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<h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Altrose</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">

<tbody><tr>
<th colspan="2" style="background:#FFDEAD; color:#202122;">Strukturformel
</th></tr>
<tr>
<td colspan="2" class="hintergrundfarbe-basis skin-invert-image" style="text-align:center;"><span typeof="mw:File"></span>
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<td colspan="2" style="text-align:center; font-size:80%;"><a href="Fischer-Projektion" title="Fischer-Projektion">Fischer-Projektion</a>, offenkettige Darstellung
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<tr>
<th colspan="2" style="background:#FFDEAD; color:#202122;">Allgemeines
</th></tr>
<tr>
<td style="width:33%;">Name
</td>
<td><small>D</small>-(+)-Altrose, <small>L</small>-(–)-Altrose
</td></tr>
<tr>
<td>Andere Namen
</td>
<td>
<ul><li>(2<i>S</i>,3<i>R</i>,4<i>R</i>,5<i>R</i>)-Pentahydroxyhexanal</li>
<li>(2<i>R</i>,3<i>S</i>,4<i>S</i>,5<i>S</i>)-Pentahydroxyhexanal</li>
<li>&nbsp;(<a href="Symbol-Nomenklatur_f%C3%BCr_Glykane" title="Symbol-Nomenklatur für Glykane">SNFG</a>-Symbol)</li></ul>
</td></tr>
<tr>
<td><a href="Summenformel" title="Summenformel">Summenformel</a>
</td>
<td>C<sub>6</sub>H<sub>12</sub>O<sub>6</sub>
</td></tr>
<tr>
<td>Kurzbeschreibung
</td>
<td>
<p>weißer Feststoff<sup id="cite_ref-TRC_D_1-0" class="reference"><a href="#cite_note-TRC_D-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-TRC_L_2-0" class="reference"><a href="#cite_note-TRC_L-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup>
</p>
</td></tr>
<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);">

<tbody><tr>
<td style="width:33%;"><a href="CAS-Nummer" title="CAS-Nummer">CAS-Nummer</a>
</td>
<td>
<ul><li><span title="Untervorlage eingebunden: CASRN"></span><span class="KeinCASLink" title="CAS-Nummer ohne Common-Chemistry-Eintrag">5987-68-8</span><span class="editoronly" style="display:none;"></span> (unspez.)</li>
<li><span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=1990-29-0">1990-29-0</a><span class="editoronly" style="display:none;"></span> (<small>D</small>-Altrose)</li>
<li><span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=1949-88-8">1949-88-8</a><span class="editoronly" style="display:none;"></span> (<small>L</small>-Altrose)</li></ul>
</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">217-870-4
</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/100.016.247">100.016.247</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/94780">94780</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.85516.html">85516</a>
</td></tr>


<tr>
<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/Q100415437" class="extiw external" title="d:Q100415437">Q100415437</a>
</td></tr></tbody></table>
</td></tr>








<tr>
<th colspan="2" style="background:#FFDEAD; color:#202122;">Eigenschaften
</th></tr>
<tr>
<td><a href="Molare_Masse" title="Molare Masse">Molare Masse</a>
</td>
<td>180,16 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
</p>
</td></tr>


<tr>
<td><a href="Schmelzpunkt" title="Schmelzpunkt">Schmelzpunkt</a>
</td>
<td>
<ul><li>111–113 <a href="Grad_Celsius" title="Grad Celsius">°C</a> (<small>D</small>-Form)<sup id="cite_ref-TRC_D_1-1" class="reference"><a href="#cite_note-TRC_D-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup></li>
<li>103–107 °C (<small>L</small>-Form)<sup id="cite_ref-TRC_L_2-1" class="reference"><a href="#cite_note-TRC_L-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup></li></ul>
</td></tr>








<tr>
<td><a href="L%C3%B6slichkeit" title="Löslichkeit">Löslichkeit</a>
</td>
<td>
<p>wenig löslich in Wasser und <a href="DMSO" class="mw-redirect" title="DMSO">DMSO</a><sup id="cite_ref-TRC_D_1-2" class="reference"><a href="#cite_note-TRC_D-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-TRC_L_2-2" class="reference"><a href="#cite_note-TRC_L-2"><span class="cite-bracket">[</span>2<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_3-0" class="reference"><a href="#cite_note-Sigma-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-SigmaL_4-0" class="reference"><a href="#cite_note-SigmaL-4"><span class="cite-bracket">[</span>4<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_3-1" class="reference"><a href="#cite_note-Sigma-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-SigmaL_4-1" class="reference"><a href="#cite_note-SigmaL-4"><span class="cite-bracket">[</span>4<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&nbsp;hPa).
</td></tr></tbody></table><p><span class="editoronly" style="display:none;"></span>
</p><p><b>Altrose</b> (kurz: <b>Alt</b>) ist ein <a href="Monosaccharid" class="mw-redirect" title="Monosaccharid">Monosaccharid</a> mit sechs <a href="Kohlenstoff" title="Kohlenstoff">Kohlenstoff</a>-Atomen. Dieser Zucker gehört zur Gruppe der nicht natürlich vorkommenden <a href="Hexosen" title="Hexosen">Aldohexosen</a> mit der Summenformel C<sub>6</sub>H<sub>12</sub>O<sub>6</sub>.
</p><p>Wie bei jedem Zucker (außer Dihydroxyaceton) gibt es zwei <a href="Enantiomer" title="Enantiomer">enantiomere</a> Formen, die sich wie Bild und Spiegelbild verhalten. Wenn in diesem Text oder in der wissenschaftlichen Literatur „Altrose“ ohne weiteren Namenszusatz (<a href="Pr%C3%A4fix" title="Präfix">Präfix</a>) erwähnt wird, ist <small>D</small>-Altrose gemeint.
</p>

<div class="mw-heading mw-heading2"><h2 id="Eigenschaften">Eigenschaften</h2></div>
<p>In wässriger Lösung kommt es teilweise zu einem intramolekularen Ringschluss, sodass sich ein Gleichgewicht zwischen der Aldehydform und den beiden Ringformen (<a href="Furanose" class="mw-redirect" title="Furanose">Furanose</a> und <a href="Pyranose" class="mw-redirect" title="Pyranose">Pyranose</a>) einstellt:<sup id="cite_ref-UNI-Bern_5-0" class="reference"><a href="#cite_note-UNI-Bern-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup>
</p>
<table class="wikitable">

<tbody><tr style="background:#FFDEAD;">
<th colspan="3"><small>D</small>-Altrose – Schreibweisen
</th></tr>
<tr class="hintergrundfarbe5">
<th>Keilstrichformel
</th>
<th colspan="2"><a href="Haworth-Formel" title="Haworth-Formel">Haworth-Schreibweise</a>
</th></tr>
<tr class="hintergrundfarbe2">
<td align="center" rowspan="2"><span typeof="mw:File"></span>
</td>
<td align="center"><span typeof="mw:File"></span><br>α-<small>D</small>-Altrofuranose<br>20&nbsp;%
</td>
<td align="center"><span typeof="mw:File"></span><br>β-<small>D</small>-Altrofuranose<br>13&nbsp;%
</td></tr>
<tr class="hintergrundfarbe2">
<td align="center"><span typeof="mw:File"></span><br>α-<small>D</small>-Altropyranose<br>27&nbsp;%
</td>
<td align="center"><span typeof="mw:File"></span><br>β-<small>D</small>-Altropyranose<br>40&nbsp;%
</td></tr>
<tr>
<th colspan="3">Sesselkonformation
</th></tr>
<tr>
<td colspan="3"><span typeof="mw:File"></span>
</td></tr></tbody></table>
<div class="mw-heading mw-heading2"><h2 id="Nachweis">Nachweis</h2></div>
<div class="mw-heading mw-heading3"><h3 id="Fehling-Reaktion">Fehling-Reaktion</h3></div>
<p>Der Nachweis der Aldehydgruppe in wässriger Lösung eines Gemisches aus <a href="Kupfersulfat" title="Kupfersulfat">Kupfer(II)-sulfat</a>- (Fehling I) und basischer <a href="Kalium-Natrium-Tartrat" class="mw-redirect" title="Kalium-Natrium-Tartrat">Kalium-Natrium-Tartrat</a>-Lösung (Fehling II) fällt positiv aus, es bildet sich festes <a href="Kupfer(I)-oxid" title="Kupfer(I)-oxid">Kupfer(I)-oxid</a> (ziegelroter Niederschlag) (siehe <a href="Fehling-Probe" title="Fehling-Probe">Fehling-Probe</a>).
</p>
<div class="mw-heading mw-heading3"><h3 id="Tollens-Reaktion_(Silberspiegelprobe)"><span id="Tollens-Reaktion_.28Silberspiegelprobe.29"></span>Tollens-Reaktion (Silberspiegelprobe)</h3></div>
<p>Das Ag<sup>+</sup>-Ion in <a href="Silbernitrat" title="Silbernitrat">Silbernitrat</a>-Lösung wird durch die Altrose zu <a href="Reinstoff" title="Reinstoff">elementarem</a> <a href="Silber" title="Silber">Silber</a> reduziert, das im Idealfall das Testgefäß mit einem Metallspiegel überzieht (siehe <a href="Tollensprobe" title="Tollensprobe">Tollensprobe</a>).
</p>
<div class="mw-heading mw-heading2"><h2 id="Weblinks">Weblinks</h2></div>
<div class="sisterproject" style="margin:0.1em 0 0 0;"><div class="noresize noviewer" style="display:inline-block; line-height:10px; min-width:1.6em; text-align:center;" aria-hidden="true" role="presentation"><span class="mw-default-size" typeof="mw:File"><span title="Commons"></span></span></div><b><span class=""><a class="external text" href="https://commons.wikimedia.org/wiki/Category:Altrose?uselang=de"><span lang="en">Commons</span>: Altrose</a></span></b>&nbsp;– Sammlung von Bildern, Videos und Audiodateien</div>
<div class="mw-heading mw-heading2"><h2 id="Einzelnachweise">Einzelnachweise</h2></div>
<ol class="references">
<li id="cite_note-TRC_D-1"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-TRC_D_1-0">a</a></sup> <sup><a href="#cite_ref-TRC_D_1-1">b</a></sup> <sup><a href="#cite_ref-TRC_D_1-2">c</a></sup></span> <span class="reference-text">Eintrag zu <span style="font-style:italic;"><a rel="nofollow" class="external text" href="https://www.trc-canada.com/product-detail/?A575700"><small>D</small>-Altrose</a></span> bei <i>Toronto Research Chemicals</i>, abgerufen am 15.&nbsp;Oktober 2023 (<a rel="nofollow" class="external text" href="https://www.trc-canada.com/prod-img/MSDS/A575700MSDS.pdf">PDF</a>).<span class="editoronly" style="display:none;"></span></span>
</li>
<li id="cite_note-TRC_L-2"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-TRC_L_2-0">a</a></sup> <sup><a href="#cite_ref-TRC_L_2-1">b</a></sup> <sup><a href="#cite_ref-TRC_L_2-2">c</a></sup></span> <span class="reference-text">Eintrag zu <span style="font-style:italic;"><a rel="nofollow" class="external text" href="https://www.trc-canada.com/product-detail/?A575710"><small>L</small>-Altrose</a></span> bei <i>Toronto Research Chemicals</i>, abgerufen am 15.&nbsp;Oktober 2023 (<a rel="nofollow" class="external text" href="https://www.trc-canada.com/prod-img/MSDS/A575710MSDS.pdf">PDF</a>).<span class="editoronly" style="display:none;"></span></span>
</li>
<li id="cite_note-Sigma-3"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-Sigma_3-0">a</a></sup> <sup><a href="#cite_ref-Sigma_3-1">b</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/63963">D-Altrose, ≥97.0% (HPLC)</a></span> bei <a href="Sigma-Aldrich" title="Sigma-Aldrich">Sigma-Aldrich</a>, abgerufen am 5.&nbsp;Februar 2013 (<a rel="nofollow" class="external text" href="https://www.sigmaaldrich.com/DE/de/sds/SIGMA/63963?userType=anonymous">PDF</a>).<span class="editoronly" style="display:none;"></span></span>
</li>
<li id="cite_note-SigmaL-4"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-SigmaL_4-0">a</a></sup> <sup><a href="#cite_ref-SigmaL_4-1">b</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/66777">L-Altrose, ≥97.0% (HPLC)</a></span> bei <a href="Sigma-Aldrich" title="Sigma-Aldrich">Sigma-Aldrich</a>, abgerufen am 5.&nbsp;Februar 2013 (<a rel="nofollow" class="external text" href="https://www.sigmaaldrich.com/DE/de/sds/SIGMA/66777?userType=anonymous">PDF</a>).<span class="editoronly" style="display:none;"></span></span>
</li>
<li id="cite_note-UNI-Bern-5"><span class="mw-cite-backlink"><a href="#cite_ref-UNI-Bern_5-0">↑</a></span> <span class="reference-text">Jürg Hunziker: <style data-mw-deduplicate="TemplateStyles:r261891140">
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.mw-parser-output .webarchiv-memento a{color:inherit}


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</style><a rel="nofollow" class="external text" href="https://web.archive.org/web/20080510045027/http://dcbwww.unibe.ch/groups/hunziker/teaching/carbohyd/Kap_02/209konfo.html"><i>Kohlenhydratchemie</i></a> (<span class="webarchiv-memento"><a href="Webarchivierung#Begrifflichkeiten" title="Webarchivierung">Memento</a></span> vom 10. Mai 2008 im <i><a href="Internet_Archive" title="Internet Archive">Internet Archive</a></i>), 1. April 2007.</span>
</li>
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