Thymol
From Wikipedia, the free encyclopedia
| Thymol | |
|---|---|
 |
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| IUPAC name | 5-methyl-2-(1-methylethyl)phenol |
| Identifiers | |
| CAS number | [89-83-8] |
| SMILES | CC1=CC(O)=C(C(C)C)C=C1 |
| Properties | |
| Molecular formula | C10H14O |
| Molar mass | 150.22 g/mol |
| Density | 0.96 g/cm3 |
| Melting point |
48-52 °C |
| Boiling point |
232 °C |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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Thymol is a monoterpene phenol derivative of cymene, C10H14OH, isomeric with carvacrol, found in oil of thyme, and extracted as a white crystalline substance of a pleasant aromatic odor and strong antiseptic properties. It is also called "hydroxy cymene".[1]
Contents |
[edit] Use
The Bee Balms (Monarda fistulosa and Monarda didyma) are natural sources of thymol, a primary active ingredient in modern commercial mouthwash formulas. The Blackfeet Indians recognized this plant's strong antiseptic action, and used poultices of the plant for skin infections and minor wounds. A tea made from the plant was also used to treat mouth and throat infections caused by dental caries and gingivitis. [2]
Thymol has been found to be useful in controlling varroa mites in bee colonies.[3]A minor use is in bookbinding: before rebinding, books with mould damage can be sealed in bags with thymol crystals to kill fungal spores. It is also used as a preservative in halothane, an anaesthetic, and as an antiseptic in mouthwash.
Recent medical research on rats concludes that "Thyme extract had relaxing effects on organs possessing β2-receptors (uterus and trachea)."[4]
In a 1994 report released by five top cigarette companies, thymol was listed as one of 599 additives to cigarettes.[5] It is added to improve the flavor.
There is also evidence supporting the belief that thymol when applied two to three times daily, can eliminate certain kinds of fungal infections that affect finger and toe nails in humans.[citation needed] Regular application to the affected nail over periods approximating three months, has been shown to eliminate the affliction by effectively preventing further progress;[citation needed] by simply cutting the nail as one normally would, all infected material is eventually eliminated.
[edit] Biological activity
Thymol has GABAnergic activity,[6] a mechanism of action similar to other depressants such as secobarbital, methaqualone and diazepam. It bears close similarity to the widely used aneasthetic propofol (2,6-diisopropylphenol). Because it is less potent, thymol could potentially be abused like the more common depressants. Propofol is extremely dangerous because of its very steep dose-response curve and high potency. It is commonly abused among aneasthesiologists and nurses, many times causing death.[citation needed] Because of thymol's lowered potency and safer dose-response curve, it could feasibly be abused as a legal depressant. Because propofol is not scheduled, thymol is neither a controlled substance nor a controlled substance analogue in the US and the UK. Because of its widespread availability in food products, it is unlikely to ever come under control.
[edit] See also
[edit] References
- ^ Webster's 1913 dictionary)
- ^ Edible and Medicinal Plants of the West, Gregory L. Tilford, ISBN 0-87842-359-1
- ^ Almond farmers seek healthy bees
- ^ Wienkötter, N.; F. Begrow, U. Kinzinger, D. Schierstedt, E.J. Verspohl (2007). "The Effect of Thyme Extract on β2-Receptors and Mucociliary Clearance". Planta Medica 73 (7): 629-635. doi:.
- ^ List of 599 Cigarette additives
- ^ Priestley, Caroline M.; E. Williamson, K. Wafford, and D. Sattelle (2003). "Thymol, a constituent of thyme essential oil, is a positive allosteric modulator of human GABAA receptors and a homo-oligomeric GABA receptor from Drosophila melanogaster". British Journal of Pharmacology (140): 1363-1372. doi:.
