Carveol

Carveol
(1R,5R)-Carveol; ((–)-cis)	(1S,5R)-Carveol; ((–)-trans)
(1R,5S)-Carveol; ((+)-trans)	(1S,5S)-Carveol; ((+)-cis)
Names
	Preferred IUPAC name 2-Methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-ol
	Other names 2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-ol; Mentha-6,8-dien-2-ol
Identifiers
CAS Number	99-48-9 ;
3D model (JSmol)	Interactive image; Interactive image;
Beilstein Reference	1861032
ChEBI	CHEBI:23046 ; CHEBI:227; CHEBI:232;
ChEMBL	ChEMBL1385229 ; ChEMBL1907992; ChEMBL1908058;
ChemSpider	7160 ; 2006207 (5R) ; 9259214 (5S) ; 292842 (1R,5R) ; 391450 (1R,5S) ;
ECHA InfoCard	100.002.507
EC Number	202-757-4;
IUPHAR/BPS	6417;
KEGG	C11395 ;
MeSH	Carveol
PubChem CID	7438; 2724032 (5R); 11084068 (5S); 330573 (1R,5R); 443178 (1R,5S);
RTECS number	OS8400000;
UNII	1L9KXT85R9 ;
CompTox Dashboard (EPA)	DTXSID3024736 ;
	InChI InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)10(11)6-9/h4,9-11H,1,5-6H2,2-3H3 Key: BAVONGHXFVOKBV-UHFFFAOYSA-N ; InChI=1/C10H16O/c1-7(2)9-5-4-8(3)10(11)6-9/h4,9-11H,1,5-6H2,2-3H3;
	SMILES CC(=C)C1CC=C(C)C(O)C1; OC1C(=C/CC(/C(=C)C)C1)\C;
Properties
Chemical formula	C10H16O
Molar mass	152.237 g·mol−1
Density	0.958 g cm−3
Boiling point	226 to 227 °C (439 to 441 °F; 499 to 500 K)
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
NFPA 704 (fire diamond)	1 1 0
Flash point	98 °C (208 °F; 371 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Carveol is a natural unsaturated, monocyclic monoterpenoid alcohol that is a constituent of spearmint essential oil in the form of cis-(−)-carveol. It is a colorless fluid soluble in oils, but insoluble in water and has an odor and flavor that resemble those of spearmint and caraway. Consequently, it is used as a fragrance in cosmetics and as a flavor additive in the food industry.

It has been found to exhibit chemoprevention of mammary carcinogenesis (prevents breast cancer).

An alpha-trans-dihydroxy derivative, (1R,2R,6S)-3-methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2-diol, possesses potent antiparkinsonian activity in animal models.

Biosynthesis

Monoterpenes such as carveol are produced from geranyl pyrophosphate. The immediate precursor in plants including peppermint and spearmint is limonene. Oxidation of the (S) enantiomer by (S)-limonene 6-monooxygenase gives (−)-trans-carveol:

(S)-limonene

(−)-trans-carveol

An alternative enzyme, (R)-limonene 6-monooxygenase is present in caraway and gives (+)-trans-carveol.

(R)-limonene

(+)-trans-carveol

References

↑ Crowell, PL; Kennan, WS; Haag, JD; Ahmad, S; Vedejs, E; Gould, MN (1992). "Chemoprevention of mammary carcinogenesis by hydroxylated derivatives of d-limonene". Carcinogenesis. 13 (7): 1261–4. doi:10.1093/carcin/13.7.1261. PMID 1638695.
↑ Ardashov, Oleg V.; Pavlova, Alla V.; Il’Ina, Irina V.; Morozova, Ekaterina A.; Korchagina, Dina V.; Karpova, Elena V.; Volcho, Konstantin P.; Tolstikova, Tat’Yana G.; Salakhutdinov, Nariman F. (2011). "Highly Potent Activity of (1R,2R,6S)-3-Methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2-diol in Animal Models of Parkinson's Disease". Journal of Medicinal Chemistry. 54 (11): 3866–3874. doi:10.1021/jm2001579. PMID 21534547.
↑ Davis, Edward M.; Croteau, Rodney (2000). "Cyclization Enzymes in the Biosynthesis of Monoterpenes, Sesquiterpenes, and Diterpenes". Topics in Current Chemistry. 209: 53–95. doi:10.1007/3-540-48146-X_2. ISBN 978-3-540-66573-1.{{cite journal}}: CS1 maint: periodical has ISBN (link)
↑ Karp F, Mihaliak CA, Harris JL, Croteau R (1990). "Monoterpene biosynthesis: specificity of the hydroxylations of (−)-limonene by enzyme preparations from peppermint (Mentha piperita), spearmint (Mentha spicata), and perilla (Perilla frutescens) leaves". Arch. Biochem. Biophys. 276 (1): 219–26. doi:10.1016/0003-9861(90)90029-X. PMID 2297225.
↑ Croteau R (1999). "Cytochrome P-450 dependent (+)-limonene-6-hydroxylation in fruits of caraway (Carum Carvi)". Phytochemistry. 50 (2): 243–248. doi:10.1016/S0031-9422(98)00516-0.

[1] Crowell, PL; Kennan, WS; Haag, JD; Ahmad, S; Vedejs, E; Gould, MN (1992). "Chemoprevention of mammary carcinogenesis by hydroxylated derivatives of d-limonene". Carcinogenesis. 13 (7): 1261–4. doi:10.1093/carcin/13.7.1261. PMID 1638695.

[2] Ardashov, Oleg V.; Pavlova, Alla V.; Il’Ina, Irina V.; Morozova, Ekaterina A.; Korchagina, Dina V.; Karpova, Elena V.; Volcho, Konstantin P.; Tolstikova, Tat’Yana G.; Salakhutdinov, Nariman F. (2011). "Highly Potent Activity of (1R,2R,6S)-3-Methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2-diol in Animal Models of Parkinson's Disease". Journal of Medicinal Chemistry. 54 (11): 3866–3874. doi:10.1021/jm2001579. PMID 21534547.

[3] Davis, Edward M.; Croteau, Rodney (2000). "Cyclization Enzymes in the Biosynthesis of Monoterpenes, Sesquiterpenes, and Diterpenes". Topics in Current Chemistry. 209: 53–95. doi:10.1007/3-540-48146-X_2. ISBN 978-3-540-66573-1.{{cite journal}}: CS1 maint: periodical has ISBN (link)

[Karp-4] Karp F, Mihaliak CA, Harris JL, Croteau R (1990). "Monoterpene biosynthesis: specificity of the hydroxylations of (−)-limonene by enzyme preparations from peppermint (Mentha piperita), spearmint (Mentha spicata), and perilla (Perilla frutescens) leaves". Arch. Biochem. Biophys. 276 (1): 219–26. doi:10.1016/0003-9861(90)90029-X. PMID 2297225.

[5] Croteau R (1999). "Cytochrome P-450 dependent (+)-limonene-6-hydroxylation in fruits of caraway (Carum Carvi)". Phytochemistry. 50 (2): 243–248. doi:10.1016/S0031-9422(98)00516-0.