Fluorooleic acid

Last updated
Fluorooleic acid
Fluorooleic Acid.svg
Names
IUPAC name
(9Z)-18-Fluoro-9-octadecenoic acid
Other names
(Z)-18-fluorooctadec-9-enoic acid
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C18H33FO2/c19-17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-18(20)21/h1-2H,3-17H2,(H,20,21)/b2-1-
    Key: XZCKFYWUUUBKNC-UPHRSURJSA-N
  • C(CCCCF)CCC/C=C\CCCCCCCC(=O)O
Properties
C18H33FO2
Molar mass 300.458 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Fluorooleic acid is a naturally occurring, unsaturated, and fluorinated fatty acid. [1] The Delta notation is 18-F-18:1-delta-9c.

Contents

Natural occurrence

Fluoroleic acid, along with some other ω-fluoro-substituted fatty acids, occurs at about 10–20% in the seed oil of Dichapetalum toxicarium , a plant native to Sierra Leone in West Africa. [2] [3] [4]

Biosynthesis

Unlike many other plants, Dichapetalum toxicarium can accumulate much more fluoride, even when the soil content is not particularly high. In young leaves, this is converted into monofluoroacetate, which is stored in the leaves around the flowers. During seed formation, the fluoroacetate is transferred there and converted into long-chain fluorinated fatty acids, including fluorooleic acid. [5] [6]

Synthesis

One method starts with 8-fluorooctanol, which is first reacted with phosphorus tribromide. The product of this reaction is then reacted with sodium acetylide in xylene/DMF. Then, the reaction takes place with 1-chloro-7-iodoheptane and metallic lithium in liquid ammonia and finally with sodium cyanide in DMSO, yielding the nitrile of fluorooleic acid. This reacts with hydrogen peroxide and potassium hydroxide in acetone to form the amide, and then with potassium hydroxide in ethanol to form the carboxylic acid. The triple bond can be converted into a (Z)-double bond by Lindlar catalyst. [7]

Fluoroleic acid can also be isolated from Dichapetalum toxicarium. A chromatography method optimized for the separation of fluorinated fatty acids has been published. [8]

Toxicology

Fluorooleic acid is responsible for the toxicity of Dichapetalum toxicariumthe fruits, which have been used as rat poison. [9] Oral LD50 values of fluorooleic acid for various animals have been determined; these are 6 mg/kg for rats, 1.5 mg/kg for guinea pigs, 2.5 mg/kg for pigeons, 0.5 mg/kg for rabbits, and 2 mg/kg for sheep. In many cases, death was delayed and sudden, presumably due to cardiac arrest. [10]

See also

References

  1. ↑ "PlantFAdb: 18-F-18:1-delta-9c; 9-Octadecenoic acid, 18-fluoro-, (Z)-; Oleic acid, 18-fluoro-". plantfadb.org. Retrieved 8 April 2025.
  2. ↑ Hamilton, John T. G.; Harper, David B. (1 March 1997). "Fluoro fatty acids in seed oil of Dichapetalum toxicarium" . Phytochemistry . 44 (6): 1129–1132. Bibcode:1997PChem..44.1129H. doi:10.1016/S0031-9422(96)00697-8. ISSN   0031-9422 . Retrieved 8 April 2025.
  3. ↑ Pattison, F. L. M.; Dear, R. E. A. (December 1961). "Synthesis of the Toxic Principle of Dichapetalum toxicarium (18-Fluoro-cis-9-Octadecenoic Acid)" . Nature . 192 (4809): 1284–1285. Bibcode:1961Natur.192.1284P. doi:10.1038/1921284a0. ISSN   1476-4687 . Retrieved 8 April 2025.
  4. ↑ Bégué, Jean-Pierre; Bonnet-Delpon, Daniele (16 May 2008). Bioorganic and Medicinal Chemistry of Fluorine. John Wiley & Sons. p. 100. ISBN   978-0-470-28187-1 . Retrieved 8 April 2025.
  5. ↑ Vickery, B.; Vickery, M. L. (1 June 1972). "Fluoride metabolism in Dichapetalum toxicarium" . Phytochemistry . 11 (6): 1905–1909. Bibcode:1972PChem..11.1905V. doi:10.1016/S0031-9422(00)90151-1. ISSN   0031-9422 . Retrieved 8 April 2025.
  6. ↑ Natural Product Biosynthesis by Microorganisms and Plants Part B. Academic Press. 1 October 2012. p. 221. ISBN   978-0-12-394628-7 . Retrieved 8 April 2025.
  7. ↑ Pattison, F. L. M.; Dear, R. E. A. (December 1961). "Synthesis of the Toxic Principle of Dichapetalum toxicarium (18-Fluoro-cis-9-Octadecenoic Acid)" . Nature . 192 (4809): 1284–1285. Bibcode:1961Natur.192.1284P. doi:10.1038/1921284a0. ISSN   1476-4687 . Retrieved 8 April 2025.
  8. ↑ Hall, R. J. (1 January 1961). "An apparatus for large scale preparative chromatography with especial application to the separation of a long chain fluoro-fatty acid" . Journal of Chromatography A . 5: 93–97. doi:10.1016/S0021-9673(01)92825-0. ISSN   0021-9673 . Retrieved 8 April 2025.
  9. ↑ Neilson, A. H. (3 July 2002). Organofluorines. Springer Science & Business Media. ISBN   978-3-540-42064-4 . Retrieved 8 April 2025.
  10. ↑ Peters, R. A.; Hall, R. J. (1960). "The toxicity to rabbits and some other animals of the fluorofatty acid present in the seeds of Dichapetalum toxicarium" . Journal of the Science of Food and Agriculture . 11 (10): 608–612. Bibcode:1960JSFA...11..608P. doi:10.1002/jsfa.2740111011. ISSN   1097-0010 . Retrieved 8 April 2025.
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