Chemistry:Carvacrol

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Carvacrol[1]
Carvacrol
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
Carvativir
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
KEGG
UNII
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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Infobox references
Tracking categories (test):

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

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

  • British Pharmacopoeia[22]

See also

Notes and references

  1. ↑ "Carvacrol data sheet from Sigma-Aldrich". http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/W224502. 
  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. ↑ 5.0 5.1 5.2  One or more of the preceding sentences incorporates text from a publication now in the public domain: Chisholm, Hugh, ed (1911). "Carvacrol". Encyclopædia Britannica. 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. http://www.ftb.com.hr/index.php/archives/67-volume-46-issue-no-4/256. 
  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.. New Crops. New York: Wiley. pp. 628–631. ISBN 0-471-59374-5. https://hort.purdue.edu/newcrop/proceedings1993/V2-628.html. 
  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". Herba Polonica. http://www.herbapolonica.pl/magazines-files/2733672-art.3.pdf. 
  11. ↑ 11.0 11.1 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. ↑ 13.0 13.1 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. 
  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". Plant Omics 4: 209–214. http://www.pomics.com/pirbalouti_4_4_2011_209_214.pdf. 
  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. 
  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 et al. (2000). "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a19_313. 
  20. ↑ 20.0 20.1 20.2 20.3 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. 
  21. ↑ Ni, Peien; Wang, Lei; Deng, Bohan; Jiu, Songtao; Ma, Chao; Zhang, Caixi; Almeida, Adelaide; Wang, Dapeng et al. (2020-06-02). "Combined Application of Bacteriophages and Carvacrol in the Control of Pseudomonas syringae pv. actinidiae Planktonic and Biofilm Forms". Microorganisms (MDPI AG) 8 (6): 837. doi:10.3390/microorganisms8060837. ISSN 2076-2607. PMID 32498472. 
  22. ↑ "Index". 2009. http://www.pharmacopoeia.co.uk/pdf/2009_index.pdf. 



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