Terpinen-4-ol

Terpinen-4-ol

Names
Preferred IUPAC name 4-Methyl-1-(propan-2-yl)cyclohex-3-en-1-ol
Identifiers
CAS Number	562-74-3^Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL507795^Y
ChemSpider	10756^Y
ECHA InfoCard	100.008.396
MeSH	terpinenol-4
PubChem CID	11230
UNII	L65MV77ZG6^Y
CompTox Dashboard (EPA)	DTXSID4044824
InChI InChI=1S/C10H18O/c1-8(2)10(11)6-4-9(3)5-7-10/h4,8,11H,5-7H2,1-3H3^Y Key: WRYLYDPHFGVWKC-UHFFFAOYSA-N^Y InChI=1/C10H18O/c1-8(2)10(11)6-4-9(3)5-7-10/h4,8,11H,5-7H2,1-3H3 Key: WRYLYDPHFGVWKC-UHFFFAOYAQ
SMILES CC1=CCC(CC1)(C(C)C)O
Properties
Chemical formula	C10H18O
Molar mass	154.253 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is ^YN ?) Infobox references

Terpinen-4-ol is an isomer of terpineol with the chemical formula C₁₀H₁₈O. A primary constituent of tea tree oil,^[1] it is obtained as an extract from the leaves, branches, and bark of Melaleuca alternifolia Cheel.^[2][3][4] 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.^[2] It may be a factor in the contact dermatitis of tea tree oil when used topically.^[2][3]

Terpinen-4-ol occurs in Juniperus communis and is thought to be the reason why this wood is highly resistant to rot. ^{[citation needed]}

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.

Synthesis of terpinen-4-ol

References

1. "Tea tree oil". Drugs and Lactation Database (LactMed), National Library of Medicine, US National Institutes of Health. 3 December 2018. Retrieved 31 July 2019.
2. "Tea tree oil". Drugs.com. 17 June 2019. Retrieved 31 July 2019.
3. de Groot, Anton C.; Schmidt, Erich (13 May 2016). "Tea tree oil: contact allergy and chemical composition". Contact Dermatitis. 75 (3): 129–143. doi:10.1111/cod.12591. ISSN 0105-1873. PMID 27173437.
4. Hammer, K. A.; Carson, C. F.; Riley, T. V. (2012). "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". Antimicrobial Agents and Chemotherapy. 56 (2): 909–915. doi:10.1128/AAC.05741-11. PMC 3264233. PMID 22083482.