Falcarinol
| Falcarinol | |
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(3S,9Z)-heptadeca-1,9-diene-4,6-diyn-3-ol |
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| Identifiers | |
| CAS number | 21852-80-2  |
| PubChem | 5281149 |
| ChemSpider | 4444589 |
| KEGG | C08450 |
| ChEMBL | CHEMBL71260 |
| Jmol-3D images | Image 1 Image 2 |
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| Properties | |
| Molecular formula | C17H24O |
| Molar mass | 244.37 g mol−1 |
 (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 | |
Falcarinol is a natural pesticide and fatty alcohol found in carrots, red ginseng (Panax ginseng) and ivy. It protects roots from fungal diseases, such as liquorice rot that causes black spots on the roots during storage. Falcarinol is a polyyne with two carbon carbon triple bonds and two double bonds.[1] Falcarinol can cause allergic and irritant contact dermatitis.[2]
It was shown that falcarinol but not falcarindiol acts as covalent cannabinoid CB1 receptor inverse agonist (antagonist) and blocks the effect of anandamide in keratinocytes, leading to pro-allergic effects in human skin.[3]
Falcarinol is thought to reduce the risk of developing cancer, as a research team from the University of Newcastle upon Tyne and Danish Universities found in February 2005 in a study on rats.[4]
[edit] References
- ^ S. G. Yates, R. E. England (1982). "Isolation and analysis of carrot constituents: myristicin, falcarinol, and falcarindiol". Journal of Agricultural and Food Chemistry 30 (2): 317–320. doi:10.1021/jf00110a025.
- ^ S. Machado, E. Silva, A. Massa (2002). "Occupational allergic contact dermatitis from falcarinol". Contact Dermatitis 47 (2): 109–125. doi:10.1034/j.1600-0536.2002.470210_5.x.
- ^ M. Leonti, S. Raduner, L. Casu, F. Cottiglia, C. Floris, KH. Altmann, J. Gertsch (2010). "Falcarinol is a covalent cannabinoid CB1 receptor antagonist and induces pro-allergic effects in skin". Biochemical Pharmacology 79 (12): 1815–1826. doi:10.1016/j.bcp.2010.02.015. PMID 20206138.
- ^ M. Kobæk-Larsen, L. P. Christensen, W. Vach, J. Ritskes-Hoitinga and K. Brandt (2005). "Inhibitory Effects of Feeding with Carrots or (-)-Falcarinol on Development of Azoxymethane-Induced Preneoplastic Lesions in the Rat Colon". Journal of Acricultural and Food Chemistry 53 (5): 1823–1827. doi:10.1021/jf048519s. PMID 15740080.
[edit] External links
- Carrots may help ward off cancer, BBC News
- Cancer boost from whole carrots, BBC News
