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Terpinen-4-ol

4-Methyl-1-(1-methylethyl)-3-cyclohexen-1-ol

Terpin-4-ol · Terpinenol-4 · 4-Terpineol · 4-Carvomenthol · p-Menth-1-en-4-ol

Monocyclic monoterpenoid alkene alcohol · C₁₀H₁₈O

Chemical structure of Terpinen-4-ol
2D structure PubChem / NCI CIR

Chemical info

CAS number CAS
20126-76-5
Molecular formula
C₁₀H₁₈O
Molecular weight
154.25 g/mol
Aroma
Fresh, lightly woody, clean, suggestive of cardamom and tea tree, with an earthy finish.

Safety

Low concern · Anti-inflammatory profile

Terpinen-4-ol is the principal constituent of tea tree oil and the main antibacterial component. Available data indicates it is safe at standard concentrations.

Skin. At 5 percent on 25 volunteers it was neither irritating nor sensitizing. Among 7 tea tree-sensitized dermatitis patients, only 1 reacted to 1 percent terpinen-4-ol. At 10 percent it was not sensitizing in 11 tea tree-sensitized patients. The compound also reduces edema associated with contact hypersensitivity.

Oral. Acute oral LD50 in rats was 1.3 g/kg. Acute dermal LD50 in rabbits exceeded 2.5 g/kg.

Kidney. Oral dosing at 400 mg/kg/day for 28 days produced no changes in kidney function or morphology.

Chronic. After chronic administration to mice, no discernible pathological changes occurred.

Mutagenicity and cancer. Not mutagenic in the Ames test. Shows in vitro anticancer activity against several human cancer cell lines including leukemia, cervical cancer, liver cancer and melanoma.


Usage guidelines

Concern level
Low
Notable property
Principal antibacterial constituent of tea tree · reduces edema in contact hypersensitivity
Oils with high content
Tea tree 30 to 48 percent · Plai 41.7 percent

Found in essential oils

Principal sources
Tea tree30.0 – 48.0 %
Plai41.7 %
Marjoram (sweet)16.4 – 31.6 %
Basil (hairy)7.5 – 26.8 %
Kewda0 – 21.0 %
Ghandi root17.2 %
Juniperberry1.5 – 17.0 %
Mace4.4 – 14.0 %
Nutmeg (East Indian)1.0 – 10.9 %
Labrador tea7.6 %
Calamint (lesser)0 – 6.8 %
Nutmeg (West Indian)3.0 – 6.4 %
Curry leaf6.1 %
Lavender0 – 6.0 %
Pteronia5.3 %
Saro3.0 – 5.0 %
Peppermint0 – 5.0 %

Notes

Terpinen-4-ol differs from α-terpinene and γ-terpinene in stability and sensitization risk. The compound rarely causes allergy and is the constituent that tea tree quality analyses use to verify antibacterial potency.