Chemistry:Prenylthiol

From HandWiki

Prenylthiol or 3-methyl-2-butene-1-thiol is an organosulfur compound with the formula (CH
3
)
2
C=CHCH
2
SH
. It is a derivative of prenyl alcohol and hydrogen sulfide.

Occurrence

Prenylthiol is a fairly common components of roasted or cooked foods such as beer,[1] including lightstruck or "skunky" beer. Some roasted coffee also owes it aroma to this thiol.[2] The "skunk-like" aroma of burnt cannabis is attributed to prenylthiol.[3][4]

References

  1. Vermeulen, C.; Lejeune, I.; Tran, T. T. H.; Collin, S. (2006). "Occurrence of Polyfunctional Thiols in Fresh Lager Beers". Journal of Agricultural and Food Chemistry 54 (14): 5061–5068. doi:10.1021/jf060669a. PMID 16819917. 
  2. Czerny, M.; Mayer, F.; Grosch, W. (1999). "Sensory Study on the Character Impact Odorants of Roasted Arabica Coffee". Journal of Agricultural and Food Chemistry 47 (2): 695–699. doi:10.1021/jf980759i. PMID 10563955. 
  3. Oswald, Iain W. H.; Ojeda, Marcos A.; Pobanz, Ryan J.; Koby, Kevin A.; Buchanan, Anthony J.; Del Rosso, Josh; Guzman, Mario A.; Martin, Thomas J. (2021-11-30). "Identification of a New Family of Prenylated Volatile Sulfur Compounds in Cannabis Revealed by Comprehensive Two-Dimensional Gas Chromatography". ACS Omega 6 (47): 31667–31676. doi:10.1021/acsomega.1c04196. PMID 34869990. PMC 8638000. https://doi.org/10.1021/acsomega.1c04196. 
  4. Remmel, Ariana (30 November 2021). "Here's the chemistry behind marijuana's skunky scent". https://www.sciencenews.org/article/marijuana-skunk-smell-cannabis-pot-plant-chemistry.