Prenylthiol

Prenylthiol
Names
	IUPAC name 3-methylbut-2-ene-1-thiol
	Other names Prenyl mercaptan; 3-Methyl-2-butene-1-thiol; MBT; Prenylthiol; UNII-FDG262156U; 2-Butene-1-thiol, 3-methyl-
Identifiers
CAS Number	5287-45-6 N;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:169260;
ChemSpider	129292;
ECHA InfoCard	100.118.632
EC Number	610-907-9;
PubChem CID	146586;
UNII	FDG262156U;
CompTox Dashboard (EPA)	DTXSID00200907 ;
	InChI InChI=1S/C5H10S/c1-5(2)3-4-6/h3,6H,4H2,1-2H3 Key: GYDPOKGOQFTYGW-UHFFFAOYSA-N;
	SMILES CC(=CCS)C;
Properties
Chemical formula	C5H10S
Molar mass	102.2 g/mol
Density	0.9012 g/cm³
Boiling point	125–127 °C (257–261 °F; 398–400 K)
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H226, H315, H319, H335
Precautionary statements	P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+P312, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P312, P330, P332+P313, P337+P313, P362, P370+P378, P403+P233, P403+P235, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Chemical compound

10.1021/jf060669a

Prenylthiol or 3-methyl-2-butene-1-thiol is an organosulfur compound with the formula (CH₃)₂C=CHCH₂SH. 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,^[2] including lightstruck or "skunky" beer. Some roasted coffee also owes it aroma to this thiol.^[3] The "skunk-like" aroma of burnt cannabis is attributed to prenylthiol.^[4]^[5]

References

^ "3-Methyl-2-butene-1-thiol". pubchem.ncbi.nlm.nih.gov.
^ 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.
^ 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.
^ 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. PMC 8638000. PMID 34869990.
^ Remmel, Ariana (30 November 2021). "Here's the chemistry behind marijuana's skunky scent". ScienceNews.org. Retrieved 30 November 2021.

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[1] "3-Methyl-2-butene-1-thiol". pubchem.ncbi.nlm.nih.gov.

[2] 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.

[3] 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.

[4] 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. PMC 8638000. PMID 34869990.

[5] Remmel, Ariana (30 November 2021). "Here's the chemistry behind marijuana's skunky scent". ScienceNews.org. Retrieved 30 November 2021.