Carveol

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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
3D model (JSmol)
1861032
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.507
EC Number
  • 202-757-4
KEGG
MeSH Carveol
RTECS number
  • OS8400000
UNII
  • 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
  • CC(=C)C1CC=C(C)C(O)C1
  • OC1C(=C/CC(/C(=C)C)C1)\C
Properties
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:
GHS07: Exclamation mark
Warning
H315, H319, H335
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)
NFPA 704 four-colored 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).
☒N verify (what is checkY☒N ?)

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
 
 
 
Rightward reaction arrow
 
 
 
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
 
 
 
Rightward reaction arrow
 
 
 
2D representation of the chemical structure of Q27089408.
(+)-trans-carveol

References

  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.
  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.