Carvacrol

Structural formula
General
Surname	Carvacrol
other names	5-isopropyl-2-methylphenol; Isothymol; Karvakrol; Isopropyl- o- cresol; Isopropyl- o- cresol; 2- p -cyymol; CARVACROL ( INCI ) ;
Molecular formula	C 10 H 14 O
Brief description	after thyme smelling liquid
External identifiers / databases
EC number	207-889-6
ECHA InfoCard	100.007.173
PubChem	10364
Wikidata	Q225543
properties
Molar mass	150.22 g mol −1
Physical state	liquid
density	0.9772 g cm −3 (20 ° C )
Melting point	~ 0 ° C
boiling point	237-238 ° C
solubility	almost insoluble in water; Easily soluble in ethanol and diethyl ether;
Refractive index	1.5230 (20 ° C)
safety instructions
H and P phrases	H: 302-315-318
	P: 280-301 + 312 + 330-305 + 351 + 338-310
Toxicological data	810 mg kg −1 ( LD 50 , rat , oral ) ; 73.3 mg kg −1 ( LD 50 , mouse , ip ) ; 80 mg kg −1 ( LD 50 , mouse , iv ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

The carvacrol is a terpenoid natural products , known under different names. The systematic name ( IUPAC ) of carvacrol is 2-methyl-5- (1-methylethyl) phenol. The compound represents a structural isomer ( constitutional isomer ) to thymol .

Occurrence

Real catnip ( Nepeta cataria )

Carvacrol is found in thyme ( Thymus ), winter savory ( Satureja montana ), summer savory ( Satureja hortensis ), oregano ( Origanum ), common catnip ( Nepeta cataria ) and goose feet (e.g. Chenopodium ambrosioides ). Oils obtained from these plant species can contain up to 85% carvacrol. A plant with a particularly high carvacrol content is the Cretan mountain tea Malotira ( Sideritis syriaca ).

Properties and structure

Carvacrol is a higher homologue of o -cresol . Legal regulations regarding carvacrol generally assume that thymol is harmless.

With iron (III) chloride, Carvacrol gives an olive green color.

Biological importance

Carvacrol has many uses, mainly as a biocide . It shows effects as an antifungal , insecticide , antibiotic and as an anthelmintic . In addition, Carvacrol inhibits the enzyme cyclooxygenase-2, which mediates inflammation reactions, and therefore corresponds in its effect to the anti-inflammatory drugs celecoxib and etoricoxib , which u. a. can be used against rheumatism and gout .

Individual evidence

↑ entry to carvacrol in CosIng database of the European Commission, accessed on 21 March 2020th
↑ ^a ^b ^c Entry on Carvacrol. In: Römpp Online . Georg Thieme Verlag, accessed on June 19, 2014.
↑ ^a ^b David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-316.
↑ ^a ^b The Merck Index Twelfth Edition. Merck Research Laboratories, 1996, ISBN 0-911910-12-3 , entry 1923.
↑ ^a ^b Carvacrol data sheet at Sigma-Aldrich , accessed on June 7, 2017 ( PDF ).

↑ ^a ^b ^c Entry on carvacrol in the ChemIDplus database of the United States National Library of Medicine (NLM) .

^ PM Jenner, EC Hagan, Jean M. Taylor, EL Cook, OG Fitzhugh: Food flavors and compounds of related structure I. Acute oral toxicity. In: Food and Cosmetics Toxicology . Vol. 2, 1964, p. 327.

^ GSB Viana, FF Matos, WL Araujo, FJA Matos, AA Craveiro: Essential Oil of Lippia grata: Pharmacological Effects and Main Constituents. In: Quarterly Journal of Crude Drug Research . Vol. 19, 1981, p. 1.

↑ Roger James, John B. Glen: Synthesis, biological evaluation, and preliminary structure-activity considerations of a series of alkylphenols as intravenous anesthetic agents. In: Journal of Medicinal Chemistry . Vol. 23, 1980, p. 1350.

↑ MS Owolabi, L. Lajide, MO Oladimeij, WN Setzer, MC Palazzo, RA Olowu, A. Ogundajo: Volatile constituents and antibacterial screening of the essential oil of Chenopodium ambrosioides L. growing in Nigeria. In: Nat. Prod. Commun. tape 4 , no. 7 , 2009, p. 989-992 , PMID 19731609 .

↑ H. Beyer, W. Walter: Textbook of organic chemistry. S. Hirzel Verlag, Stuttgart 1981, ISBN 3-7776-0356-2 , p. 643.

↑ thymol; Exemption from the Requirement of a Tolerance. In: Federal Register . 71 (11), 2006, pp. 2889-2895.

↑ Harry Auterhoff , Joachim Knabe, Hans-Dieter Höltje: Textbook of pharmaceutical chemistry. Wissenschaftliche Verlagsgesellschaft, Stuttgart 1999, ISBN 3-8047-1645-8 .

↑ S. Kordali, A. Cakir, H. Ozer, R. Cakmakci, M. Kesdek, E. Mete: Antifungal, phytotoxic and insecticidal properties of essential oil isolated from Turkish Origanum acutidens and its three components, carvacrol, thymol and p- cymene. In: J. Bior. Tech. tape 99 , no. 18 , 2008, p. 8788-8795 , doi : 10.1016 / j.biortech.2008.04.048 , PMID 18513954 .

↑ MM Obaidat, JF Frank: Inactivation of Escherichia coli O157: H7 on the Intact and Damaged Portions of Lettuce and Spinach Leaves by Using Allyl Isothiocyanate, Carvacrol, and Cinnamaldehyde in Vapor Phase. In: J. Food Prot. Band 72 , no. 10 , 2009, p. 2046-2055 , PMID 19833026 .

↑ M. Hotta, R. Nakata, M. Katsukawa, K. Hori, S. Takahashi, HJ Inoue: Carvacrol, a component of thyme oil, activates PPARalpha and gamma and suppresses COX-2 expression. In: Lipid Res. 51 (1), Jan 2010, pp. 132-139. PMID 19578162 .

Web links

Commons : Carvacrol - collection of pictures, videos and audio files

[CosIng-1] try to carvacrol in CosIng database of the European Commission, accessed on 21 March 2020th

[Römpp-2] Entry on Carvacrol. In: Römpp Online . Georg Thieme Verlag, accessed on June 19, 2014.

[CRC90_3_316-3] David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-316.

[Merck_12_1923-4] The Merck Index Twelfth Edition. Merck Research Laboratories, 1996, ISBN 0-911910-12-3 , entry 1923.

[Sigma-5] Carvacrol data sheet at Sigma-Aldrich , accessed on June 7, 2017 ( PDF ).

[chemid-6] Entry on carvacrol in the ChemIDplus database of the United States National Library of Medicine (NLM) .

[7] PM Jenner, EC Hagan, Jean M. Taylor, EL Cook, OG Fitzhugh: Food flavors and compounds of related structure I. Acute oral toxicity. In: Food and Cosmetics Toxicology . Vol. 2, 1964, p. 327.

[8] GSB Viana, FF Matos, WL Araujo, FJA Matos, AA Craveiro: Essential Oil of Lippia grata: Pharmacological Effects and Main Constituents. In: Quarterly Journal of Crude Drug Research . Vol. 19, 1981, p. 1.

[9] Roger James, John B. Glen: Synthesis, biological evaluation, and preliminary structure-activity considerations of a series of alkylphenols as intravenous anesthetic agents. In: Journal of Medicinal Chemistry . Vol. 23, 1980, p. 1350.

[Owalabi_2009-10] MS Owolabi, L. Lajide, MO Oladimeij, WN Setzer, MC Palazzo, RA Olowu, A. Ogundajo: Volatile constituents and antibacterial screening of the essential oil of Chenopodium ambrosioides L. growing in Nigeria. In: Nat. Prod. Commun. tape 4 , no. 7 , 2009, p. 989-992 , PMID 19731609 .

[Beyer_Kresol-11] H. Beyer, W. Walter: Textbook of organic chemistry. S. Hirzel Verlag, Stuttgart 1981, ISBN 3-7776-0356-2 , p. 643.

[FR_71_11_2889-12] thymol; Exemption from the Requirement of a Tolerance. In: Federal Register . 71 (11), 2006, pp. 2889-2895.

[13] Harry Auterhoff , Joachim Knabe, Hans-Dieter Höltje: Textbook of pharmaceutical chemistry. Wissenschaftliche Verlagsgesellschaft, Stuttgart 1999, ISBN 3-8047-1645-8 .

[Kordali_2008-14] S. Kordali, A. Cakir, H. Ozer, R. Cakmakci, M. Kesdek, E. Mete: Antifungal, phytotoxic and insecticidal properties of essential oil isolated from Turkish Origanum acutidens and its three components, carvacrol, thymol and p- cymene. In: J. Bior. Tech. tape 99 , no. 18 , 2008, p. 8788-8795 , doi : 10.1016 / j.biortech.2008.04.048 , PMID 18513954 .

[Obaidat_2009-15] MM Obaidat, JF Frank: Inactivation of Escherichia coli O157: H7 on the Intact and Damaged Portions of Lettuce and Spinach Leaves by Using Allyl Isothiocyanate, Carvacrol, and Cinnamaldehyde in Vapor Phase. In: J. Food Prot. Band 72 , no. 10 , 2009, p. 2046-2055 , PMID 19833026 .

[Hotta_2010-16] M. Hotta, R. Nakata, M. Katsukawa, K. Hori, S. Takahashi, HJ Inoue: Carvacrol, a component of thyme oil, activates PPARalpha and gamma and suppresses COX-2 expression. In: Lipid Res. 51 (1), Jan 2010, pp. 132-139. PMID 19578162 .