![]() | |
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). |
Carvacrol, or cymophenol, C6H3(CH3)(OH)C3H7, is a monoterpenoid phenol. It has a characteristic pungent, warm odor of oregano. [4]
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]
Marjoram is a cold-sensitive perennial herb or undershrub with sweet pine and citrus flavours. In some Middle Eastern countries, marjoram is synonymous with oregano, and there the names sweet marjoram and knotted marjoram are used to distinguish it from other plants of the genus Origanum. It is also called pot marjoram, although this name is also used for other cultivated species of Origanum.
Oregano is a species of flowering plant in the mint family Lamiaceae. It was native to the Mediterranean region, but widely naturalised elsewhere in the temperate Northern Hemisphere.
Satureja is a genus of aromatic plants of the family Lamiaceae, related to rosemary and thyme. It is native to North Africa, southern and southeastern Europe, the Middle East, and Central Asia. A few New World species were formerly included in Satureja, but they have all been moved to other genera. Several species are cultivated as culinary herbs called savory, and they have become established in the wild in a few places.
Thyme is a culinary herb consisting of the dried aerial parts of some members of the genus Thymus of flowering plants in the mint family Lamiaceae. Thymes are native to Eurasia and north Africa. Thymes have culinary, medicinal, and ornamental uses. The species most commonly cultivated and used for culinary purposes is Thymus vulgaris, native to Southeast Europe.
Coleus amboinicus, synonym Plectranthus amboinicus, is a semi-succulent perennial plant in the family Lamiaceae with a pungent oregano-like flavor and odor. Coleus amboinicus is considered to be native to parts of Africa, the Arabian Peninsula, and India, although it is widely cultivated and naturalized elsewhere in the tropics where it is used as a spice and ornamental plant. Common names in English include Indian borage, country borage, French thyme, Indian mint, Mexican mint, Cuban oregano, broad leaf thyme, soup mint, Spanish thyme. The species epithet, amboinicus refers to Ambon Island, in Indonesia, where it was apparently encountered and described by João de Loureiro (1717–1791).
Thymol, C10H14O, is a natural monoterpenoid phenol derivative of p-Cymene, isomeric with carvacrol, found in oil of thyme, and extracted from Thymus vulgaris, ajwain, and various other plants as a white crystalline substance of a pleasant aromatic odor and strong antiseptic properties. Thymol also provides the distinctive, strong flavor of the culinary herb thyme, also produced from T. vulgaris. Thymol is only slightly soluble in water at neutral pH, but it is extremely soluble in alcohols and other organic solvents. It is also soluble in strongly alkaline aqueous solutions due to deprotonation of the phenol. Its dissociation constant (pKa) is 10.59±0.10. Thymol absorbs maximum UV radiation at 274 nm.
Monarda is a genus of flowering plants in the mint family, Lamiaceae. The genus is endemic to North America. Common names include bergamot, bee balm, horsemint, and oswego tea, the first being inspired by the fragrance of the leaves, which is reminiscent of bergamot orange. The genus was named for the Spanish botanist Nicolás Monardes, who wrote a book in 1574 describing plants of the New World.
Origanum dictamnus, the dittany of Crete, Cretan dittany or hop marjoram, is a tender perennial plant that grows 20–30 cm high. It is known in Greek as δίκταμο or in the Cretan dialect as έρωντας. It is a therapeutic and aromatic plant that grows wild only on the mountainsides and gorges of the Greek island of Crete. It is widely used for food flavouring and medicinal purposes, in addition to featuring as an ornamental plant in gardens. This small, lanate shrub is easily recognised by the distinctive soft, woolly covering of white-grey hair on its stems and round green leaves, giving it a velvety texture. Its tiny rose-pink flowers are surrounded by brighter purple-pink bracts in summer and autumn. The dittany is classified as vulnerable on the IUCN Red List of Threatened Plant Species 1997.
Carvone is a member of a family of chemicals called terpenoids. Carvone is found naturally in many essential oils, but is most abundant in the oils from seeds of caraway, spearmint, and dill.
Origanum is a genus of herbaceous perennial flowering plants and subshrubs in the family Lamiaceae. They are native to Europe, North Africa, and much of temperate Asia, where they are found in open or mountainous habitats. A few species also naturalized in scattered locations in North America and other regions.
Summer savory is among the best known of the savory genus. It is an annual, but otherwise is similar in use and flavor to the perennial winter savory. It is used more often than winter savory, which has a slightly more bitter flavor.
Caryophyllene, more formally (−)-β-caryophyllene (BCP), is a natural bicyclic sesquiterpene that is a constituent of many essential oils, especially clove oil, the oil from the stems and flowers of Syzygium aromaticum (cloves), the essential oil of Cannabis sativa, copaiba, rosemary, and hops. It is usually found as a mixture with isocaryophyllene and α-humulene, a ring-opened isomer. Caryophyllene is notable for having a cyclobutane ring, as well as a trans-double bond in a 9-membered ring, both rarities in nature.
Monoterpenes are a class of terpenes that consist of two isoprene units and have the molecular formula C10H16. Monoterpenes may be linear (acyclic) or contain rings (monocyclic and bicyclic). Modified terpenes, such as those containing oxygen functionality or missing a methyl group, are called monoterpenoids. Monoterpenes and monoterpenoids are diverse. They have relevance to the pharmaceutical, cosmetic, agricultural, and food industries.
Monarda fistulosa, the wild bergamot or bee balm, is a wildflower in the mint family Lamiaceae, widespread and abundant as a native plant in much of North America. This plant, with showy summer-blooming pink to lavender flowers, is often used as a honey plant, medicinal plant, and garden ornamental. The species is quite variable, and several subspecies or varieties have been recognized within it.
Cedrol is a sesquiterpene alcohol found in the essential oil of conifers, especially in the genera Cupressus (cypress) and Juniperus (juniper). It has also been identified in Origanum onites, a plant related to oregano. Its main uses are in the chemistry of aroma compounds. It makes up about 19% of cedarwood oil Texas and 15.8% of cedarwood oil Virginia.
Origanum onites, the Cretan oregano, Greek oregano, pot marjoram or Ellinikí rίgani in Greek, is a plant species in the genus Origanum found in Sicily, Greece and Turkey. It has similar flavors as common oregano.It has antimicrobial activities.
γ-Terpinene synthase is an enzyme with systematic name geranyl-diphosphate diphosphate-lyase . This enzyme catalyses the following chemical reaction
2,5-Dimethoxy-p-cymene, or thymohydroquinone dimethyl ether, is a phytochemical found in the essential oils of plants within the family Asteraceae. These essential oils, which contain the compound as a major component of the oil, have antifungal, antibacterial, and insecticidal properties.
Thymus zygis is a type of flowering plant in the family Lamiaceae native to the Iberian Peninsula and northern Morocco.
Satureja thymbra, commonly known as savory of Crete, whorled savory, pink savory, and Roman hyssop, is a perennial-green dwarf shrub of the family Lamiaceae, having strongly scented leaves, native to Libya, southeastern Europe from Sardinia to Turkey; Cyprus, Lebanon, Israel and the Palestinian Authority. The plant is noted for its dark-green leaves which grow on numerous, closely compacted branches, reaching a height of 20–50 cm. The plant bears pink to purple flowers that blossom between March and June.