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Available in 22 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-22" 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">22 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%A7%D9%84%D8%A8%D8%A7%D8%AA%D9%88%D9%84%D9%8A%D9%86" title="الباتولين – Arabic" lang="ar" hreflang="ar" data-title="الباتولين" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Patulina" title="Patulina – Catalan" lang="ca" hreflang="ca" data-title="Patulina" 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/Patulin" title="Patulin – Czech" lang="cs" hreflang="cs" data-title="Patulin" 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/Patulin" title="Patulin – German" lang="de" hreflang="de" data-title="Patulin" 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/Patulina" title="Patulina – Spanish" lang="es" hreflang="es" data-title="Patulina" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Patuline" title="Patuline – French" lang="fr" hreflang="fr" data-title="Patuline" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%ED%8C%8C%ED%88%B4%EB%A6%B0" title="파툴린 – Korean" lang="ko" hreflang="ko" data-title="파툴린" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Patulina" title="Patulina – Italian" lang="it" hreflang="it" data-title="Patulina" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-la mw-list-item"><a href="https://la.wikipedia.org/wiki/Patulinum" title="Patulinum – Latin" lang="la" hreflang="la" data-title="Patulinum" data-language-autonym="Latina" data-language-local-name="Latin" class="interlanguage-link-target"><span>Latina</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Patulin" title="Patulin – Hungarian" lang="hu" hreflang="hu" data-title="Patulin" 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/Patuline" title="Patuline – Dutch" lang="nl" hreflang="nl" data-title="Patuline" 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%91%E3%83%84%E3%83%AA%E3%83%B3" title="パツリン – Japanese" lang="ja" hreflang="ja" data-title="パツリン" 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/Patulina" title="Patulina – Polish" lang="pl" hreflang="pl" data-title="Patulina" 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/Patulina" title="Patulina – Portuguese" lang="pt" hreflang="pt" data-title="Patulina" 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/Patulin%C4%83" title="Patulină – Romanian" lang="ro" hreflang="ro" data-title="Patulină" 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%B0%D1%82%D1%83%D0%BB%D0%B8%D0%BD" title="Патулин – Russian" lang="ru" hreflang="ru" data-title="Патулин" 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/Patulin" title="Patulin – Serbian" lang="sr" hreflang="sr" data-title="Patulin" 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/Patulin" title="Patulin – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Patulin" 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/Patuliini" title="Patuliini – Finnish" lang="fi" hreflang="fi" data-title="Patuliini" 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/Patulin" title="Patulin – Swedish" lang="sv" hreflang="sv" data-title="Patulin" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Patulin" title="Patulin – Vietnamese" lang="vi" hreflang="vi" data-title="Patulin" 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/%E5%B1%95%E9%9D%92%E9%9C%89%E7%B4%A0" title="展青霉素 – Chinese" lang="zh" hreflang="zh" data-title="展青霉素" 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 href="https://www.wikidata.org/wiki/Special:EntityPage/Q414526#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></div> </div> </div> </div> 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For the botany and zoology term, see <a href="/wiki/Glossary_of_entomology_terms#clavate" title="Glossary of entomology terms">Glossary of entomology terms § clavate</a>.</div> <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> <table class="infobox ib-chembox"> <caption>Patulin<sup id="cite_ref-merck_1-0" class="reference"><a href="#cite_note-merck-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </caption> <tbody><tr> <td colspan="2" class="borderless" style="text-align:center"> <table border="0" style="width:100%;display:inline-table;"> <tbody><tr> <td style="border-right:1px solid #aaa; width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Patulin.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/7b/Patulin.png/110px-Patulin.png" decoding="async" width="110" height="76" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/7b/Patulin.png/165px-Patulin.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/7b/Patulin.png/220px-Patulin.png 2x" data-file-width="1170" data-file-height="813" /></a><figcaption></figcaption></figure> </td> <td style="width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Patulin_3d_structure.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/47/Patulin_3d_structure.png/110px-Patulin_3d_structure.png" decoding="async" width="110" height="94" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/47/Patulin_3d_structure.png/165px-Patulin_3d_structure.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/47/Patulin_3d_structure.png/220px-Patulin_3d_structure.png 2x" data-file-width="821" data-file-height="699" /></a><figcaption></figcaption></figure> </td></tr></tbody></table> </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 name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">4-hydroxy-4<i>H</i>-furo[3,2-<i>c</i>]pyran-2(6<i>H</i>)-one</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;">2-Hydroxy-3,7-dioxabicyclo[4.3.0]nona-5,9-dien-8-one<br /> Clairformin<br />Claviform<br />Expansine<br />Clavacin<br />Clavatin<br />Expansin<br />Gigantin<br />Leucopin<br />Patuline</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=149-29-1">149-29-1</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;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=O%3DC%5C1O%2FC2%3DC%2FCOC%28O%29C2%3DC%2F1">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</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/chebi/searchId.do?chebiId=74926">CHEBI:74926</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/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/ChEMBL294018">ChEMBL294018</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><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><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.4534.html">4534</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><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/100.005.215">100.005.215</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q414526#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/European_Community_number" title="European Community number"><span title="European Community number (chemical identifier)">EC Number</span></a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>205-735-2</li></ul></div> </td></tr> <tr> <td><a href="/wiki/KEGG" title="KEGG">KEGG</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/C16748">C16748</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><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/4696">4696</a></span></li></ul></div> </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/95X2BV4W8R">95X2BV4W8R</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/DTXSID2021101">DTXSID2021101</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q414526#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> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C7H6O4/c8-6-3-4-5(11-6)1-2-10-7(4)9/h1,3,7,9H,2H2<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></div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: ZRWPUFFVAOMMNM-UHFFFAOYSA-N<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></div></div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1/C7H6O4/c8-6-3-4-5(11-6)1-2-10-7(4)9/h1,3,7,9H,2H2</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: ZRWPUFFVAOMMNM-UHFFFAOYAU</div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">O=C\1O/C2=C/COC(O)C2=C/1</div></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><span title="Carbon">C</span><sub>7</sub><span title="Hydrogen">H</span><sub>6</sub><span title="Oxygen">O</span><sub>4</sub> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td>154.12 g/mol    </td></tr> <tr> <td>Appearance </td> <td>Compact prisms </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>1.52 g/mL </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>110 °C (230 °F; 383 K) </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Aqueous_solution" title="Aqueous solution">Solubility in water</a></div> </td> <td>Soluble </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=462273608&page2=Patulin">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>Patulin</b> is an <a href="/wiki/Organic_compound" title="Organic compound">organic compound</a> classified as a <a href="/wiki/Polyketide" title="Polyketide">polyketide</a>. It is named after the <a href="/wiki/Fungus" title="Fungus">fungus</a> from which it was isolated, <i><a href="/wiki/Penicillium_patulum" class="mw-redirect" title="Penicillium patulum">Penicillium patulum</a></i>. It is a white powder soluble in acidic water and in <a href="/wiki/Organic_solvent" class="mw-redirect" title="Organic solvent">organic solvents</a>. It is a <a href="/wiki/Lactone" title="Lactone">lactone</a> that is heat-stable, so it is not destroyed by <a href="/wiki/Pasteurization" title="Pasteurization">pasteurization</a> or thermal <a href="/wiki/Denaturation_(biochemistry)" title="Denaturation (biochemistry)">denaturation</a>.<sup id="cite_ref-sigma_2-0" class="reference"><a href="#cite_note-sigma-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> However, stability following <a href="/wiki/Fermentation" title="Fermentation">fermentation</a> is lessened.<sup id="cite_ref-ucm212520_3-0" class="reference"><a href="#cite_note-ucm212520-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> It is a <a href="/wiki/Mycotoxin" title="Mycotoxin">mycotoxin</a> produced by a variety of molds, in particular, <i><a href="/wiki/Aspergillus" title="Aspergillus">Aspergillus</a></i> and <i><a href="/wiki/Penicillium" title="Penicillium">Penicillium</a></i> and <i><a href="/wiki/Byssochlamys" title="Byssochlamys">Byssochlamys</a></i>. Most commonly found in rotting <a href="/wiki/Apples" class="mw-redirect" title="Apples">apples</a>, the amount of patulin in apple products is generally viewed as a measure of the quality of the apples used in production. In addition, patulin has been found in other foods such as grains, fruits, and vegetables. Its presence is highly regulated. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Biosynthesis,_synthesis,_and_reactivity"><span id="Biosynthesis.2C_synthesis.2C_and_reactivity"></span>Biosynthesis, synthesis, and reactivity</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Patulin&action=edit&section=1" title="Edit section: Biosynthesis, synthesis, and reactivity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Patulin is biosynthesized from <a href="/wiki/6-Methylsalicylic_acid" title="6-Methylsalicylic acid">6-methylsalicylic acid</a> via multiple chemical transformations.<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> </p><p>Isoepoxydon dehydrogenase (IDH) is an important <a href="/wiki/Enzyme" title="Enzyme">enzyme</a> in the multi-step biosynthesis of patulin. Its gene is present in other fungi that may potentially produce the toxin.<sup id="cite_ref-Puel_5-0" class="reference"><a href="#cite_note-Puel-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> It is reactive with <a href="/wiki/Sulfur_dioxide" title="Sulfur dioxide">sulfur dioxide</a>, so antioxidant and antimicrobial agents may be useful to destroy it.<sup id="cite_ref-Llewellyn_6-0" class="reference"><a href="#cite_note-Llewellyn-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> Levels of nitrogen, manganese, and pH as well as abundance of necessary enzymes regulate the biosynthetic pathway of patulin.<sup id="cite_ref-Puel_5-1" class="reference"><a href="#cite_note-Puel-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <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=Patulin&action=edit&section=2" title="Edit section: Uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Patulin was originally used as an antibiotic against Gram-positive and Gram-negative bacteria, but after several toxicity reports, it is no longer used for that purpose.<sup id="cite_ref-MRC_7-0" class="reference"><a href="#cite_note-MRC-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> Isolated by <a href="/wiki/Nancy_Atkinson" title="Nancy Atkinson">Nancy Atkinson</a> in 1943, it was specifically trialed to be used against the common cold.<sup id="cite_ref-MRC_7-1" class="reference"><a href="#cite_note-MRC-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> Patulin is used as a potassium-uptake inhibitor in laboratory applications.<sup id="cite_ref-sigma_2-1" class="reference"><a href="#cite_note-sigma-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Kashif Jilani and co-workers reported that patulin stimulates suicidal <a href="/wiki/Erythrocyte" class="mw-redirect" title="Erythrocyte">erythrocyte</a> death under physiological concentrations.<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Sources_of_exposure">Sources of exposure</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Patulin&action=edit&section=3" title="Edit section: Sources of exposure"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Frequently, patulin is found in apples and apple products such as juices, jams, and ciders. It has also been detected in other fruits including cherries, blueberries, plums, bananas, strawberries, and grapes.<sup id="cite_ref-Llewellyn_6-1" class="reference"><a href="#cite_note-Llewellyn-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> Fungal growth leading to patulin production is most common on damaged fruits.<sup id="cite_ref-pippin_9-0" class="reference"><a href="#cite_note-pippin-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> Patulin has also been detected in grains like barley, wheat, corn and their processed products as well as in shellfish.<sup id="cite_ref-Llewellyn_6-2" class="reference"><a href="#cite_note-Llewellyn-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Pouchous_10-0" class="reference"><a href="#cite_note-Pouchous-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup><sup class="noprint Inline-Template" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citing_sources#What_information_to_include" title="Wikipedia:Citing sources"><span title="A complete citation is needed. (January 2024)">full citation needed</span></a></i>]</sup> Dietary intake of patulin from apple juice has been estimated at between 0.03 and 0.26 μg per kg body weight per day in various age groups and populations.<sup id="cite_ref-wouters_11-0" class="reference"><a href="#cite_note-wouters-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> Content of patulin in apple juice is estimated to be less than 10–15 μg/L.<sup id="cite_ref-wouters_11-1" class="reference"><a href="#cite_note-wouters-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> A number of studies have looked into comparisons of organic vs conventional harvest of apples and levels of patulin contamination.<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><sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup><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> For example, one study showed 0.9% of children drinking organic apple juice exceeded the <a href="/wiki/Tolerable_daily_intake" title="Tolerable daily intake">tolerable daily intake</a> (TDI) for patulin.<sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup><sup class="noprint Inline-Template" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citing_sources#What_information_to_include" title="Wikipedia:Citing sources"><span title="A complete citation is needed. (January 2024)">full citation needed</span></a></i>]</sup> A recent article described detection of patulin in marine strains of Penicillium, indicating a potential risk in shellfish consumption.<sup id="cite_ref-Pouchous_10-1" class="reference"><a href="#cite_note-Pouchous-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Toxicity">Toxicity</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Patulin&action=edit&section=4" title="Edit section: Toxicity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A subacute rodent <a href="/wiki/NOAEL" class="mw-redirect" title="NOAEL">NOAEL</a> of 43 μg/kg body weight as well as <a href="/wiki/Genotoxicity" title="Genotoxicity">genotoxicity</a> studies were primarily the cause for setting limits for patulin exposure, although a range of other types of toxicity also exist.<sup id="cite_ref-ucm212520_3-1" class="reference"><a href="#cite_note-ucm212520-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p><p>While not a particularly potent toxin, patulin is <a href="/wiki/Genotoxic" class="mw-redirect" title="Genotoxic">genotoxic</a>. Some theorize that it may be a carcinogen, although animal studies have remained inconclusive.<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> Patulin has shown antimicrobial properties against some microorganisms.<sup id="cite_ref-merck_1-1" class="reference"><a href="#cite_note-merck-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Several countries have instituted patulin restrictions in apple products. The <a href="/wiki/World_Health_Organization" title="World Health Organization">World Health Organization</a> recommends a maximum concentration of 50 μg/L in apple juice.<sup id="cite_ref-FHWHO_17-0" class="reference"><a href="#cite_note-FHWHO-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> In the European Union, the limit is also set at 50 micrograms per kilogram (μg/kg) in apple juice and cider, at 25 μg/kg in solid apple products, and at 10 μg/kg in products for infants and young children. These limits came into force on 1 November 2003.<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><sup class="noprint Inline-Template" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citing_sources#What_information_to_include" title="Wikipedia:Citing sources"><span title="A complete citation is needed. (January 2024)">full citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading3"><h3 id="Acute">Acute</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Patulin&action=edit&section=5" title="Edit section: Acute"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Patulin is toxic primarily through affinity to sulfhydryl groups (SH), which results in inhibition of enzymes. Oral <a href="/wiki/Median_lethal_dose" title="Median lethal dose">LD<sub>50</sub></a> in rodent models have ranged between 20 and 100 mg/kg.<sup id="cite_ref-ucm212520_3-2" class="reference"><a href="#cite_note-ucm212520-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> In poultry, the oral LD<sub>50</sub> range was reported between 50 and 170 mg/kg.<sup id="cite_ref-Puel_5-2" class="reference"><a href="#cite_note-Puel-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Other routes of exposure are more toxic, yet less likely to occur. Major acute toxicity findings include gastrointestinal problems, <a href="/wiki/Neurotoxicity" title="Neurotoxicity">neurotoxicity</a> (i.e. convulsions), <a href="/wiki/Pulmonary_congestion" class="mw-redirect" title="Pulmonary congestion">pulmonary congestion</a>, and <a href="/wiki/Edema" title="Edema">edema</a>.<sup id="cite_ref-ucm212520_3-3" class="reference"><a href="#cite_note-ucm212520-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Subacute">Subacute</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Patulin&action=edit&section=6" title="Edit section: Subacute"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Studies in rats showed decreased weight, and gastric, intestinal, and renal function changes, while repetitive doses lead to neurotoxicity. Reproductive toxicity in males was also reported.<sup id="cite_ref-Puel_5-3" class="reference"><a href="#cite_note-Puel-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> A <a href="/wiki/NOAEL" class="mw-redirect" title="NOAEL">NOAEL</a> in rodents was observed at 43 μg/kg body weight.<sup id="cite_ref-ucm212520_3-4" class="reference"><a href="#cite_note-ucm212520-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Genotoxicity">Genotoxicity</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Patulin&action=edit&section=7" title="Edit section: Genotoxicity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/WHO" class="mw-redirect" title="WHO">WHO</a> concluded that patulin is genotoxic based on variable <a href="/wiki/Genotoxicity" title="Genotoxicity">genotoxicity</a> data, however it is considered a group 3 carcinogen by the <a href="/wiki/International_Agency_for_Research_on_Cancer" title="International Agency for Research on Cancer">International Agency for Research on Cancer</a> (IARC) since data was inconclusive.<sup id="cite_ref-ucm212520_3-5" class="reference"><a href="#cite_note-ucm212520-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Reproduction_studies">Reproduction studies</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Patulin&action=edit&section=8" title="Edit section: Reproduction studies"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Patulin decreased sperm count and altered sperm morphology in the rat.<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> Also, it resulted in abortion of <a href="/wiki/F1_generation" class="mw-redirect" title="F1 generation">F1</a> litters in rats and mice after i.p. injection.<sup id="cite_ref-Puel_5-4" class="reference"><a href="#cite_note-Puel-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Embryotoxicity and <a href="/wiki/Teratogenicity" class="mw-redirect" title="Teratogenicity">teratogenicity</a> were also reported in chick eggs.<sup id="cite_ref-Puel_5-5" class="reference"><a href="#cite_note-Puel-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Immunotoxicity">Immunotoxicity</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Patulin&action=edit&section=9" title="Edit section: Immunotoxicity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Patulin was found to be <a href="/wiki/Immunotoxic" class="mw-redirect" title="Immunotoxic">immunotoxic</a> in a number of animal and even human studies. Reduced cytokine secretion, oxidative burst in macrophages, increased splenic <a href="/wiki/T_lymphocytes" class="mw-redirect" title="T lymphocytes">T lymphocytes</a>, and increased <a href="/wiki/Neutrophil" title="Neutrophil">neutrophil</a> numbers are a few endpoints noticed.<sup id="cite_ref-Puel_5-6" class="reference"><a href="#cite_note-Puel-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> However, dietary relevant exposure would not be likely to alter immune response.<sup id="cite_ref-Llewellyn_6-3" class="reference"><a href="#cite_note-Llewellyn-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Human_health">Human health</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Patulin&action=edit&section=10" title="Edit section: Human health"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Although there are only very few reported cases and epidemiological data, the <a href="/wiki/FDA" class="mw-redirect" title="FDA">FDA</a> has set an action limit of 50 ppb in cider due to its potential <a href="/wiki/Carcinogenicity" class="mw-redirect" title="Carcinogenicity">carcinogenicity</a> and other reported adverse effects.<sup id="cite_ref-ucm212520_3-6" class="reference"><a href="#cite_note-ucm212520-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> In humans, it was tested as an <a href="/wiki/Antiviral" class="mw-redirect" title="Antiviral">antiviral</a> intranasally for use against the <a href="/wiki/Common_cold" title="Common cold">common cold</a> with few significant <a href="/wiki/Adverse_effect" title="Adverse effect">adverse effects</a>, yet also had negligible or no beneficial effect.<sup id="cite_ref-MRC_7-2" class="reference"><a href="#cite_note-MRC-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Risk_management_and_regulations">Risk management and regulations</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Patulin&action=edit&section=11" title="Edit section: Risk management and regulations"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Patulin exposure can be successfully managed by following <a href="/wiki/Good_agricultural_practices" class="mw-redirect" title="Good agricultural practices">good agricultural practices</a> such as removing mold, washing, and not using rotten or damaged apples for baking, canning, or juice production.<sup id="cite_ref-ucm212520_3-7" class="reference"><a href="#cite_note-ucm212520-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pippin_9-1" class="reference"><a href="#cite_note-pippin-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p><p><b>US</b> </p><p>The provisional <a href="/wiki/Tolerable_daily_intake" title="Tolerable daily intake">tolerable daily intake</a> (PTDI) for patulin was set at 0.43 μg/kg body weight by the FDA<sup id="cite_ref-ucm212520_3-8" class="reference"><a href="#cite_note-ucm212520-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> based on a <a href="/wiki/NOAEL" class="mw-redirect" title="NOAEL">NOAEL</a> of 0.3 mg/kg body weight per week.<sup id="cite_ref-ucm212520_3-9" class="reference"><a href="#cite_note-ucm212520-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Monte_Carlo_analysis" class="mw-redirect" title="Monte Carlo analysis">Monte Carlo analysis</a> was done on apple juice to compare exposure and the PTDI. Without controls or an action limit, the 90th percentile of consumers would not be above the PTDI. However, the concentration in children 1–2 years old would be three times as high as the PDTI, hence an action limit of 50 μg/kg.<sup id="cite_ref-ucm212520_3-10" class="reference"><a href="#cite_note-ucm212520-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p><p><b>WHO</b> </p><p>The <a href="/wiki/World_Health_Organization" title="World Health Organization">World Health Organization</a> recommends a maximum concentration of 50 μg/L in apple juice.<sup id="cite_ref-FHWHO_17-1" class="reference"><a href="#cite_note-FHWHO-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p><p><b>EU</b> </p><p>The <a href="/wiki/European_Union" title="European Union">European Union</a> (EU) has set a maximum limit of 50 μg/kg on fruit juices and drinks, while solid apple products have a limit of 25 μg/kg. For certain foods intended for infants, an even lower limit of 10 μg/kg is observed. </p><p>To test for patulin contamination, a variety of methods and sample preparation methods have been employed, including <a href="/wiki/Thin_layer_chromatography" class="mw-redirect" title="Thin layer chromatography">thin layer chromatography</a> (TLC), <a href="/wiki/Gas_chromatography" title="Gas chromatography">gas chromatography</a> (GC), <a href="/wiki/High-performance_liquid_chromatography" title="High-performance liquid chromatography">high-performance liquid chromatography</a> (HPLC), and <a href="/wiki/Capillary_electrophoresis" title="Capillary electrophoresis">capillary electrophoresis</a>.<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> </p> <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=Patulin&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 reflist-columns references-column-width reflist-columns-2"> <ol class="references"> <li id="cite_note-merck-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-merck_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-merck_1-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text">Merck Index, 11th Edition, 7002</span> </li> <li id="cite_note-sigma-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-sigma_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-sigma_2-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><a rel="nofollow" class="external text" href="http://www.sigmaaldrich.com/catalog/product/sigma/p1639?lang=en&region=US">Patulin</a> sigmaaldrich.com</span> </li> <li id="cite_note-ucm212520-3"><span class="mw-cite-backlink">^ <a href="#cite_ref-ucm212520_3-0"><sup><i><b>a</b></i></sup></a> 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Perishables Handling Quarterly (91): 5. August 1997</span> </li> <li id="cite_note-FHWHO-17"><span class="mw-cite-backlink">^ <a href="#cite_ref-FHWHO_17-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-FHWHO_17-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text">"Foodborne hazards (World Health Organization". Retrieved 2007-01-22.</span> </li> <li id="cite_note-18"><span class="mw-cite-backlink"><b><a href="#cite_ref-18">^</a></b></span> <span class="reference-text">Patulin information leaf from Fermentek</span> </li> <li id="cite_note-19"><span class="mw-cite-backlink"><b><a href="#cite_ref-19">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSelmanoglu2006" class="citation journal cs1">Selmanoglu, G (2006). "Evaluation of the reproductive toxicity of patulin in growing male rats". <i>Food Chem. Toxicol</i>. <b>44</b> (12): <span class="nowrap">2019–</span>2024. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.fct.2006.06.022">10.1016/j.fct.2006.06.022</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/16905234">16905234</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Food+Chem.+Toxicol.&rft.atitle=Evaluation+of+the+reproductive+toxicity+of+patulin+in+growing+male+rats&rft.volume=44&rft.issue=12&rft.pages=%3Cspan+class%3D%22nowrap%22%3E2019-%3C%2Fspan%3E2024&rft.date=2006&rft_id=info%3Adoi%2F10.1016%2Fj.fct.2006.06.022&rft_id=info%3Apmid%2F16905234&rft.aulast=Selmanoglu&rft.aufirst=G&rfr_id=info%3Asid%2Fen.wikipedia.org%3APatulin" class="Z3988"></span></span> </li> <li id="cite_note-20"><span class="mw-cite-backlink"><b><a href="#cite_ref-20">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBaertDe_MeulenaerVerdonckHuybrechts2007" class="citation journal cs1">Baert, Katleen; De Meulenaer, Bruno; Verdonck, Frederik; Huybrechts, Inge; De Henauw, Stefaan; Vanrolleghem, Peter A.; Debevere, Johan; Devlieghere, Frank (2007). "Variability and uncertainty assessment of patulin exposure for preschool children in Flanders". <i>Food and Chemical Toxicology</i>. <b>45</b> (9): <span class="nowrap">1745–</span>1751. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.fct.2007.03.008">10.1016/j.fct.2007.03.008</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/17459555">17459555</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Food+and+Chemical+Toxicology&rft.atitle=Variability+and+uncertainty+assessment+of+patulin+exposure+for+preschool+children+in+Flanders&rft.volume=45&rft.issue=9&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1745-%3C%2Fspan%3E1751&rft.date=2007&rft_id=info%3Adoi%2F10.1016%2Fj.fct.2007.03.008&rft_id=info%3Apmid%2F17459555&rft.aulast=Baert&rft.aufirst=Katleen&rft.au=De+Meulenaer%2C+Bruno&rft.au=Verdonck%2C+Frederik&rft.au=Huybrechts%2C+Inge&rft.au=De+Henauw%2C+Stefaan&rft.au=Vanrolleghem%2C+Peter+A.&rft.au=Debevere%2C+Johan&rft.au=Devlieghere%2C+Frank&rfr_id=info%3Asid%2Fen.wikipedia.org%3APatulin" class="Z3988"></span></span> </li> </ol></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=Patulin&action=edit&section=13" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a rel="nofollow" class="external text" href="http://www.foodsafetywatch.org/factsheets/patulin/">Patulin</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20171219144226/http://www.foodsafetywatch.org/factsheets/patulin/">Archived</a> 2017-12-19 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a>, Food Safety Watch</li></ul>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?useformat=desktop&type=1x1&usesul3=0" alt="" width="1" height="1" style="border: none; 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