Carvacrol

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Carvacrol[1]
Carvacrol
Names
Preferred IUPAC name
2-Methyl-5-(propan-2-yl)phenol
Other names
5-Isopropyl-2-methylphenol
2-Methyl-5-(1-methylethyl)phenol
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.007.173
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[2]
−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

Carvacrol, or cymophenol, C6H3(CH3)(OH)C3H7, is a monoterpenoid phenol. It has a characteristic pungent, warm odor of oregano.[3]

Natural occurrence[edit]

Carvacrol is present in the essential oil of Origanum vulgare (oregano), oil of thyme, oil obtained from pepperwort, and wild bergamot. The essential oil of thyme subspecies contains between 5% and 75% of carvacrol, while Satureja (savory) subspecies have a content between 1% and 45%.[4] Origanum majorana (marjoram) and Dittany of Crete are rich in carvacrol, 50% and 60–80% respectively.[5]

It is also found in tequila[6] and Lippia graveolens (Mexican oregano) in the verbena family.

Research[edit]

In vitro, carvacrol inhibits the growth of several bacteria strains, e.g. Escherichia coli.[7] In Pseudomonas aeruginosa in vitro, it disrupts cell membranes of these bacteria and inhibits their proliferation.[8]

Application of carvacrol on the human tongue, as well as activation of TRPV3, causes a sensation of warmth. Both pro- and anti-apoptotic effect of this compound have been proposed in various cellular systems, but conclusive evidence to support a direct effect has not been proven.[9][10]

Synthesis and derivatives[edit]

Carvacrol may be synthetically prepared by the fusion of cymol sulfonic acid with caustic potash; by the action of nitrous acid on 1-methyl-2-amino-4-propyl benzene; by prolonged heating of five parts of camphor with one part of iodine; or by heating carvol with glacial phosphoric acid or by performing a dehydrogenation of carvone with a palladium-carbon catalyst. 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.

List of the plants that contain the chemical[edit]

Toxicology[edit]

Carvacrol does not have many long-term genotoxic risks. The cytotoxic effect of carvacrol can make it an effective antiseptic and antimicrobial agent. Carvacrol has been found to show antioxidant activity.[21]

Carvacrol has antimicrobial activity against 25 different periodontopathic bacteria and strains, [22] Cladosporium herbarum,[22] Penicillium glabrum,[22] and fungi such as F. moniliforme, R. solani, S. sclerotirum, and P. capisci.[22]

Compendial status[edit]

See also[edit]

Notes and references[edit]

  1. ^ "Carvacrol data sheet from Sigma-Aldrich".
  2. ^ 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.
  3. ^ 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): 620–4. doi:10.4315/0362-028x-63.5.620. PMID 10826719.
  4. ^ Vladić, Jelena; Zeković, Zoran; Jokić, Stela; Svilović, Sandra; Kovačević, Strahinja; Vidović, Senka (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. Retrieved 28 September 2017.
  5. ^ De Vincenzi, M.; Stammati, A.; De Vincenzi, A.; Silano, M. (2004). "Constituents of aromatic plants: Carvacrol". Fitoterapia. 75 (7–8): 801–4. doi:10.1016/j.fitote.2004.05.002. PMID 15567271.
  6. ^ De León Rodríguez, Antonio; Escalante Minakata, Pilar; Jiménez García, María I.; Ordóñez Acevedo, Leandro G.; Flores Flores, José L.; Barba de la Rosa, Ana P. (2008). "Characterization of volatile compounds from ethnic Agave alcoholic beverages by gas chromatography-mass spectrometry". Food Technology and Biotechnology. 46 (4): 448–55.
  7. ^ Du, Wen-Xian; Olsen, Carl W.; Avena-Bustillos, Roberto J.; McHugh, Tara H.; Levin, Carol E.; Friedman, Mendel (2008). "Storage Stability and Antibacterial Activity against Escherichia coli O157:H7 of Carvacrol in Edible Apple Films Made by Two Different Casting Methods". Journal of Agricultural and Food Chemistry. 56 (9): 3082–8. doi:10.1021/jf703629s. PMID 18366181.
  8. ^ Cox, S. D.; Markham, J. L. (2007). "Susceptibility and intrinsic tolerance of Pseudomonas aeruginosato selected plant volatile compounds". Journal of Applied Microbiology. 103 (4): 930–6. doi:10.1111/j.1365-2672.2007.03353.x. PMID 17897196.
  9. ^ Bhakkiyalakshmi, E; Suganya, N; Sireesh, D; Krishnamurthi, K; Saravana Devi, S; Rajaguru, P; Ramkumar, K. M. (2016). "Carvacrol induces mitochondria-mediated apoptosis in HL-60 promyelocytic and Jurkat T lymphoma cells". European Journal of Pharmacology. 772: 92–8. doi:10.1016/j.ejphar.2015.12.046. PMID 26724845.
  10. ^ Zhang, Q; Fan, K; Wang, P; Yu, J; Liu, R; Qi, H; Sun, H; Cao, Y (2016). "Carvacrol induces the apoptosis of pulmonary artery smooth muscle cells under hypoxia". European Journal of Pharmacology. 770: 134–46. doi:10.1016/j.ejphar.2015.11.037. PMID 26607464.
  11. ^ https://hort.purdue.edu/newcrop/proceedings1993/V2-628.html[full citation needed]
  12. ^ http://www.herbapolonica.pl/magazines-files/2733672-art.3.pdf[full citation needed]
  13. ^ a b Bouchra, Chebli; Achouri, Mohamed; Idrissi Hassani, L.M; Hmamouchi, Mohamed (2003). "Chemical composition and antifungal activity of essential oils of seven Moroccan Labiatae against Botrytis cinerea Pers: Fr". Journal of Ethnopharmacology. 89 (1): 165–9. doi:10.1016/S0378-8741(03)00275-7. PMID 14522450.
  14. ^ 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.
  15. ^ a b Aligiannis, N.; Kalpoutzakis, E.; Mitaku, Sofia; Chinou, Ioanna B. (2001). "Composition and Antimicrobial Activity of the Essential Oils of Two Origanum Species". Journal of Agricultural and Food Chemistry. 49 (9): 4168–70. doi:10.1021/jf001494m. PMID 11559104.
  16. ^ Coskun, Sevki; Girisgin, Oya; Kürkcüoglu, Mine; Malyer, Hulusi; Girisgin, Ahmet Onur; Kırımer, Nese; Baser, Kemal Hüsnü (2008). "Acaricidal efficacy of Origanum onites L. Essential oil against Rhipicephalus turanicus (Ixodidae)". Parasitology Research. 103 (2): 259–61. doi:10.1007/s00436-008-0956-x. PMID 18438729.
  17. ^ Ruberto, Giuseppe; Biondi, Daniela; Meli, Rosa; Piattelli, Mario (1993). "Volatile flavour components of Sicilian Origanum onites L". Flavour and Fragrance Journal. 8 (4): 197–200. doi:10.1002/ffj.2730080406.
  18. ^ https://www.researchgate.net/profile/Abdollah_Ghasemi_Pirbalouti/publication/235329752_Variation_in_antibacterial_activity_thymol_and_carvacrol_contents_of_wild_populations_of_Thymus_daenensis_subsp_daenensis_Celak/links/0fcfd510dedb8868ac000000.pdf[full citation needed]
  19. ^ 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.
  20. ^ Figiel, Adam; Szumny, Antoni; Gutiérrez-Ortíz, Antonio; Carbonell-Barrachina, Ángel A. (2010). "Composition of oregano essential oil (Origanum vulgare) as affected by drying method". Journal of Food Engineering. 98 (2): 240–7. doi:10.1016/j.jfoodeng.2010.01.002.
  21. ^ Özkan, Aysun; Erdoğan, Ayşe (2011). "A comparative evaluation of antioxidant and anticancer activity of essential oil from Origanum onites (Lamiaceae) and its two major phenolic components". Tübitak. 35 (6): 735–42. doi:10.3906/biy-1011-170.
  22. ^ a b c d 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.
  23. ^ The British Pharmacopoeia Secretariat (2009). "Index, BP 2009" (PDF). Archived from the original (PDF) on 11 April 2009. Retrieved 29 March 2010.