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<h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Melibiose</span></h1>
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<div id="mw-content-text" class="mw-body-content mw-content-ltr" lang="de" dir="ltr"><div class="mw-content-ltr mw-parser-output" lang="de" dir="ltr"><table class="wikitable infobox float-right" id="Vorlage_Infobox_Chemikalie" style="font-size:90%; margin-top:0; width:350px;" summary="Infobox Chemikalie">
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<th colspan="2" style="background:#FFDEAD; color:#202122;">Strukturformel
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<td colspan="2" class="hintergrundfarbe-basis skin-invert-image" style="text-align:center;"><span typeof="mw:File"></span>
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<th colspan="2" style="background:#FFDEAD; color:#202122;">Allgemeines
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<td style="width:33%;">Name
</td>
<td>Melibiose
</td></tr>
<tr>
<td>Andere Namen
</td>
<td>
<p>6-<i>O</i>-α-<small>D</small>-Galactopyranosyl-<small>D</small>-glucopyranose (<a href="IUPAC-Nomenklatur" class="mw-redirect" title="IUPAC-Nomenklatur">IUPAC</a>)
</p>
</td></tr>
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<td><a href="Summenformel" title="Summenformel">Summenformel</a>
</td>
<td>C<sub>12</sub>H<sub>22</sub>O<sub>11</sub>
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<tr>
<th colspan="2" style="background:#FFDEAD; color:#202122;">Externe Identifikatoren/Datenbanken
</th></tr>
<tr>
<td colspan="2" style="padding:0;">
<table class="mw-collapsible mw-collapsed wikitable" data-expandtext="+" data-collapsetext="−" style="border-top:none; margin:-1px; width:calc(100% + 2px);">
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<td style="width:33%;"><a href="CAS-Nummer" title="CAS-Nummer">CAS-Nummer</a>
</td>
<td><span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=585-99-9">585-99-9</a><span class="editoronly" style="display:none;"></span>
</td>
<td style="background:#FFDEAD; color:#202122; border-top:1px solid #FFDEAD; padding:0.2em 0; vertical-align:bottom; width:5%;">
</td></tr>
<tr>
<td><a href="EG-Nummer" title="EG-Nummer">EG-Nummer</a>
</td>
<td colspan="2">209-568-6
</td></tr>
<tr>
<td><a href="Europ%C3%A4ische_Chemikalienagentur" title="Europäische Chemikalienagentur">ECHA</a>-InfoCard
</td>
<td colspan="2"><a rel="nofollow" class="external text" href="https://www.echa.europa.eu/de/substance-information/-/substanceinfo/100.008.700">100.008.700</a>
</td></tr>
<tr>
<td><a href="PubChem" title="PubChem">PubChem</a>
</td>
<td colspan="2"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/440658">440658</a>
</td></tr>
<tr>
<td><a href="ChemSpider" title="ChemSpider">ChemSpider</a>
</td>
<td colspan="2"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.389538.html">389538</a>
</td></tr>
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<td style="border-right:1px solid #a2a9b1;"><a href="Wikidata" title="Wikidata">Wikidata</a>
</td>
<td colspan="2"><a href="https://www.wikidata.org/wiki/Q74411440" class="extiw external" title="d:Q74411440">Q74411440</a>
</td></tr></tbody></table>
</td></tr>
<tr>
<th colspan="2" style="background:#FFDEAD; color:#202122;">Eigenschaften
</th></tr>
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<td><a href="Molare_Masse" title="Molare Masse">Molare Masse</a>
</td>
<td>342,3 g·<a href="Mol" title="Mol">mol</a><sup>−1</sup>
</td></tr>
<tr>
<td><a href="Aggregatzustand" title="Aggregatzustand">Aggregatzustand</a>
</td>
<td>
<p>fest<sup id="cite_ref-Sigma_1-0" class="reference"><a href="#cite_note-Sigma-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>
</p>
</td></tr>
<tr>
<td><a href="Schmelzpunkt" title="Schmelzpunkt">Schmelzpunkt</a>
</td>
<td>
<p>182 °C (Zersetzung)<sup id="cite_ref-Sigma_1-1" class="reference"><a href="#cite_note-Sigma-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>
</p>
</td></tr>
<tr>
<th colspan="2" style="background:#FFDEAD; color:#202122;">Sicherheitshinweise
</th></tr>
<tr>
<td colspan="2">
<table cellspacing="0" cellpadding="2" style="width:100%;">
<tbody><tr>
<td colspan="2" style="text-align:center"><b><a href="Global_harmonisiertes_System_zur_Einstufung_und_Kennzeichnung_von_Chemikalien" title="Global harmonisiertes System zur Einstufung und Kennzeichnung von Chemikalien">GHS-Gefahrstoffkennzeichnung</a></b><sup id="cite_ref-Sigma_1-2" class="reference"><a href="#cite_note-Sigma-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>
<table class="hintergrundfarbe-neutral" style="text-align:center; margin-left:auto; margin-right:auto; display:flex; justify-content:center;">
<tbody><tr>
<td><i>keine GHS-Piktogramme</i>
</td></tr></tbody></table>
<p>
</p>
</td></tr>
<tr>
<td rowspan="2" width="33%" style="border-top:1px #A7A7A7 dashed; border-right:1px #A7A7A7 dashed;"><a href="H-_und_P-S%C3%A4tze" title="H- und P-Sätze">H- und P-Sätze</a>
</td>
<td style="border-top:1px #A7A7A7 dashed;">H: <span title="Untervorlage eingebunden: H-Sätze"></span><i>keine H-Sätze</i>
</td></tr>
<tr>
<td style="border-top:1px #A7A7A7 dashed;">P: <span title="Untervorlage eingebunden: P-Sätze"></span><i>keine P-Sätze</i><sup id="cite_ref-Sigma_1-3" class="reference"><a href="#cite_note-Sigma-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>
</td></tr>
</tbody></table>
</td></tr>
<tr>
<td colspan="2" style="background:#FFDEAD; color:#202122; font-size:80%; text-align:center; line-height:150%; padding:.25em;">Wenn nicht anders vermerkt, gelten die angegebenen Daten bei <a href="Standardbedingungen" title="Standardbedingungen">Standardbedingungen</a> (0 °C, 1000 hPa).
</td></tr></tbody></table><p><span class="editoronly" style="display:none;"></span>
</p>
<p><b>Melibiose</b> ist eine natürlich vorkommende <a href="Chemische_Verbindung" title="Chemische Verbindung">organische Verbindung</a> aus der Gruppe der <a href="Disaccharide" title="Disaccharide">Disaccharide</a>. Es setzt sich ebenso wie <a href="Lactose" title="Lactose">Lactose</a> aus <a href="Glucose" title="Glucose">Glucose</a> und <a href="Galactose" title="Galactose">Galactose</a> zusammen, die jedoch eine andere Verknüpfung aufweisen, konkret eine (α1→6)-<a href="Glycosidische_Bindung" title="Glycosidische Bindung">glycosidische Bindung</a>. Somit ist es das <a href="Anomere" title="Anomere">Anomer</a> von <a href="Allolactose" title="Allolactose">Allolactose</a>.
</p>
<div class="mw-heading mw-heading2"><h2 id="Vorkommen_und_biologische_Bedeutung">Vorkommen und biologische Bedeutung</h2></div>
<p>Melibiose kommt beispielsweise in <a href="Birkensaft" title="Birkensaft">Birkensaft</a> vor.<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> Sie entsteht neben <a href="Fructose" title="Fructose">Fructose</a> bei der Hydrolyse von <a href="Raffinose" title="Raffinose">Raffinose</a>, beispielsweise durch Mikroorganismen. Nicht alle Mikroorganismen verfügen auch über Enzyme zum Spalten der Melibiose, was schon zur Unterscheidung von <a href="Hefen" title="Hefen">Hefe</a>-Arten herangezogen wurde, da von den in der Lebensmittelproduktion häufig eingesetzten Arten <i><a href="Backhefe" title="Backhefe">Saccharomyces cerevisiae</a></i> keine Melibiose abbauen kann, <i><a href="Saccharomyces_carlsbergensis" title="Saccharomyces carlsbergensis">Saccharomyces carlsbergensis</a></i> jedoch dazu in der Lage ist.<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> Menschen können (α1→6)-verknüpfte Saccharide nicht verdauen, sie werden jedoch von Darmbakterien metabolisiert.<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>
<div class="mw-heading mw-heading2"><h2 id="Einzelnachweise">Einzelnachweise</h2></div>
<div class="mw-references-wrap"><ol class="references">
<li id="cite_note-Sigma-1"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-Sigma_1-0">a</a></sup> <sup><a href="#cite_ref-Sigma_1-1">b</a></sup> <sup><a href="#cite_ref-Sigma_1-2">c</a></sup> <sup><a href="#cite_ref-Sigma_1-3">d</a></sup></span> <span class="reference-text">Datenblatt <span style="font-style:italic;"><a rel="nofollow" class="external text" href="https://www.sigmaaldrich.com/catalog/product/SIGMA/M5500">Melibiose</a></span> bei <a href="Sigma-Aldrich" title="Sigma-Aldrich">Sigma-Aldrich</a>, abgerufen am 7. Juni 2025 (<a rel="nofollow" class="external text" href="https://www.sigmaaldrich.com/DE/de/sds/SIGMA/M5500?userType=anonymous">PDF</a>).<span class="editoronly" style="display:none;"></span></span>
</li>
<li id="cite_note-2"><span class="mw-cite-backlink"><a href="#cite_ref-2">↑</a></span> <span class="reference-text">S. Haq, G. A. Adams: <cite style="font-style:italic">OLIGOSACCHARIDES OF BIRCH SAP</cite>. In: <cite style="font-style:italic"><a href="Canadian_Journal_of_Biochemistry_and_Physiology" class="mw-redirect" title="Canadian Journal of Biochemistry and Physiology">Canadian Journal of Biochemistry and Physiology</a></cite>. <span style="white-space:nowrap">Band<span style="display:inline-block;width:.2em"> </span>40</span>, <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em"> </span>8</span>, 1. August 1962, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>989–997</span>, <a href="Digital_Object_Identifier" title="Digital Object Identifier">doi</a>:<span class="uri-handle" style="white-space:nowrap"><a rel="nofollow" class="external text" href="https://doi.org/10.1139/o62-111">10.1139/o62-111</a></span>.<span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rfr_id=info:sid/de.wikipedia.org:Melibiose&rft.atitle=OLIGOSACCHARIDES+OF+BIRCH+SAP&rft.au=S.+Haq%2C+G.+A.+Adams&rft.date=1962-08-01&rft.doi=10.1139%2Fo62-111&rft.genre=journal&rft.issue=8&rft.jtitle=Canadian+Journal+of+Biochemistry+and+Physiology&rft.pages=989-997&rft.volume=40" style="display:none"> </span></span>
</li>
<li id="cite_note-3"><span class="mw-cite-backlink"><a href="#cite_ref-3">↑</a></span> <span class="reference-text">C. E. Skinner, R. Bouthilet: <cite style="font-style:italic">Melibiose Broth for Classifying Yeasts</cite>. In: <cite style="font-style:italic">Journal of Bacteriology</cite>. <span style="white-space:nowrap">Band<span style="display:inline-block;width:.2em"> </span>53</span>, <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em"> </span>1</span>, Januar 1947, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>37–43</span>, <a href="Digital_Object_Identifier" title="Digital Object Identifier">doi</a>:<span class="uri-handle" style="white-space:nowrap"><a rel="nofollow" class="external text" href="https://doi.org/10.1128/jb.53.1.37-43.1947">10.1128/jb.53.1.37-43.1947</a></span>.<span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rfr_id=info:sid/de.wikipedia.org:Melibiose&rft.atitle=Melibiose+Broth+for+Classifying+Yeasts&rft.au=C.+E.+Skinner%2C+R.+Bouthilet&rft.date=1947-01&rft.doi=10.1128%2Fjb.53.1.37-43.1947&rft.genre=journal&rft.issue=1&rft.jtitle=Journal+of+Bacteriology&rft.pages=37-43&rft.volume=53" style="display:none"> </span></span>
</li>
<li id="cite_note-4"><span class="mw-cite-backlink"><a href="#cite_ref-4">↑</a></span> <span class="reference-text">Kaarel Adamberg, Signe Adamberg, Karin Ernits, Anneli Larionova, Tiia Voor, Madis Jaagura, Triinu Visnapuu, Tiina Alamäe: <cite style="font-style:italic">Composition and metabolism of fecal microbiota from normal and overweight children are differentially affected by melibiose, raffinose and raffinose-derived fructans</cite>. In: <cite style="font-style:italic">Anaerobe</cite>. <span style="white-space:nowrap">Band<span style="display:inline-block;width:.2em"> </span>52</span>, August 2018, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>100–110</span>, <a href="Digital_Object_Identifier" title="Digital Object Identifier">doi</a>:<span class="uri-handle" style="white-space:nowrap"><a rel="nofollow" class="external text" href="https://doi.org/10.1016/j.anaerobe.2018.06.009">10.1016/j.anaerobe.2018.06.009</a></span>.<span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rfr_id=info:sid/de.wikipedia.org:Melibiose&rft.atitle=Composition+and+metabolism+of+fecal+microbiota+from+normal+and+overweight+children+are+differentially+affected+by+melibiose%2C+raffinose+and+raffinose-derived+fructans&rft.au=Kaarel+Adamberg%2C+Signe+Adamberg%2C+Karin+Ernits%2C+...&rft.btitle=Anaerobe&rft.date=2018-08&rft.doi=10.1016%2Fj.anaerobe.2018.06.009&rft.genre=book&rft.pages=100-110&rft.volume=52" style="display:none"> </span></span>
</li>
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