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Ácido cafeico – Wikipédia, a enciclopédia livre
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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">Início</div> </a> </li> <li id="toc-Notas_e_referências" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Notas_e_referências"> <div class="vector-toc-text"> <span class="vector-toc-numb">1</span> <span>Notas e referências</span> </div> </a> <ul id="toc-Notas_e_referências-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="Conteúdo" 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="Alternar o índice" > <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">Alternar o índice</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">Ácido cafeico</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="Ir para um artigo noutra língua. Disponível em 27 línguas" > <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 línguas</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 — árabe" lang="ar" hreflang="ar" data-title="حمض الكافئيك" data-language-autonym="العربية" data-language-local-name="árabe" 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 — búlgaro" lang="bg" hreflang="bg" data-title="Кафеена киселина" data-language-autonym="Български" data-language-local-name="búlgaro" 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 — bósnio" lang="bs" hreflang="bs" data-title="Kofeinska kiselina" data-language-autonym="Bosanski" data-language-local-name="bósnio" 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 — catalão" lang="ca" hreflang="ca" data-title="Àcid cafeic" data-language-autonym="Català" data-language-local-name="catalão" 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 — checo" lang="cs" hreflang="cs" data-title="Kyselina kávová" data-language-autonym="Čeština" data-language-local-name="checo" 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 — alemão" lang="de" hreflang="de" data-title="Kaffeesäure" data-language-autonym="Deutsch" data-language-local-name="alemão" 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 — inglês" lang="en" hreflang="en" data-title="Caffeic acid" data-language-autonym="English" data-language-local-name="inglês" 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 — esperanto" lang="eo" hreflang="eo" data-title="Kafeata acido" data-language-autonym="Esperanto" data-language-local-name="esperanto" 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 — espanhol" lang="es" hreflang="es" data-title="Ácido cafeico" data-language-autonym="Español" data-language-local-name="espanhol" 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 — basco" lang="eu" hreflang="eu" data-title="Azido kafeiko" data-language-autonym="Euskara" data-language-local-name="basco" 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 — persa" lang="fa" hreflang="fa" data-title="کافئیک اسید" data-language-autonym="فارسی" data-language-local-name="persa" 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 — finlandês" lang="fi" hreflang="fi" data-title="Kahvihappo" data-language-autonym="Suomi" data-language-local-name="finlandês" 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 — francês" lang="fr" hreflang="fr" data-title="Acide caféique" data-language-autonym="Français" data-language-local-name="francês" 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 — húngaro" lang="hu" hreflang="hu" data-title="Kávésav" data-language-autonym="Magyar" data-language-local-name="húngaro" 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 — italiano" lang="it" hreflang="it" data-title="Acido caffeico" data-language-autonym="Italiano" data-language-local-name="italiano" 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 — japonês" lang="ja" hreflang="ja" data-title="コーヒー酸" data-language-autonym="日本語" data-language-local-name="japonês" 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 — coreano" lang="ko" hreflang="ko" data-title="커피산" data-language-autonym="한국어" data-language-local-name="coreano" 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 — neerlandês" lang="nl" hreflang="nl" data-title="Koffiezuur" data-language-autonym="Nederlands" data-language-local-name="neerlandês" 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 — polaco" lang="pl" hreflang="pl" data-title="Kwas kawowy" data-language-autonym="Polski" data-language-local-name="polaco" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Acid_cafeic" title="Acid cafeic — romeno" lang="ro" hreflang="ro" data-title="Acid cafeic" data-language-autonym="Română" data-language-local-name="romeno" 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 — russo" lang="ru" hreflang="ru" data-title="Кофейная кислота" data-language-autonym="Русский" data-language-local-name="russo" 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 — servo-croata" lang="sh" hreflang="sh" data-title="Kofeinska kiselina" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="servo-croata" 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 — eslovaco" lang="sk" hreflang="sk" data-title="Kyselina kávová" data-language-autonym="Slovenčina" data-language-local-name="eslovaco" 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 — sérvio" lang="sr" hreflang="sr" data-title="Kofeinska kiselina" data-language-autonym="Српски / srpski" data-language-local-name="sérvio" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%9A%D0%B0%D0%B2%D0%BE%D0%B2%D0%B0_%D0%BA%D0%B8%D1%81%D0%BB%D0%BE%D1%82%D0%B0" title="Кавова кислота — ucraniano" lang="uk" hreflang="uk" data-title="Кавова кислота" data-language-autonym="Українська" data-language-local-name="ucraniano" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E5%92%96%E5%95%A1%E9%85%B8" title="咖啡酸 — chinês" lang="zh" hreflang="zh" data-title="咖啡酸" data-language-autonym="中文" data-language-local-name="chinês" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet 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livre.</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="pt" dir="ltr"><table class="toccolours" style="width: 300px; float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"> <tbody><tr> <th style="background: #F8EABA; text-align: center;" colspan="2">Caffeic acid<br /><small><a href="/wiki/Wikip%C3%A9dia:Aviso_m%C3%A9dico" title="Wikipédia:Aviso médico">Alerta sobre risco à saúde</a></small> </th></tr> <tr> <td align="center" colspan="2" bgcolor="#ffffff"><span typeof="mw:File"><a href="/wiki/Ficheiro:Caffeic_acid.svg" class="mw-file-description"><img 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, 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/>(E)-3-(3,4-dihydroxyphenyl)-2-propenoic acid<br />3,4-Dihydroxybenzeneacrylicacid<br />3-(3,4-Dihydroxyphenyl)-2-propenoic acid </td></tr> <tr> <th style="background: #F8EABA; text-align: center;" colspan="2">Identificadores </th></tr> <tr> <td bgcolor=""><a href="/wiki/Registro_CAS" class="mw-redirect" title="Registro CAS">Número CAS</a> </td> <td bgcolor=""><span class="reflink plainlinksneverexpand"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=331-39-5">331-39-5</a></span> </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><span class="reflink plainlinksneverexpand"><a rel="nofollow" class="external text" href="http://www.chemspider.com/Chemical-Structure.600426">600426</a></span> </td></tr> <tr> <td><a href="/wiki/SMILES" title="SMILES">SMILES</a> </td> <td><small><tt><div class="NavFrame collapsed" style="border: none; padding: 0;"> <div class="NavHead" style="font-size: 105%; background: transparent; text-align: left;"> </div> <ul class="NavContent" style="list-style: none none; margin-left: 0; text-align: left; font-size: 105%; margin-top: 0; margin-bottom: 0; line-height: inherit;"><li style="line-height: inherit; margin: 0">Oc1ccc(/C=C/C(O)=O)cc1O</li></ul> </div></tt></small> </td></tr> <tr> <th style="background: #F8EABA; text-align: center;" colspan="2">Propriedades </th></tr> <tr> <td><a href="/wiki/F%C3%B3rmula_qu%C3%ADmica" title="Fórmula química">Fórmula molecular</a> </td> <td>C<sub>9</sub>H<sub>8</sub>O<sub>4</sub> </td></tr> <tr> <td><a href="/wiki/Massa_molar" title="Massa molar">Massa molar</a> </td> <td>180.16 g/mol </td></tr> <tr> <td><a href="/wiki/Densidade" title="Densidade">Densidade</a> </td> <td>1.478 g/cm³ </td></tr> <tr> <td><a href="/wiki/Ponto_de_fus%C3%A3o" title="Ponto de fusão">Ponto de fusão</a> </td> <td> <p>223-225 °C </p> </td></tr> <tr> <th style="background: #F8EABA; text-align: center;" colspan="2">Compostos relacionados </th></tr> <tr> <td><a href="/w/index.php?title=%C3%81cidos_fen%C3%B3licos&action=edit&redlink=1" class="new" title="Ácidos fenólicos (página não existe)">Ácidos fenólicos</a> relacionados </td> <td><a href="/wiki/%C3%81cido_cin%C3%A2mico" title="Ácido cinâmico">Ácido cinâmico</a> ((E)-3-fenil-propenoico)<br /><a href="/wiki/%C3%81cido_fer%C3%BAlico" title="Ácido ferúlico">Ácido ferúlico</a> (3-(4-hidróxi-3-metóxifenil)propenoico)<br /><a href="/wiki/%C3%81cido_sinap%C3%ADnico" title="Ácido sinapínico">Ácido sinapínico</a> (3-(4-hidróxi-3,5-dimetóxifenil)propenoico) </td></tr> <tr> <td>Compostos relacionados </td> <td><a href="/w/index.php?title=%C3%81lcool_cafeico&action=edit&redlink=1" class="new" title="Álcool cafeico (página não existe)">Álcool cafeico</a> </td></tr> <tr> <th style="background: #F8EABA; text-align: center;" colspan="2"><a class="mw-selflink selflink">Página de dados suplementares</a> </th></tr> <tr> <td><a class="mw-selflink-fragment" href="#Estrutura_e_propriedades">Estrutura e propriedades</a> </td> <td><a href="/wiki/%C3%8Dndice_de_refrac%C3%A7%C3%A3o" class="mw-redirect" title="Índice de refracção"><i>n</i></a>, <a href="/wiki/Constante_diel%C3%A9ctrica" class="mw-redirect" title="Constante dieléctrica">ε<sub>r</sub></a>, etc. </td></tr> <tr> <td><a class="mw-selflink-fragment" href="#Propriedades_termodinâmicas">Dados termodinâmicos</a> </td> <td>Phase behaviour<br />Solid, liquid, gas </td></tr> <tr> <td><a class="mw-selflink-fragment" href="#Dados_espectrais">Dados espectrais</a> </td> <td><a href="/wiki/Espectroscopia_UV/vis%C3%ADvel" title="Espectroscopia UV/visível">UV</a>, <a href="/wiki/Espectroscopia_de_infravermelho" title="Espectroscopia de infravermelho">IV</a>, <a href="/wiki/Espectroscopia_de_resson%C3%A2ncia_magn%C3%A9tica_nuclear" class="mw-redirect" title="Espectroscopia de ressonância magnética nuclear">RMN</a>, <a href="/wiki/Espectroscopia_de_massa" class="mw-redirect" title="Espectroscopia de massa">EM</a> </td></tr> <tr> <td style="background: #F8EABA; text-align: center;" colspan="2"><small><b>Exceto onde denotado, os dados referem-se a<br /> materiais sob <a href="/wiki/Condi%C3%A7%C3%B5es_normais_de_temperatura_e_press%C3%A3o" title="Condições normais de temperatura e pressão">condições normais de temperatura e pressão</a></b><br /><b><a href="/wiki/Wikip%C3%A9dia:Informa%C3%A7%C3%A3o_nas_infocaixas_de_qu%C3%ADmica" title="Wikipédia:Informação nas infocaixas de química">Referências e avisos gerais sobre esta caixa</a>.</b><br /><b><a href="/wiki/Wikip%C3%A9dia:Aviso_m%C3%A9dico" title="Wikipédia:Aviso médico">Alerta sobre risco à saúde</a>.</b> </small> </td></tr> </tbody></table> <p><b>Ácido caféico</b> é um <a href="/wiki/%C3%81cido_fen%C3%B3lico" title="Ácido fenólico">ácido fenólico</a> que tem como propriedade a ligação entre si e outros compostos. Possui atividade <a href="/wiki/Antioxidante" title="Antioxidante">antioxidante</a>.<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span>[</span>1<span>]</span></a></sup> </p> <p> É classificado como agente possivelmente carcinogênico para humanos na <a href="/wiki/Lista_Nacional_de_Agentes_Cancer%C3%ADgenos_para_Humanos" title="Lista Nacional de Agentes Cancerígenos para Humanos">Lista Nacional de Agentes Cancerígenos para Humanos</a> - LINACH, publicada pelos Ministérios do Trabalho e Emprego, da Saúde, e da Previdência Social (Portaria Interministerial 9, de 7/10/2014)<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span>[</span>2<span>]</span></a></sup>, com base em estudos da Agência de Pesquisa em Câncer da Organização Mundial da Saúde (IARC/OMS)<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span>[</span>3<span>]</span></a></sup>. </p><h2 id="Notas_e_referências" style="cursor: help;" title="Esta seção foi configurada para não ser editável diretamente. Edite a página toda ou a seção anterior em vez disso."><span id="Notas_e_refer.C3.AAncias"></span>Notas e referências</h2> <div class="reflist" style="list-style-type: decimal;"><div class="mw-references-wrap"><ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><a href="#cite_ref-1">↑</a></span> <span class="reference-text"><cite class="citation web">Rev. Nutr. vol.15 no.1 Campinas Jan. 2002. <a rel="nofollow" class="external text" href="http://www.scielo.br/scielo.php?pid=S1415-52732002000100008&script=sci_arttext">«Ácidos fenólicos como antioxidantes»</a><span class="reference-accessdate">. Consultado em 15 de outubro de 2009</span></cite><span title="ctx_ver=Z39.88-2004&rfr_id=info%3Asid%2Fpt.wikipedia.org%3A%C3%81cido+cafeico&rft.au=Rev.+Nutr.+vol.15+no.1+Campinas+Jan.+2002&rft.btitle=%C3%81cidos+fen%C3%B3licos+como+antioxidantes&rft.genre=unknown&rft_id=http%3A%2F%2Fwww.scielo.br%2Fscielo.php%3Fpid%3DS1415-52732002000100008%26script%3Dsci_arttext&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook" class="Z3988"><span style="display:none;"> </span></span></span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><a href="#cite_ref-2">↑</a></span> <span class="reference-text"><cite class="citation web"><a rel="nofollow" class="external text" href="http://pesquisa.in.gov.br/imprensa/jsp/visualiza/index.jsp?jornal=1&pagina=140&data=08/10/2014">«Portaria Interministerial número 9»</a>. Ministérios do Trabalho e Emprego, da Saúde; da previdência Social. 8 de outubro de 2014<span class="reference-accessdate">. Consultado em 8 de fevereiro de 2016</span></cite><span title="ctx_ver=Z39.88-2004&rfr_id=info%3Asid%2Fpt.wikipedia.org%3A%C3%81cido+cafeico&rft.btitle=Portaria+Interministerial+n%C3%BAmero+9&rft.date=2014-10-08&rft.genre=unknown&rft.pub=Minist%C3%A9rios+do+Trabalho+e+Emprego%2C+da+Sa%C3%BAde%3B+da+previd%C3%AAncia+Social.&rft_id=http%3A%2F%2Fpesquisa.in.gov.br%2Fimprensa%2Fjsp%2Fvisualiza%2Findex.jsp%3Fjornal%3D1%26pagina%3D140%26data%3D08%2F10%2F2014&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook" class="Z3988"><span style="display:none;"> </span></span></span> </li> <li id="cite_note-3"><span class="mw-cite-backlink"><a href="#cite_ref-3">↑</a></span> <span class="reference-text"><cite class="citation web"><a rel="nofollow" class="external text" href="http://monographs.iarc.fr/ENG/Monographs/vol56/mono56-8.pdf">«Monografia sobre Ácido cafeico (em inglês)»</a> <span style="font-size:85%;">(PDF)</span>. IARC - Agência de Pesquisa em Câncer da Organização Mundial da Saúde<span class="reference-accessdate">. Consultado em 8 de fevereiro de 2016</span></cite><span title="ctx_ver=Z39.88-2004&rfr_id=info%3Asid%2Fpt.wikipedia.org%3A%C3%81cido+cafeico&rft.btitle=Monografia+sobre+%C3%81cido+cafeico+%28em+ingl%C3%AAs%29&rft.genre=unknown&rft.pub=IARC+-+Ag%C3%AAncia+de+Pesquisa+em+C%C3%A2ncer+da+Organiza%C3%A7%C3%A3o+Mundial+da+Sa%C3%BAde.&rft_id=http%3A%2F%2Fmonographs.iarc.fr%2FENG%2FMonographs%2Fvol56%2Fmono56-8.pdf&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook" class="Z3988"><span style="display:none;"> </span></span></span> </li> </ol></div></div><ul class="noprint navigation-box" style="border-top: solid silver 1px; border-right: solid silver 1px; border-bottom:1px solid silver; border-left: solid silver 1px; padding:3px; background-color: #F9F9F9; text-align: center; margin-top:10px; margin-left: 0; clear: both;"><li style="display: inline;"><span style="white-space: nowrap; margin: auto 1.5em"><span style="margin-right: 0.5em"><span typeof="mw:File"><a href="/wiki/Ficheiro:Sciences_exactes.svg" title="Portal da química"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/3/37/Sciences_exactes.svg/25px-Sciences_exactes.svg.png" decoding="async" width="25" height="25" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/37/Sciences_exactes.svg/38px-Sciences_exactes.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/37/Sciences_exactes.svg/50px-Sciences_exactes.svg.png 2x" data-file-width="256" data-file-height="256" /></a></span></span> <span style="font-weight:bold"><a href="/wiki/Portal:Qu%C3%ADmica" title="Portal:Química">Portal da química</a></span></span></li> </ul> <!-- NewPP limit report Parsed by mw‐web.codfw.main‐6b7f745dd4‐kwdbg Cached time: 20241125104201 Cache expiry: 2592000 Reduced expiry: false Complications: [] CPU time usage: 0.164 seconds Real time usage: 0.305 seconds Preprocessor visited node count: 3035/1000000 Post‐expand include size: 22941/2097152 bytes Template argument size: 5481/2097152 bytes Highest expansion depth: 15/100 Expensive parser function count: 0/500 Unstrip recursion depth: 0/20 Unstrip post‐expand size: 3585/5000000 bytes Lua time usage: 0.034/10.000 seconds Lua memory usage: 1679402/52428800 bytes Number of Wikibase entities loaded: 0/400 --> <!-- Transclusion expansion time report (%,ms,calls,template) 100.00% 187.908 1 -total 56.52% 106.212 1 Predefinição:Info/Química 29.83% 56.058 1 Predefinição:Referências 29.33% 55.110 84 Predefinição:Chembox_entry 25.43% 47.787 3 Predefinição:Citar_web 18.16% 34.131 1 Predefinição:Info/Química/Identifiers 15.26% 28.670 1 Predefinição:Chembox_Properties 11.86% 22.279 1 Predefinição:Portal3 10.46% 19.663 1 Predefinição:Portal3/Portais 10.36% 19.473 1 Predefinição:Chembox_SMILES --> <!-- Saved in parser cache with key ptwiki:pcache:2435599:|#|:idhash:canonical and timestamp 20241125104201 and revision id 44748238. 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