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Thymol (also known as 2-isopropyl-5-methylphenol, IPMP), , is a Monoterpene, Phenols derivative of p-Cymene, with carvacrol. It occurs naturally in the oil of thyme, and it is extracted from Thymus vulgaris (common thyme), ajwain,
and various other plants as a white crystal substance of a pleasant Aromaticity odor.Thymol provides the distinctive flavor of the Herb thyme, also produced from T. vulgaris. Thymol is only slightly solubility in water at neutral pH, but is highly soluble in alcohols, other organic solvents, and in strongly aqueous solutions due to deprotonation of the phenol.
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 .CAS Registry: Data obtained from SciFinder Thymol absorbs maximum ultraviolet radiation at 274 nm.
Thymol was first isolated by German chemist Caspar Neumann in 1719. 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.) In 1853, French chemist Alexandre LallemandMarie-Étienne-Alexandre Lallemand (December 25, 1816 - March 16, 1886) (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.
Thymol is a fragrance ingredient in some cosmetics. Thymol has been used to successfully control and prevent fermentation and the growth of mold in bees. Thymol is also used as a rapidly degrading, non-persisting pesticide, such as insecticides and fungicides which are leveraged in plant care products. Thymol can also be used as a medical disinfectant and general purpose disinfectant. Thymol is also used in the production of menthol through the hydrogenation of the aromatic ring.
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