Carvacrol

Last updated
Carvacrol [1]
Carvacrol structure.png
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 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C10H14O/c1-7(2)9-5-4-8(3)10(11)6-9/h4-7,11H,1-3H3 Yes check.svgY
    Key: RECUKUPTGUEGMW-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C10H14O/c1-7(2)9-5-4-8(3)10(11)6-9/h4-7,11H,1-3H3
    Key: RECUKUPTGUEGMW-UHFFFAOYAI
  • Cc1ccc(cc1O)C(C)C
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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Carvacrol, or cymophenol, C6H3(CH3)(OH)C3H7, is a monoterpenoid phenol. It has a characteristic pungent, warm odor of oregano. [4]

Contents

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

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]

Antimicrobial effects

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]

Compendial status

See also

Notes and references

  1. "Carvacrol data sheet from Sigma-Aldrich".
  2. "Front Matter". Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 691. doi:10.1039/9781849733069-FP001. ISBN   978-0-85404-182-4.
  3. Lide, David R. (1998). Handbook of Chemistry and Physics (87 ed.). Boca Raton, FL: CRC Press. pp. 3–346. ISBN   978-0-8493-0594-8.
  4. Ultee, A.; Slump, R. A.; Steging, G.; Smid, E. J. (2000). "Antimicrobial activity of carvacrol toward Bacillus cereus on rice". Journal of Food Protection. 63 (5): 620–624. doi: 10.4315/0362-028x-63.5.620 . PMID   10826719.
  5. 1 2 3 Wikisource-logo.svg One or more of the preceding sentences incorporates text from a publication now in the public domain :  Chisholm, Hugh, ed. (1911). "Carvacrol". Encyclopædia Britannica . Vol. 5 (11th ed.). Cambridge University Press. p. 437.
  6. Vladić, J.; Zeković, Z.; Jokić, S.; Svilović, S.; Kovačević, S.; Vidović, S. (November 2016). "Winter savory: Supercritical carbon dioxide extraction and mathematical modeling of extraction process". The Journal of Supercritical Fluids. 117: 89–97. doi:10.1016/j.supflu.2016.05.027.
  7. De Vincenzi, M.; Stammati, A.; De Vincenzi, A.; Silano, M. (2004). "Constituents of aromatic plants: Carvacrol". Fitoterapia. 75 (7–8): 801–804. doi:10.1016/j.fitote.2004.05.002. PMID   15567271.
  8. De León Rodríguez, A.; Escalante Minakata, P.; Jiménez García, M. I.; Ordóñez Acevedo, L. G.; Flores Flores, J. L.; Barba de la Rosa, A. P. (2008). "Characterization of volatile compounds from ethnic Agave alcoholic beverages by gas chromatography-mass spectrometry". Food Technology and Biotechnology. 46 (4): 448–455.
  9. Mazza, G.; Kiehn, F. A.; Marshall, H. H. (1993). "Monarda: A source of geraniol, linalool, thymol and carvacrol-rich essential oils". In Janick, J.; Simon, J. E. (eds.). New Crops. New York: Wiley. pp. [https ://archive.org/details/newcrops0000nati/page/628 628–631]. ISBN   0-471-59374-5.
  10. Zawirska-Wojtasiak, R.; Mildner-Szkudlarz, S.; Wąsowicz, E.; Pacyński, M. (2010). "Gas chromatography, sensory analysis and electronic nose in the evaluation of black cumin (Nigella sativa L.) aroma quality" (PDF). Herba Polonica. Archived from the original (PDF) on 2023-05-14. Retrieved 2014-01-24.
  11. 1 2 Bouchra, C.; Achouri, M.; Idrissi Hassani, L. M.; Hmamouchi, M. (2003). "Chemical composition and antifungal activity of essential oils of seven Moroccan Labiatae against Botrytis cinerea Pers: Fr". Journal of Ethnopharmacology. 89 (1): 165–169. doi:10.1016/S0378-8741(03)00275-7. PMID   14522450.
  12. Liolios, C. C.; Gortzi, O.; Lalas, S.; Tsaknis, J.; Chinou, I. (2009). "Liposomal incorporation of carvacrol and thymol isolated from the essential oil of Origanum dictamnus L. and in vitro antimicrobial activity". Food Chemistry. 112 (1): 77–83. doi:10.1016/j.foodchem.2008.05.060.
  13. 1 2 Aligiannis, N.; Kalpoutzakis, E.; Mitaku, S.; Chinou, I. B. (2001). "Composition and antimicrobial activity of the essential oils of two Origanum species". Journal of Agricultural and Food Chemistry. 49 (9): 4168–4170. doi:10.1021/jf001494m. PMID   11559104.
  14. Coşkun, Ş.; Girişgin, O.; Kürkçüoğlu, M.; Malyer, H.; Girişgin, A. O.; Kırımer, N.; Başer, K. H. (2008). "Acaricidal efficacy of Origanum onites L. essential oil against Rhipicephalus turanicus (Ixodidae)". Parasitology Research. 103 (2): 259–261. doi:10.1007/s00436-008-0956-x. PMID   18438729. S2CID   5771248.
  15. Ruberto, G.; Biondi, D.; Meli, R.; Piattelli, M. (1993). "Volatile flavour components of Sicilian Origanum onites L.". Flavour and Fragrance Journal. 8 (4): 197–200. doi:10.1002/ffj.2730080406.
  16. Ghasemi Pirbalouti, A.; Rahimmalek, M.; Malekpoor, F.; Karimi, A. (2011). "Variation in antibacterial activity, thymol and carvacrol contents of wild populations of Thymus daenensis subsp. daenensis Celak" (PDF). Plant Omics. 4: 209–214.
  17. Kanias, G. D.; Souleles, C.; Loukis, A.; Philotheou-Panou, E. (1998). "Trace elements and essential oil composition in chemotypes of the aromatic plant Origanum vulgare". Journal of Radioanalytical and Nuclear Chemistry. 227 (1–2): 23–31. doi:10.1007/BF02386426. S2CID   94582250.
  18. Figiel, A.; Szumny, A.; Gutiérrez Ortiz, A.; Carbonell Barrachina, Á. A. (2010). "Composition of oregano essential oil (Origanum vulgare) as affected by drying method". Journal of Food Engineering. 98 (2): 240–247. doi:10.1016/j.jfoodeng.2010.01.002.
  19. Fiege, Helmut; Voges, Heinz-Werner; Hamamoto, Toshikazu; Umemura, Sumio; Iwata, Tadao; Miki, Hisaya; Fujita, Yasuhiro; Buysch, Hans-Josef; Garbe, Dorothea; Paulus, Wilfried (2000). "Phenol Derivatives". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a19_313. ISBN   3527306730.
  20. 1 2 3 4 Andersen, A. (2006). "Final report on the safety assessment of sodium p-chloro-m-cresol, p-chloro-m-cresol, chlorothymol, mixed cresols, m-cresol, o-cresol, p-cresol, isopropyl cresols, thymol, o-cymen-5-ol, and carvacrol". International Journal of Toxicology. 25: 29–127. doi: 10.1080/10915810600716653 . PMID   16835130. S2CID   33675413.
  21. Ni, Peien; Wang, Lei; Deng, Bohan; Jiu, Songtao; Ma, Chao; Zhang, Caixi; Almeida, Adelaide; Wang, Dapeng; Xu, Wenping; Wang, Shiping (2020-06-02). "Combined Application of Bacteriophages and Carvacrol in the Control of Pseudomonas syringae pv. actinidiae Planktonic and Biofilm Forms". Microorganisms. 8 (6). MDPI AG: 837. doi: 10.3390/microorganisms8060837 . ISSN   2076-2607. PMC   7356356 . PMID   32498472.
  22. "Index" (PDF). British Pharmacopoeia. 2009. Archived from the original (PDF) on 11 April 2009. Retrieved 29 March 2010.

Related Research Articles

<span class="mw-page-title-main">Marjoram</span> Perennial herb

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.

<span class="mw-page-title-main">Oregano</span> Species of flowering plant

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.

<span class="mw-page-title-main">Thyme</span> Herb

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.

<i>Coleus amboinicus</i> Species of plant

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).

<span class="mw-page-title-main">Thymol</span> Chemical compound found in plants including thyme

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.

<i>Monarda</i> Genus of flowering plants

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.

<i>Origanum dictamnus</i> Species of flowering plant

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.

<span class="mw-page-title-main">Carvone</span> Chemical compound

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.

<i>Origanum</i> Genus of flowering plants

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.

<span class="mw-page-title-main">Summer savory</span> Species of flowering plant

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.

<span class="mw-page-title-main">Caryophyllene</span> Chemical compound

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.

<i>Lippia graveolens</i> Species of flowering plant

Lippia graveolens, a species of flowering plant in the verbena or vervain family, Verbenaceae, is native to the southwestern United States, Mexico, and Central America as far south as Nicaragua. Common names include: Mexican oregano, redbrush lippia, orégano cimarrón, scented lippia, and scented matgrass. The specific epithet is derived from two Latin words: gravis, meaning 'heavy', and olens, meaning 'smelling'. It is a shrub or small tree, reaching 1–2.7 m (3.3–8.9 ft) in height. Fragrant white or yellowish flowers can be found on the plant throughout the year, especially after rains.

<span class="mw-page-title-main">Cedrol</span> Chemical compound

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.

<i>Origanum onites</i> Species of plant

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-<i>p</i>-cymene Chemical compound

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.

<i>Thymus zygis</i> Species of flowering plant

Thymus zygis is a type of flowering plant in the family Lamiaceae native to the Iberian Peninsula and northern Morocco.

<i>Satureja thymbra</i> Species of plant

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.