Terpinen-4-ol

Last updated
Terpinen-4-ol
Terpinen-4-ol.svg
Names
Preferred IUPAC name
4-Methyl-1-(propan-2-yl)cyclohex-3-en-1-ol
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.008.396 OOjs UI icon edit-ltr-progressive.svg
MeSH terpinenol-4
PubChem CID
UNII
  • InChI=1S/C10H18O/c1-8(2)10(11)6-4-9(3)5-7-10/h4,8,11H,5-7H2,1-3H3 Yes check.svgY
    Key: WRYLYDPHFGVWKC-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C10H18O/c1-8(2)10(11)6-4-9(3)5-7-10/h4,8,11H,5-7H2,1-3H3
    Key: WRYLYDPHFGVWKC-UHFFFAOYAQ
  • CC1=CCC(CC1)(C(C)C)O
Properties
C10H18O
Molar mass 154.253 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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. [ citation needed ]

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.

Synthesis of terpinen-4-ol Terpinen-4-ol-Synthese.svg
Synthesis of terpinen-4-ol

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References

  1. "Tea tree oil". Drugs and Lactation Database (LactMed), National Library of Medicine, US National Institutes of Health. 3 December 2018. Retrieved 31 July 2019.
  2. 1 2 3 "Tea tree oil". Drugs.com. 17 June 2019. Retrieved 31 July 2019.
  3. 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.
  4. 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)