Terpinen-4-ol
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| Names | |
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| Preferred IUPAC name
4-Methyl-1-(propan-2-yl)cyclohex-3-en-1-ol | |
| Identifiers | |
3D model (JSmol) |
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| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.008.396 |
| MeSH | terpinenol-4 |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C10H18O | |
| Molar mass | 154.253 g·mol−1 |
| Density | 0.9315 g/cm3 |
| Melting point | −66 °C (−87 °F; 207 K) |
| Boiling point | 212 °C (414 °F; 485 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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 the "tea tree" 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. [citation needed]
Synthesis
[edit]Terpinen-4-ol can be synthesized from terpinolene (1) via photooxygenation, reduction of the resulting hydroperoxide (2), and selective hydrogenation of the terminal double bond in 3.[5]
Synthesis of terpinen-4-ol
References
[edit]- ↑ "Tea tree oil". Drugs and Lactation Database (LactMed), National Library of Medicine, US National Institutes of Health. 3 December 2018. Retrieved 31 July 2019.
- 1 2 3 "Tea tree oil". Drugs.com. 17 June 2019. Retrieved 31 July 2019.
- 1 2 de Groot, Anton C.; Schmidt, Erich (13 May 2016). "Tea tree oil: contact allergy and chemical composition". Contact Dermatitis. 75 (3): 129–143. doi:10.1111/cod.12591. ISSN 0105-1873. PMID 27173437.
- ↑ 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): 909–915. doi:10.1128/AAC.05741-11. PMC 3264233. PMID 22083482.
{{cite journal}}: CS1 maint: multiple names: authors list (link) - ↑ Panten, Johannes; Surburg, Horst (26 November 2015). "Flavors and Fragrances, 2. Aliphatic Compounds". Ullmann's Encyclopedia of Industrial Chemistry: 28. doi:10.1002/14356007.t11_t01.