Terpinen-4-ol

Terpinen-4-ol
Identifiers
562-74-3 YesY
3D model (Jmol) Interactive image
ChEMBL ChEMBL507795 YesY
ChemSpider 10756 YesY
ECHA InfoCard 100.008.396
MeSH terpinenol-4
PubChem 11230
UNII L65MV77ZG6 YesY
Properties
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, also known as 4-Terpineol, is an organic compound in the terpene family. Its molecular formula is C10H18O and its molecular weight is 154.24932 g/mol.[1]

Terpinen-4-ol is used in multiple skin related diseases including blepharitis, rosacea, Demodex, meibomian gland dysfunction, chalazion and dry eye. It’s also used in lid margin diseases. 4-Terpineol has miticidal, anti-inflammatory, antibacterial and antifungal effect.

Terpinen-4-ol is the main component of the essential oil of tea tree oil.[2] Tea tree oil (TTO) is a natural essential oil steam-distilled from the Australian native plant Melaleuca alternifolia and has long been used by the Aborigines for wounds and cutaneous infections. Terpinen-4-ol is the most abundant component.

Therapeutic Uses

Extensive research has been conducted on 4-Terpineol properties. It makes an ideal topical solution to treat ocular and face diseases like blepharitis, rosacea, meibomian gland dysfunction (MGD), dry eye, acne, demodicosis and chalazia.

Demodex Blepharitis

Demodex is a microscopic mite that is a normal inhabitant of human facial skin. About 65 species of Demodex are known. New scientific evidence has shown its role in triggering or enhancing the signs and symptoms of rosacea or blepharitis.[3][4]

Study by Sean Tighe, Ying-Ying Gao, and Scheffer C. G. Tseng [5] have demonstrated the efficiency of 4-terpineol against demodex mites. Terpinen-4-ol, the most abundant ingredient in TTO, was more potent than TTO at equivalent concentrations and its killing effect was even observable at a mere concentration of 1%. Terpinen-4-ol can be adopted in formulations of acaricides to treat a number of ocular and cutaneous diseases caused by demodicosis.

Anti-inflammatory

Hart et al (2000) showed the anti-inflammatory properties of terpinen-4-ol.[6] The water-soluble components of tea tree oil can suppress pro-inflammatory mediator production by activated human monocytes. Nogueira et al (2014) showed the efficacy of terpinen-4-ol and alpha-terpineol to suppress the production of inflammatory mediators in LPS stimulated human macrophages (mites).[7]

Additional images

Synthesis

References

  1. ↑ Terpinen-4-ol from PubChem
  2. ↑ 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): 909–15. doi:10.1128/AAC.05741-11. PMC 3264233Freely accessible. PMID 22083482.
  3. ↑ Jarmuda, S.; O'Reilly, N.; Zaba, R.; Jakubowicz, O.; Szkaradkiewicz, A.; Kavanagh, K. (2012). "Potential role of Demodex mites and bacteria in the induction of rosacea". Journal of Medical Microbiology. 61 (Pt 11): 1504–10. doi:10.1099/jmm.0.048090-0. PMID 22933353.
  4. ↑ Forton, F.M.N. (2012). "Papulopustular rosacea, skin immunity and Demodex: pityriasis folliculorum as a missing link". Journal of the European Academy of Dermatology and Venereology. 26 (1): 19–28. doi:10.1111/j.1468-3083.2011.04310.x. PMID 22017468.
  5. ↑ Tighe, Sean; Gao, Ying-Ying; Tseng, Scheffer C. G. (2013). "Terpinen-4-ol is the Most Active Ingredient of Tea Tree Oil to Kill Demodex Mites". Translational Vision Science & Technology. 2 (7): 2. doi:10.1167/tvst.2.7.2. PMC 3860352Freely accessible. PMID 24349880.
  6. ↑ Hart, P.H.; Brand, C.; Carson, C.F.; Riley, T.V.; Prager, R.H.; Finlay-Jones, J.J. (2000). "Terpinen-4-ol, the main component of the essential oil of Melaleuca alternifolia (tea tree oil), suppresses inflammatory mediator production by activated human monocytes". Inflammation Research. 49 (11): 619–26. doi:10.1007/s000110050639. PMID 11131302.
  7. ↑ Nogueira, M. N. M.; Aquino, S. G.; Rossa Junior, C.; Spolidorio, 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): 769–78. doi:10.1007/s00011-014-0749-x. PMID 24947163.
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