(-)-trans-carveol

Carveol
1R,5R-Carveol.png
(1R,5R)-Carveol
((–)-cis)
1S,5R-Carveol.png
(1S,5R)-Carveol
((–)-trans)
1R,5S-Carveol.png
(1R,5S)-Carveol
((+)-trans)
1S,5S-Carveol.png
(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)
3DMet
1861032
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.507 Edit this at Wikidata
EC Number
  • 202-757-4
KEGG
MeSH Carveol
RTECS number
  • OS8400000
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 pictograms GHS07: Harmful
GHS Signal word Warning
H315, H319, H335
P261, P264, P271, P280, P302+352, P304+340, P305+351+338, P312, P321, P332+313, P337+313, P362, P403+233, P405, P501
NFPA 704 (fire diamond)
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilHealth code 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no codeNFPA 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).
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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).[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]

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.