Carvacrol

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Carvacrol[1]
Carvacrol
Names
IUPAC names
5-isopropyl-2-methylphenol[citation needed]
2-Methyl-5-(1-methylethyl)-phenol
Identifiers
499-75-2 YesY
ChEMBL ChEMBL281202 YesY
ChemSpider 21105867 YesY
2497
Jmol 3D model Interactive image
KEGG C09840 YesY
PubChem 10364
UNII 9B1J4V995Q YesY
  • InChI=1S/C10H14O/c1-7(2)9-5-4-8(3)10(11)6-9/h4-7,11H,1-3H3 YesY
    Key: RECUKUPTGUEGMW-UHFFFAOYSA-N YesY
  • 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[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY verify (what is YesYN ?)
Infobox references

Carvacrol, or cymophenol, C6H3CH3(OH)(C3H7), is a monoterpenoid phenol. It has a characteristic pungent, warm odor of oregano.[3]

Natural occurrence

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%. Origanum majorana (marjoram) and Dittany of Crete are rich in carvacrol, 50% resp. 60-80%.[4]

It is also found in tequila.[5]

Biological properties and use

Carvacrol inhibits the growth of several bacteria strains, e.g. Escherichia coli[6] and Bacillus cereus. Its low toxicity together with its pleasant taste and smell suggests its use as a food additive to prevent bacterial contamination.[7] In Pseudomonas aeruginosa it causes damages to the cell membrane of these bacteria and, unlike other terpenes, inhibits their proliferation.[8] The cause of the antimicrobial properties is believed to be disruption of the bacteria membrane.[9][10]
It is a potent activator of the human ion channels transient receptor potential V3 (TRPV3) and A1 (TRPA1).[11] Application of carvacrol on the human tongue, as well as activation of TRPV3, causes a sensation of warmth. In addition, carvacrol also activates, but then rapidly desensitizes, the pain receptor TRPA1; this explains its pungency.[11]

It activates PPAR and suppresses COX-2 inflammation.[12]

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.[13]

A study led by Supriya Bavadekar reports that carvacrol stimulates apoptosis in prostate cancer cells.[14]

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 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

Toxicology

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.[24]

Antimicrobial activity:

Compendial status

See also

Notes and references

  1. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  2. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  4. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ Characterization of volatile compounds from ethnic Agave alcoholic beverages by gas chromatography-mass spectrometry. León-Rodríguez, A. de, Escalante-Minakata, P., Jiménez-García, M. I., Ordoñez-Acevedo, L. G., Flores Flores, J. L. and Barba de la Rosa, A. P., Food Technology and Biotechnology, 2008, Volume 46, Number 4, pages 448-455 (abstract)
  6. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  7. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  8. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  9. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  10. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  11. ↑ 11.0 11.1 Lua error in package.lua at line 80: module 'strict' not found.
  12. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  13. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  14. ↑ http://www.liu.edu/Brooklyn/About/News/Press-Releases/2012/April/BK-PR-Apr25-2012.aspx
  15. ↑ http://www.hort.purdue.edu/newcrop/proceedings1993../V2-628.html
  16. ↑ http://www.herbapolonica.pl/magazines-files/2733672-art.3.pdf
  17. ↑ 17.0 17.1 Lua error in package.lua at line 80: module 'strict' not found.
  18. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  19. ↑ 19.0 19.1 Lua error in package.lua at line 80: module 'strict' not found.
  20. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  21. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  22. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  23. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  24. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  25. ↑ 25.0 25.1 25.2 25.3 Lua error in package.lua at line 80: module 'strict' not found.
  26. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  • Public Domain This article incorporates text from a publication now in the public domain: Lua error in package.lua at line 80: module 'strict' not found.
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