Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Terpinen-4-ol: Difference between pages

| Watchedfields = changed

| verifiedrevid = 470602523

| PIN = 4-Methyl-1-(propan-2-yl)cyclohex-3-en-1-ol

|Section1={{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| PubChem = 11230

| SMILES = CC1=CCC(CC1)(C(C)C)O

| MeSHName = terpinenol-4

|Section2={{Chembox Properties

| C=10 | H=18 | O=1

| Appearance =

| Density =

| MeltingPt =

| BoilingPt =

|Section3={{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt =

'''Terpinen-4-ol''' is an isomer of [[terpineol]] with the chemical formula C₁₀H₁₈O. A primary constituent of [[tea tree oil]],<ref name="lact">{{cite web |title=Tea tree oil |url=https://www.ncbi.nlm.nih.gov/books/NBK501884/ |publisher=Drugs and Lactation Database (LactMed), National Library of Medicine, US National Institutes of Health |accessdate=31 July 2019 |date=3 December 2018}}</ref> it is obtained as an [[extract]] from the leaves, branches, and bark of ''[[Melaleuca alternifolia]]'' Cheel.<ref name="drugs">{{cite web |title=Tea tree oil |url=https://www.drugs.com/npp/tea-tree-oil.html |publisher=Drugs.com |accessdate=31 July 2019 |date=17 June 2019}}</ref><ref name="Groot">{{cite journal | last1=de Groot | first1=Anton C. | last2=Schmidt | first2=Erich | title=Tea tree oil: contact allergy and chemical composition | journal=Contact Dermatitis | volume=75 | issue=3 | date=13 May 2016 | issn=0105-1873 | doi=10.1111/cod.12591 | pages=129–143| pmid=27173437 | doi-access=free }}</ref><ref>{{ cite journal | author = Hammer, K. A.; Carson, C. F.; Riley, T. V. | title = Effects of ''Melaleuca alternifolia'' (Tea Tree) Essential Oil and the Major Monoterpene Component Terpinen-4-ol on the Development of Single- and Multistep Antibiotic Resistance and Antimicrobial Susceptibility | journal = Antimicrobial Agents and Chemotherapy | year = 2012 | volume = 56 | issue = 2 | pages = 909–915 | doi = 10.1128/AAC.05741-11 | pmid = 22083482 | pmc = 3264233 }}</ref> Despite considerable [[basic research|basic]] and preliminary [[clinical research]] of terpinen-4-ol and tea tree oil, its biological properties and potential for clinical uses have not been established as of 2019.<ref name=drugs/> It may be a factor in the [[contact dermatitis]] of tea tree oil when used [[topical medication|topically]].<ref name=drugs/><ref name=Groot/>

Terpinen-4-ol occurs in ''[[Juniperus communis]]'' and is thought to be the reason why this wood is highly resistant to [[Decomposition|rot]]. {{citation needed|date=July 2019}}

==Synthesis==

Terpinen-4-ol can be synthesized from [[terpinolene]] ('''1''') by [[photooxidation]], reduction of the resulting hydroperoxide ('''2'''), and selective [[hydrogenation]] of the terminal double bond in '''3'''.

:[[Image:Terpinen-4-ol-Synthese.svg|thumb|left|500px|Synthesis of terpinen-4-ol]]{{clear-left}}

==References==

{{reflist}}

[[Category:Monoterpenes]]

[[Category:Cyclohexenols]]