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Thymol
Thymol (also known as 2-isopropyl-5-methylphenol, IPMP), C10H14O, is a monoterpenoid, phenol derivative of p-cymene, isomeric with carvacrol. It occurs naturally in oil of thyme and is extracted from Thymus vulgaris (common thyme), ajwain, and various other plants, as a white crystalline substance with a pleasant aromatic odor.
Thymol provides the distinctive flavor of the culinary herb thyme, also produced from T. vulgaris. Thymol is only slightly soluble in water at neutral pH, but due to deprotonation of the phenol, it is highly soluble in alcohols, other organic solvents, and strongly alkaline aqueous solutions.
Thymol is produced by the alkylation of m-cresol and propene. CH3C6H4OH + CH2CHCH3 → ((CH3)2CH)CH3C6H3OH
A predicted method of biosynthesis of thymol in thyme and oregano begins with the cyclization of geranyl diphosphate by TvTPS2 to γ-terpinene. Oxidation by a cytochrome P450 in the CYP71D subfamily creates a dienol intermediate, which is then converted into a ketone by short-chain dehydrogenase. Lastly, keto-enol tautomerization gives thymol. Its dissociation constant (pKa) is 10.59±0.10. Thymol absorbs maximum UV radiation at 274 nm.
The bee balms Monarda fistulosa and Monarda didyma, North American wildflowers, are natural sources of thymol. The Blackfoot Native Americans recognized these plants' strong antiseptic action and used poultices of the plants for skin infections and minor wounds. A tisane made from them was also used to treat mouth and throat infections caused by dental caries and gingivitis.
Thymol was first isolated by German chemist Caspar Neumann in 1719. In 1853, French chemist Alexandre Lallemand (1816-1886) named thymol and determined its empirical formula. Possible antiseptic properties of thymol were discovered in 1875, and it was first synthesized by Swedish chemist Oskar Widman (1852-1930) in 1882.
The conventional method of extracting is 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.
During the 1910s, thymol was used for hookworm infection in the United States. People of the Middle East continue to use za'atar, a delicacy made with large amounts of thyme, to reduce and eliminate internal parasites. It is also used as a preservative in halothane, an anaesthetic, and as an antiseptic in mouthwash. When used to reduce plaque and gingivitis, thymol has been found to be more effective when used in combination with chlorhexidine than when used purely by itself.
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Thymol
Thymol (also known as 2-isopropyl-5-methylphenol, IPMP), C10H14O, is a monoterpenoid, phenol derivative of p-cymene, isomeric with carvacrol. It occurs naturally in oil of thyme and is extracted from Thymus vulgaris (common thyme), ajwain, and various other plants, as a white crystalline substance with a pleasant aromatic odor.
Thymol provides the distinctive flavor of the culinary herb thyme, also produced from T. vulgaris. Thymol is only slightly soluble in water at neutral pH, but due to deprotonation of the phenol, it is highly soluble in alcohols, other organic solvents, and strongly alkaline aqueous solutions.
Thymol is produced by the alkylation of m-cresol and propene. CH3C6H4OH + CH2CHCH3 → ((CH3)2CH)CH3C6H3OH
A predicted method of biosynthesis of thymol in thyme and oregano begins with the cyclization of geranyl diphosphate by TvTPS2 to γ-terpinene. Oxidation by a cytochrome P450 in the CYP71D subfamily creates a dienol intermediate, which is then converted into a ketone by short-chain dehydrogenase. Lastly, keto-enol tautomerization gives thymol. Its dissociation constant (pKa) is 10.59±0.10. Thymol absorbs maximum UV radiation at 274 nm.
The bee balms Monarda fistulosa and Monarda didyma, North American wildflowers, are natural sources of thymol. The Blackfoot Native Americans recognized these plants' strong antiseptic action and used poultices of the plants for skin infections and minor wounds. A tisane made from them was also used to treat mouth and throat infections caused by dental caries and gingivitis.
Thymol was first isolated by German chemist Caspar Neumann in 1719. In 1853, French chemist Alexandre Lallemand (1816-1886) named thymol and determined its empirical formula. Possible antiseptic properties of thymol were discovered in 1875, and it was first synthesized by Swedish chemist Oskar Widman (1852-1930) in 1882.
The conventional method of extracting is 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.
During the 1910s, thymol was used for hookworm infection in the United States. People of the Middle East continue to use za'atar, a delicacy made with large amounts of thyme, to reduce and eliminate internal parasites. It is also used as a preservative in halothane, an anaesthetic, and as an antiseptic in mouthwash. When used to reduce plaque and gingivitis, thymol has been found to be more effective when used in combination with chlorhexidine than when used purely by itself.