terpinen-4-ol

{{Chembox

| Watchedfields = changed

| verifiedrevid = 470602523

| ImageFile = Terpinen-4-ol.svg

| ImageSize = 100px

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

| OtherNames =

|Section1={{Chembox Identifiers

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

| ChemSpiderID = 10756

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = L65MV77ZG6

| InChI = 1/C10H18O/c1-8(2)10(11)6-4-9(3)5-7-10/h4,8,11H,5-7H2,1-3H3

| InChIKey = WRYLYDPHFGVWKC-UHFFFAOYAQ

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 507795

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C10H18O/c1-8(2)10(11)6-4-9(3)5-7-10/h4,8,11H,5-7H2,1-3H3

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = WRYLYDPHFGVWKC-UHFFFAOYSA-N

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 562-74-3

| 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 =

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|Section3={{Chembox Hazards

| MainHazards =

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| AutoignitionPt =

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Terpinen-4-ol is an isomer of terpineol with the chemical formula C₁₀H₁₈O. A primary constituent of tea tree oil,{{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}} it is obtained as an extract from the leaves, branches, and bark of Melaleuca alternifolia Cheel.{{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}}{{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 }}{{ 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 }} Despite considerable 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. It may be a factor in the contact dermatitis of tea tree oil when used topically.

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