Thymol

Source: Wikipedia, the free encyclopedia.
Not to be confused with Thymeol, Thymine, or Thiamine.

Thymol
Thymol
Names
Preferred IUPAC name
5-Methyl-2-(propan-2-yl)phenol[1]
Systematic IUPAC name
5-Methyl-2-(propan-2-yl)benzenol
Other names
2-Isopropyl-5-methylphenol, isopropyl-m-cresol, 1-methyl-3-hydroxy-4-isopropylbenzene, 3-methyl-6-isopropylphenol, 5-methyl-2-(1-methylethyl)phenol, 5-methyl-2-isopropyl-1-phenol, 5-methyl-2-isopropylphenol, 6-isopropyl-3-methylphenol, 6-isopropyl-m-cresol, Apiguard, NSC 11215, NSC 47821, NSC 49142, thyme camphor, m-thymol, and p-cymen-3-ol
Identifiers
3D model (
JSmol
)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard
 100.001.768 Edit this at Wikidata
EC Number
  • 201-944-8
IUPHAR/BPS
KEGG
UNII
  • InChI=1S/C10H14O/c1-7(2)9-5-4-8(3)6-10(9)11/h4-7,11H,1-3H3 checkY
    Key: MGSRCZKZVOBKFT-UHFFFAOYSA-N checkY
  • InChI=1/C10H14O/c1-7(2)9-5-4-8(3)6-10(9)11/h4-7,11H,1-3H3
    Key: MGSRCZKZVOBKFT-UHFFFAOYAS
  • CC(C)c1ccc(C)cc1O
Properties
C10H14O
Molar mass 150.221 g·mol−1
Density 0.96 g/cm3
Melting point 49 to 51 °C (120 to 124 °F; 322 to 324 K)
Boiling point 232 °C (450 °F; 505 K)
0.9 g/L (20 °C)[2]
1.5208[3]
Pharmacology
QP53AX22 (WHO
)
Hazards
GHS labelling:
GHS05: CorrosiveGHS07: Exclamation markGHS09: Environmental hazard
Warning
H302, H314, H411
P260, P264, P270, P273, P280, P301+P312, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P330, P363, P391, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Thymol (also known as 2-isopropyl-5-methylphenol, IPMP), C10H14O, is a natural

pKa) is 10.59±0.10.[5] Thymol absorbs maximum UV radiation at 274 nm.[6]

Chemical synthesis

Thymol is produced by the

propene:[7][8]

CH3C6H4OH + CH2CHCH3 → ((CH3)2CH)CH3C6H3OH

History

funerals, because it was supposed to ensure passage into the next life.[12]

The bee balms

caries and gingivitis.[13]

Thymol was first isolated by German chemist Caspar Neumann in 1719.[14] In 1853, French chemist Alexandre Lallemand[15] (1816-1886) named thymol and determined its empirical formula.[16] Thymol was first synthesized by Swedish chemist Oskar Widman[17] (1852-1930) in 1882.[18]

Extraction

The conventional method of

hydro-distillation (HD), but can also be extracted with solvent-free microwave extraction (SFME). In 30 minutes, SFME yields similar amounts of thymol with more oxygenated compounds than 4.5 hours of hydro-distillation at atmospheric pressures without the need for solvent.[19]

Uses

Thymol

Thymol during the 1910s was the treatment of choice for

bee colonies.[24] Thymol is also used as a rapidly degrading, non-persisting pesticide.[25] Thymol can also be used as a medical disinfectant and general purpose disinfectant.[26] Thymol is also used in the production of menthol through the hydrogenation of the aromatic ring.[27]

List of plants that contain thymol

Toxicology and environmental impacts

In 2009, the U.S. Environmental Protection Agency (EPA) reviewed the research literature on the toxicology and environmental impact of thymol and concluded that "thymol has minimal potential toxicity and poses minimal risk".[42]

Environmental breakdown and use as a pesticide

Studies have shown that hydrocarbon

monoterpenes and thymol in particular degrade rapidly (DT50 16 days in water, 5 days in soil[25]) in the environment and are, thus, low risks because of rapid dissipation and low bound residues,[25] supporting the use of thymol as a pesticide agent that offers a safe alternative to other more persistent chemical pesticides that can be dispersed in runoff and produce subsequent contamination. Though, there has been recent research into sustained released systems for botanically derived pesticides, such as using natural polysaccharides which would be biodegradable and biocompatible.[43]

Compendial status

See also

Notes and references

  1. ISBN 978-0-85404-182-4
    .
  2. ^ "Thymol". PubChem. Retrieved 1 April 2016.
  3. ^ Mndzhoyan, A. L. (1940). "Thymol from Thymus kotschyanus". Sbornik Trudov Armyanskogo Filial. Akad. Nauk. 1940: 25–28.
  4. OCLC 959875923
    .
  5. ^ CAS Registry: Data obtained from SciFinder[full citation needed]
  6. doi:10.1021/ac00294a034
    .
  7. ISBN 9780323150422
    .
  8. ISBN 3527306730
    .
  9. ^ "A Brief History of Thyme - Hungry History". HISTORY.com. Archived from the original on 13 June 2016. Retrieved 9 June 2016.
  10. ^ Grieve, Mrs. Maud. "Thyme. A Modern Herbal". botanical.com (Hypertext version of the 1931 ed.). Archived from the original on 23 February 2011. Retrieved 9 February 2008.
  11. ^ Huxley, A., ed. (1992). New RHS Dictionary of Gardening. Macmillan.
  12. ^ "Thyme (thymus)". englishplants.co.uk. The English Cottage Garden Nursery. Archived from the original on 27 September 2006.
  13. ISBN 978-0-87842-359-0
    .
  14. doi:10.1098/rstl.1724.0061. On page 324, Neumann mentions that in 1719 he distilled some essential oils from various herbs. On page 326, he mentions that during these experiments, he obtained a crystalline substance from thyme oil, which he called "Camphora Thymi" (camphor
    of thyme). (Neumann gave the name "camphor" not only to the specific substance that today is called camphor but to any crystalline substance that precipitated from a volatile, fragrant oil from some plant.)
  15. ^ Marie-Étienne-Alexandre Lallemand (December 25, 1816 - March 16, 1886)
  16. ^ Lallemand, A. (1853). "Sur la composition de l'huile essentielle de thym" [On the composition of the essential oil of thyme]. Comptes Rendus (in French). 37: 498–500.
  17. ^ Karl Oskar Widman (aka Carl Oskar Widman) (January 2, 1852 - August 26, 1930)
  18. doi:10.1002/cber.18820150139
    .
  19. PMID 15330107
    .
  20. ^ Ferrell, John Atkinson (1914). The Rural School and Hookworm Disease. US Bureau of Education Bulletin. Vol. 20, Whole No. 593. Washington, DC: U.S. Government Printing Office.
  21. ^ Milton, Joseph Rosenau (1913). Preventive Medicine and Hygiene. D. Appleton. p. 119.
  22. ^ Inskeep, Steve; Godoy, Maria (11 June 2013). "Za'atar: A Spice Mix With Biblical Roots And Brain Food Reputation". NPR. Retrieved 24 February 2022.
  23. PMID 15943766
    .
  24. ^ Ward, Mark (8 March 2006). "Almond farmers seek healthy bees". BBC News. BBC.
  25. ^
    PMID 18381775
    .
  26. ^ "Thymol" (PDF). US Environmental Protection Agency. September 1993.
  27. ^ "Menthol | Definition, Structure, & Uses | Britannica". www.britannica.com. 6 October 2023. Retrieved 30 October 2023.
  28. PMID 26000025
    .
  29. doi:10.1080/10412905.1994.9698448
    .
  30. PMID 28157176
    .
  31. S2CID 24267822
    .
  32. ISSN 1878-5352
    .
  33. ^
    PMID 14522450
    .
  34. doi:10.1016/j.foodchem.2008.05.060
    .
  35. PMID 20355032
    .
  36. S2CID 81307357
    .
  37. S2CID 94582250
    .
  38. doi:10.1016/j.jfoodeng.2010.01.002
    .
  39. ^
    doi:10.1016/j.indcrop.2006.06.006
    .
  40. doi:10.1016/j.foodchem.2004.05.056
    .
  41. doi:10.1016/S0896-8446(00)00047-4
    .
  42. ^ 74 FR 12613
  43. S2CID 89798604
    .
  44. ^ The British Pharmacopoeia Secretariat (2009). "Index, BP 2009" (PDF). Archived from the original (PDF) on 11 April 2009. Retrieved 5 July 2009.
  45. ^ "Japanese Pharmacopoeia" (PDF). Archived from the original (PDF) on 22 July 2011. Retrieved 21 April 2010.

External links

Media related to Thymol at Wikimedia Commons

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