Editing Thymol (section)

== Chemical synthesis ==
Thymol is produced by the [[alkylation]] of [[M-Cresol|''m''-cresol]] and [[propene]]:<ref>{{cite book|last1=Stroh|first1=R.|last2=Sydel|first2=R.|last3=Hahn|first3=W.|editor1-last=Foerst|editor1-first=Wilhelm|title=Newer Methods of Preparative Organic Chemistry, Volume 2|date=1963|publisher=Academic Press|location=New York|isbn=9780323150422|page=344|edition= 1st|url=https://books.google.com/books?id=LG2J6i1sUAMC&pg=PA344}}</ref><ref>{{Ullmann |doi=10.1002/14356007.a19_313|title=Phenol Derivatives |year=2000 |last1=Fiege |first1=Helmut |last2=Voges |first2=Heinz-Werner |last3=Hamamoto |first3=Toshikazu |last4=Umemura |first4=Sumio |last5=Iwata |first5=Tadao |last6=Miki |first6=Hisaya |last7=Fujita |first7=Yasuhiro |last8=Buysch |first8=Hans-Josef |last9=Garbe |first9=Dorothea |last10=Paulus |first10=Wilfried |isbn=3527306730 }}</ref>
: {{chem2|CH3C6H4OH + CH2CHCH3  -> ((CH3)2CH)CH3C6H3OH}}

A predicted method of biosynthesis of thymol in thyme and oregano begins with the cyclization of geranyl diphosphate by TvTPS2 to γ-terpinene. Oxidation by a [[cytochrome P450]] in the CYP71D subfamily creates a [[dienol]] intermediate, which is then converted into a ketone by short-chain dehydrogenase. Lastly, [[keto-enol tautomerization]] gives thymol.

[[File:Thymol biosynthesis.svg|center|thumb|800px|Predicted biosynthesis of thymol in thyme and oregano. Reconstruction of figure 4 in Krause et. al. (2021).<ref name="r505">{{cite journal | last=Krause | first=Sandra T. | last2=Liao | first2=Pan | last3=Crocoll | first3=Christoph | last4=Boachon | first4=Benoît | last5=Förster | first5=Christiane | last6=Leidecker | first6=Franziska | last7=Wiese | first7=Natalie | last8=Zhao | first8=Dongyan | last9=Wood | first9=Joshua C. | last10=Buell | first10=C. Robin | last11=Gershenzon | first11=Jonathan | last12=Dudareva | first12=Natalia | last13=Degenhardt | first13=Jörg | title=The biosynthesis of thymol, carvacrol, and thymohydroquinone in Lamiaceae proceeds via cytochrome P450s and a short-chain dehydrogenase | journal=Proceedings of the National Academy of Sciences | volume=118 | issue=52 | date=2021-12-28 | issn=0027-8424 | pmid=34930840 | pmc=8719858 | doi=10.1073/pnas.2110092118 | page=}}</ref>]]