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Terpinen-4-ol

Terpinen-4-ol is a monoterpene originally found in many plants and is one of the primary active ingredients in tea tree oil. Terpinen-4-ol exhibits anticancer chemotherapeutic, anti-inflammatory, antibacterial, and antifungal activities. In leukemia cells, terpinen-4-ol induces release of cytochrome c and activation of caspase 8, resulting in autophagy, apoptosis, and cell death. In non-small cell lung cancer (NSCLC) cells, terpinen-4-ol induces cleavage of poly(ADP)-ribose polymerase (PARP), activates caspases 3 and 9, decreases mitochondrial membrane potential, increases the Bax/Bcl-2 ratio, and increases levels of p53, resulting in apoptosis and cell death. Additionally, this compound decreases myeloperoxidase activity and expression of MIP-2 and other cytokines in animal models of oral candidiasis. Terpinen-4-ol displays antimicrobial activity against gram positive and gram negative bacteria such as Campylobacter as well as fungi such as Aspergillus and Fusarium.

References PubMed ID::http://www.ncbi.nlm.nih.gov/pubmed/18975754

Cas No.

562-74-3

Purity

≥98%

Formula

C10H18O

Formula Wt.

154.25

IUPAC Name

4-methyl-1-propan-2-ylcyclohex-3-en-1-ol

Appearance

Colorless to yellowish slightly viscous liquid

Banjerdpongchai R, Khaw-On P. Terpinen-4-ol Induces Autophagic and Apoptotic Cell Death in Human Leukemic HL-60 Cells. Asian Pac J Cancer Prev. 2013;14(12):7537-42. PMID: 24460330.

Kurekci C, Padmanabha J, Bishop-Hurley SL, et al. Antimicrobial activity of essential oils and five terpenoid compounds against Campylobacter jejuni in pure and mixed culture experiments. Int J Food Microbiol. 2013 Sep 16;166(3):450-7. PMID: 24041998.

Ninomiya K, Hayama K, Ishijima SA, et al. Suppression of inflammatory reactions by terpinen-4-ol, a main constituent of tea tree oil, in a murine model of oral candidiasis and its suppressive activity to cytokine production of macrophages in vitro. Biol Pharm Bull. 2013;36(5):838-44. PMID: 23649340.

Morcia C, Malnati M, Terzi V. In vitro antifungal activity of terpinen-4-ol, eugenol, carvone, 1,8-cineole (eucalyptol) and thymol against mycotoxigenic plant pathogens. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2012;29(3):415-22. PMID: 22257275.

Wu CS, Chen YJ, Chen JJ, et al. Terpinen-4-ol Induces Apoptosis in Human Nonsmall Cell Lung Cancer In Vitro and In Vivo. Evid Based Complement Alternat Med. 2012;2012:818261. PMID: 21760828.

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