Carvacrol

Source: Wikipedia, the free encyclopedia.
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
ECHA InfoCard
 100.007.173 Edit this at Wikidata
IUPHAR/BPS
KEGG
UNII
  • InChI=1S/C10H14O/c1-7(2)9-5-4-8(3)10(11)6-9/h4-7,11H,1-3H3 checkY
    Key: RECUKUPTGUEGMW-UHFFFAOYSA-N checkY
  • 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).
checkY verify (what is checkY☒N ?)

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

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

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. 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. PMID 10826719
    .
  5. ^ a b c  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. doi:10.1016/j.supflu.2016.05.027
    .
  7. 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. 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. ^
    PMID 14522450
    .
  12. doi:10.1016/j.foodchem.2008.05.060
    .
  13. ^
    PMID 11559104
    .
  14. S2CID 5771248
    .
  15. 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. S2CID 94582250
    .
  18. doi:10.1016/j.jfoodeng.2010.01.002
    .
  19. ISBN 978-3527306732
    .
  20. ^
    S2CID 33675413
    .
  21. PMID 32498472
    .
  22. ^ "Index" (PDF). British Pharmacopoeia. 2009. Archived from the original (PDF) on 11 April 2009. Retrieved 29 March 2010.
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