Falcarinol
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| Names | |
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| IUPAC name
(3S,9Z)-Heptadeca-1,9-diene-4,6-diyn-3-ol
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| Other names
Carotatoxin
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| Identifiers | |
21852-80-2  |
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| ChemSpider | 4580244  |
| Jmol 3D model | Interactive image |
| KEGG | C08450 |
| PubChem | 5469789 |
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| Properties | |
| C17H24O | |
| Molar mass | 244.38 g·mol−1 |
| Vapor pressure | {{{value}}} |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 verify (what is ?) |
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| Infobox references | |
Falcarinol (carotatoxin) is a natural pesticide and fatty alcohol found in carrots (Daucus carota), red ginseng (Panax ginseng) and ivy. In carrots, it occurs in a concentration of approximately 2 mg/kg.[1][2] As a toxin, it protects roots from fungal diseases, such as liquorice rot that causes black spots on the roots during storage.
Chemistry
Falcarinol is a polyyne with two carbon-carbon triple bonds and two double bonds.[3] Falcarinol can cause allergic and irritant contact dermatitis.[4] It is structurally related to the oenanthotoxin and cicutoxin.
Biological effects
It was shown that falcarinol acts as a covalent cannabinoid receptor type 1 inverse agonist and blocks the effect of anandamide in keratinocytes, leading to pro-allergic effects in human skin.[5]
Preliminary research in animal models suggest that falcarinol may have a protective effect against certain types of cancer. Laboratory rats fed a diet containing raw carrots or isolated falcarinol were a third less likely to develop full-scale tumors induced by azoxymethane than those in a control group.[6]
Normal consumption of carrots doesn't cause any toxic effect in humans. However, when falcarinol is delivered in high doses to laboratory animals, it causes neurotoxical problems.[7]
See also
References
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External links
- Carrots may help ward off cancer, BBC News
- Cancer boost from whole carrots, BBC News
