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<tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Estragole_acsv.svg" class="mw-file-description"><img alt="Skeletal formula of estragole" src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8b/Estragole_acsv.svg/220px-Estragole_acsv.svg.png" decoding="async" width="220" height="97" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8b/Estragole_acsv.svg/330px-Estragole_acsv.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/8b/Estragole_acsv.svg/440px-Estragole_acsv.svg.png 2x" data-file-width="1069" data-file-height="472" /></a></span> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Estragole-3D-balls.png" class="mw-file-description"><img alt="Ball-and-stick model of the estragole molecule" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/45/Estragole-3D-balls.png/220px-Estragole-3D-balls.png" decoding="async" width="220" height="131" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/45/Estragole-3D-balls.png/330px-Estragole-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/45/Estragole-3D-balls.png/440px-Estragole-3D-balls.png 2x" data-file-width="2000" data-file-height="1187" /></a></span> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Preferred_IUPAC_name" title="Preferred IUPAC name">Preferred IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">1-Methoxy-4-(prop-2-en-1-yl)benzene</div></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;">1-Methoxy-4-(2-propenyl)-benzene<br />1-Allyl-4-methoxybenzene<br />Estragol<br />Estragon<br /><i>p</i>-Allylanisole<br />Chavicyl methylether<br />Methylchavicol<br />Chavicol methylether<br />Isoanethole<br />4-Allylanisole</div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; 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=140-67-0">140-67-0</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=COc1ccc%28CC%3DC%29cc1">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=4867">CHEBI:4867</a></span></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/ChEMBL470671">ChEMBL470671</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.13850247.html">13850247</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/100.004.935">100.004.935</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q419495#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>205-427-8</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/C10452">C10452</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/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/8815">8815</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/9NIW07V3ET">9NIW07V3ET</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/DTXSID0020575">DTXSID0020575</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q419495#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; background:transparent;"><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/C10H12O/c1-3-4-9-5-7-10(11-2)8-6-9/h3,5-8H,1,4H2,2H3<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: ZFMSMUAANRJZFM-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/C10H12O/c1-3-4-9-5-7-10(11-2)8-6-9/h3,5-8H,1,4H2,2H3</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: ZFMSMUAANRJZFM-UHFFFAOYAS</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; background:transparent;"><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%;">COc1ccc(CC=C)cc1</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; 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>10</sub>H<sub>12</sub>O  </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td>148.20 g/mol    </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>0.946 g/cm<sup>3</sup> </td></tr> <tr> <td><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a> </td> <td>216 °C (421 °F; 489 K) <br />95–96 °C (203–205 °F; 368–369 K) at 12 mmHg </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; 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="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/12px-Yes_check.svg.png" decoding="async" width="12" height="12" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/18px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/24px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=414461450&page2=Estragole">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>Estragole</b> (<b><i>p</i>-allylanisole</b>, <b>methyl chavicol</b>) is a <a href="/wiki/Phenylpropene" title="Phenylpropene">phenylpropene</a>, a natural organic compound. Its chemical structure consists of a <a href="/wiki/Benzene" title="Benzene">benzene</a> ring substituted with a <a href="/wiki/Methoxy_group" title="Methoxy group">methoxy group</a> and an <a href="/wiki/Allyl" class="mw-redirect" title="Allyl">allyl</a> group. It is an isomer of <a href="/wiki/Anethole" title="Anethole">anethole</a>, differing with respect to the location of the <a href="/wiki/Double_bond" title="Double bond">double bond</a>. It is a colorless liquid, although impure samples can appear yellow. It is a component of various trees and plants, including <a href="/wiki/Turpentine" title="Turpentine">turpentine</a> (pine oil), <a href="/wiki/Anise" title="Anise">anise</a>, <a href="/wiki/Fennel" title="Fennel">fennel</a>, <a href="/wiki/Pimenta_racemosa" title="Pimenta racemosa">bay</a>, <a href="/wiki/Tarragon" title="Tarragon">tarragon</a>, and <a href="/wiki/Basil" title="Basil">basil</a>. It is used in the preparation of fragrances.<sup id="cite_ref-Ullmann_1-0" class="reference"><a href="#cite_note-Ullmann-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p><p>The compound is named for <i>estragon</i>, the French name of tarragon. </p> <meta property="mw:PageProp/toc" /> <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=Estragole&action=edit&section=1" title="Edit section: Production"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Hundreds of tonnes of <a href="/wiki/Basil_oil" class="mw-redirect" title="Basil oil">basil oil</a> are produced annually by steam distillation of <i><a href="/wiki/Ocimum_basilicum" class="mw-redirect" title="Ocimum basilicum">Ocimum basilicum</a></i> (common basil). This oil is mainly estragole but also contains substantial amounts of <a href="/wiki/Linalool" title="Linalool">linalool</a>. Estragole is the primary constituent of <a href="/wiki/Essential_oil" title="Essential oil">essential oil</a> of <a href="/wiki/Tarragon" title="Tarragon">tarragon</a> (comprising 60–75%). It is also present in <a href="/wiki/Pine_oil" title="Pine oil">pine oil</a>, <a href="/wiki/Turpentine" title="Turpentine">turpentine</a>, <a href="/wiki/Fennel" title="Fennel">fennel</a>, <a href="/wiki/Anise" title="Anise">anise</a> (2%<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup>), <a href="/wiki/Frankincense" title="Frankincense">frankincense</a> (4%<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup>), <i><a href="/wiki/Clausena_anisata" title="Clausena anisata">Clausena anisata</a></i>, and <i><a href="/wiki/Syzygium_anisatum" title="Syzygium anisatum">Syzygium anisatum</a></i>. </p><p>Estragole is used in perfumes and in <a href="/wiki/Flavoring" title="Flavoring">flavorings</a> for foods. In the European Union, it can only be present in a flavor by using an essential oil.<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> Upon treatment with <a href="/wiki/Potassium_hydroxide" title="Potassium hydroxide">potassium hydroxide</a>, estragole converts to <a href="/wiki/Anethole" title="Anethole">anethole</a>.<sup id="cite_ref-Ullmann_1-1" class="reference"><a href="#cite_note-Ullmann-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Estragole is used in the synthesis of <a href="/wiki/Magnolol" title="Magnolol">magnolol</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. (June 2024)">citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading2"><h2 id="Safety">Safety</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Estragole&action=edit&section=2" title="Edit section: Safety"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Estragole is suspected to be <a href="/wiki/Carcinogenic" class="mw-redirect" title="Carcinogenic">carcinogenic</a> and <a href="/wiki/Genotoxic" class="mw-redirect" title="Genotoxic">genotoxic</a>, as is indicated by a report of the European Union <a href="/wiki/Committee_on_Herbal_Medicinal_Products" title="Committee on Herbal Medicinal Products">Committee on Herbal Medicinal Products</a>.<sup id="cite_ref-EMEA2005_5-0" class="reference"><a href="#cite_note-EMEA2005-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Several studies have clearly established that the profiles of metabolism, metabolic activation, and covalent binding are dose dependent and that the relative importance diminishes markedly at low levels of exposure (that is, these events are not linear with respect to dose).<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. (March 2020)">citation needed</span></a></i>]</sup> In particular, <a href="/wiki/Animal_testing_on_rodents" title="Animal testing on rodents">rodent studies</a> show that these events are minimal probably in the dose range of 1–10 mg/kg body weight, which is approximately 100 to 1,000 times the anticipated human exposure to this substance. For these reasons it is concluded that the present exposure to estragole resulting from consumption of herbal medicinal products (short time use in adults at recommended posology) does not pose a significant cancer risk. In the meantime exposure of estragole to sensitive groups such as young children, pregnant and breastfeeding women should be minimized.<sup id="cite_ref-EMEA2005_5-1" class="reference"><a href="#cite_note-EMEA2005-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p><p>The <a href="/wiki/Scientific_Committee_on_Food" title="Scientific Committee on Food">Scientific Committee on Food</a> from the <a href="/wiki/Health_and_Consumer_Protection_Directorate" class="mw-redirect" title="Health and Consumer Protection Directorate">Health and Consumer Protection Directorate</a> took a more concerned position and concluded that "Estragole has been demonstrated to be genotoxic and carcinogenic. Therefore the existence of a threshold cannot be assumed and the Committee could not establish a safe exposure limit. Consequently, reductions in exposure and restrictions in use levels are indicated."<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> </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=Estragole&action=edit&section=3" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Anethole" title="Anethole">Anethole</a>, an isomer</li> <li><a href="/wiki/Chavicol" title="Chavicol">Chavicol</a>, the <a href="/wiki/Phenol" title="Phenol">phenol</a> analog</li> <li><a href="/wiki/Safrole" title="Safrole">Safrole</a>, a methylenedioxy analog</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=Estragole&action=edit&section=4" 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"><ol class="references"> <li id="cite_note-Ullmann-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-Ullmann_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Ullmann_1-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFFahlbuschHammerschmidtPantenPickenhagen" class="citation encyclopaedia cs1">Fahlbusch, Karl-Georg; Hammerschmidt, Franz-Josef; Panten, Johannes; et al. "Flavors and Fragrances". <i><a href="/wiki/Ullmann%27s_Encyclopedia_of_Industrial_Chemistry" title="Ullmann's Encyclopedia of Industrial Chemistry">Ullmann's Encyclopedia of Industrial Chemistry</a></i>. Weinheim: Wiley-VCH. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F14356007.a11_141">10.1002/14356007.a11_141</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3527306732" title="Special:BookSources/978-3527306732"><bdi>978-3527306732</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Flavors+and+Fragrances&rft.btitle=Ullmann%27s+Encyclopedia+of+Industrial+Chemistry&rft.place=Weinheim&rft.pub=Wiley-VCH&rft_id=info%3Adoi%2F10.1002%2F14356007.a11_141&rft.isbn=978-3527306732&rft.aulast=Fahlbusch&rft.aufirst=Karl-Georg&rft.au=Hammerschmidt%2C+Franz-Josef&rft.au=Panten%2C+Johannes&rft.au=Pickenhagen%2C+Wilhelm&rft.au=Schatkowski%2C+Dietmar&rft.au=Bauer%2C+Kurt&rft.au=Garbe%2C+Dorothea&rft.au=Surburg%2C+Horst&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstragole" class="Z3988"></span>.</span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFAshurst1999" class="citation book cs1">Ashurst, Philip R. (1999). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=hrWuqmtwJiEC&pg=PA18"><i>Food Flavorings</i></a>. Springer. p. 11. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780834216211" title="Special:BookSources/9780834216211"><bdi>9780834216211</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Food+Flavorings&rft.pages=11&rft.pub=Springer&rft.date=1999&rft.isbn=9780834216211&rft.aulast=Ashurst&rft.aufirst=Philip+R.&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DhrWuqmtwJiEC%26pg%3DPA18&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstragole" class="Z3988"></span></span> </li> <li id="cite_note-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-3">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSharmaChhikaraGhodekarBhatia2009" class="citation journal cs1">Sharma, A.; Chhikara, S.; Ghodekar, S. N.; et al. (2009). <a rel="nofollow" class="external text" href="https://www.phcogrev.com/sites/default/files/PhcogRev-3-5-206.pdf">"Phytochemical and Pharmacological investigations on Boswellia serrata"</a> <span class="cs1-format">(PDF)</span>. <i>Pharmacognosy Reviews</i>. <b>3</b> (5): 206–215.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Pharmacognosy+Reviews&rft.atitle=Phytochemical+and+Pharmacological+investigations+on+Boswellia+serrata&rft.volume=3&rft.issue=5&rft.pages=206-215&rft.date=2009&rft.aulast=Sharma&rft.aufirst=A.&rft.au=Chhikara%2C+S.&rft.au=Ghodekar%2C+S.+N.&rft.au=Bhatia%2C+S.&rft.au=Kharya%2C+M.+D.&rft.au=Gajbhiye%2C+V.&rft.au=Mann%2C+A.+S.&rft.au=Namdeo%2C+A.+G.&rft.au=Mahadik%2C+K.+R.&rft_id=https%3A%2F%2Fwww.phcogrev.com%2Fsites%2Fdefault%2Ffiles%2FPhcogRev-3-5-206.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstragole" class="Z3988"></span></span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://eur-lex.europa.eu/LexUriServ/LexUriServ.do?uri=OJ:L:2008:354:0034:0050:en:PDF">"Regulation EC 1334/2008"</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Regulation+EC+1334%2F2008&rft_id=https%3A%2F%2Feur-lex.europa.eu%2FLexUriServ%2FLexUriServ.do%3Furi%3DOJ%3AL%3A2008%3A354%3A0034%3A0050%3Aen%3APDF&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstragole" class="Z3988"></span></span> </li> <li id="cite_note-EMEA2005-5"><span class="mw-cite-backlink">^ <a href="#cite_ref-EMEA2005_5-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-EMEA2005_5-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCommittee_on_Herbal_Medicinal_Products" class="citation web cs1">Committee on Herbal Medicinal Products. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20150722205214/http://www.ema.europa.eu/docs/en_GB/document_library/Scientific_guideline/2010/04/WC500089960.pdf">"EMEA/HMPC/137212/2005 Final Public Statement on the Use of Herbal Medicinal Products Containing Estragole"</a> <span class="cs1-format">(PDF)</span>. Archived from <a rel="nofollow" class="external text" href="http://www.ema.europa.eu/docs/en_GB/document_library/Scientific_guideline/2010/04/WC500089960.pdf">the original</a> <span class="cs1-format">(PDF)</span> on 2015-07-22.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=EMEA%2FHMPC%2F137212%2F2005+Final+Public+Statement+on+the+Use+of+Herbal+Medicinal+Products+Containing+Estragole&rft.au=Committee+on+Herbal+Medicinal+Products&rft_id=http%3A%2F%2Fwww.ema.europa.eu%2Fdocs%2Fen_GB%2Fdocument_library%2FScientific_guideline%2F2010%2F04%2FWC500089960.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstragole" class="Z3988"></span></span> </li> <li id="cite_note-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-6">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFScientific_Committee_on_Food2001" class="citation report cs1">Scientific Committee on Food (26 September 2001). <a rel="nofollow" class="external text" href="http://ec.europa.eu/food/fs/sc/scf/out104_en.pdf">Opinion of the Scientific Committee on Food on Estragole (1-Allyl-4-methoxybenzene</a> <span class="cs1-format">(PDF)</span> (Report). European Commission Health and Consumer Protection Directorate-General. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20070302102822/http://ec.europa.eu/food/fs/sc/scf/out104_en.pdf">Archived</a> <span class="cs1-format">(PDF)</span> from the original on 2007-03-02<span class="reference-accessdate">. Retrieved <span class="nowrap">2007-02-16</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=report&rft.btitle=Opinion+of+the+Scientific+Committee+on+Food+on+Estragole+%281-Allyl-4-methoxybenzene&rft.pub=European+Commission+Health+and+Consumer+Protection+Directorate-General&rft.date=2001-09-26&rft.au=Scientific+Committee+on+Food&rft_id=http%3A%2F%2Fec.europa.eu%2Ffood%2Ffs%2Fsc%2Fscf%2Fout104_en.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstragole" 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=Estragole&action=edit&section=5" 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="https://web.archive.org/web/20070302102822/http://ec.europa.eu/food/fs/sc/scf/out104_en.pdf">Opinion by the Scientific Committee on Food of the European Union on Estragole</a></li></ul> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline dl,.mw-parser-output .hlist.inline ol,.mw-parser-output .hlist.inline ul,.mw-parser-output .hlist dl dl,.mw-parser-output .hlist dl ol,.mw-parser-output .hlist dl ul,.mw-parser-output .hlist ol dl,.mw-parser-output .hlist ol ol,.mw-parser-output .hlist ol ul,.mw-parser-output .hlist ul dl,.mw-parser-output .hlist ul ol,.mw-parser-output .hlist ul ul{display:inline}.mw-parser-output .hlist .mw-empty-li{display:none}.mw-parser-output .hlist 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