Carvacrol

Carvacrol, or cymophenol, C6H3(CH3)(OH)C3H7, is a monoterpenoid phenol. It has a characteristic pungent, warm odor of oregano. Carvacrol, or cymophenol, C6H3(CH3)(OH)C3H7, is a monoterpenoid phenol. It has a characteristic pungent, warm odor of oregano. Carvacrol is present in the essential oil of Origanum vulgare (oregano), oil of thyme, oil obtained from pepperwort, and wild bergamot. The essential oil of thyme subspecies contains between 5% and 75% of carvacrol, while Satureja (savory) subspecies have a content between 1% and 45%. Origanum majorana (marjoram) and Dittany of Crete are rich in carvacrol, 50% and 60–80% respectively. It is also found in tequila and Lippia graveolens (Mexican oregano) in the verbena family. In vitro, carvacrol inhibits the growth of several bacteria strains, e.g. Escherichia coli. In Pseudomonas aeruginosa in vitro, it disrupts cell membranes of these bacteria and inhibits their proliferation. Application of carvacrol on the human tongue, as well as activation of TRPV3, causes a sensation of warmth. Both pro- and anti-apoptotic effect of this compound have been proposed in various cellular systems, but conclusive evidence to support a direct effect has not been proven. Carvacrol may be synthetically prepared by the fusion of cymol sulfonic acid with caustic potash; by the action of nitrous acid on 1-methyl-2-amino-4-propyl benzene; by prolonged heating of five parts of camphor with one part of iodine; or by heating carvol with glacial phosphoric acid or by performing a dehydrogenation of carvone with a palladium-carbon catalyst. It is extracted from Origanum oil by means of a 50% potash solution. It is a thick oil that sets at 20 °C to a mass of crystals of melting point 0 °C, and boiling point 236–237 °C. Oxidation with ferric chloride converts it into dicarvacrol, whilst phosphorus pentachloride transforms it into chlorcymol. Carvacrol does not have many long-term genotoxic risks. The cytotoxic effect of carvacrol can make it an effective antiseptic and antimicrobial agent. Carvacrol has been found to show antioxidant activity. Carvacrol has antimicrobial activity against 25 different periodontopathic bacteria and strains, Cladosporium herbarum, Penicillium glabrum, and fungi such as F. moniliforme, R. solani, S. sclerotirum, and P. capisci.