Carvacrol, or cymophenol, C6H3(CH3)(OH)C3H7, is a monoterpenoid phenol. It has a characteristic pungent, warm odor of oregano.[4]
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Preferred IUPAC name
2-Methyl-5-(propan-2-yl)phenol[2] | |
Systematic IUPAC name
2-Methyl-5-(propan-2-yl)benzenol | |
Other names
Carvacrol
5-Isopropyl-2-methylphenol 2-Methyl-5-(1-methylethyl)phenol Isothymol Carvativir | |
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ECHA InfoCard | 100.007.173 |
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Properties | |
C10H14O | |
Molar mass | 150.217 g/mol |
Density | 0.9772 g/cm3 at 20 °C |
Melting point | 1 °C (34 °F; 274 K) |
Boiling point | 237.7 °C (459.9 °F; 510.8 K) |
insoluble | |
Solubility | soluble in ethanol, diethyl ether, carbon tetrachloride, acetone[3] |
−1.091×10−4 cm3/mol | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Carvacrol is present in the essential oil of Origanum vulgare (oregano), oil of thyme, oil obtained from pepperwort, and wild bergamot.[5] The essential oil of thyme subspecies contains between 5% and 75% of carvacrol, while Satureja (savory) subspecies have a content between 1% and 45%.[6] Origanum majorana (marjoram) and Dittany of Crete are rich in carvacrol, 50% and 60–80% respectively.[7]
It is also found in tequila[8] and Lippia graveolens (Mexican oregano) in the verbena family.
Carvacrol may be synthetically prepared by a number of routes. The fusion of cymol sulfonic acid with caustic potash results in desulfonation. By the action of nitrous acid on 1-methyl-2-amino-4-propyl benzene, one effects diazotization. Prolonged heating of camphor and iodine or carvone with glacial phosphoric acid have also been demonstrated. The dehydrogenation of carvone with a palladium-carbon catalyst has been established.[5]
It has also been prepared by transalkylation of isopropylated cresols.[19]
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.[5]
In vitro, carvacrol has antimicrobial activity against 25 different phytopathogenic bacteria and strains including:[20] Cladosporium herbarum,[20] Penicillium glabrum,[20] Pseudomonas syringae,[21] and fungi such as Fusarium verticillioides/F. moniliforme, Rhizoctonia solani/R. solani, Sclerotinia sclerotiorum, and Phytophthora capsici.[20]