Carveol

Carveol

Names
IUPAC name 2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-ol
Systematic IUPAC name 2-Methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-ol[1]
Other names Mentha-6,8-dien-2-ol
Identifiers
CAS Number	99-48-9
3DMet	B04241
Beilstein Reference	1861032
ChEBI	CHEBI:23046
ChEMBL	ChEMBL1908058
ChemSpider	7160 2006207 (5R) 9259214 (5S) 292842 (1R,5R) 391450 (1R,5S)
EC Number	202-757-4
IUPHAR/BPS	6417
Jmol interactive 3D	Image Image
KEGG	C11395
MeSH	Carveol
PubChem	7438 2724032 (5R) 11084068 (5S) 330573 (1R,5R) 443178 (1R,5S)
RTECS number	OS8400000
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	152.24 g·mol^−1
Density	0.958 g cm^−3
Boiling point	226 to 227 °C (439 to 441 °F; 499 to 500 K)
Hazards
EU classification (DSD)	Xi
R-phrases	R36/37/38
S-phrases	S26 S37/39
NFPA 704	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).
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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).^[2]

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.^[3]

References

1. "Carveol". Chemical Entities of Biological Interest. UK: European Bioinformatics Institute.
2. 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.
3. 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.