Carvacrol
Carvacrol, or cymophenol, C6H3(CH3)(OH)C3H7, is a monoterpenoid phenol. It has a characteristic pungent, warm odor of oregano.[1]
Natural occurrence
Carvacrol is present in the essential oil of Origanum vulgare (oregano), oil of thyme, oil obtained from pepperwort, and wild bergamot.[2] The essential oil of thyme subspecies contains between 5% and 75% of carvacrol, while Satureja (savory) subspecies have a content between 1% and 45%.[3] Origanum majorana (marjoram) and Dittany of Crete are rich in carvacrol, 50% and 60–80% respectively.[4]
It is also found in tequila[5] and Lippia graveolens (Mexican oregano) in the verbena family.
Sources
- Coleus amboinicus
- Lavandula multifida
- Lepidium
- Lippia graveolens
- Monarda didyma[6]
- Monarda fistulosa
- Nigella sativa[7]
- Origanum compactum[8]
- Origanum dictamnus[9]
- Origanum majorana
- Origanum microphyllum[10]
- Origanum minutiflorum
- Origanum onites[11][12]
- Origanum scabrum[10]
- Origanum syriacum[13]
- Origanum vulgare[14][15]
- Plectranthus amboinicus
- Satureja
- Satureja thymbra
- tequila
- Thymbra spicata
- oil of thyme
- Thymus glandulosus[8]
Synthesis and derivatives
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.[2]
It has also been prepared by transalkylation of isopropylated cresols.[16]
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.[2]
Antimicrobial effects
In vitro, carvacrol has antimicrobial activity against 25 different phytopathogenic bacteria and strains including:[17] Cladosporium herbarum,[17] Penicillium glabrum,[17] Pseudomonas syringae,[18] and fungi such as Fusarium verticillioides/F. moniliforme, Rhizoctonia solani/R. solani, Sclerotinia sclerotiorum, and Phytophthora capsici.[17]
Compendial status
See also
Notes and references
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