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vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Human_health_effects"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Human health effects</span> </div> </a> <ul id="toc-Human_health_effects-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Available_forms_and_nomenclature" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Available_forms_and_nomenclature"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Available forms and nomenclature</span> </div> </a> <ul id="toc-Available_forms_and_nomenclature-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Production" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Production"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Production</span> </div> </a> <ul id="toc-Production-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>External links</span> </div> </a> <ul id="toc-External_links-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="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" title="Table of Contents" > <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="Toggle the table of contents" > <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">Toggle the table of contents</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">Polyethylene glycol</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="Go to an article in another language. Available in 28 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-28" 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">28 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/%D8%A8%D9%88%D9%84%D9%8A_%D8%A5%D9%8A%D8%AB%D9%8A%D9%84%D9%8A%D9%86_%D8%AC%D9%84%D8%A7%D9%8A%D9%83%D9%88%D9%84" title="بولي إيثيلين جلايكول – Arabic" lang="ar" hreflang="ar" data-title="بولي إيثيلين جلايكول" data-language-autonym="العربية" data-language-local-name="Arabic" 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/%D9%BE%D9%88%D9%84%DB%8C%D8%A7%D8%AA%DB%8C%D9%84%D9%86_%D9%82%D9%84%DB%8C%DA%A9%D9%88%D9%84" title="پولیاتیلن قلیکول – South Azerbaijani" lang="azb" hreflang="azb" data-title="پولیاتیلن قلیکول" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Polietilenglicol" title="Polietilenglicol – Catalan" lang="ca" hreflang="ca" data-title="Polietilenglicol" data-language-autonym="Català" data-language-local-name="Catalan" 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/Polyethylenglykol" title="Polyethylenglykol – Czech" lang="cs" hreflang="cs" data-title="Polyethylenglykol" 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/Polyethylenglycol" title="Polyethylenglycol – German" lang="de" hreflang="de" data-title="Polyethylenglycol" 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/Polietilenglicol" title="Polietilenglicol – Spanish" lang="es" hreflang="es" data-title="Polietilenglicol" 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/Polietilen_glikol" title="Polietilen glikol – Basque" lang="eu" hreflang="eu" data-title="Polietilen glikol" 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/%D9%BE%D9%84%DB%8C%E2%80%8C%D8%A7%D8%AA%DB%8C%D9%84%D9%86_%DA%AF%D9%84%DB%8C%DA%A9%D9%88%D9%84" title="پلی‌اتیلن گلیکول – Persian" lang="fa" hreflang="fa" data-title="پلی‌اتیلن گلیکول" 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/Poly%C3%A9thyl%C3%A8ne_glycol" title="Polyéthylène glycol – French" lang="fr" hreflang="fr" data-title="Polyéthylène glycol" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Polietilenglicol" title="Polietilenglicol – Galician" lang="gl" hreflang="gl" data-title="Polietilenglicol" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Polietilen_glikol" title="Polietilen glikol – Indonesian" lang="id" hreflang="id" data-title="Polietilen glikol" 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/Glicole_polietilenico" title="Glicole polietilenico – Italian" lang="it" hreflang="it" data-title="Glicole polietilenico" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%9F%D0%BE%D0%BB%D0%B8%D0%B5%D1%82%D0%B8%D0%BB%D0%B5%D0%BD_%D0%B3%D0%BB%D0%B8%D0%BA%D0%BE%D0%BB" title="Полиетилен гликол – Macedonian" lang="mk" hreflang="mk" data-title="Полиетилен гликол" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Polyethyleenglycol" title="Polyethyleenglycol – Dutch" lang="nl" hreflang="nl" data-title="Polyethyleenglycol" 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%83%9D%E3%83%AA%E3%82%A8%E3%83%81%E3%83%AC%E3%83%B3%E3%82%B0%E3%83%AA%E3%82%B3%E3%83%BC%E3%83%AB" title="ポリエチレングリコール – Japanese" lang="ja" hreflang="ja" data-title="ポリエチレングリコール" 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/Poli(tlenek_etylenu)" title="Poli(tlenek etylenu) – Polish" lang="pl" hreflang="pl" data-title="Poli(tlenek etylenu)" 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/Polietilenoglicol" title="Polietilenoglicol – Portuguese" lang="pt" hreflang="pt" data-title="Polietilenoglicol" 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/Polietilenglicol" title="Polietilenglicol – Romanian" lang="ro" hreflang="ro" data-title="Polietilenglicol" 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%9F%D0%BE%D0%BB%D0%B8%D1%8D%D1%82%D0%B8%D0%BB%D0%B5%D0%BD%D0%B3%D0%BB%D0%B8%D0%BA%D0%BE%D0%BB%D1%8C" title="Полиэтиленгликоль – Russian" lang="ru" hreflang="ru" data-title="Полиэтиленгликоль" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Polyetyl%C3%A9nglykol" title="Polyetylénglykol – Slovak" lang="sk" hreflang="sk" data-title="Polyetylénglykol" data-language-autonym="Slovenčina" data-language-local-name="Slovak" 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/Polietilen_glikol" title="Polietilen glikol – Serbian" lang="sr" hreflang="sr" data-title="Polietilen glikol" 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-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Polietilen_glikol" title="Polietilen glikol – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Polietilen glikol" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Polyetyleeniglykoli" title="Polyetyleeniglykoli – Finnish" lang="fi" hreflang="fi" data-title="Polyetyleeniglykoli" 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/Polyetylenglykol" title="Polyetylenglykol – Swedish" lang="sv" hreflang="sv" data-title="Polyetylenglykol" 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/Polietilen_glikol" title="Polietilen glikol – Turkish" lang="tr" hreflang="tr" data-title="Polietilen glikol" 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%9F%D0%BE%D0%BB%D1%96%D0%B5%D1%82%D0%B8%D0%BB%D0%B5%D0%BD%D0%B3%D0%BB%D1%96%D0%BA%D0%BE%D0%BB%D1%8C" title="Поліетиленгліколь – Ukrainian" lang="uk" hreflang="uk" data-title="Поліетиленгліколь" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Polyethylen_glycol" title="Polyethylen glycol – Vietnamese" lang="vi" hreflang="vi" data-title="Polyethylen glycol" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E8%81%9A%E4%B9%99%E4%BA%8C%E9%86%87" title="聚乙二醇 – Chinese" lang="zh" hreflang="zh" data-title="聚乙二醇" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a 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searchaux" style="display:none">Chemical compound</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/Ethylene_glycol" title="Ethylene glycol">Ethylene glycol</a> or <a href="/wiki/Diethylene_glycol" title="Diethylene glycol">Diethylene glycol</a> or <a href="/wiki/Polypropylene_glycol" title="Polypropylene glycol">Polypropylene glycol</a> or <a href="/wiki/Propylene_glycol" title="Propylene glycol">Propylene glycol</a>.</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">For medical uses of polyethylene glycol, see <a href="/wiki/Macrogol" title="Macrogol">Macrogol</a>.</div> <p> <style data-mw-deduplicate="TemplateStyles:r1268415487">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}</style> </p> <table class="infobox ib-chembox"> <caption>Polyethylene glycol </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:PEG_Structural_Formula_V1.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/64/PEG_Structural_Formula_V1.svg/220px-PEG_Structural_Formula_V1.svg.png" decoding="async" width="220" height="94" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/64/PEG_Structural_Formula_V1.svg/330px-PEG_Structural_Formula_V1.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/64/PEG_Structural_Formula_V1.svg/440px-PEG_Structural_Formula_V1.svg.png 2x" data-file-width="248" data-file-height="106" /></a><figcaption></figcaption></figure> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Polyethylene_glycol_400.jpg" class="mw-file-description" title="Polyethylene glycol 400"><img alt="Polyethylene glycol 400" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5e/Polyethylene_glycol_400.jpg/220px-Polyethylene_glycol_400.jpg" decoding="async" width="220" height="330" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5e/Polyethylene_glycol_400.jpg/330px-Polyethylene_glycol_400.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5e/Polyethylene_glycol_400.jpg/440px-Polyethylene_glycol_400.jpg 2x" data-file-width="2848" data-file-height="4272" /></a><figcaption>Polyethylene glycol 400</figcaption></figure> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature" title="Chemical nomenclature">IUPAC names</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">poly(oxyethylene) <small>{structure-based}</small>,<br /> poly(ethylene oxide) <small>{source-based}</small><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></div> </td></tr> <tr> <td colspan="2" style="text-align:left;">Other names <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">Kollisolv, Carbowax, GoLYTELY, GlycoLax, Fortrans, TriLyte, Colyte, Halflytely, <a href="/wiki/Macrogol" title="Macrogol">macrogol</a>, MiraLAX, MoviPrep</div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=25322-68-3">25322-68-3</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td>Abbreviations </td> <td>PEG </td></tr> <tr> <td><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL1201478">ChEMBL1201478</a></span><sup> <span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>none</li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.105.546">100.105.546</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q410083#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span> </td></tr> <tr> <td><a href="/wiki/E_number" title="E number"><span title="E number (food additive code)">E number</span></a> </td> <td>E1521 <a href="/wiki/E_number#E1000–E1599" title="E number">(additional chemicals)</a> </td></tr> <tr> <td><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/3WJQ0SDW1A">3WJQ0SDW1A</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID4027862">DTXSID4027862</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q410083#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td>C<sub>2n</sub>H<sub>4n+2</sub>O<sub>n+1</sub>  </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap">44.05n + 18.02<i> g/mol</i></span><i>   </i> </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>1.125<sup id="cite_ref-ChemSrc-2020_2-0" class="reference"><a href="#cite_note-ChemSrc-2020-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Pharmacology </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Anatomical_Therapeutic_Chemical_Classification_System" title="Anatomical Therapeutic Chemical Classification System">ATC code</a></div> </td> <td><a href="/wiki/ATC_code_A06" title="ATC code A06">A06AD15</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=A06AD15">WHO</a></span>)  </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Hazards </th></tr> <tr> <td><a href="/wiki/Flash_point" title="Flash point">Flash point</a> </td> <td>182–287 °C; 360–549 °F; 455–560 K </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; color:inherit; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/12px-X_mark.svg.png" decoding="async" width="12" height="14" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/18px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/24px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=477163023&page2=Polyethylene+glycol">verify</a></span> (<a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">what is</a> <sup><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup> ?) </div></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> <p><b>Polyethylene glycol</b> (<b>PEG</b>; <span class="rt-commentedText nowrap"><span class="IPA nopopups noexcerpt" lang="en-fonipa"><a href="/wiki/Help:IPA/English" title="Help:IPA/English">/<span style="border-bottom:1px dotted"><span title="/ˌ/: secondary stress follows">ˌ</span><span title="'p' in 'pie'">p</span><span title="/ɒ/: 'o' in 'body'">ɒ</span><span title="'l' in 'lie'">l</span><span title="/i/: 'y' in 'happy'">i</span><span title="/ˈ/: primary stress follows">ˈ</span><span title="/ɛ/: 'e' in 'dress'">ɛ</span><span title="/θ/: 'th' in 'thigh'">θ</span><span title="/əl/: 'le' in 'bottle'">əl</span><span title="/ˌ/: secondary stress follows">ˌ</span><span title="/iː/: 'ee' in 'fleece'">iː</span><span title="'n' in 'nigh'">n</span></span><span class="wrap"> </span><span style="border-bottom:1px dotted"><span title="/ˈ/: primary stress follows">ˈ</span><span title="/ɡ/: 'g' in 'guy'">ɡ</span><span title="'l' in 'lie'">l</span><span title="/aɪ/: 'i' in 'tide'">aɪ</span><span title="/ˌ/: secondary stress follows">ˌ</span><span title="'k' in 'kind'">k</span><span title="/ɒ/: 'o' in 'body'">ɒ</span><span title="'l' in 'lie'">l</span></span>,<span class="wrap"> </span>-<span style="border-bottom:1px dotted"><span title="/ˈ/: primary stress follows">ˈ</span><span title="/ɛ/: 'e' in 'dress'">ɛ</span><span title="/θ/: 'th' in 'thigh'">θ</span><span title="/ɪ/: 'i' in 'kit'">ɪ</span><span title="'l' in 'lie'">l</span></span>-,<span class="wrap"> </span>-<span style="border-bottom:1px dotted"><span title="/ˌ/: secondary stress follows">ˌ</span><span title="'k' in 'kind'">k</span><span title="/ɔː/: 'au' in 'fraud'">ɔː</span><span title="'l' in 'lie'">l</span></span>/</a></span></span>) is a <a href="/wiki/Polyether" class="mw-redirect" title="Polyether">polyether</a> compound derived from <a href="/wiki/Petroleum" title="Petroleum">petroleum</a> with many applications, from industrial manufacturing to <a href="/wiki/Medicine" title="Medicine">medicine</a>. PEG is also known as <b>polyethylene oxide</b> (<b>PEO</b>) or <b>polyoxyethylene</b> (<b>POE</b>), depending on its <a href="/wiki/Molecular_weight" class="mw-redirect" title="Molecular weight">molecular weight</a>. The structure of PEG is commonly expressed as H−(O−CH<sub>2</sub>−CH<sub>2</sub>)<sub>n</sub>−OH.<sup id="cite_ref-Ullmann'Encyclo-2000_3-0" class="reference"><a href="#cite_note-Ullmann'Encyclo-2000-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Uses">Uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polyethylene_glycol&action=edit&section=1" title="Edit section: Uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Medical_uses">Medical uses</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polyethylene_glycol&action=edit&section=2" title="Edit section: Medical uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main articles: <a href="/wiki/Macrogol" title="Macrogol">Macrogol</a> and <a href="/wiki/PEGylation" title="PEGylation">PEGylation</a></div> <ul><li>Pharmaceutical-grade PEG is used as an <a href="/wiki/Excipient" title="Excipient">excipient</a> in many pharmaceutical products, in oral, topical, and parenteral dosage forms.<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></li> <li>PEG is the basis of a number of <a href="/wiki/Laxative" title="Laxative">laxatives</a> (as <i>MiraLax, RestoraLAX, MoviPrep, etc.</i>).<sup id="cite_ref-Kean-2017_5-0" class="reference"><a href="#cite_note-Kean-2017-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Whole_bowel_irrigation" title="Whole bowel irrigation">Whole bowel irrigation</a> with polyethylene glycol and added <a href="/wiki/Electrolyte" title="Electrolyte">electrolytes</a> is used for bowel preparation before <a href="/wiki/Surgery" title="Surgery">surgery</a> or <a href="/wiki/Colonoscopy" title="Colonoscopy">colonoscopy</a> or for children with constipation.<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> <a href="/wiki/Macrogol" title="Macrogol">Macrogol</a> (with brand names such as Laxido, Movicol and Miralax) is the generic name for polyethylene glycol used as a laxative. The name may be followed by a number that represents the average molecular weight (e.g. macrogol 3350, macrogol 4000, or macrogol 6000).</li> <li>The possibility that PEG could be used to fuse <a href="/wiki/Axon" title="Axon">axons</a> is being explored by researchers studying <a href="/wiki/Nerve_injury" title="Nerve injury">peripheral nerve</a> and <a href="/wiki/Spinal_cord_injury" title="Spinal cord injury">spinal cord injury</a>.<sup id="cite_ref-Kean-2017_5-1" class="reference"><a href="#cite_note-Kean-2017-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup></li> <li>An example of PEG <a href="/wiki/Hydrogel" title="Hydrogel">hydrogels</a> (see <a href="#Biological_uses">Biological uses</a> section) in a therapeutic has been theorized by Ma et al. They propose using the hydrogel to address <a href="/wiki/Periodontal_disease" title="Periodontal disease">periodontitis</a> (gum disease) by encapsulating <a href="/wiki/Stem_cell" title="Stem cell">stem cells</a> in the gel that promote healing in the gums.<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> The gel with encapsulated stem cells was to be injected into the site of disease and crosslinked to create the microenvironment required for the stem cells to function.</li> <li><a href="/wiki/PEGylation" title="PEGylation">PEGylation</a> of <a href="/wiki/Adenoviridae" title="Adenoviridae">adenoviruses</a> for <a href="/wiki/Gene_therapy" title="Gene therapy">gene therapy</a> can help prevent adverse reactions due to pre-existing adenovirus immunity.<sup id="cite_ref-Seregin-2009_8-0" class="reference"><a href="#cite_note-Seregin-2009-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup></li> <li>A <a href="/wiki/PEGylation" title="PEGylation">PEGylated</a> lipid is used as an excipient in both the <a href="/wiki/Moderna#COVID-19_vaccine" title="Moderna">Moderna</a> and <a href="/wiki/Tozinameran" class="mw-redirect" title="Tozinameran">Pfizer–BioNTech vaccines</a> for <a href="/wiki/SARS-CoV-2" title="SARS-CoV-2">SARS-CoV-2</a>. Both <a href="/wiki/RNA_vaccines" class="mw-redirect" title="RNA vaccines">RNA vaccines</a> consist of <a href="/wiki/Messenger_RNA" title="Messenger RNA">messenger RNA</a>, or mRNA, encased in a bubble of oily molecules called <a href="/wiki/Lipid" title="Lipid">lipids</a>. Proprietary lipid technology is used for each. In both vaccines, the bubbles are coated with a stabilizing molecule of polyethylene glycol.<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> PEG could trigger allergic reaction,<sup id="cite_ref-Cabanillas-2021_10-0" class="reference"><a href="#cite_note-Cabanillas-2021-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> and allergic reactions are the driver for both the United Kingdom and Canadian regulators to issue an advisory, noting that: two "individuals in the U.K. ... were treated and have recovered" from <a href="/wiki/Anaphylactic" class="mw-redirect" title="Anaphylactic">anaphylactic</a> shock.<sup id="cite_ref-Bostock-2020_11-0" class="reference"><a href="#cite_note-Bostock-2020-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-HealthCanada-2020_12-0" class="reference"><a href="#cite_note-HealthCanada-2020-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> The US CDC stated that in their jurisdiction six cases of "severe allergic reaction" had been recorded from more than 250,000 vaccinations, and of those six only one person had a "history of vaccination reactions".<sup id="cite_ref-Furtula-2020_13-0" class="reference"><a href="#cite_note-Furtula-2020-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup></li></ul> <div class="mw-heading mw-heading3"><h3 id="Chemical_uses">Chemical uses</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polyethylene_glycol&action=edit&section=3" title="Edit section: Chemical uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:MaryRose-conservation2.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/92/MaryRose-conservation2.jpg/220px-MaryRose-conservation2.jpg" decoding="async" width="220" height="223" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/92/MaryRose-conservation2.jpg/330px-MaryRose-conservation2.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/92/MaryRose-conservation2.jpg/440px-MaryRose-conservation2.jpg 2x" data-file-width="750" data-file-height="761" /></a><figcaption>The remains of the 16th century <a href="/wiki/Carrack" title="Carrack">carrack</a> <i><a href="/wiki/Mary_Rose" title="Mary Rose">Mary Rose</a></i> undergoing conservation treatment with PEG in the 1980s</figcaption></figure> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Terra_Cotta_Warriors,_Guardians_of_China%E2%80%99s_First_Emperor_1.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/bc/Terra_Cotta_Warriors%2C_Guardians_of_China%E2%80%99s_First_Emperor_1.jpg/220px-Terra_Cotta_Warriors%2C_Guardians_of_China%E2%80%99s_First_Emperor_1.jpg" decoding="async" width="220" height="330" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/bc/Terra_Cotta_Warriors%2C_Guardians_of_China%E2%80%99s_First_Emperor_1.jpg/330px-Terra_Cotta_Warriors%2C_Guardians_of_China%E2%80%99s_First_Emperor_1.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/bc/Terra_Cotta_Warriors%2C_Guardians_of_China%E2%80%99s_First_Emperor_1.jpg/440px-Terra_Cotta_Warriors%2C_Guardians_of_China%E2%80%99s_First_Emperor_1.jpg 2x" data-file-width="1365" data-file-height="2048" /></a><figcaption>Terra cotta warrior, showing traces of original color</figcaption></figure> <ul><li>Polyethylene glycol is also commonly used as a polar stationary phase for <a href="/wiki/Gas_chromatography" title="Gas chromatography">gas chromatography</a>, as well as a <a href="/wiki/Coolant" title="Coolant">heat transfer fluid</a> in electronic testers.</li> <li>PEG is frequently used to <a href="/wiki/Conservation_and_restoration_of_waterlogged_wood" title="Conservation and restoration of waterlogged wood">preserve waterlogged wood</a> and other organic artifacts that have been salvaged from underwater archaeological contexts, as was the case with the warship <i><a href="/wiki/Vasa_(ship)" title="Vasa (ship)">Vasa</a></i> in Stockholm,<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> and similar cases. It replaces water in wooden objects, making the wood dimensionally stable and preventing the warping or shrinking of the wood when it dries.<sup id="cite_ref-Kean-2017_5-2" class="reference"><a href="#cite_note-Kean-2017-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> In addition, PEG is used when working with <a href="/wiki/Green_wood" title="Green wood">green wood</a> as a stabilizer, and to prevent shrinkage.<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></li> <li>PEG has been used to preserve the painted colors on <a href="/wiki/Terracotta_Army" title="Terracotta Army">Terracotta Warriors</a> unearthed at a UNESCO World Heritage site in China.<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> These painted artifacts were created during the <a href="/wiki/Qin_Shi_Huang" title="Qin Shi Huang">Qin Shi Huang</a> (first emperor of China) era. Within 15 seconds of the terra-cotta pieces being unearthed during excavations, the lacquer beneath the paint begins to curl after being exposed to the dry <a href="/wiki/Xi%27an" title="Xi'an">Xi'an</a> air. The paint would subsequently flake off in about four minutes. The German Bavarian State Conservation Office developed a PEG preservative that when immediately applied to unearthed artifacts has aided in preserving the colors painted on the pieces of clay soldiers.<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></li> <li>PEG is often used (as an internal calibration compound) in <a href="/wiki/Mass_spectrometry" title="Mass spectrometry">mass spectrometry</a> experiments, with its characteristic fragmentation pattern allowing accurate and reproducible tuning.</li> <li>PEG derivatives, such as <a href="/wiki/Narrow_range_ethoxylate" class="mw-redirect" title="Narrow range ethoxylate">narrow range ethoxylates</a>, are used as <a href="/wiki/Surfactant" title="Surfactant">surfactants</a>.</li> <li>PEG has been used as the hydrophilic block of <a href="/wiki/Amphiphilic" class="mw-redirect" title="Amphiphilic">amphiphilic</a> block <a href="/wiki/Copolymers" class="mw-redirect" title="Copolymers">copolymers</a> used to create some <a href="/wiki/Polymersome" title="Polymersome">polymersomes</a>.<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></li> <li>PEG is a component of the propellent used in <a href="/wiki/UGM-133_Trident_II" title="UGM-133 Trident II">UGM-133M Trident II Missiles</a>, in service with the <a href="/wiki/United_States_Navy" title="United States Navy">United States Navy</a>.<sup id="cite_ref-Strategic_Systems_Programs_19-0" class="reference"><a href="#cite_note-Strategic_Systems_Programs-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup></li> <li>PEG has been used as a solvent for aryl <a href="/wiki/Thioether" class="mw-redirect" title="Thioether">thioether</a> synthesis.<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup></li></ul> <div class="mw-heading mw-heading3"><h3 id="Biological_uses">Biological uses</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polyethylene_glycol&action=edit&section=4" title="Edit section: Biological uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li>An example study was done using PEG-diacrylate hydrogels to recreate vascular environments with the encapsulation of <a href="/wiki/Endothelium" title="Endothelium">endothelial</a> cells and <a href="/wiki/Macrophage" title="Macrophage">macrophages</a>. This model furthered vascular disease modeling and isolated macrophage phenotype's effect on blood vessels.<sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup></li> <li>PEG is commonly used as a crowding agent in <i>in vitro</i> assays to mimic highly crowded cellular conditions.<sup id="cite_ref-Ganji-2016_22-0" class="reference"><a href="#cite_note-Ganji-2016-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> Although polyethylene glycol is considered biologically inert, it can form <a href="/wiki/Non-covalent_interaction" title="Non-covalent interaction">non-covalent</a> complexes with monovalent <a href="/wiki/Cations" class="mw-redirect" title="Cations">cations</a> such as <a href="/wiki/Na%E2%81%BA" class="mw-redirect" title="Na⁺">Na<sup>+</sup></a>, <a href="/wiki/Potassium" title="Potassium">K<sup>+</sup></a>, Rb<sup>+</sup>, and Cs<sup>+</sup>, affecting <a href="/wiki/Equilibrium_constant" title="Equilibrium constant">equilibrium constants</a> of biochemical reactions.<sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup></li> <li>PEG is commonly used as a <a href="/wiki/Precipitant" class="mw-redirect" title="Precipitant">precipitant</a> for plasmid DNA isolation and <a href="/wiki/X-ray_crystallography" title="X-ray crystallography">protein crystallization</a>. <a href="/wiki/X-ray_diffraction" title="X-ray diffraction">X-ray diffraction</a> of protein crystals can reveal the atomic structure of the proteins.</li> <li>PEG is used to fuse two different types of cells, most often B-cells and myelomas to create <a href="/wiki/Hybridomas" class="mw-redirect" title="Hybridomas">hybridomas</a>. <a href="/wiki/C%C3%A9sar_Milstein" title="César Milstein">César Milstein</a> and <a href="/wiki/Georges_J._F._K%C3%B6hler" title="Georges J. F. Köhler">Georges J. F. Köhler</a> originated this technique, which they used for antibody production, winning a <a href="/wiki/Nobel_Prize_in_Physiology_or_Medicine" title="Nobel Prize in Physiology or Medicine">Nobel Prize in Physiology or Medicine</a> in 1984.<sup id="cite_ref-Kean-2017_5-3" class="reference"><a href="#cite_note-Kean-2017-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup></li> <li>In <a href="/wiki/Microbiology" title="Microbiology">microbiology</a>, PEG precipitation is used to concentrate viruses. PEG is also used to induce complete fusion (mixing of both inner and outer leaflets) in liposomes reconstituted <i>in vitro</i>.</li> <li><a href="/wiki/Gene_therapy" title="Gene therapy">Gene therapy</a> vectors (such as viruses) can be PEG-coated to shield them from inactivation by the immune system and to de-target them from organs where they may build up and have a toxic effect.<sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> The size of the PEG polymer is important, with larger polymers achieving the best immune protection.</li> <li>PEG is a component of <a href="/wiki/Stable_nucleic_acid_lipid_particle" title="Stable nucleic acid lipid particle">stable nucleic acid lipid particles</a> (SNALPs) used to package <a href="/wiki/SiRNA" class="mw-redirect" title="SiRNA">siRNA</a> for use <i>in vivo</i>.<sup id="cite_ref-26" class="reference"><a href="#cite_note-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-27" class="reference"><a href="#cite_note-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup></li> <li>In <a href="/wiki/Blood_banking" class="mw-redirect" title="Blood banking">blood banking</a>, PEG is used as a <a href="/wiki/Potentiator" title="Potentiator">potentiator</a> to enhance detection of <a href="/wiki/Antigen" title="Antigen">antigens</a> and <a href="/wiki/Antibodies" class="mw-redirect" title="Antibodies">antibodies</a>.<sup id="cite_ref-Kean-2017_5-4" class="reference"><a href="#cite_note-Kean-2017-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-28" class="reference"><a href="#cite_note-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup></li> <li>When working with <a href="/wiki/Phenol" title="Phenol">phenol</a> in a laboratory situation, <a href="/w/index.php?title=PEG_300&action=edit&redlink=1" class="new" title="PEG 300 (page does not exist)">PEG 300</a> can be used on phenol skin burns to deactivate any residual phenol.<sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup></li> <li>In <a href="/wiki/Biophysics" title="Biophysics">biophysics</a>, polyethylene glycols are the molecules of choice for the functioning ion channel diameter studies, because in aqueous solutions they have a spherical shape and can block ion channel conductance.<sup id="cite_ref-30" class="reference"><a href="#cite_note-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-31" class="reference"><a href="#cite_note-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup></li></ul> <div class="mw-heading mw-heading3"><h3 id="Commercial_uses">Commercial uses</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polyethylene_glycol&action=edit&section=5" title="Edit section: Commercial uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li>PEG is the basis of many <a href="/wiki/Moisturizer" title="Moisturizer">skin creams</a> (as <i><a href="/wiki/Cetomacrogol" class="mw-redirect" title="Cetomacrogol">cetomacrogol</a></i>) and <a href="/wiki/Personal_lubricant" title="Personal lubricant">personal lubricants</a>.</li> <li>PEG is used in a number of <a href="/wiki/Toothpaste" title="Toothpaste">toothpastes</a><sup id="cite_ref-Kean-2017_5-5" class="reference"><a href="#cite_note-Kean-2017-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> as a <a href="/wiki/Dispersant" title="Dispersant">dispersant</a>. In this application, it binds water and helps keep <a href="/wiki/Xanthan_gum" title="Xanthan gum">xanthan gum</a> uniformly distributed throughout the toothpaste.</li> <li>PEG is under investigation for use in <a href="/wiki/Liquid_Armor" class="mw-redirect" title="Liquid Armor">liquid body armor</a>, and in <a href="/wiki/Tattoo" title="Tattoo">tattoos</a> to monitor <a href="/wiki/Diabetes" title="Diabetes">diabetes</a>.<sup id="cite_ref-32" class="reference"><a href="#cite_note-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup></li> <li>Polymer segments derived from PEG <a href="/wiki/Polyols" class="mw-redirect" title="Polyols">polyols</a> impart flexibility to <a href="/wiki/Polyurethane" title="Polyurethane">polyurethanes</a> for applications such as elastomeric <a href="/wiki/Fiber" title="Fiber">fibers</a> (<a href="/wiki/Spandex" title="Spandex">spandex</a>) and <a href="/wiki/Foam" title="Foam">foam</a> cushions.</li> <li>In low-<a href="/wiki/Molecular_weight" class="mw-redirect" title="Molecular weight">molecular-weight</a> formulations (e.g. <a href="/wiki/PEG_400" title="PEG 400">PEG 400</a>), it is used in <a href="/wiki/Hewlett-Packard" title="Hewlett-Packard">Hewlett-Packard</a> designjet <a href="/wiki/Printer_(computing)" title="Printer (computing)">printers</a> as an ink solvent and lubricant for the print heads.</li> <li>PEG is used as an anti-foaming agent in food and drinks<sup id="cite_ref-33" class="reference"><a href="#cite_note-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> – its <a href="/wiki/INS_number" class="mw-redirect" title="INS number">INS number</a> is 1521<sup id="cite_ref-34" class="reference"><a href="#cite_note-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> or E1521 in the EU.<sup id="cite_ref-35" class="reference"><a href="#cite_note-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup></li></ul> <div class="mw-heading mw-heading3"><h3 id="Industrial_uses">Industrial uses</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polyethylene_glycol&action=edit&section=6" title="Edit section: Industrial uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li>A <a href="/wiki/Nitrate" title="Nitrate">nitrate</a> <a href="/wiki/Ester" title="Ester">ester</a>-plasticized polyethylene glycol (<a href="/wiki/Solid-fuel_rocket#Composite_modified_double_base_propellants" class="mw-redirect" title="Solid-fuel rocket">NEPE-75</a>) is used in <a href="/wiki/UGM-133_Trident_II#Design" title="UGM-133 Trident II">Trident II</a> <a href="/wiki/Submarine-launched_ballistic_missile" title="Submarine-launched ballistic missile">submarine-launched ballistic missile</a> solid rocket fuel.<sup id="cite_ref-Spinardi-1994_36-0" class="reference"><a href="#cite_note-Spinardi-1994-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup></li> <li>Dimethyl ethers of PEG are the key ingredient of <a href="/wiki/Selexol" title="Selexol">Selexol</a>, a solvent used by <a href="/wiki/Coal" title="Coal">coal</a>-burning, <a href="/wiki/Integrated_gasification_combined_cycle" title="Integrated gasification combined cycle">integrated gasification combined cycle</a> (IGCC) power plants to remove <a href="/wiki/Carbon_dioxide" title="Carbon dioxide">carbon dioxide</a> and <a href="/wiki/Hydrogen_sulfide" title="Hydrogen sulfide">hydrogen sulfide</a> from the <a href="/wiki/Syngas" title="Syngas">syngas</a> stream.</li> <li>PEG has been used as the gate insulator in an electric double-layer transistor to induce superconductivity in an insulator.<sup id="cite_ref-37" class="reference"><a href="#cite_note-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup></li> <li>PEG is used as a polymer host for solid polymer electrolytes. Although not yet in commercial production, many groups around the globe are engaged in research on solid polymer electrolytes involving PEG, to improve their properties, and in permitting their use in batteries, electro-chromic display systems, and other products in the future.</li> <li>PEG is injected into industrial processes to reduce foaming in separation equipment.</li> <li>PEG is used as a <a href="/wiki/Binder_(material)" title="Binder (material)">binder</a> in the preparation of technical <a href="/wiki/Ceramic" title="Ceramic">ceramics</a>.<sup id="cite_ref-38" class="reference"><a href="#cite_note-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup></li> <li>PEG was used as an additive to silver halide photographic <a href="/wiki/Photolith_film" title="Photolith film">emulsions</a>.</li> <li>PEG is used as an active ingredient in agricultural soil wetter, which improves water-retention and seedling growth.<sup id="cite_ref-39" class="reference"><a href="#cite_note-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup></li></ul> <div class="mw-heading mw-heading3"><h3 id="Entertainment_uses">Entertainment uses</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polyethylene_glycol&action=edit&section=7" title="Edit section: Entertainment uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li>PEG is used to extend the size and durability of very large <a href="/wiki/Soap_bubbles" class="mw-redirect" title="Soap bubbles">soap bubbles</a>.</li> <li>PEG is an ingredient in some <a href="/wiki/Personal_lubricant" title="Personal lubricant">personal lubricants</a>.<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. (February 2024)">citation needed</span></a></i>]</sup> (Not to be confused with <a href="/wiki/Propylene_glycol" title="Propylene glycol">propylene glycol</a>.)</li> <li>PEG is the main ingredient in the paint (known as "fill") in <a href="/wiki/Paintball" title="Paintball">paintballs</a>.</li></ul> <div class="mw-heading mw-heading2"><h2 id="Human_health_effects">Human health effects</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polyethylene_glycol&action=edit&section=8" title="Edit section: Human health effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>PEO's<sup class="noprint Inline-Template" style="margin-left:0.1em; white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Please_clarify" title="Wikipedia:Please clarify"><span title="Why are we suddenly talking about PEO, not PEG? What is the difference, if any? (October 2024)">clarification needed</span></a></i>]</sup> have "very low single dose oral toxicity", on the order of tens of <a href="/wiki/Gram" title="Gram">grams</a> per <a href="/wiki/Kilogram" title="Kilogram">kilogram</a> of human body weight when ingested by mouth.<sup id="cite_ref-Ullmann'Encyclo-2000_3-1" class="reference"><a href="#cite_note-Ullmann'Encyclo-2000-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Because of its low toxicity, PEO is used in a variety of edible products.<sup id="cite_ref-40" class="reference"><a href="#cite_note-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup> It is also used as a <a href="/wiki/Lubrication" title="Lubrication">lubricating</a> coating for various surfaces in <a href="/wiki/Aqueous_solution" title="Aqueous solution">aqueous</a> and non-aqueous applications.<sup id="cite_ref-41" class="reference"><a href="#cite_note-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> </p><p>The precursor to PEGs is <a href="/wiki/Ethylene_oxide" title="Ethylene oxide">ethylene oxide</a>, which is hazardous.<sup id="cite_ref-42" class="reference"><a href="#cite_note-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup> Ethylene glycol and its <a href="/wiki/Ether" title="Ether">ethers</a> are <a href="/wiki/Nephrotoxicity" title="Nephrotoxicity">nephrotoxic</a> (<a href="/wiki/Poison" title="Poison">poisonous</a> to the <a href="/wiki/Kidney" title="Kidney">kidneys</a>) if applied to damaged skin.<sup id="cite_ref-Andersen-1999_43-0" class="reference"><a href="#cite_note-Andersen-1999-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> </p><p>The United States <a href="/wiki/Food_and_Drug_Administration" title="Food and Drug Administration">Food and Drug Administration</a> (FDA or US FDA) regards PEG as biologically inert and safe.<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. (September 2024)">citation needed</span></a></i>]</sup> </p><p>A 2015 study appears to challenge the FDA's conclusion. In the study, a high-sensitivity <a href="/wiki/ELISA" title="ELISA">ELISA</a> assay detected anti-PEG <a href="/wiki/Antibody" title="Antibody">antibodies</a> in 72% of random <a href="/wiki/Blood_plasma" title="Blood plasma">blood plasma</a> samples collected from 1990 to 1999. According to the study's authors, this result suggests that anti-PEG antibodies may be present, typically at low levels, in people who were never treated with <a href="/wiki/PEGylated" class="mw-redirect" title="PEGylated">PEGylated</a> drugs.<sup id="cite_ref-44" class="reference"><a href="#cite_note-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Yang-2016_45-0" class="reference"><a href="#cite_note-Yang-2016-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup> Due to its ubiquity in many products and the large percentage of the population with antibodies to PEG, which indicates an <a href="/wiki/Allergy" title="Allergy">allergic</a> reaction, hypersensitive reactions to PEG are an increasing health concern.<sup id="cite_ref-Wenande-2016_46-0" class="reference"><a href="#cite_note-Wenande-2016-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-47" class="reference"><a href="#cite_note-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup> Allergy to PEG is usually discovered after a person has been diagnosed with an allergy to several seemingly unrelated products—including processed foods, cosmetics, drugs, and other substances—that contain or were manufactured with PEG.<sup id="cite_ref-Wenande-2016_46-1" class="reference"><a href="#cite_note-Wenande-2016-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Available_forms_and_nomenclature">Available forms and nomenclature</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polyethylene_glycol&action=edit&section=9" title="Edit section: Available forms and nomenclature"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><i>PEG</i>, <i>PEO</i>, and <i>POE</i> refer to an <a href="/wiki/Oligomer" title="Oligomer">oligomer</a> or polymer of <a href="/wiki/Ethylene_oxide" title="Ethylene oxide">ethylene oxide</a>. The three names are chemically synonymous, but historically <i>PEG</i> is preferred in the biomedical field, whereas <i>PEO</i> is more prevalent in the field of polymer chemistry. Because different applications require different polymer chain lengths, <i>PEG</i> has tended to refer to oligomers and polymers with a molecular mass below 20,000<span class="nowrap"> </span>g/mol, <i>PEO</i> to polymers with a molecular mass above 20,000<span class="nowrap"> </span>g/mol, and <i>POE</i> to a polymer of any molecular mass.<sup id="cite_ref-48" class="reference"><a href="#cite_note-48"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup> PEGs are prepared by <a href="/wiki/Polymerization" title="Polymerization">polymerization</a> of <a href="/wiki/Ethylene_oxide" title="Ethylene oxide">ethylene oxide</a> and are commercially available over a wide range of molecular weights from 300<span class="nowrap"> </span>g/mol to 10,000,000<span class="nowrap"> </span>g/mol.<sup id="cite_ref-French-2009_49-0" class="reference"><a href="#cite_note-French-2009-49"><span class="cite-bracket">[</span>49<span class="cite-bracket">]</span></a></sup> </p><p>PEG and PEO are liquids or low-melting solids, depending on their <a href="/wiki/Molecular_weight" class="mw-redirect" title="Molecular weight">molecular weights</a>. While PEG and PEO with different molecular weights find use in different applications and have different physical properties (e.g. <a href="/wiki/Viscosity" title="Viscosity">viscosity</a>) due to chain length effects, their chemical properties are nearly identical. Different forms of PEG are also available, depending on the <a href="/wiki/Radical_initiator" title="Radical initiator">initiator</a> used for the polymerization process – the most common initiator is a monofunctional methyl ether PEG, or methoxypoly(ethylene glycol), abbreviated mPEG. Lower-molecular-weight PEGs are also available as purer oligomers, referred to as monodisperse, uniform, or discrete. Very high-purity PEG has recently been shown to be crystalline, allowing the determination of a crystal structure by <a href="/wiki/X-ray_crystallography" title="X-ray crystallography">x-ray crystallography</a>.<sup id="cite_ref-French-2009_49-1" class="reference"><a href="#cite_note-French-2009-49"><span class="cite-bracket">[</span>49<span class="cite-bracket">]</span></a></sup> Since purification and separation of pure oligomers is difficult, the price for this type of quality is often 10–1000 fold that of polydisperse PEG. </p><p>PEGs are also available with different geometries. </p> <ul><li><i>Branched</i> PEGs have three to ten PEG chains emanating from a central core group.</li> <li><i>Star</i> PEGs have 10 to 100 PEG chains emanating from a central core group.</li> <li><i>Comb</i> PEGs have multiple PEG chains normally grafted onto a polymer backbone.</li></ul> <p>The numbers that are often included in the names of PEGs indicate their average molecular weights (e.g. a PEG with <span class="nowrap"><i>n</i> = 9</span> would have an average molecular weight of approximately 400 <a href="/wiki/Atomic_mass_unit" class="mw-redirect" title="Atomic mass unit">daltons</a>, and would be labeled <a href="/wiki/PEG_400" title="PEG 400">PEG 400</a>). Most PEGs include molecules with a distribution of molecular weights (i.e. they are polydisperse). The size distribution can be characterized statistically by its <a href="/wiki/Weight_average_molecular_weight" class="mw-redirect" title="Weight average molecular weight">weight average molecular weight</a> (<i>M</i><sub>w</sub>) and its <a href="/wiki/Number_average_molecular_weight" class="mw-redirect" title="Number average molecular weight">number average molecular weight</a> (<i>M</i><sub>n</sub>), the ratio of which is called the <a href="/wiki/Polydispersity_index" class="mw-redirect" title="Polydispersity index">polydispersity index</a> (<i>Đ</i><sub>M</sub>). <i>M</i><sub>w</sub> and <i>M</i><sub>n</sub> can be measured by <a href="/wiki/Mass_spectrometry" title="Mass spectrometry">mass spectrometry</a>. </p><p><a href="/wiki/PEGylation" title="PEGylation">PEGylation</a> is the act of covalently coupling a PEG structure to another larger molecule, for example, a <a href="/wiki/Therapeutic_protein" class="mw-redirect" title="Therapeutic protein">therapeutic protein</a>, which is then referred to as a <i>PEGylated</i> protein. <a href="/wiki/PEGylated_interferon_alfa-2a" class="mw-redirect" title="PEGylated interferon alfa-2a">PEGylated interferon alfa-2a</a> or <a href="/wiki/PEGylated_interferon_alfa-2b" class="mw-redirect" title="PEGylated interferon alfa-2b">alfa-2b</a> are commonly used injectable treatments for <a href="/wiki/Hepatitis_C" title="Hepatitis C">hepatitis C</a> infection. </p><p>PEG is soluble in <a href="/wiki/Water" title="Water">water</a>, <a href="/wiki/Methanol" title="Methanol">methanol</a>, <a href="/wiki/Ethanol" title="Ethanol">ethanol</a>, <a href="/wiki/Acetonitrile" title="Acetonitrile">acetonitrile</a>, <a href="/wiki/Benzene" title="Benzene">benzene</a>, and <a href="/wiki/Dichloromethane" title="Dichloromethane">dichloromethane</a>, and is insoluble in <a href="/wiki/Diethyl_ether" title="Diethyl ether">diethyl ether</a> and <a href="/wiki/Hexane" title="Hexane">hexane</a>. It is coupled to hydrophobic molecules to produce non-ionic <a href="/wiki/Surfactant" title="Surfactant">surfactants</a>.<sup id="cite_ref-50" class="reference"><a href="#cite_note-50"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:SArfus_PEO.3D.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a6/SArfus_PEO.3D.jpg/220px-SArfus_PEO.3D.jpg" decoding="async" width="220" height="145" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a6/SArfus_PEO.3D.jpg/330px-SArfus_PEO.3D.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a6/SArfus_PEO.3D.jpg/440px-SArfus_PEO.3D.jpg 2x" data-file-width="719" data-file-height="473" /></a><figcaption>Polyethylene oxide (PEO, <a href="/wiki/Molar_mass_distribution" title="Molar mass distribution">M<sub>w</sub></a> 4<span class="nowrap"> </span><a href="/wiki/Atomic_mass_unit" class="mw-redirect" title="Atomic mass unit">kDa</a>) nanometric crystallites (4 nm)</figcaption></figure> <p>PEG and related polymers (PEG phospholipid constructs) are often <a href="/wiki/Sonication" title="Sonication">sonicated</a> when used in biomedical applications. However, as reported by Murali et al., PEG is very sensitive to sonolytic degradation and PEG degradation products can be toxic to mammalian cells. It is, thus, imperative to assess potential PEG degradation to ensure that the final material does not contain undocumented contaminants that can introduce artifacts into experimental results.<sup id="cite_ref-51" class="reference"><a href="#cite_note-51"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup> </p><p>PEGs and methoxypolyethylene glycols are manufactured by <a href="/wiki/Dow_Chemical_Company" title="Dow Chemical Company">Dow Chemical</a> under the trade name <i>Carbowax</i> for industrial use, and <i>Carbowax Sentry</i> for food and pharmaceutical use. They vary in consistency from liquid to solid, depending on the molecular weight, as indicated by a number following the name. They are used commercially in numerous applications, including foods, <a href="/wiki/Cosmetics" title="Cosmetics">cosmetics</a>, pharmaceutics, <a href="/wiki/Biomedicine" title="Biomedicine">biomedicine</a>, dispersing agents, solvents, <a href="/wiki/Ointment" class="mw-redirect" title="Ointment">ointments</a>, <a href="/wiki/Suppository" title="Suppository">suppository</a> bases, as tablet <a href="/wiki/Excipient" title="Excipient">excipients</a>, and as <a href="/wiki/Laxative" title="Laxative">laxatives</a>. Some specific groups are <a href="/wiki/Lauromacrogol" class="mw-redirect" title="Lauromacrogol">lauromacrogols</a>, <a href="/wiki/Nonoxynol" class="mw-redirect" title="Nonoxynol">nonoxynols</a>, <a href="/wiki/Octoxynol" class="mw-redirect" title="Octoxynol">octoxynols</a>, and <a href="/wiki/Poloxamer" title="Poloxamer">poloxamers</a>. </p> <div class="mw-heading mw-heading2"><h2 id="Production">Production</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polyethylene_glycol&action=edit&section=10" title="Edit section: Production"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Polyethylene_glycol_400.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5e/Polyethylene_glycol_400.jpg/220px-Polyethylene_glycol_400.jpg" decoding="async" width="220" height="330" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5e/Polyethylene_glycol_400.jpg/330px-Polyethylene_glycol_400.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5e/Polyethylene_glycol_400.jpg/440px-Polyethylene_glycol_400.jpg 2x" data-file-width="2848" data-file-height="4272" /></a><figcaption>Polyethylene glycol 400, pharmaceutical quality</figcaption></figure> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Polyethylene_glycol_4000.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/74/Polyethylene_glycol_4000.jpg/220px-Polyethylene_glycol_4000.jpg" decoding="async" width="220" height="147" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/74/Polyethylene_glycol_4000.jpg/330px-Polyethylene_glycol_4000.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/74/Polyethylene_glycol_4000.jpg/440px-Polyethylene_glycol_4000.jpg 2x" data-file-width="4272" data-file-height="2848" /></a><figcaption>Polyethylene glycol 4000, pharmaceutical quality</figcaption></figure> <p>The production of polyethylene glycol was first reported in 1859. Both <a href="/w/index.php?title=A._V._Louren%C3%A7o&action=edit&redlink=1" class="new" title="A. V. Lourenço (page does not exist)">A. V. Lourenço</a> and <a href="/wiki/Charles_Adolphe_Wurtz" title="Charles Adolphe Wurtz">Charles Adolphe Wurtz</a> independently isolated products that were polyethylene glycols.<sup id="cite_ref-Bailey-1990_52-0" class="reference"><a href="#cite_note-Bailey-1990-52"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup> Polyethylene glycol is produced by the interaction of <a href="/wiki/Ethylene_oxide" title="Ethylene oxide">ethylene oxide</a> with water, <a href="/wiki/Ethylene_glycol" title="Ethylene glycol">ethylene glycol</a>, or ethylene glycol oligomers.<sup id="cite_ref-53" class="reference"><a href="#cite_note-53"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup> The reaction is catalyzed by acidic or basic catalysts. Ethylene glycol and its oligomers are preferable as a starting material instead of water because they allow the creation of polymers with a low <a href="/wiki/Polydispersity" class="mw-redirect" title="Polydispersity">polydispersity</a> (narrow molecular weight distribution). Polymer chain length depends on the ratio of reactants. </p> <dl><dd>HOCH<sub>2</sub>CH<sub>2</sub>OH + n(CH<sub>2</sub>CH<sub>2</sub>O) → HO(CH<sub>2</sub>CH<sub>2</sub>O)<sub>n+1</sub>H</dd></dl> <p>Depending on the catalyst type, the mechanism of <a href="/wiki/Polymerization" title="Polymerization">polymerization</a> can be cationic or anionic. The anionic mechanism is preferable because it allows one to obtain PEG with a low <a href="/wiki/Polydispersity" class="mw-redirect" title="Polydispersity">polydispersity</a>. Polymerization of ethylene oxide is an exothermic process. Overheating or contaminating ethylene oxide with catalysts, such as alkalis or metal oxides, can lead to runaway polymerization, which can end in an explosion after a few hours. </p><p>Polyethylene oxide, or high-molecular-weight polyethylene glycol, is synthesized by <a href="/wiki/Suspension_polymerization" title="Suspension polymerization">suspension polymerization</a>. It is necessary to hold the growing polymer chain in <a href="/wiki/Polymer_solution" title="Polymer solution">solution</a> in the course of the <a href="/wiki/Polycondensation" class="mw-redirect" title="Polycondensation">polycondensation</a> process. The reaction is catalyzed by magnesium-, aluminium-, or calcium-organoelement compounds. To prevent <a href="/wiki/Coagulation" title="Coagulation">coagulation</a> of polymer chains from solution, chelating additives, such as <a href="/wiki/Dimethylglyoxime" title="Dimethylglyoxime">dimethylglyoxime</a>, are used. </p><p>Alkaline catalysts, such as <a href="/wiki/Sodium_hydroxide" title="Sodium hydroxide">sodium hydroxide</a> (NaOH), <a href="/wiki/Potassium_hydroxide" title="Potassium hydroxide">potassium hydroxide</a> (KOH), or <a href="/wiki/Sodium_carbonate" title="Sodium carbonate">sodium carbonate</a> (Na<sub>2</sub>CO<sub>3</sub>), are used to prepare low-molecular-weight polyethylene glycol.<sup id="cite_ref-54" class="reference"><a href="#cite_note-54"><span class="cite-bracket">[</span>54<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=Polyethylene_glycol&action=edit&section=11" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Lauryl_methyl_gluceth-10_hydroxypropyl_dimonium_chloride" title="Lauryl methyl gluceth-10 hydroxypropyl dimonium chloride">Lauryl methyl gluceth-10 hydroxypropyl dimonium chloride</a></li> <li><a href="/wiki/Lysozyme_PEGylation" title="Lysozyme PEGylation">Lysozyme PEGylation</a></li> <li><a href="/wiki/PEG-PVA" title="PEG-PVA">PEG-PVA</a></li> <li><a href="/wiki/Polyethylene_glycol_propylene_glycol_cocoates" title="Polyethylene glycol propylene glycol cocoates">Polyethylene glycol propylene glycol cocoates</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=Polyethylene_glycol&action=edit&section=12" 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 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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 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New York: Dekker. pp. <span class="nowrap">27–</span>28. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780824783846" title="Special:BookSources/9780824783846"><bdi>9780824783846</bdi></a><span class="reference-accessdate">. Retrieved <span class="nowrap">17 July</span> 2017</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Alkylene+oxides+and+their+polymers&rft.place=New+York&rft.pages=%3Cspan+class%3D%22nowrap%22%3E27-%3C%2Fspan%3E28&rft.pub=Dekker&rft.date=1990&rft.isbn=9780824783846&rft.aulast=Bailey&rft.aufirst=FE&rft.au=Koleske%2C+JV&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DLfmJuNNl5bwC%26pg%3DPA27&rfr_id=info%3Asid%2Fen.wikipedia.org%3APolyethylene+glycol" class="Z3988"></span></span> </li> <li id="cite_note-53"><span class="mw-cite-backlink"><b><a href="#cite_ref-53">^</a></b></span> <span class="reference-text"><a rel="nofollow" class="external text" href="http://chemindustry.ru/Polyethylene_Glycol.php">Polyethylene glycol</a>, Chemindustry.ru</span> </li> <li id="cite_note-54"><span class="mw-cite-backlink"><b><a href="#cite_ref-54">^</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.venus-goa.com/Polyethylene-glycol.php">"PEG 4000, 6000, 8000, 12000 | Polyethylene glycol"</a>. <i>www.venus-goa.com</i><span class="reference-accessdate">. Retrieved <span class="nowrap">19 January</span> 2023</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=www.venus-goa.com&rft.atitle=PEG+4000%2C+6000%2C+8000%2C+12000+%7C+Polyethylene+glycol&rft_id=https%3A%2F%2Fwww.venus-goa.com%2FPolyethylene-glycol.php&rfr_id=info%3Asid%2Fen.wikipedia.org%3APolyethylene+glycol" class="Z3988"></span></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polyethylene_glycol&action=edit&section=13" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1235681985">.mw-parser-output .side-box{margin:4px 0;box-sizing:border-box;border:1px solid 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phosphate">Sodium phosphate</a></li> <li><a href="/wiki/Sodium_sulfate" title="Sodium sulfate">Sodium sulfate</a></li> <li><a href="/wiki/Sodium_tartrate" title="Sodium tartrate">Sodium tartrate</a></li> <li><a href="/wiki/Sorbitol" title="Sorbitol">Sorbitol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Enema" title="Enema">Enemas</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Bisacodyl" title="Bisacodyl">Bisacodyl</a></li> <li><a href="/wiki/Dantron" title="Dantron">Dantron</a></li> <li><a href="/wiki/Glycerol" title="Glycerol">Glycerol</a></li> <li><a href="/wiki/Oil" title="Oil">Oil</a></li> <li><a href="/wiki/Sodium_dodecyl_sulfate" title="Sodium dodecyl sulfate">Sodium laurilsulfate</a></li> <li><a href="/wiki/Sodium_lauryl_sulfoacetate" title="Sodium lauryl sulfoacetate">Sodium lauryl sulfoacetate</a></li> <li><a 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title="Methylnaltrexone">Methylnaltrexone</a></li> <li><a href="/wiki/Naldemedine" title="Naldemedine">Naldemedine</a></li> <li><a href="/wiki/Naloxegol" title="Naloxegol">Naloxegol</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Others</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Linaclotide" title="Linaclotide">Linaclotide</a></li> <li><a href="/wiki/Lubiprostone" title="Lubiprostone">Lubiprostone</a></li> <li><a href="/wiki/Oxyphenisatine" title="Oxyphenisatine">Oxyphenisatine</a></li> <li><a href="/wiki/Plecanatide" title="Plecanatide">Plecanatide</a></li> <li><a href="/wiki/Prucalopride" title="Prucalopride">Prucalopride</a></li> <li><a href="/wiki/Tegaserod" title="Tegaserod">Tegaserod</a></li> <li><a href="/wiki/Tenapanor" title="Tenapanor">Tenapanor</a></li> <li><a href="/wiki/Ulimorelin" 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