Alpha Terpinyl Acetate

Anticancer.png
Tooth.png
Antiinflammatory.png
Gut.png
Wound.png
Antibacterial.png
Brain.png

The monoterpenoid ester α‐terpinyl acetate, a natural acetylated derivative of α‐terpineol derived from the essential oils of Salvia desoleana (Sardinian Sage) and Ziziphora clinopodioides (Kakouti Kohi), has a diverse array of physiological functions. It is also metabolised via hydrolysis in-vivo into α‐terpineol (a component of tea tree oil), giving it a wide scope of potential effects.

The metabolite alpha-terpineol has demonstrated anti-proliferative effects via inhibition of overactive NF-κB pathways (1). It has also been linked to the antiproliferative effects of various essential oils in a variety of deleterious cells, without damaging normal reference cell lines, and encouraging differentiation of deleterious cells thus reducing their ability to adapt and survive (2, 3).

Alpha-terpineol has also been demonstrated to elicit anti-inflammatory effects via suppression of various pro-inflammatory interleukins, accounting for a large component of the beneficial effect of tea-tree oil (4). Furthermore, this molecule has shown gastroprotective activity against gastric ulceration independent of prostaglandins, and without altering gastric acid secretion (5), and has also demonstrated broader wound-healing effects in burns, ulcers and cuts (6).

Alpha-terpineol is antimicrobial, inhibiting bacterial growth (7) and protecting teeth and gums against periodontopathic and cariogenic bacteria when used at 0.4 mg/ml in a gargling solution, particularly in combination with linalool (8).

Alpha-terpinyl acetate itself has also been demonstrated to protect against the aggregation of amyloid fibrils in the brain, inhibiting acetylcholinesterase and eliciting in-vivo neuroprotective effects (9).

Alpha-terpineol and Alpha-terpinyl acetate should not be taken in large doses in conjunction with medications without consultation of a registered health professional, as they are metabolised by Cytochrome P450 2B6, an enzyme responsible for the metabolism for many drugs, and as such may compete for metabolism and affect the potency of the drug (10).

 Key references:

  • Anti-proliferative (1,2,3)

  • Anti-inflammatory (4)

  • Gastroprotective (5)

  • Wound-healing (6)

  • Antimicrobial (7,8)

  • Tooth/gum health (8)

  • Neuroprotective (9)

Terpinyl Acetate.png

1 - Hassan, S. B., Gali-Muhtasib, H., Göransson, H., & Larsson, R. (2010). Alpha terpineol: a potential anticancer agent which acts through suppressing NF-κB signalling. Anticancer Research, 30(6), 1911-1919.

2 - Sobral, M. V., Xavier, A. L., Lima, T. C., & de Sousa, D. P. (2014). Antitumor activity of monoterpenes found in essential oils. The Scientific World Journal, 2014.

3 - Lampronti, I., Saab, A. M., & Gambari, R. (2006). Antiproliferative activity of essential oils derived from plants belonging to the Magnoliophyta division. International journal of oncology, 29(4), 989-995.

4 - Nogueira, M. N. M., Aquino, S. G., Junior, C. R., & Spolidório, D. M. P. (2014). Terpinen-4-ol and alpha-terpineol (tea tree oil components) inhibit the production of IL-1β, IL-6 and IL-10 on human macrophages. Inflammation research, 63(9), 769-778.

5 - Souza, R. H. L., Cardoso, M. S. P., Menezes, C. T., Silva, J. P., De Sousa, D. P., & Batista, J. S. (2011). Gastroprotective activity of α-terpineol in two experimental models of gastric ulcer in rats. DARU: Journal of Faculty of Pharmacy, Tehran University of Medical Sciences, 19(4), 277.

6 - Villegas, L. F., Marcalo, A., Martin, J., Fernandez, I. D., Maldonado, H., Vaisberg, A. J., & Hammond, G. B. (2001). (+)-epi-Alpha-bisabolol is the wound-healing principle of Peperomia galioides: investigation of the in vivo wound-healing activity of related terpenoids. Journal of Natural Products, 64(10), 1357-1359.

7 - Deans, S. G., & Svoboda, K. P. (1989). Antibacterial activity of summer savory (Satureja hortensis L) essential oil and its constituents. Journal of Horticultural Science, 64(2), 205-210.

8 - Park, S. N., Lim, Y. K., Freire, M. O., Cho, E., Jin, D., & Kook, J. K. (2012). Antimicrobial effect of linalool and α-terpineol against periodontopathic and cariogenic bacteria. Anaerobe, 18(3), 369-372.

9 - Chowdhury, S., & Kumar, S. (2020). Alpha-terpinyl acetate: A natural monoterpenoid from Elettaria cardamomum as multi-target directed ligand in Alzheimer’s disease. Journal of Functional Foods, 68, 103892.

10 - Lee, Y., Park, H. G., Kim, V., Cho, M. A., Kim, H., Ho, T. H., & Kim, D. (2018). Inhibitory effect of α-terpinyl acetate on cytochrome P450 2B6 enzymatic activity. Chemico-biological interactions, 289, 90-97.