Terpinen-4-ol explained

Terpinen-4-ol is an isomer of terpineol with the chemical formula C10H18O. A primary constituent of tea tree oil,[1] it is obtained as an extract from the leaves, branches, and bark of Melaleuca alternifolia Cheel.[2] [3] [4] Despite considerable basic and preliminary clinical research of terpinen-4-ol and tea tree oil, its biological properties and potential for clinical uses have not been established as of 2019.[2] It may be a factor in the contact dermatitis of tea tree oil when used topically.[2] [3]

Terpinen-4-ol occurs in Juniperus communis and is thought to be the reason why this wood is highly resistant to rot.

Synthesis

Terpinen-4-ol can be synthesized from terpinolene (1) by photooxidation, reduction of the resulting hydroperoxide (2), and selective hydrogenation of the terminal double bond in 3.

Notes and References

  1. Web site: Tea tree oil . Drugs and Lactation Database (LactMed), National Library of Medicine, US National Institutes of Health . 31 July 2019 . 3 December 2018.
  2. Web site: Tea tree oil . Drugs.com . 31 July 2019 . 17 June 2019.
  3. de Groot . Anton C. . Schmidt . Erich . Tea tree oil: contact allergy and chemical composition . Contact Dermatitis . 75 . 3 . 13 May 2016 . 0105-1873 . 10.1111/cod.12591 . 129–143. 27173437 . free .
  4. Hammer, K. A.; Carson, C. F.; Riley, T. V. . 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 . 2012 . 56 . 2 . 909–915 . 10.1128/AAC.05741-11 . 22083482 . 3264233 .

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