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
3DMet B04241
1861032
99-48-9 
ChEBI CHEBI:23046 
ChEMBL ChEMBL1908058 
ChemSpider 7160 
2006207 (5R) Yes
9259214 (5S) Yes
292842 (1R,5R) Yes
391450 (1R,5S) Yes
EC number 202-757-4
Jmol-3D images Image
Image
KEGG C11395 
MeSH Carveol
PubChem 7438
2724032 (5R)
11084068 (5S)
330573 (1R,5R)
443178 (1R,5S)
RTECS number OS8400000
Properties
Molecular formula
 C10H16O
Molar mass 152.23 g·mol−1
Density 0.958 g cm−3
Boiling point 226 °C (439 °F; 499 K)
Hazards
EU classification Xi
R-phrases R36/37/38
S-phrases S26 S37/39
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentine Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
1
1
0
Flash point 98 °C (208 °F; 371 K)
Except where noted otherwise, data is 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.