Prenylthiol

{{Chembox  | ImageFile = 3-Methyl-2-buten-1-thiol V1.svg | ImageSize = | ImageFile1 = Prenyl-mercaptan-3D-balls.png  | IUPACName = 3-methylbut-2-ene-1-thiol | OtherNames = Prenyl mercaptan; 3-Methyl-2-butene-1-thiol; MBT; Prenylthiol; UNII-FDG262156U; 2-Butene-1-thiol, 3-methyl-  | Section1 = {{Chembox Identifiers | CASNo = 5287-45-6 | CASNo_Ref = {{Cascite|changed|CAS}} | ChEBI = 169260 | ChEMBL = | ChemSpiderID = 129292 | DrugBank = | EC_number = 610-907-9 | KEGG = | MeSHName = | PubChem = 146586 | UNII = FDG262156U | InChI = 1S/C5H10S/c1-5(2)3-4-6/h3,6H,4H2,1-2H3 | InChIKey = GYDPOKGOQFTYGW-UHFFFAOYSA-N | SMILES = CC(=CCS)C }} | Section2 = {{Chembox Properties | C=5 | H=10 | S=1 | MolarMass = 102.2 g/mol | Appearance = | Density = 0.9012 g/cm³ | MeltingPt = | BoilingPtC = 125-127 | Solubility = }} | Section3 = {{Chembox Hazards | Hazards_ref=<ref>{{cite web |title=3-Methyl-2-butene-1-thiol |url=https://pubchem.ncbi.nlm.nih.gov/compound/3-Methyl-2-butene-1-thiol#section=Safety-and-Hazards |website=pubchem.ncbi.nlm.nih.gov |language=en}}</ref> | GHSPictograms = {{GHS02}}{{GHS07}} | GHSSignalWord = Warning | HPhrases = {{H-phrases|226|315|319|335}} | PPhrases = {{P-phrases|210|233|240|241|242|243|261|264|270|271|280|301+312|302+352|303+361+353|304+340|305+351+338|312|330|332+313|337+313|362|370+378|403+233|403+235|405|501}} | MainHazards = | FlashPt = | AutoignitionPt = }} }}10.1021/jf060669a '''Prenylthiol''' or '''3-methyl-2-butene-1-thiol''' is an organosulfur compound with the formula {{chem2|(CH3)2C\dCHCH2SH}}. 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,<ref>{{cite journal |last1=Vermeulen |first1=C. |last2=Lejeune |first2=I. |last3=Tran |first3=T. T. H. |last4=Collin |first4=S. |title=Occurrence of Polyfunctional Thiols in Fresh Lager Beers |journal=Journal of Agricultural and Food Chemistry |date=2006 |volume=54 |issue=14 |pages=5061–5068 |doi=10.1021/jf060669a |pmid=16819917 }}</ref> including lightstruck or "skunky" beer. Some roasted coffee also owes it aroma to this thiol.<ref>{{cite journal |last1=Czerny |first1=M. |last2=Mayer |first2=F. |last3=Grosch |first3=W. |title=Sensory Study on the Character Impact Odorants of Roasted Arabica Coffee |journal=Journal of Agricultural and Food Chemistry |date=1999 |volume=47 |issue=2 |pages=695–699 |doi=10.1021/jf980759i |pmid=10563955 }}</ref> The "skunk-like" aroma of burnt cannabis is attributed to prenylthiol.<ref>{{Cite journal|last1=Oswald|first1=Iain W. H.|last2=Ojeda|first2=Marcos A.|last3=Pobanz|first3=Ryan J.|last4=Koby|first4=Kevin A.|last5=Buchanan|first5=Anthony J.|last6=Del Rosso|first6=Josh|last7=Guzman|first7=Mario A.|last8=Martin|first8=Thomas J.|date=2021-11-30|title=Identification of a New Family of Prenylated Volatile Sulfur Compounds in Cannabis Revealed by Comprehensive Two-Dimensional Gas Chromatography|url=https://doi.org/10.1021/acsomega.1c04196|journal=ACS Omega|volume=6|issue=47|pages=31667–31676|doi=10.1021/acsomega.1c04196|doi-access=free|pmid=34869990 |pmc=8638000}}</ref><ref>{{cite web |last1=Remmel |first1=Ariana |title=Here's the chemistry behind marijuana's skunky scent |url=https://www.sciencenews.org/article/marijuana-skunk-smell-cannabis-pot-plant-chemistry |website=ScienceNews.org |date=30 November 2021 |access-date=30 November 2021}}</ref>

==References== {{Reflist}}

Category:Thiols