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).^[1]

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.^[2]

Biosynthesis

Monoterpenes such as carveol are produced from geranyl pyrophosphate.^[3] The immediate precursor in plants including peppermint and spearmint is limonene.^[4] Oxidation of the (S) enantiomer by (S)-limonene 6-monooxygenase gives (−)-trans-carveol:

2D representation of the chemical structure of Q27089405.

(S)-limonene

2D representation of the chemical structure of Q27089409.

(−)-trans-carveol

An alternative enzyme, (R)-limonene 6-monooxygenase is present in caraway and gives (+)-trans-carveol.^[5]

2D representation of the chemical structure of Q27888324.

(R)-limonene

2D representation of the chemical structure of Q27089408.

(+)-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.
↑ 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.

[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.

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Biosynthesis

References