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Fusel alcohol
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<h2 id="usage">Usage</h2> <p>Fusel oil and fusel-oil acetates are used in the <a href="/facts/Lacquer/83C6H1IW">lacquer</a> industry as high boiling point <a href="/facts/Solvent/LoMPMz8S">solvents</a>.<a class="footnote-ref" id="fnref:4" href="#fn:4"><sup>4</sup></a> </p> <h2 id="compounds">Compounds</h2> <p class="note">Further information: <a href="/facts/Congener_(alcohol)/lzNtGYvv">Congener (alcohol)</a></p> <p>Excessive concentrations of some alcohols other than ethanol may cause off-flavors, sometimes described as "spicy", "hot", or "solvent-like". Some beverages, such as <a href="/facts/Rum/a146KQB5">rum</a>, <a href="/facts/Whisky/sfmuHmyL">whisky</a> (especially <a href="/facts/Bourbon_whiskey/KyDJH6Ht">bourbon</a>), incompletely <a href="/facts/Rectified_spirit/EngsegCD">rectified</a> vodka (e.g. <a href="/facts/Siwucha_vodka/hIgJCQRu">Siwucha</a>) and traditional <a href="/facts/Ale/tcpd1FVh">ales</a> and <a href="/facts/Cider/3B1PDMuL">ciders</a>, are expected to have relatively high concentrations of non-hazardous alcohols as part of their flavor profile. However, in other beverages, such as <a href="/facts/Korn_(liquor)/30l2juux">Korn</a>, <a href="/facts/Vodka/49G9hEo8">vodka</a> and <a href="/facts/Lager/wzdV80Qo">lagers</a>, the presence of alcohols other than ethanol is considered a <a href="/facts/Wine_fault/XmWUxr7e">fault</a>.<a class="footnote-ref" id="fnref:5" href="#fn:5"><sup>5</sup></a> </p><p>The compounds involved are chiefly the following:<a class="footnote-ref" id="fnref:6" href="#fn:6"><sup>6</sup></a> </p> <ul><li><a href="/facts/Isoamyl_alcohol/dqKX0Hn0">isoamyl alcohol</a> (isopentanol)</li> <li><a href="/facts/2-methyl-1-butanol/amhKNqX1">2-methyl-1-butanol</a> - sometimes called "active" <a href="/facts/Amyl_alcohol/0kFT94lx">amyl alcohol</a></li> <li><a href="/facts/Isobutyl_alcohol/JNB4Hh9W">isobutyl alcohol</a> - one of the least toxic of the butanols.</li> <li><a href="/facts/1-propanol/NoSmhEhh">1-propanol</a></li></ul> <p>Other higher alcohols that can be produced during fermentation include: </p> <ul><li><a href="/facts/Isopropanol/7KqgIkUd">isopropanol</a> (isopropyl alcohol), oxidized to form acetone by <a href="/facts/Alcohol_dehydrogenase/XWwHgyad">alcohol dehydrogenase</a> in the liver, leading to <a href="/facts/Ketosis/GIzSt3mL">ketosis</a> when ingested in large quantities.</li> <li><a href="/facts/1-butanol/GlSNHexW">1-butanol</a></li> <li><a href="/facts/1-pentanol/noK6jWws">1-pentanol</a> (<i>n</i>-amyl alcohol)</li> <li><a href="/facts/1-hexanol/6XnzVeYQ">1-hexanol</a></li> <li><a href="/facts/2-phenylethanol/pSj94eAT">2-phenylethanol</a></li> <li><a href="/facts/Tyrosol/NcIfbj1F">tyrosol</a></li> <li><a href="/facts/Tryptophol/sbpjfRje">tryptophol</a></li> <li>methionol</li></ul> <h2 id="distillation">Distillation</h2> <p>During <a href="/facts/Distillation/plDvUMxn">distillation</a>, fusel alcohols are concentrated in the feints or "tails" at the end of the distillation run. They have an oily consistency, which is noticeable to the distiller, hence the other name "fusel oil". If desired, these heavier alcohols can be almost completely separated in a <a href="/facts/Reflux_still/Elav2kgM">reflux still</a>. On the other hand, <a href="/facts/Freeze_distillation/PgMRowMd">freeze distillation</a> does not remove fusel alcohols. </p><p>Fusel alcohols can be reduced during <a href="/facts/Fermentation_(biochemistry)/rxaDr28b">fermentation</a> by lowering the fermenter's temperature or increasing the oxygen content.<a class="footnote-ref" id="fnref:7" href="#fn:7"><sup>7</sup></a> </p> <h2 id="see-also">See also</h2> <ul><li><a href="/facts/Alcohol_(drug)/IeK2fVd5">Alcohol (drug)</a></li> <li><a href="/facts/Reinheitsgebot/4fkAcVg7">Beer purity law (1516)</a></li> <li><a href="/facts/Biofuel/RWu7b6Y3">Biofuel</a></li> <li><a href="/facts/Cellulosic_ethanol/NyHYapwq">Cellulosic ethanol</a></li> <li><a href="/facts/Moonshine/zTBTC34m">Moonshine</a></li> <li><a href="/facts/Beer_in_South_Africa/QdMmghbh">Sorghum beer</a></li> <li><a href="/facts/Wine_chemistry/vBaWpCfh">Wine chemistry</a></li></ul> <h2 id="external-links">External links</h2> <ul><li><a href="https://en.wikisource.org/wiki/1911_Encyclop%C3%A6dia_Britannica/Fusel_Oil">"Fusel Oil" </a>. <i><a href="/facts/Encyclop%C3%A6dia_Britannica_Eleventh_Edition/mPElbCRY">Encyclopædia Britannica</a></i> (11th ed.). 1911.</li></ul> <h2 id="references">References</h2> <ol> <li id="fn:1"><p>"Fusel oil". Oxford Dictionaries. Archived from the original on 2013-01-26. Retrieved 2013-01-21.- Blazquez, Rodrigo (March 2019). "Higher Alcohols". Waterhouse Lab. UC Davis. Retrieved 22 September 2020. <a href="https://web.archive.org/web/20130126224105/http://oxforddictionaries.com/definition/english/fusel%2Boil" target="_blank">https://web.archive.org/web/20130126224105/http://oxforddictionaries.com/definition/english/fusel%2Boil</a> <a href="#fnref:1" class="footnote-back-ref">↩</a></p></li> <li id="fn:2"><p>Hazelwood, Lucie A.; Daran, Jean-Marc; van Maris, Antonius J. A.; Pronk, Jack T.; Dickinson, J. Richard (2008). "The Ehrlich pathway for fusel alcohol production: a century of research on Saccharomyces cerevisiae metabolism". Appl. Environ. Microbiol. 74 (8): 2259–66. Bibcode:2008ApEnM..74.2259H. doi:10.1128/AEM.02625-07. PMC 2293160. PMID 18281432. <a href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2293160" target="_blank">https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2293160</a> <a href="#fnref:2" class="footnote-back-ref">↩</a></p></li> <li id="fn:3"><p>Hori H, Fujii W, Hatanaka Y, Suwa Y (27 August 2003). "Effects of fusel oil on animal hangover models". Alcohol Clin Exp Res. 27 (8 Suppl): 37S – 41S. doi:10.1097/01.ALC.0000078828.49740.48. PMID 12960505. <a href="https://doi.org/10.1097%2F01.ALC.0000078828.49740.48" target="_blank">https://doi.org/10.1097%2F01.ALC.0000078828.49740.48</a> <a href="#fnref:3" class="footnote-back-ref">↩</a></p></li> <li id="fn:4"><p>Kenyon, Richard L.; Inskeep, Gordon C.; Gillette, Leslie; Price, J. Frank (1950). "Amyl Compounds from Pentane". Industrial & Engineering Chemistry. 42 (12): 2388–2401. doi:10.1021/ie50492a004. <a href="/wiki/Industrial_%26_Engineering_Chemistry" target="_blank">/wiki/Industrial_%26_Engineering_Chemistry</a> <a href="#fnref:4" class="footnote-back-ref">↩</a></p></li> <li id="fn:5"><p>Aroma of Beer, Wine and Distilled Alcoholic Beverages <a href="#fnref:5" class="footnote-back-ref">↩</a></p></li> <li id="fn:6"><p>MERCK INDEX (10th ed.). 1983. <a href="#fnref:6" class="footnote-back-ref">↩</a></p></li> <li id="fn:7"><p>"Avoid the Dreaded Cheap Booze Flavour: 5 Strategies for Fusel Alcohols". <a href="https://escarpmentlabs.com/en-us/blogs/resources/avoid-the-dreaded-cheap-booze-flavour-5-strategies-for-fusel-alcohols" target="_blank">https://escarpmentlabs.com/en-us/blogs/resources/avoid-the-dreaded-cheap-booze-flavour-5-strategies-for-fusel-alcohols</a> <a href="#fnref:7" class="footnote-back-ref">↩</a></p></li> </ol>