To install click the Add extension button. That's it.

The source code for the WIKI 2 extension is being checked by specialists of the Mozilla Foundation, Google, and Apple. You could also do it yourself at any point in time.

How to transfigure the Wikipedia

Would you like Wikipedia to always look as professional and up-to-date? We have created a browser extension. It will enhance any encyclopedic page you visit with the magic of the WIKI 2 technology.

Try it — you can delete it anytime.

Install in 5 seconds
4,5
Kelly Slayton
Congratulations on this excellent venture… what a great idea!
Alexander Grigorievskiy
I use WIKI 2 every day and almost forgot how the original Wikipedia looks like.
What we do. Every page goes through several hundred of perfecting techniques; in live mode. Quite the same Wikipedia. Just better.
Great Wikipedia has got greater.
.
Leo
Newton
Brights
Milds

Carvacrol

From 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
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]

YouTube Encyclopedic

  • 1/5
    Views:
    7 984
    872 880
    831
    512 248
    3 792
  • Oregano (Carvacrol) in 60 Seconds
  • 14 Amazing Benefits of Oregano Oil
  • Vocabulário Ciência: CARVACROL
  • Episodio #1307 El Problema No Es El Oregano
  • CHEM 2212L Experiment 4 - Conversion of Carvone to Carvacrol

Transcription

Carvacrol is the active ingredient which is found in a number of plants such as thyme and pepperwort, but is most abundant in oregano where it can make up to 75% of the oil. Carvacrol has demonstrated powerful bacteriostatic properties against a number of pathogens including e.coli and staph. Aureus which are known to cause serious illness. These bacteriostatic properties are minimal against probiotics such as bifidobacter and lactobacillius, which shows that carvacrol can help balance out the gut microflora. Carvacrol can also inhibit an enzyme called COX-2 in the gut. This enzyme is responsible for causing inflammation which may lead to stomach ulcers. In human cells, carvacrol has shown an ability to protect DNA form damage, prevent cancer cells from developing, and cause apoptosis in cancer cells which have already developed. There are no known toxic effects of carvacrol, and it has been part of the human diet for hundreds of years. For more information on Carvacrol please click the link in the description.

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

See also

Notes and references

  1. ^ "Carvacrol data sheet from Sigma-Aldrich".
  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. ^ 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. ^ 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.
  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. (eds.). New Crops. New York: Wiley. pp. 628–631. 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. ^ a b 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. ^ a b 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. S2CID 5771248.
  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" (PDF). Plant Omics. 4: 209–214.
  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. S2CID 94582250.
  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; Garbe (2000). "Phenol Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a19_313.
  20. ^ 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. S2CID 33675413.
  21. ^ Ni, Peien; Wang, Lei; Deng, Bohan; Jiu, Songtao; Ma, Chao; Zhang, Caixi; Almeida, Adelaide; Wang, Dapeng; Xu, Wenping; Wang, Shiping (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. PMC 7356356. PMID 32498472.
  22. ^ "Index" (PDF). British Pharmacopoeia. 2009. Archived from the original (PDF) on 11 April 2009. Retrieved 29 March 2010.
This page was last edited on 18 November 2023, at 11:54
Basis of this page is in Wikipedia. Text is available under the CC BY-SA 3.0 Unported License. Non-text media are available under their specified licenses. Wikipedia® is a registered trademark of the Wikimedia Foundation, Inc. WIKI 2 is an independent company and has no affiliation with Wikimedia Foundation.
Contact WIKI 2
Introduction
Terms of Service
Privacy Policy