3-Methyl-2-buten-1-thiol

Soweit möglich und gebräuchlich, werden SI-Einheiten verwendet.
Wenn nicht anders vermerkt, gelten die angegebenen Daten bei Standardbedingungen (0 °C, 1000 hPa). Brechungsindex: Na-D-Linie, 20 °C

3-Methyl-2-buten-1-thiol (MBT) ist ein schwefelhaltiges Terpenoid. Es ist ein stark geruchsaktives Thiol, das einen intensiven, schwefligen Geruch aufweist. Aufgrund dieser Eigenschaft und seiner Verwandtschaft mit 3-Methylbutanthiol, einer im Analdrüsensekret von Stinktieren enthaltenen Verbindung, wird es im englischen Sprachraum auch als Skunk Thiol bezeichnet.

Die Verbindung entsteht, wenn man helles Bier dem Tageslicht aussetzt. Dabei kommt es zur Zersetzung der im Bier enthaltenen iso-Alphasäuren. In Anwesenheit von schwefelhaltigen Aminosäuren wie dem Cystein reagieren die Zersetzungsprodukte zu MBT. Im Brauereiwesen wird dieses unerwünschte Fehlaroma als Lichtgeschmack bezeichnet. Auch beim Rösten der Kaffeesorten Robusta und Arabica kann es zur Bildung von MBT kommen. Forscher des niederländischen Plant Research International in Wageningen haben 2006 entdeckt, dass dieser Stoff auch von der Kaiserkrone als Fraßschutz gegen Wühlmäuse produziert wird.^[3]

Der charakteristische Geruch von Cannabis kommt von MBT.^[4]

Einzelnachweise

↑ ^a ^b ^c ^d ^e ^f FAO: Specifications for Flavourings.
↑ Vorlage:CL Inventory/nicht harmonisiertFür diesen Stoff liegt noch keine harmonisierte Einstufung vor. Wiedergegeben ist eine von einer Selbsteinstufung durch Inverkehrbringer abgeleitete Kennzeichnung von 3-Methyl-2-buten-1-thiol im Classification and Labelling Inventory der Europäischen Chemikalienagentur (ECHA), abgerufen am 8. Juli 2020.
↑ Johannes Petrus Franciscus Gerardus Helsper, Mark Bücking, Sorel Muresan, Jan Blaas, Willem Anne Wietsma: Identification of the volatile component(s) causing the characteristic foxy odor in various cultivars of Fritillaria imperialis L. (Liliaceae). In: Journal of Agricultural and Food Chemistry. Band 54, Nr. 14, 12. Juli 2006, S. 5087–5091, doi:10.1021/jf0605594, PMID 16819920.
↑ Iain W. H. Oswald, Marcos A. Ojeda, Ryan J. Pobanz, Kevin A. Koby, Anthony J. Buchanan, Josh Del Rosso, Mario A. Guzman, Thomas J. Martin: Identification of a New Family of Prenylated Volatile Sulfur Compounds in Cannabis Revealed by Comprehensive Two-Dimensional Gas Chromatography. In: ACS Omega. Band 6, Nr. 47, 30. November 2021, S. 31667–31676, doi:10.1021/acsomega.1c04196, PMID 34869990, PMC 8638000 (freier Volltext).

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