Carveol

Carveol
IUPAC name 2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-ol
Systematic 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 N
PubChem	7438, 2724032 (5R), 11084068 (5S), 330573 (1R,5R), 443178 (1R,5S)
ChemSpider	7160 N, 2006207 (5R) Y, 9259214 (5S) Y, 292842 (1R,5R) Y, 391450 (1R,5S) Y
EC number	202-757-4
KEGG	C11395 N
MeSH	Carveol
ChEBI	CHEBI:23046 N
RTECS number	OS8400000
Beilstein Reference	1861032
3DMet	B04241
Jmol-3D images	Image 1 Image 2
SMILES CC(=C)C1CC=C(C)C(O)C1 OC1C(=C/CC(/C(=C)C)C1)\C
InChI InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)10(11)6-9/h4,9-11H,1,5-6H2,2-3H3 N Key: BAVONGHXFVOKBV-UHFFFAOYSA-N N InChI=1/C10H16O/c1-7(2)9-5-4-8(3)10(11)6-9/h4,9-11H,1,5-6H2,2-3H3
Properties
Molecular formula	C10H16O
Molar mass	152.23 g mol−1
Exact mass	152.120115134 g mol-1
Density	0.958 g cm-3
Boiling point	226-227 °C, 499-500 K, 439-441 °F
Hazards
EU classification	Xi
R-phrases	R36/37/38
S-phrases	S26 S37/39
NFPA 704	1 1 0
Flash point	98 °C (208 °F)
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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 water and 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. https://www.ebi.ac.uk/chebi/searchId.do?chebiId=23046. 
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. et al. (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.