title="国际化合物标识">InChI</a> </td> <td><div style="word-break:break-all;"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div> </div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0;"><li style="line-height: inherit; margin: 0">1/C9H8O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1-5,10-11H,(H,12,13)/b4-2+</li></ul> </div></div> </td></tr> <tr> <td><a href="/wiki/%E5%9B%BD%E9%99%85%E5%8C%96%E5%90%88%E7%89%A9%E6%A0%87%E8%AF%86" title="国际化合物标识">InChIKey</a> </td> <td><small>QAIPRVGONGVQAS-DUXPYHPUBE</small> </td></tr> <tr> <th style="background:#D6E0DC; text-align:center;" colspan="2">性质 </th></tr> <tr> <td><a href="/wiki/%E5%8C%96%E5%AD%A6%E5%BC%8F" title="化学式">化学式</a> </td> <td><span lang="en">C<sub>9</sub>H<sub>8</sub>O<sub>4</sub></span> </td></tr> <tr> <td><a href="/wiki/%E6%91%A9%E5%B0%94%E8%B4%A8%E9%87%8F" title="摩尔质量">摩尔质量</a> </td> <td>180.16 g·mol⁻¹ </td></tr> <tr> <td><a href="/wiki/%E5%AF%86%E5%BA%A6" title="密度">密度</a> </td> <td>1.478 g/cm³ </td></tr> <tr> <td><a href="/wiki/%E7%86%94%E7%82%B9" title="熔点">熔点</a> </td> <td>223-225 °C </td></tr> <tr> <td><a href="/w/index.php?title=%E7%B4%AB%E5%A4%96%E5%8F%AF%E8%A7%81%E5%90%B8%E6%94%B6%E5%85%89%E8%B0%B1&action=edit&redlink=1" class="new" title="紫外可见吸收光谱（页面不存在）">λ<sub>max<sub></sub></sub></a> </td> <td>327<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> <a href="/wiki/%E7%BA%B3%E7%B1%B3" title="纳米">nm</a> </td></tr> <tr> <th style="background:#D6E0DC; text-align:center;" colspan="2">危险性 </th></tr> <tr> <td colspan="2" style="text-align: center;"><a href="/wiki/%E5%85%A8%E7%90%83%E5%8C%96%E5%AD%A6%E5%93%81%E7%BB%9F%E4%B8%80%E5%88%86%E7%B1%BB%E5%92%8C%E6%A0%87%E7%AD%BE%E5%88%B6%E5%BA%A6" title="全球化学品统一分类和标签制度">GHS危险性符号</a><br /><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-exclam.svg" class="mw-file-description" title="《全球化学品统一分类和标签制度》（简称“GHS”）中有害物质的标签图案"><img alt="《全球化学品统一分类和标签制度》（简称“GHS”）中有害物质的标签图案" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/50px-GHS-pictogram-exclam.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/75px-GHS-pictogram-exclam.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/100px-GHS-pictogram-exclam.svg.png 2x" data-file-width="512" data-file-height="512" /></a></span><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-silhouette.svg" class="mw-file-description" title="《全球化学品统一分类和标签制度》（简称“GHS”）中对人体有害物质的标签图案"><img alt="《全球化学品统一分类和标签制度》（简称“GHS”）中对人体有害物质的标签图案" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/50px-GHS-pictogram-silhouette.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/75px-GHS-pictogram-silhouette.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/100px-GHS-pictogram-silhouette.svg.png 2x" data-file-width="724" data-file-height="724" /></a></span> </td></tr> <tr> <td><a href="/wiki/%E5%85%A8%E7%90%83%E5%8C%96%E5%AD%A6%E5%93%81%E7%BB%9F%E4%B8%80%E5%88%86%E7%B1%BB%E5%92%8C%E6%A0%87%E7%AD%BE%E5%88%B6%E5%BA%A6" title="全球化学品统一分类和标签制度">GHS提示词</a> </td> <td>Warning </td></tr> <tr> <td><a href="/wiki/GHS%E5%8D%B1%E9%99%A9%E8%AF%B4%E6%98%8E" title="GHS危险说明">H-术语</a> </td> <td><span class="abbr skin-invert" style="color: blue; border-bottom: 1px dotted blue" title="造成皮肤刺激">H315</span>, <span class="abbr skin-invert" style="color: blue; border-bottom: 1px dotted blue" title="造成严重眼刺激">H319</span>, <span class="abbr skin-invert" style="color: blue; border-bottom: 1px dotted blue" title="可能引起呼吸道刺激">H335</span>, <span class="abbr skin-invert" style="color: blue; border-bottom: 1px dotted blue" title="怀疑会致癌">H351</span>, <span class="abbr skin-invert" style="color: blue; border-bottom: 1px dotted blue" title="怀疑会可能对生育能力或胎儿造成伤害">H361</span> </td></tr> <tr> <td><a href="/wiki/GHS%E9%98%B2%E8%8C%83%E8%AF%B4%E6%98%8E" title="GHS防范说明">P-术语</a> </td> <td><span class="abbr skin-invert" style="color: blue; border-bottom: 1px dotted blue" title="在使用前获取特别指示">P201</span>, <span class="abbr skin-invert" style="color: blue; border-bottom: 1px dotted blue" title="在读懂所有安全防范措施之前切勿搬动">P202</span>, <span class="abbr skin-invert" style="color: blue; border-bottom: 1px dotted blue" title="避免吸入粉尘/烟/气体/烟雾/蒸气/喷雾">P261</span>, <span class="abbr skin-invert" style="color: blue; border-bottom: 1px dotted blue" title="作业后彻底清洗……">P264</span>, <span class="abbr skin-invert" style="color: blue; border-bottom: 1px dotted blue" title="只能在室外或通风良好处使用">P271</span>, <span class="abbr skin-invert" style="color: blue; border-bottom: 1px dotted blue" title="戴防护手套/穿防护服/戴防护眼罩/戴防护面具">P280</span>, <span class="abbr skin-invert" style="color: blue; border-bottom: 1px dotted blue" title="按要求使用个人防护设备">P281</span>, <span class="abbr skin-invert" style="color: blue; border-bottom: 1px dotted blue" title="如皮肤沾染：用大量肥皂和水清洗">P302+352</span>, <span class="abbr skin-invert" style="color: blue; border-bottom: 1px dotted blue" title="如误吸入：将伤者转移到空气新鲜处，使其保持呼吸舒适的休息姿势">P304+340</span>, <span class="abbr skin-invert" style="color: blue; border-bottom: 1px dotted blue" title="如进入眼睛：用水小心冲洗几分钟。如戴隐形眼镜并可方便地取出，取出隐形眼镜再继续冲洗">P305+351+338</span>, <span class="abbr skin-invert" style="color: blue; border-bottom: 1px dotted blue" title="如接触到或有疑虑：求医/就诊">P308+313</span>, <span class="abbr skin-invert" style="color: blue; border-bottom: 1px dotted blue" title="如感觉不适，呼叫解毒中心或医生">P312</span>, <span class="abbr skin-invert" style="color: blue; border-bottom: 1px dotted blue" title="具体治疗（见本标签上的……）">P321</span>, <span class="abbr skin-invert" style="color: blue; border-bottom: 1px dotted blue" title="如发生皮肤刺激：求医/就诊">P332+313</span> </td></tr> <tr> <td><a href="/wiki/NFPA_704" title="NFPA 704">NFPA 704</a> </td> <td> <div style="position: relative; height: 85px; width: 75px;"> <div style="position: absolute; height: 75px; width: 75px;"><span typeof="mw:File"><a href="/wiki/File:NFPA_704.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/75px-NFPA_704.svg.png" decoding="async" width="75" height="75" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/113px-NFPA_704.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/150px-NFPA_704.svg.png 2x" data-file-width="512" data-file-height="512" /></a></span></div> <div title="可燃性" style="background: transparent; width: 75px; height: 2em; text-align: center; vertical-align: middle; position: absolute; top: 3px; font-size: large;"><span class="abbr" style="color: black;" title="可燃性1級。必須預熱才可能引燃（如菜籽油）。閃點高於93°C。"><b>1</b></span></div> <div title="健康" style="background: transparent; width: 37.5px; height: 2em; text-align: center; vertical-align: middle; position: absolute; top: 21px; font-size: large;"><span class="abbr" style="color: black;" title="健康危險1級。暴露可能導致不適，但是僅可能有輕微持續性傷害（如松節油）。"><b>1</b></span></div> <div title="反應性" style="background: transparent; width: 37.5px; height: 2em; text-align: center; vertical-align: middle; position: absolute; top: 21px; left: 37.5px; font-size: large;"><span class="abbr" style="color: black;" title="反應性0級。通常情況下穩定，即使暴露於明火中也不反應，並且不與水反應（如液氮）。"><b>0</b></span></div> <div title="其它危險" style="background: transparent; width: 75px; height: 2em; text-align: center; vertical-align: middle; position: absolute; top: 44px; font-size: small;"> </div> </div> </td></tr> <tr> <th style="background:#D6E0DC; text-align:center;" colspan="2">相关物质 </th></tr> <tr> <td>相关化学品 </td> <td><a href="/wiki/%E7%B6%A0%E5%8E%9F%E9%85%B8" title="綠原酸">绿原酸</a><br /><a href="/wiki/%E5%A5%8E%E5%B0%BC%E9%85%B8" title="奎尼酸">奎尼酸</a> </td></tr> <tr> <td style="background:#D6E0DC; text-align:center;" colspan="2">若非注明，所有数据均出自<a href="/wiki/%E6%A0%87%E5%87%86%E7%8A%B6%E6%80%81" title="标准状态">标准状态（25 ℃，100 kPa）</a>下。 </td></tr></tbody></table> <p><b>咖啡酸</b>（英語：<span lang="en"><b>Caffeic acid</b></span>）是一种归属于羟基肉桂酸的有机化合物，同时具有<a href="/wiki/%E8%8B%AF%E9%85%9A" title="苯酚">酚羟基</a>和<a href="/wiki/%E4%B8%99%E7%83%AF%E9%85%B8" title="丙烯酸">丙烯酸</a>两种官能团结构。因为咖啡酸是生物合成植物生物质及其残留物的主要组分之一<a href="/wiki/%E6%9C%A8%E8%B4%A8%E7%B4%A0" title="木质素">木质素</a>的关键中间体，所以它广泛存在于各种植物中<sup id="cite_ref-Boerjan_2-0" class="reference"><a href="#cite_note-Boerjan-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup>。它可以在热水和<a href="/wiki/%E4%B9%99%E9%86%87" title="乙醇">乙醇</a>中溶解，冷水中微溶。常温下为黄白色<a href="/wiki/%E7%BB%93%E6%99%B6" title="结晶">结晶</a>体。 </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="自然中的含量"><span id=".E8.87.AA.E7.84.B6.E4.B8.AD.E7.9A.84.E5.90.AB.E9.87.8F"></span>自然中的含量</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%E5%92%96%E5%95%A1%E9%85%B8&action=edit&section=1" title="编辑章节：自然中的含量"><span>编辑</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>自然界中，咖啡酸可以在<a href="/wiki/%E8%93%9D%E6%A1%89" title="蓝桉">蓝桉</a>的树皮中找到<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup>，也可以在淡水蕨类<a href="/wiki/%E6%A7%90%E5%8F%B6%E8%8B%B9" class="mw-redirect" title="槐叶苹">槐叶苹</a><sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup>或<a href="/w/index.php?title=%E6%A1%91%E9%BB%84%E8%98%91%E8%8F%87&action=edit&redlink=1" class="new" title="桑黄蘑菇（页面不存在）">桑黄蘑菇</a>中发现<sup id="cite_ref-pmid18827365_5-0" class="reference"><a href="#cite_note-pmid18827365-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup>。 </p> <div class="mw-heading mw-heading3"><h3 id="食物中的含量"><span id=".E9.A3.9F.E7.89.A9.E4.B8.AD.E7.9A.84.E5.90.AB.E9.87.8F"></span>食物中的含量</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%E5%92%96%E5%95%A1%E9%85%B8&action=edit&section=2" title="编辑章节：食物中的含量"><span>编辑</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>咖啡酸在<a href="/wiki/%E5%92%96%E5%95%A1" title="咖啡">咖啡</a>中的含量非常低，仅为0.03毫克/ 100毫升。它是<a href="/w/index.php?title=%E6%91%A9%E6%B4%9B%E5%93%A5%E5%9D%9A%E6%9E%9C%E6%B2%B9&action=edit&redlink=1" class="new" title="摩洛哥坚果油（页面不存在）">摩洛哥坚果油</a>所含的主要天然酚类之一<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup>，在一些草药，特别是百里香、鼠尾草和留兰香中咖啡酸的含量较高（约20mg/100g）。在<a href="/wiki/%E9%94%A1%E5%85%B0%E8%82%89%E6%A1%82" title="锡兰肉桂">锡兰肉桂</a>和<a href="/wiki/%E5%85%AB%E8%A7%92%E8%8C%B4%E9%A6%99" class="mw-redirect" title="八角茴香">八角茴香</a>中的含量约22mg/100g。向日葵种子中的咖啡酸含量较高（8mg/100g），在红葡萄酒存在一定量的咖啡酸（1.88mg/100ml），苹果酱，杏和李子中也含有咖啡酸（1mg/100g）。南美州的草药<a href="/wiki/%E5%B7%B4%E6%8B%89%E5%9C%AD%E5%86%AC%E9%9D%92" title="巴拉圭冬青">巴拉圭冬青</a>中也有相当高含量的咖啡酸（基于薄层色谱密度测定<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup>和<a href="/wiki/%E9%AB%98%E6%95%88%E6%B6%B2%E7%9B%B8%E8%89%B2%E8%B0%B1%E6%B3%95" title="高效液相色谱法">高效液相色谱法</a><sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup>测得的含量为150mg /100g）。同时也存在于大麦谷物中<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup>。 </p> <div class="mw-heading mw-heading2"><h2 id="代谢途径"><span id=".E4.BB.A3.E8.B0.A2.E9.80.94.E5.BE.84"></span>代谢途径</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%E5%92%96%E5%95%A1%E9%85%B8&action=edit&section=3" title="编辑章节：代谢途径"><span>编辑</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="生源合成"><span id=".E7.94.9F.E6.BA.90.E5.90.88.E6.88.90"></span>生源合成</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%E5%92%96%E5%95%A1%E9%85%B8&action=edit&section=4" title="编辑章节：生源合成"><span>编辑</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>咖啡酸的生源合成是从<a href="/wiki/%E7%B6%A0%E5%8E%9F%E9%85%B8" title="綠原酸">绿原酸</a>的香豆酸酯（酯化的侧链醇）经<a href="/wiki/%E7%BE%9F%E5%9F%BA%E5%8C%96" title="羟基化">羟基化</a>产生的。这种羟基化过程产生莽草酸的咖啡酸酯，进而转化为绿原酸。它是阿魏酸，松柏醇和芥子醇的前体，它们是形成木质素的重要结构单元<sup id="cite_ref-Boerjan_2-1" class="reference"><a href="#cite_note-Boerjan-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup>。 </p><p>许多种植物能产生咖啡酸及其衍生物咖啡酸苯乙醇酯<sup id="cite_ref-pmid11208940_10-0" class="reference"><a href="#cite_note-pmid11208940-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup>。 </p> <dl><dd><figure class="mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:CaffeicAcIn.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/65/CaffeicAcIn.png/300px-CaffeicAcIn.png" decoding="async" width="300" height="140" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/65/CaffeicAcIn.png/450px-CaffeicAcIn.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/65/CaffeicAcIn.png/600px-CaffeicAcIn.png 2x" data-file-width="1464" data-file-height="681" /></a><figcaption>在植物中，从4-羟基肉桂酸（左）形成咖啡酸（中间），并进而转化为阿魏酸。</figcaption></figure></dd></dl> <div style="clear:left;"></div> <div class="mw-heading mw-heading3"><h3 id="生物转化"><span id=".E7.94.9F.E7.89.A9.E8.BD.AC.E5.8C.96"></span>生物转化</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%E5%92%96%E5%95%A1%E9%85%B8&action=edit&section=5" title="编辑章节：生物转化"><span>编辑</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>咖啡因O-甲基转移酶是负责将咖啡酸转化为<a href="/wiki/%E9%98%BF%E9%AD%8F%E9%85%B8" title="阿魏酸">阿魏酸</a>的酶。咖啡酸和相关的邻二酚被组织提取物中的邻二酚氧化酶快速氧化<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup>。 </p> <div class="mw-heading mw-heading2"><h2 id="药理作用"><span id=".E8.8D.AF.E7.90.86.E4.BD.9C.E7.94.A8"></span>药理作用</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%E5%92%96%E5%95%A1%E9%85%B8&action=edit&section=6" title="编辑章节：药理作用"><span>编辑</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>在体外研究和动物模型中发现咖啡酸具有多种潜在的药理作用，通过氧化机制咖啡酸对人HT-1080纤维肉瘤细胞系中的对癌细胞增殖的抑制作用。<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> 咖啡酸在体外和活体内都是一种抗氧化剂<sup id="cite_ref-pmid11208940_10-1" class="reference"><a href="#cite_note-pmid11208940-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup>。咖啡酸还显示出免疫调节和抗炎活性，咖啡酸能使黄曲霉毒素产量降低超过95％，优于其他抗氧化剂。研究表明否则触发<a href="/wiki/%E9%BB%84%E6%9B%B2%E9%9C%89" class="mw-redirect" title="黄曲霉">黄曲霉</a>产生<a href="/wiki/%E9%BB%83%E9%BA%B4%E6%AF%92%E7%B4%A0" title="黃麴毒素">黃麴毒素</a>的应激氧化可被咖啡酸阻碍。对咖啡酸致癌性的研究具有混合的结果<sup id="cite_ref-Hirose_13-0" class="reference"><a href="#cite_note-Hirose-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup>。一部分研究结果表明它抑制致癌作用，另一部分结果显示咖啡酸有致癌作用<sup id="cite_ref-Hirose_13-1" class="reference"><a href="#cite_note-Hirose-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup>。对大鼠进行高剂量咖啡酸的口服给药会引起胃乳头状瘤<sup id="cite_ref-Hirose_13-2" class="reference"><a href="#cite_note-Hirose-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup>。在相同的研究中，高剂量包含咖啡酸的组合抗氧化剂则能显著减少相同种类大鼠<a href="/wiki/%E7%BB%93%E8%82%A0" title="结肠">结肠</a><a href="/wiki/%E8%82%BF%E7%98%A4" class="mw-redirect" title="肿瘤">肿瘤</a>的生长<sup id="cite_ref-Hirose_13-3" class="reference"><a href="#cite_note-Hirose-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup>。在一些危险物数据表中咖啡酸被列为潜在致癌物，它已被<a href="/wiki/%E5%9B%BD%E9%99%85%E7%99%8C%E7%97%87%E7%A0%94%E7%A9%B6%E6%9C%BA%E6%9E%84" title="国际癌症研究机构">国际癌症研究机构</a>列为<a href="/wiki/2B%E9%A1%9E%E8%87%B4%E7%99%8C%E7%89%A9" class="mw-redirect" title="2B類致癌物">2B类致癌物</a>（“可能对人类致癌”）<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup>。一些研究数据显示，大鼠肠道中的细菌可能改变咖啡酸<a href="/wiki/%E4%BB%A3%E8%B0%A2%E4%BA%A7%E7%89%A9" class="mw-redirect" title="代谢产物">代谢产物</a>的形成<sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup>。 </p> <div class="mw-heading mw-heading2"><h2 id="化学性质"><span id=".E5.8C.96.E5.AD.A6.E6.80.A7.E8.B4.A8"></span>化学性质</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%E5%92%96%E5%95%A1%E9%85%B8&action=edit&section=7" title="编辑章节：化学性质"><span>编辑</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>咖啡酸易于自动氧化。<a href="/wiki/%E8%B0%B7%E8%83%B1%E7%94%98%E8%82%BD" title="谷胱甘肽">谷胱甘肽</a>以及<a href="/wiki/%E7%A1%AB%E9%86%87" title="硫醇">硫醇</a>类化合物（例如<a href="/wiki/%E5%8D%8A%E8%83%B1%E6%B0%A8%E9%85%B8" title="半胱氨酸">半胱氨酸</a>，<a href="/wiki/%E5%B7%AF%E5%9F%BA%E4%B9%99%E9%85%B8" title="巯基乙酸">巯基乙酸</a>或甲琉酚）或抗坏血酸对咖啡酸的褐变和消失具有抑制作用<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup>，咖啡酸的褐变是由邻二酚被氧化为邻二醌造成的。在酸性条件下用<a href="/wiki/%E9%AB%98%E7%A2%98%E9%85%B8%E9%92%A0" title="高碘酸钠">高碘酸钠</a>对咖啡酸进行化学氧化会生成具有呋喃结构的二聚体（2,5-（3'，4'-二羟基苯基）四氢呋喃3,4-二羧酸的异构体）<sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup>。使用<a href="/wiki/%E8%BE%A3%E6%A0%B9%E8%BF%87%E6%B0%A7%E5%8C%96%E7%89%A9%E9%85%B6" title="辣根过氧化物酶">辣根过氧化物酶</a>/<a href="/wiki/%E8%BF%87%E6%B0%A7%E5%8C%96%E6%B0%A2" title="过氧化氢">过氧化氢</a>的氧化系统能使咖啡酸聚合<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup>。 </p> <div class="mw-heading mw-heading2"><h2 id="其他用途"><span id=".E5.85.B6.E4.BB.96.E7.94.A8.E9.80.94"></span>其他用途</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%E5%92%96%E5%95%A1%E9%85%B8&action=edit&section=8" title="编辑章节：其他用途"><span>编辑</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>咖啡酸也用于<a href="/wiki/%E8%9B%8B%E7%99%BD%E8%B4%A8" title="蛋白质">蛋白质</a>的<a href="/wiki/%E5%9F%BA%E8%B4%A8%E8%BE%85%E5%8A%A9%E6%BF%80%E5%85%89%E8%A7%A3%E5%90%B8/%E7%94%B5%E7%A6%BB" title="基质辅助激光解吸/电离">基质辅助激光解吸/电离</a><a href="/wiki/%E8%B4%A8%E8%B0%B1%E6%B3%95" title="质谱法">质谱</a>分析的辅助基质<sup id="cite_ref-pmid2520223_20-0" class="reference"><a href="#cite_note-pmid2520223-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup>。 </p> <div class="mw-heading mw-heading2"><h2 id="同分异构体"><span id=".E5.90.8C.E5.88.86.E5.BC.82.E6.9E.84.E4.BD.93"></span>同分异构体</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%E5%92%96%E5%95%A1%E9%85%B8&action=edit&section=9" title="编辑章节：同分异构体"><span>编辑</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>咖啡酸有三个同属于羟基苯丙烯酸的同分异构体，分别是： </p> <ul><li><a href="/wiki/%E4%BC%9E%E5%BD%A2%E9%85%B8" title="伞形酸">伞形酸</a>（2,4-二羟基肉桂酸）</li> <li><a href="/wiki/2,3-%E4%BA%8C%E7%BE%A5%E5%9F%BA%E8%82%89%E6%A1%82%E9%85%B8" title="2,3-二羥基肉桂酸">2,3-二羟基肉桂酸</a></li> <li><a href="/wiki/2,5-%E4%BA%8C%E7%BE%9F%E5%9F%BA%E8%82%89%E6%A1%82%E9%85%B8" title="2,5-二羟基肉桂酸">2,5-二羟基肉桂酸</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="参考文献"><span id=".E5.8F.82.E8.80.83.E6.96.87.E7.8C.AE"></span>参考文献</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%E5%92%96%E5%95%A1%E9%85%B8&action=edit&section=10" title="编辑章节：参考文献"><span>编辑</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="reflist" style="list-style-type: decimal;"> <ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><cite class="citation journal">Gould, Kevin S.; Markham, Kenneth R.; Smith, Richard H.; Goris, Jessica J. <a 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