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Available in 30 languages" > <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-30" 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">30 languages</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/%D9%83%D8%B1%D9%8A%D8%B3%D9%88%D9%84" title="كريسول – Arabic" lang="ar" hreflang="ar" data-title="كريسول" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/Krezol" title="Krezol – Azerbaijani" lang="az" hreflang="az" data-title="Krezol" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target"><span>Azərbaycanca</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Kresol" title="Kresol – Czech" lang="cs" hreflang="cs" data-title="Kresol" data-language-autonym="Čeština" data-language-local-name="Czech" 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/Kresole" title="Kresole – German" lang="de" hreflang="de" data-title="Kresole" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Cresol" title="Cresol – Spanish" lang="es" hreflang="es" data-title="Cresol" data-language-autonym="Español" data-language-local-name="Spanish" 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/Kresol" title="Kresol – Basque" lang="eu" hreflang="eu" data-title="Kresol" data-language-autonym="Euskara" data-language-local-name="Basque" 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%B1%D8%B3%D9%88%D9%84" title="کرسول – Persian" lang="fa" hreflang="fa" data-title="کرسول" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Cr%C3%A9sol" title="Crésol – French" lang="fr" hreflang="fr" data-title="Crésol" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ga mw-list-item"><a href="https://ga.wikipedia.org/wiki/Cr%C3%A9as%C3%B3l" title="Créasól – Irish" lang="ga" hreflang="ga" data-title="Créasól" data-language-autonym="Gaeilge" data-language-local-name="Irish" class="interlanguage-link-target"><span>Gaeilge</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%ED%81%AC%EB%A0%88%EC%A1%B8" title="크레졸 – Korean" lang="ko" hreflang="ko" data-title="크레졸" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D4%BF%D6%80%D5%A5%D5%A6%D5%B8%D5%AC%D5%B6%D5%A5%D6%80" title="Կրեզոլներ – Armenian" lang="hy" hreflang="hy" data-title="Կրեզոլներ" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%95%E0%A5%8D%E0%A4%B0%E0%A5%87%E0%A4%B8%E0%A5%8B%E0%A4%B2" title="क्रेसोल – Hindi" lang="hi" hreflang="hi" data-title="क्रेसोल" data-language-autonym="हिन्दी" data-language-local-name="Hindi" class="interlanguage-link-target"><span>हिन्दी</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Kresol" title="Kresol – Indonesian" lang="id" hreflang="id" data-title="Kresol" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Cresolo" title="Cresolo – Italian" lang="it" hreflang="it" data-title="Cresolo" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%A7%D7%A8%D7%A1%D7%95%D7%9C_(%D7%AA%D7%A8%D7%9B%D7%95%D7%91%D7%AA_%D7%90%D7%95%D7%A8%D7%92%D7%A0%D7%99%D7%AA)" title="קרסול (תרכובת אורגנית) – Hebrew" lang="he" hreflang="he" data-title="קרסול (תרכובת אורגנית)" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-ky mw-list-item"><a href="https://ky.wikipedia.org/wiki/%D0%9A%D1%80%D0%B5%D0%B7%D0%BE%D0%BB" title="Крезол – Kyrgyz" lang="ky" hreflang="ky" data-title="Крезол" data-language-autonym="Кыргызча" data-language-local-name="Kyrgyz" class="interlanguage-link-target"><span>Кыргызча</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Krezoli" title="Krezoli – Latvian" lang="lv" hreflang="lv" data-title="Krezoli" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Krezol" title="Krezol – Hungarian" lang="hu" hreflang="hu" data-title="Krezol" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Cresol" title="Cresol – Dutch" lang="nl" hreflang="nl" data-title="Cresol" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%AF%E3%83%AC%E3%82%BE%E3%83%BC%E3%83%AB" title="クレゾール – Japanese" lang="ja" hreflang="ja" data-title="クレゾール" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Krezol" title="Krezol – Polish" lang="pl" hreflang="pl" data-title="Krezol" data-language-autonym="Polski" data-language-local-name="Polish" 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/Cresol" title="Cresol – Portuguese" lang="pt" hreflang="pt" data-title="Cresol" data-language-autonym="Português" data-language-local-name="Portuguese" 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/Crezol" title="Crezol – Romanian" lang="ro" hreflang="ro" data-title="Crezol" data-language-autonym="Română" data-language-local-name="Romanian" 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%D1%80%D0%B5%D0%B7%D0%BE%D0%BB%D1%8B" title="Крезолы – Russian" lang="ru" hreflang="ru" data-title="Крезолы" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Krezol" title="Krezol – Serbian" lang="sr" hreflang="sr" data-title="Krezol" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Kresoli" title="Kresoli – Finnish" lang="fi" hreflang="fi" data-title="Kresoli" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Kresol" title="Kresol – Swedish" lang="sv" hreflang="sv" data-title="Kresol" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Krezol" title="Krezol – Turkish" lang="tr" hreflang="tr" data-title="Krezol" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%9A%D1%80%D0%B5%D0%B7%D0%BE%D0%BB%D0%B8" title="Крезоли – Ukrainian" lang="uk" hreflang="uk" data-title="Крезоли" data-language-autonym="Українська" data-language-local-name="Ukrainian" 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free encyclopedia</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="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Group of chemical compounds</div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">Not to be confused with <a href="/wiki/Creosol" title="Creosol">creosol</a>.</div> <table align="right" border="1" cellspacing="0" cellpadding="3" style="margin: 0 0 0 0.5em; background: #FFFFFF; border-collapse: collapse; border-color: #C0C090;"> <tbody><tr> <th style="background: #F8EABA; text-align: center;" colspan="4" align="center">Isomers of Cresol<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><sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><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><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> </th></tr> <tr> <td><a href="/wiki/Skeletal_formula" title="Skeletal formula">Skeletal formula</a> </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:O-Kresol.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0b/O-Kresol.svg/90px-O-Kresol.svg.png" decoding="async" width="90" height="83" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0b/O-Kresol.svg/135px-O-Kresol.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0b/O-Kresol.svg/180px-O-Kresol.svg.png 2x" data-file-width="138" data-file-height="128" /></a><figcaption></figcaption></figure> </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:M-Kresol.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/51/M-Kresol.svg/90px-M-Kresol.svg.png" decoding="async" width="90" height="92" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/51/M-Kresol.svg/135px-M-Kresol.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/51/M-Kresol.svg/180px-M-Kresol.svg.png 2x" data-file-width="138" data-file-height="141" /></a><figcaption></figcaption></figure> </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:P-Kresol.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9e/P-Kresol.svg/45px-P-Kresol.svg.png" decoding="async" width="45" height="116" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9e/P-Kresol.svg/68px-P-Kresol.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/9e/P-Kresol.svg/90px-P-Kresol.svg.png 2x" data-file-width="70" data-file-height="181" /></a><figcaption></figcaption></figure> </td></tr> <tr> <td><a href="/wiki/Ball-and-stick_model" title="Ball-and-stick model">Ball-and-stick model</a> </td> <td><span typeof="mw:File"><a href="/wiki/File:Ortho-cresol-3D-balls.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/69/Ortho-cresol-3D-balls.png/100px-Ortho-cresol-3D-balls.png" decoding="async" width="100" height="105" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/69/Ortho-cresol-3D-balls.png/150px-Ortho-cresol-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/69/Ortho-cresol-3D-balls.png/200px-Ortho-cresol-3D-balls.png 2x" data-file-width="1100" data-file-height="1156" /></a></span> </td> <td><span typeof="mw:File"><a href="/wiki/File:Meta-cresol-3D-balls.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/96/Meta-cresol-3D-balls.png/100px-Meta-cresol-3D-balls.png" decoding="async" width="100" height="101" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/96/Meta-cresol-3D-balls.png/150px-Meta-cresol-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/96/Meta-cresol-3D-balls.png/200px-Meta-cresol-3D-balls.png 2x" data-file-width="1092" data-file-height="1100" /></a></span> </td> <td><span typeof="mw:File"><a href="/wiki/File:Para-cresol-3D-balls.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b7/Para-cresol-3D-balls.png/100px-Para-cresol-3D-balls.png" decoding="async" width="100" height="111" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b7/Para-cresol-3D-balls.png/150px-Para-cresol-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b7/Para-cresol-3D-balls.png/200px-Para-cresol-3D-balls.png 2x" data-file-width="995" data-file-height="1100" /></a></span> </td></tr> <tr> <th style="background: #F8EABA; text-align: center;" colspan="4" align="center">General </th></tr> <tr> <td>Common name </td> <td><b><a href="/wiki/O-cresol" class="mw-redirect" title="O-cresol"><i>o</i>-cresol</a></b> </td> <td><b><a href="/wiki/M-cresol" class="mw-redirect" title="M-cresol"><i>m</i>-cresol</a></b> </td> <td><b><a href="/wiki/P-cresol" class="mw-redirect" title="P-cresol"><i>p</i>-cresol</a></b> </td></tr> <tr> <td><a href="/wiki/Preferred_IUPAC_name" title="Preferred IUPAC name">Preferred IUPAC name</a> </td> <td>2-methylphenol </td> <td>3-methylphenol </td> <td>4-methylphenol </td></tr> <tr> <td><a href="/wiki/Chemical_nomenclature#Systematic_name" title="Chemical nomenclature">Systematic name</a> </td> <td>2-methylbenzenol </td> <td>3-methylbenzenol </td> <td>4-methylbenzenol </td></tr> <tr> <td>Other names </td> <td><i>ortho</i>-cresol<br />2-hydroxytoluene </td> <td><i>meta</i>-cresol<br />3-hydroxytoluene </td> <td><i>para</i>-cresol<br />4-hydroxytoluene </td></tr> <tr> <td><a href="/wiki/Chemical_formula" title="Chemical formula">Molecular formula</a> </td> <td align="center" colspan="4">C<sub>7</sub>H<sub>8</sub>O </td></tr> <tr> <td><a href="/wiki/Simplified_molecular_input_line_entry_specification" class="mw-redirect" title="Simplified molecular input line entry specification">SMILES</a> </td> <td>oc1c(C)cccc1 </td> <td>oc1cc(C)ccc1 </td> <td>oc1ccc(C)cc1 </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td align="center" colspan="4">108.14 g/mol </td></tr> <tr> <td>Appearance at room<br /> temperature and pressure </td> <td>colorless crystals </td> <td>thicker liquid </td> <td>greasy-looking solid </td></tr> <tr> <td rowspan="2"><a href="/wiki/CAS_registry_number" class="mw-redirect" title="CAS registry number">CAS number</a> </td> <td>[95-48-7] </td> <td>[108-39-4] </td> <td>[106-44-5] </td></tr> <tr> <td align="center" colspan="3">mixture of cresols (tricresol): [1319-77-3] </td></tr> <tr> <th style="background: #F8EABA; text-align: center;" colspan="4" align="center">Properties </th></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> and <a href="/wiki/Phase_(matter)" title="Phase (matter)">phase</a> </td> <td>1.05 g/cm<sup>3</sup>, solid </td> <td>1.03 g/cm<sup>3</sup>, liquid </td> <td>1.02 g/cm<sup>3</sup>, liquid </td></tr> <tr> <td><a href="/wiki/Soluble" class="mw-redirect" title="Soluble">Solubility</a> in <a href="/wiki/Water_(molecule)" class="mw-redirect" title="Water (molecule)">pure water</a><br /> at 20−25 °C </td> <td>2.5 g/100 ml </td> <td>2.4 g/100 ml </td> <td>1.9 g/100 ml </td></tr> <tr> <td align="center" colspan="4">soluble in strongly <a href="/wiki/Alkaline" class="mw-redirect" title="Alkaline">alkaline</a> water </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>29.8 °C (303.0 K) </td> <td>11.8 °C (285.0 K) </td> <td>35.5 °C (309.7 K) </td></tr> <tr> <td><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a> </td> <td>191.0 °C (464.2 K) </td> <td>202.0 °C (475.2 K) </td> <td>201.9 °C (475.1 K) </td></tr> <tr> <td><a href="/wiki/Acid_dissociation_constant" title="Acid dissociation constant">Acidity</a> (p<i>K</i><sub>a</sub>) </td> <td>10.287 </td> <td>10.09 </td> <td>10.26 </td></tr> <tr> <td><a href="/wiki/Viscosity" title="Viscosity">Viscosity</a> </td> <td>solid at 25 °C </td> <td>? c<a href="/wiki/Poise_(unit)" title="Poise (unit)">P</a> at 25 °C </td> <td>solid at 25 °C </td></tr> <tr> <th style="background: #F8EABA; text-align: center;" colspan="4" align="center">Structure </th></tr> <tr> <td><a href="/wiki/Dipole#Molecular_dipoles" title="Dipole">Dipole moment</a> </td> <td>1.35 <a href="/wiki/Debye" title="Debye">D</a> </td> <td>1.61 <a href="/wiki/Debye" title="Debye">D</a> </td> <td>1.58 <a href="/wiki/Debye" title="Debye">D</a> </td></tr> <tr> <th style="background: #F8EABA; text-align: center;" colspan="4" align="center">Hazards </th></tr> <tr> <td><a href="/wiki/Safety_data_sheet" title="Safety data sheet">SDS</a> </td> <td> </td> <td> </td> <td> </td></tr> <tr> <td>Main <a href="/wiki/Worker_safety_and_health" class="mw-redirect" title="Worker safety and health">hazards</a> </td> <td align="center" colspan="4"><a href="/wiki/Flammable" class="mw-redirect" title="Flammable">flammable</a>, ingestion and inhalation toxicity hazard </td></tr> <tr> <td><a href="/wiki/Flash_point" title="Flash point">Flash point</a> </td> <td>81 °C c.c. </td> <td>86 °C </td> <td>86 °C c.c. </td></tr> <tr> <td><a href="/wiki/GHS_pictograms" class="mw-redirect" title="GHS pictograms">GHS pictograms</a> </td> <td align="center" colspan="4"><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-acid.svg" class="mw-file-description" title="GHS05: Corrosive"><img alt="GHS05: Corrosive" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a1/GHS-pictogram-acid.svg/50px-GHS-pictogram-acid.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a1/GHS-pictogram-acid.svg/75px-GHS-pictogram-acid.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a1/GHS-pictogram-acid.svg/100px-GHS-pictogram-acid.svg.png 2x" data-file-width="724" data-file-height="724" /></a></span><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-skull.svg" class="mw-file-description" title="GHS06: Toxic"><img alt="GHS06: Toxic" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/58/GHS-pictogram-skull.svg/50px-GHS-pictogram-skull.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/58/GHS-pictogram-skull.svg/75px-GHS-pictogram-skull.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/58/GHS-pictogram-skull.svg/100px-GHS-pictogram-skull.svg.png 2x" data-file-width="724" data-file-height="724" /></a></span> </td></tr> <tr> <td><a href="/wiki/RTECS" class="mw-redirect" title="RTECS">RTECS</a> number </td> <td>GO6300000 </td> <td>GO6125000 </td> <td>GO6475000 </td></tr> <tr> <th style="background: #F8EABA; text-align: center;" colspan="4" align="center">Related compounds </th></tr> <tr> <td>Related <a href="/wiki/Phenols" title="Phenols">phenols</a> </td> <td colspan="3"><a href="/wiki/Xylenol" title="Xylenol">xylenols</a> </td></tr> <tr> <td>Related compounds </td> <td colspan="3"><a href="/wiki/Bromocresol_green" title="Bromocresol green">bromocresol green</a>, <a href="/wiki/Cresol_red" class="mw-redirect" title="Cresol red">cresol red</a> </td></tr> <tr> <td style="background: #F8EABA; text-align: center;" colspan="4" align="center"><small>Except where noted otherwise, data are given for<br /> materials in their <a href="/wiki/Standard_state" title="Standard state">standard state (at 25 °C, 100 kPa)</a><br /><a href="/wiki/Wikipedia:Chemical_infobox" title="Wikipedia:Chemical infobox">Infobox disclaimer and references</a></small> </td></tr> </tbody></table> <p><b>Cresols</b> (also known as <b>hydroxytoluene</b>, <b>toluenol</b>, <b>benzol</b> or <b>cresylic acid</b>) are a group of <a href="/wiki/Aromatic" class="mw-redirect" title="Aromatic">aromatic</a> <a href="/wiki/Organic_compound" title="Organic compound">organic compounds</a>. They are widely-occurring <a href="/wiki/Phenols" title="Phenols">phenols</a> (sometimes called <i>phenolics</i>) which may be either natural or manufactured. They are also categorized as <b><a href="/wiki/Methyl_group" title="Methyl group">methyl</a> <a href="/wiki/Phenol" title="Phenol">phenols</a></b>. Cresols commonly occur as either solids or liquids because their <a href="/wiki/Melting_point" title="Melting point">melting points</a> are generally close to room temperature. Like other types of phenols, they are slowly <a href="/wiki/Oxidation" class="mw-redirect" title="Oxidation">oxidized</a> by exposure to <a href="/wiki/Air" class="mw-redirect" title="Air">air</a>, and the resulting impurities often give the samples a yellow to brownish red tint. Cresols have an <a href="/wiki/Odor" title="Odor">odor</a> characteristic to that of other simple phenols, reminiscent to some of a "<a href="/wiki/Coal_tar" title="Coal tar">coal tar</a>" smell. The name "cresol" is an adduct of phenol and their traditional source, <a href="/wiki/Creosote" title="Creosote">creosote</a>. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Structure_and_production">Structure and production</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cresol&action=edit&section=1" title="Edit section: Structure and production"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In its <a href="/wiki/Chemical_structure" title="Chemical structure">chemical structure</a>, a <a href="/wiki/Molecule" title="Molecule">molecule</a> of cresol has a <a href="/wiki/Methyl_group" title="Methyl group">methyl group</a> substituted onto the ring of phenol. There are three forms (<a href="/wiki/Isomers" class="mw-redirect" title="Isomers">isomers</a>) of cresol: <i>ortho</i>-cresol (<a href="/wiki/O-Cresol" title="O-Cresol"><i>o</i>-cresol</a>), <i>meta</i>-cresol (<a href="/wiki/M-Cresol" title="M-Cresol"><i>m</i>-cresol</a>), and <i>para</i>-cresol (<a href="/wiki/P-Cresol" title="P-Cresol"><i>p</i>-cresol</a>). These forms occur separately or as a mixture, which can also be called cresol or more specifically, <b>tricresol</b>.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (December 2017)">citation needed</span></a></i>]</sup> About half of the world's supply of cresols are extracted from coal tar. The rest is produced by <a href="/wiki/Hydrolysis" title="Hydrolysis">hydrolysis</a> of <a href="/wiki/Chlorotoluene" title="Chlorotoluene">chlorotoluenes</a> or the related sulfonates. Another method entails methylation of phenol with methanol over a solid acid catalyst, often comprising magnesium oxide or alumina. Temperatures above 300 °C are typical. <a href="/wiki/Anisole" title="Anisole">Anisole</a> converts to cresols under these conditions.<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Ullmann_6-0" class="reference"><a href="#cite_note-Ullmann-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p><p>Another <a href="/wiki/Isomer" title="Isomer">isomer</a> of cresol is called <a href="/wiki/Benzyl_alcohol" title="Benzyl alcohol">Benzyl alcohol</a>, or <i>alpha</i>-cresol (α-cresol). Benzyl alcohol has a hydroxy group inside a methyl group on the <a href="/wiki/Benzene" title="Benzene">benzene</a> ring. </p> <div class="mw-heading mw-heading2"><h2 id="Applications">Applications</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cresol&action=edit&section=2" title="Edit section: Applications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Cresols are precursors or synthetic intermediates to other compounds and materials, including plastics, pesticides, pharmaceuticals, and dyes.<sup id="cite_ref-Ullmann_6-1" class="reference"><a href="#cite_note-Ullmann-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p><p>For cresol bactericides or disinfectants the mechanism of action is due to the destruction of bacterial <a href="/wiki/Cell_membranes" class="mw-redirect" title="Cell membranes">cell membranes</a>.<sup id="cite_ref-judis62_7-0" class="reference"><a href="#cite_note-judis62-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-dboc_8-0" class="reference"><a href="#cite_note-dboc-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p><p>Most recently, cresols have been used to create a breakthrough in manufacturing <a href="/wiki/Carbon_nanotubes" class="mw-redirect" title="Carbon nanotubes">carbon nanotubes</a> at scale that are separated and not twisted, without additional chemicals that change the surface properties of the nanotubes.<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><sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Commercial_examples">Commercial examples</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cresol&action=edit&section=3" title="Edit section: Commercial examples"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Creolin" title="Creolin">Creolin</a>, a 19th-century disinfectant.</li> <li><a href="/wiki/Carbolic_soap" title="Carbolic soap">Carbolic soap</a>, 19th-century.</li> <li>The original <a href="/wiki/Lysol" title="Lysol">Lysol</a> formulation, essentially a water solution of carbolic soap.<sup id="cite_ref-LysolCresolReference_11-0" class="reference"><a href="#cite_note-LysolCresolReference-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> "Lysol" has been used as a <a href="/wiki/Generic_trademark" title="Generic trademark">generic trademark</a> to refer to such a cresol soap solution and remains used as such in some professional settings. The CAS number is 12772-68-8.</li></ul> <div class="mw-heading mw-heading3"><h3 id="Derivatives">Derivatives</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cresol&action=edit&section=4" title="Edit section: Derivatives"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Derivatives of <i>p</i>-cresol include: </p> <ul><li><a href="/wiki/Butylated_hydroxytoluene" title="Butylated hydroxytoluene">Butylated hydroxytoluene</a>, a common <a href="/wiki/Antioxidant" title="Antioxidant">antioxidant</a></li></ul> <p>Derivatives of <i>o</i>-cresol include: </p> <ul><li><a href="/wiki/Indo-1" title="Indo-1">Indo-1</a>, a popular calcium indicator</li> <li><a href="/wiki/MCPA" title="MCPA">MCPA</a>, (4-chloro-2-methylphenoxy)acetic acid</li> <li><a href="/wiki/MCPB" title="MCPB">MCPB</a>, 4-(4-chloro-2-methylphenoxy)butanoic acid</li> <li><a href="/wiki/Mecoprop" title="Mecoprop">Mecoprop</a>, (<i>RS</i>)-2-(4-chloro-2-methylphenoxy)propanoic acid</li> <li>the <a href="/wiki/Amine" title="Amine">amine</a> <a href="/wiki/Atomoxetine" title="Atomoxetine">atomoxetine</a>, (3<i>R</i>)-<i>N</i>-methyl-3-(2-methylphenoxy)-3-phenylpropan-1-amine</li> <li>the <a href="/wiki/Diol" title="Diol">diol</a> <a href="/wiki/Mephenesin" title="Mephenesin">mephenesin</a>, 3-(2-methylphenoxy)propane-1,2-diol</li></ul> <p>Derivatives of <i>m</i>-cresol include: </p> <ul><li><a href="/wiki/Amylmetacresol" title="Amylmetacresol">Amylmetacresol</a>, an <a href="/wiki/Antiseptic" title="Antiseptic">antiseptic</a></li> <li><a href="/wiki/Bevantolol" title="Bevantolol">Bevantolol</a>, (<i>RS</i>)-[2-(3,4-dimethoxyphenyl)ethyl] [2-hydroxy-3-(3-methylphenoxy)propyl]amine</li> <li><a href="/wiki/Bromocresol_green" title="Bromocresol green">Bromocresol green</a></li> <li><a href="/wiki/Bupranolol" title="Bupranolol">Bupranolol</a>, a non-selective <a href="/wiki/Beta_blocker" title="Beta blocker">beta blocker</a></li> <li><a href="/wiki/Chloro-m-cresol" class="mw-redirect" title="Chloro-m-cresol">Chloro-<i>m</i>-cresol</a> which is used as a household disinfectant</li> <li><a href="/wiki/Tolimidone" title="Tolimidone">Tolimidone</a>, 5-(3-methylphenoxy)pyrimidin-2(1<i>H</i>)-one</li></ul> <div class="mw-heading mw-heading2"><h2 id="Health_effects">Health effects</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cresol&action=edit&section=5" title="Edit section: Health effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>When cresols are inhaled, ingested, or applied to the <a href="/wiki/Skin" title="Skin">skin</a>, they can be very harmful. Effects observed in people include <a href="/wiki/Irritation" title="Irritation">irritation</a> and burning of skin, <a href="/wiki/Eye" title="Eye">eyes</a>, <a href="/wiki/Mouth" title="Mouth">mouth</a>, and <a href="/wiki/Throat" title="Throat">throat</a>; abdominal pain and vomiting; <a href="/wiki/Heart" title="Heart">heart</a> damage; <a href="/wiki/Anemia" title="Anemia">anemia</a>; <a href="/wiki/Liver" title="Liver">liver</a> and <a href="/wiki/Kidney" title="Kidney">kidney</a> damage; facial paralysis; <a href="/wiki/Coma" title="Coma">coma</a>; and <a href="/wiki/Death" title="Death">death</a>. </p><p>Breathing high levels of cresols for a short time results in irritation of the <a href="/wiki/Human_nose" title="Human nose">nose</a> and throat. Aside from these effects, very little is known about the effects of breathing cresols, for example, at lower levels over longer times. </p><p>Ingesting high levels results in kidney problems, mouth and throat burns, abdominal pain, vomiting, and effects on the <a href="/wiki/Blood" title="Blood">blood</a> and <a href="/wiki/Nervous_system" title="Nervous system">nervous system</a>. </p><p>Skin contact with high levels of cresols can burn the skin and damage the kidneys, liver, blood, <a href="/wiki/Brain" title="Brain">brain</a>, and <a href="/wiki/Lung" title="Lung">lungs</a>. </p><p>Short-term and long-term studies with animals have shown similar effects from exposure to cresols. No human or animal studies have shown harmful effects from cresols on reproduction. </p><p>It is not known what the effects are from long-term ingestion or skin contact with low levels of cresols. </p><p>The <a href="/wiki/Occupational_Safety_and_Health_Administration" title="Occupational Safety and Health Administration">Occupational Safety and Health Administration</a> has set a <a href="/wiki/Permissible_exposure_limit" title="Permissible exposure limit">permissible exposure limit</a> at 5 ppm (22 mg/m<sup>3</sup>) over an eight-hour time-weighted average, while the <a href="/wiki/National_Institute_for_Occupational_Safety_and_Health" title="National Institute for Occupational Safety and Health">National Institute for Occupational Safety and Health</a> <a href="/wiki/Recommended_exposure_limit" title="Recommended exposure limit">recommends a limit</a> of 2.3 ppm (10 mg/m<sup>3</sup>).<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> </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cresol&action=edit&section=6" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Dihydroxytoluene" class="mw-redirect" title="Dihydroxytoluene">Dihydroxytoluene</a></li> <li><a href="/wiki/Trihydroxytoluene" title="Trihydroxytoluene">Trihydroxytoluene</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cresol&action=edit&section=7" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><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"><a rel="nofollow" class="external text" href="http://www.inchem.org/documents/icsc/icsc/eics0030.htm">o-CRESOL (ICSC)</a></span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text"><a rel="nofollow" class="external text" href="http://www.inchem.org/documents/icsc/icsc/eics0646.htm">m-CRESOL (ICSC)</a></span> </li> <li id="cite_note-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-3">^</a></b></span> <span class="reference-text"><a rel="nofollow" class="external text" href="http://www.inchem.org/documents/icsc/icsc/eics0031.htm">p-CRESOL (ICSC)</a></span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFPubchem" class="citation web cs1">Pubchem. <a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/o-cresol#section=Odor-Threshold">"o-cresol"</a>. <i>pubchem.ncbi.nlm.nih.gov</i><span class="reference-accessdate">. Retrieved <span class="nowrap">2018-01-16</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=pubchem.ncbi.nlm.nih.gov&rft.atitle=o-cresol&rft.au=Pubchem&rft_id=https%3A%2F%2Fpubchem.ncbi.nlm.nih.gov%2Fcompound%2Fo-cresol%23section%3DOdor-Threshold&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACresol" class="Z3988"></span></span> </li> <li id="cite_note-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-5">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFW._W._Hartman1923" class="citation journal cs1">W. W. Hartman (1923). "<i>p</i>-Cresol". <i>Organic Syntheses</i>. <b>3</b>: 37. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.15227%2Forgsyn.003.0037">10.15227/orgsyn.003.0037</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Organic+Syntheses&rft.atitle=p-Cresol&rft.volume=3&rft.pages=37&rft.date=1923&rft_id=info%3Adoi%2F10.15227%2Forgsyn.003.0037&rft.au=W.+W.+Hartman&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACresol" class="Z3988"></span></span> </li> <li id="cite_note-Ullmann-6"><span class="mw-cite-backlink">^ <a href="#cite_ref-Ullmann_6-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Ullmann_6-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text">Helmut Fiegein "Cresols and Xylenols" in Ullmann's Encyclopedia of Industrial Chemistry" 2007; Wiley-VCH, Weinheim. <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F14356007.a08_025">10.1002/14356007.a08_025</a></span> </li> <li id="cite_note-judis62-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-judis62_7-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFJudis1962" class="citation journal cs1">Judis, Joseph (1962). "Studies on the Mechanism of Action of Phenolic Disinfectants I". <i>Journal of Pharmaceutical Sciences</i>. <b>51</b> (3): <span class="nowrap">261–</span>265. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fjps.2600510317">10.1002/jps.2600510317</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/14452711">14452711</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Pharmaceutical+Sciences&rft.atitle=Studies+on+the+Mechanism+of+Action+of+Phenolic+Disinfectants+I&rft.volume=51&rft.issue=3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E261-%3C%2Fspan%3E265&rft.date=1962&rft_id=info%3Adoi%2F10.1002%2Fjps.2600510317&rft_id=info%3Apmid%2F14452711&rft.aulast=Judis&rft.aufirst=Joseph&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACresol" class="Z3988"></span></span> </li> <li id="cite_note-dboc-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-dboc_8-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation news cs1"><a rel="nofollow" class="external text" href="https://go.drugbank.com/drugs/DB11143">"IDENTIFICATION Name Cresol"</a>. DrugBank Online. 12 June 2020.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=IDENTIFICATION+Name+Cresol&rft.date=2020-06-12&rft_id=https%3A%2F%2Fgo.drugbank.com%2Fdrugs%2FDB11143&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACresol" class="Z3988"></span></span> </li> <li id="cite_note-9"><span class="mw-cite-backlink"><b><a href="#cite_ref-9">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.sciencedaily.com/releases/2018/05/180515162801.htm">"Making carbon nanotubes as usable as common plastics: Researchers discover that cresols disperse carbon nanotubes at unprecedentedly high concentrations"</a>. ScienceDaily, Northwestern University. 15 May 2018. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20180516060704/http://www.sciencedaily.com/releases/2018/05/180515162801.htm">Archived</a> from the original on 2018-05-16.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Making+carbon+nanotubes+as+usable+as+common+plastics%3A+Researchers+discover+that+cresols+disperse+carbon+nanotubes+at+unprecedentedly+high+concentrations&rft.pub=ScienceDaily%2C+Northwestern+University&rft.date=2018-05-15&rft_id=http%3A%2F%2Fwww.sciencedaily.com%2Freleases%2F2018%2F05%2F180515162801.htm&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACresol" class="Z3988"></span></span> </li> <li id="cite_note-10"><span class="mw-cite-backlink"><b><a href="#cite_ref-10">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFChiouByunKimHuang2018" class="citation journal cs1">Chiou, Kevin; Byun, Segi; Kim, Jaemyung; Huang, Jiaxing (29 May 2018). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5984515">"Additive-free carbon nanotube dispersions, pastes, gels, and doughs in cresols"</a>. <i>Proceedings of the National Academy of Sciences</i>. <b>115</b> (22): <span class="nowrap">5703–</span>5708. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2018PNAS..115.5703C">2018PNAS..115.5703C</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1073%2Fpnas.1800298115">10.1073/pnas.1800298115</a></span>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5984515">5984515</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/29760075">29760075</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Proceedings+of+the+National+Academy+of+Sciences&rft.atitle=Additive-free+carbon+nanotube+dispersions%2C+pastes%2C+gels%2C+and+doughs+in+cresols&rft.volume=115&rft.issue=22&rft.pages=%3Cspan+class%3D%22nowrap%22%3E5703-%3C%2Fspan%3E5708&rft.date=2018-05-29&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC5984515%23id-name%3DPMC&rft_id=info%3Apmid%2F29760075&rft_id=info%3Adoi%2F10.1073%2Fpnas.1800298115&rft_id=info%3Abibcode%2F2018PNAS..115.5703C&rft.aulast=Chiou&rft.aufirst=Kevin&rft.au=Byun%2C+Segi&rft.au=Kim%2C+Jaemyung&rft.au=Huang%2C+Jiaxing&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC5984515&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACresol" class="Z3988"></span> <span style="position:relative; top: -2px;"><span typeof="mw:File"><a href="/wiki/Open_access" title="open access publication – free to read"><img alt="Open access icon" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/77/Open_Access_logo_PLoS_transparent.svg/9px-Open_Access_logo_PLoS_transparent.svg.png" decoding="async" width="9" height="14" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/77/Open_Access_logo_PLoS_transparent.svg/14px-Open_Access_logo_PLoS_transparent.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/77/Open_Access_logo_PLoS_transparent.svg/18px-Open_Access_logo_PLoS_transparent.svg.png 2x" data-file-width="640" data-file-height="1000" /></a></span></span></span> </li> <li id="cite_note-LysolCresolReference-11"><span class="mw-cite-backlink"><b><a href="#cite_ref-LysolCresolReference_11-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFSIMMONS1908" class="citation book cs1">SIMMONS, W.H. (1908). <a rel="nofollow" class="external text" href="http://www.gutenberg.org/files/21724/21724-h/21724-h.htm"><i>THE HANDBOOK OF SOAP MANUFACTURE no</i></a>. SCOTT, GREENWOOD & SON.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=THE+HANDBOOK+OF+SOAP+MANUFACTURE+no&rft.pub=SCOTT%2C+GREENWOOD+%26+SON&rft.date=1908&rft.aulast=SIMMONS&rft.aufirst=W.H.&rft_id=http%3A%2F%2Fwww.gutenberg.org%2Ffiles%2F21724%2F21724-h%2F21724-h.htm&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACresol" class="Z3988"></span></span> </li> <li id="cite_note-12"><span class="mw-cite-backlink"><b><a href="#cite_ref-12">^</a></b></span> <span class="reference-text"><a rel="nofollow" class="external text" href="https://www.cdc.gov/niosh/idlh/cresol.html">Documentation for Immediately Dangerous To Life or Health Concentrations (IDLHs) - Cresol (o, m, p isomers)</a></span> </li> </ol></div></div> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist 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mw-ui-icon-wikimedia-history mw-ui-icon-wikimedia-wikimedia-history"></span> <span></span> </a> <a href="#" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only mw-watchlink" id="ca-watchstar-sticky-header" tabindex="-1" data-event-name="watch-sticky-header"><span class="vector-icon mw-ui-icon-wikimedia-star mw-ui-icon-wikimedia-wikimedia-star"></span> <span></span> </a> <a href="#" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only" id="ca-edit-sticky-header" tabindex="-1" data-event-name="wikitext-edit-sticky-header"><span class="vector-icon mw-ui-icon-wikimedia-wikiText mw-ui-icon-wikimedia-wikimedia-wikiText"></span> <span></span> </a> <a href="#" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only" id="ca-ve-edit-sticky-header" tabindex="-1" data-event-name="ve-edit-sticky-header"><span class="vector-icon mw-ui-icon-wikimedia-edit mw-ui-icon-wikimedia-wikimedia-edit"></span> <span></span> </a> <a href="#" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only" id="ca-viewsource-sticky-header" tabindex="-1" data-event-name="ve-edit-protected-sticky-header"><span class="vector-icon mw-ui-icon-wikimedia-editLock mw-ui-icon-wikimedia-wikimedia-editLock"></span> <span></span> </a> </div> <div class="vector-sticky-header-buttons"> <button class="cdx-button cdx-button--weight-quiet mw-interlanguage-selector" id="p-lang-btn-sticky-header" tabindex="-1" data-event-name="ui.dropdown-p-lang-btn-sticky-header"><span class="vector-icon mw-ui-icon-wikimedia-language mw-ui-icon-wikimedia-wikimedia-language"></span> <span>30 languages</span> </button> <a href="#" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive" id="ca-addsection-sticky-header" tabindex="-1" data-event-name="addsection-sticky-header"><span class="vector-icon mw-ui-icon-speechBubbleAdd-progressive mw-ui-icon-wikimedia-speechBubbleAdd-progressive"></span> <span>Add topic</span> </a> </div> <div class="vector-sticky-header-icon-end"> <div class="vector-user-links"> </div> </div> </div> </div> </div> <div class="mw-portlet mw-portlet-dock-bottom emptyPortlet" id="p-dock-bottom"> <ul> </ul> </div> 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