Falcarinol

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Falcarinol
Falcarinol.svg
Names
IUPAC name
(3S,9Z)-Heptadeca-1,9-diene-4,6-diyn-3-ol
Other names
Carotatoxin
Identifiers
21852-80-2 YesY
ChemSpider 4580244 N
Jmol 3D model Interactive image
KEGG C08450 YesY
PubChem 5469789
Properties
C17H24O
Molar mass 244.38 g·mol−1
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
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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  2. Badui (1988). Diccionario de Tecnología de Alimentos. D. F. Mexico: Alhambra Mexicana. ISBN 968-444-071-5.<templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>
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  7. Deshpande (2002). Handbook of Food Toxicology. Hyderabad, India: CRC Press. ISBN 978-0-8247-0760-6.<templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>

External links