Terpinen-4-ol

Terpinen-4-ol

Identifiers
CAS Number	562-74-3
ChEMBL	ChEMBL507795
ChemSpider	10756
Jmol interactive 3D	Image
MeSH	terpinenol-4
PubChem	11230
UNII	L65MV77ZG6
InChI InChI=1S/C10H18O/c1-8(2)10(11)6-4-9(3)5-7-10/h4,8,11H,5-7H2,1-3H3 Key: WRYLYDPHFGVWKC-UHFFFAOYSA-N 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	154.25 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Terpinen-4-ol is a terpene with a molecular weight of 154.249. It has an antibacterial and antifungal effect.

It is considered the primary active ingredient of tea tree oil.^[1] It is also the compound of highest concentration in the essential oil of nutmeg.

Terpinen-4-ol occurs in Juniperus communis and is thought to be the reason this wood is highly resistant to rot. Norwegian farmers used to exploit this by making fence poles out of juniper. The concentration is higher in the alpine subspecies of juniper, but occurs in both subspecies.

Additional images

Synthesis

References

1. 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.