Carveol
| Carveol | |
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2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-ol |
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2-Methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-ol[1] |
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Other names
Mentha-6,8-dien-2-ol |
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| Identifiers | |
| CAS number | 99-48-9  |
| PubChem | 7438, 2724032 (5R), 11084068 (5S), 330573 (1R,5R), 443178 (1R,5S) |
| ChemSpider | 7160 , 2006207 (5R)  , 9259214 (5S) , 292842 (1R,5R) , 391450 (1R,5S) |
| EC number | 202-757-4 |
| KEGG | C11395 |
| MeSH | Carveol |
| ChEBI | CHEBI:23046 |
| RTECS number | OS8400000 |
| Beilstein Reference | 1861032 |
| 3DMet | B04241 |
| Jmol-3D images | Image 1 Image 2 |
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| 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
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| Flash point | 98 °C (208 °F) |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 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 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]
[edit] References
- ^ "Carveol". Chemical Entities of Biological Interest. UK: European Bioinformatics Institute. https://www.ebi.ac.uk/chebi/searchId.do?chebiId=23046.
- ^ 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. 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.
