Carvacrol
Chemical compound
From Wikipedia, the free encyclopedia
Carvacrol, or cymophenol, C6H3(CH3)(OH)C3H7, is a monoterpenoid phenol. It has a characteristic pungent, warm odor of oregano.[4]
 | |
| Names | |
|---|---|
| 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 | |
| Identifiers | |
3D model (JSmol) |
|
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.007.173 |
| KEGG | |
PubChem CID |
|
| UNII | |
CompTox Dashboard (EPA) |
|
| |
| |
| 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).
| |
Natural occurrence
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.
Sources
- Coleus amboinicus
- Lavandula multifida
- Lepidium species
- Lippia graveolens (Mexican oregano)
- Monarda didyma[9]
- Monarda fistulosa (bergamot)
- Nigella sativa[10]
- Origanum compactum[11]
- Origanum dictamnus (dittany of Crete)[12]
- Origanum majorana (marjoram)
- Origanum microphyllum[13]
- Origanum minutiflorum
- Origanum onites[14][15]
- Origanum scabrum[13]
- Origanum syriacum[16]
- Origanum vulgare (oregan)[17][18]
- Plectranthus amboinicus
- Satureja spp.
- Satureja thymbra
- Tequila
- Thymbra spicata
- Oil of thyme
- Thymus glandulosus[11]
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.[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]
Thymoquinone is a quinone derivative that can be synthesized through the catalytic oxidation of carvacrol.[20][21]
Antimicrobial effects
In vitro, carvacrol has antimicrobial activity against 25 different phytopathogenic bacteria and strains including:[22] Cladosporium herbarum,[22] Penicillium glabrum,[22] Pseudomonas syringae,[23] and fungi such as Fusarium verticillioides/F. moniliforme, Rhizoctonia solani/R. solani, Sclerotinia sclerotiorum, and Phytophthora capsici.[22]
