Terpinen-4-ol

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

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
Density	0.9315 g/cm3
Melting point	−66 °C (−87 °F; 207 K)
Boiling point	212 °C (414 °F; 485 K)
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 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