Carvacrol

From Wikipedia, the free encyclopedia

Carvacrol[1]
Carvacrol
IUPAC name 2-methyl-5-propan-2-ylphenol
PubChem 10364
Identifiers
CAS number [499-75-2]
SMILES CC1=C(C=C(C=C1)C(C)C)O
Properties
Molecular formula C10H14O
Molar mass 150.22 g/mol
Density 0.976 g/mL
Melting point

3-4 °C
Boiling point

236-237 °C
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references

Carvacrol, or cymophenol, C6H3CH3(OH)(C3H7), is a monoterpenoid phenol. It has a characteristic pungent, warm odor of oregano and a pizza-like taste.[2]


Contents

[edit] Natural occurrence

Carvacrol is present in the essential oil of Origanum vulgaris, oil of thyme, oil obtained from pepperwort, and wi€ld 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%. The Origanum species majorana and Dittany of Crete are rich in carvacrol, 50% resp. 60-80%.[3]

[edit] Biological properties and use

Carvacrol inhibits the growth of several bacteria strains, e.g. Escheria coli[4] and Bacillus cereus. Its low toxicity together with its pleasant taste and smell suggests its use as a food additive to prevent bacterial contamination.[5] In Pseudomonas aeruginosa it causes damages to the cell membrane of these bacteria and, unlike other terpenes, inhibits the proliferation of this germ.[6] The cause of the antimicrobial properties is believed to be disruption of the bacteria membrane.[7][8]
It is a potent activator of the human ion channels transient receptor potential V3 (TRPV3) and A1 (TRPA1).[9] Application of carvacrol on the human tongue, as well as activation of TRPV3, causes a sensation of warmth. In addition carvacrol also activates, but rapidly desensitizes the pain receptor TRPA1 explaining its pungency.[9]
In rats carvacrol is quickly metabolized and excreted. The main metabolic route is esterification of the phenolic group with sulfuric acid and glucuronic acid. A minor pathway is oxidation of the terminal methyl groups to primary alcohols. After 24 hours only very small amounts of carvacrol or its metabolites could be found in urine, indicating an almost complete excretion within one day.[10]

[edit] Synthesis and derivatives

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 Pd/C catalyst. It is extracted from Origanum oil by means of a 50% potash solution. It is a thick oil which 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.

[edit] References

  1. ^ Carvacrol data sheet from Sigma-Aldrich.
  2. ^ Ultee A, Slump RA, Steging G, Smid EJ (2000). "Antimicrobial activity of carvacrol toward Bacillus cereus on rice". J. Food Prot. 63 (5): 620–4. PMID 10826719. 
  3. ^ 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. 
  4. ^ Du WX, Olsen CE, Avena-Bustillos RJ, McHugh TH, Levin CE, Friedman M (2008). "Storage Stability and Antibacterial Activity against Escherichia coli O157:H7 of Carvacrol in Edible Apple Films Made by Two Different Casting Methods". J. Agric. Food Chem.. doi:10.1021/jf703629s. PMID 18366181. 
  5. ^ Ultee A, Smid EJ (2001). "Influence of carvacrol on growth and toxin production by Bacillus cereus". Int. J. Food Microbiol. 64 (3): 373-8. PMID 11294360. 
  6. ^ Cox SD, Markham JL (2007). "Susceptibility and intrinsic tolerance of Pseudomonas aeruginosa to selected plant volatile compounds". J. Appl. Microbiol. 103 (4): 930-6. doi:10.1111/j.1365-2672.2007.03353.x. PMID 17897196. 
  7. ^ Di Pasqua R, Betts G, Hoskins N, Edwards M, Ercolini D, Mauriello G (2007). "Membrane toxicity of antimicrobial compounds from essential oils". J. Agric. Food Chem. 55 (12): 4863-70. doi:10.1021/jf0636465. PMID 17497876. 
  8. ^ Cristani M, D'Arrigo M, Mandalari G, et al (2007). "Interaction of four monoterpenes contained in essential oils with model membranes: implications for their antibacterial activity". J. Agric. Food Chem. 55 (15): 6300-8. doi:10.1021/jf070094x. PMID 17602646. 
  9. ^ a b Xu H, Delling M, Jun JC, Clapham DE (2006). "Oregano, thyme and clove-derived flavors and skin sensitizers activate specific TRP channels". Nat. Neurosci. 9 (5): 628–35. doi:10.1038/nn1692. PMID 16617338. 
  10. ^ Austgulen LT, Solheim E, Scheline RR (1987). "Metabolism in rats of p-cymene derivatives: carvacrol and thymol". Pharmacol. Toxicol. 61 (2): 98–102. PMID 2959918.