Arsenobetaine

Arsenobetaine
Structural formula of arsenobetaine
Ball-and-stick model of arsenobetaine
Names
Preferred IUPAC name
2-Trimethylarsoniumylacetate
Systematic IUPAC name
2-(Trimethylarsaniumyl)acetate
Identifiers
3D model (JSmol)
3933180
ChemSpider
ECHA InfoCard 100.162.654
KEGG
MeSH Arsenobetaine
RTECS number CH9750000
Properties
C5H11AsO2
Molar mass 177.997501013 g mol−1
Hazards
Toxic (T); Dangerous for the environment (N)
R-phrases (outdated) R23/25 R50/53
S-phrases (outdated) S20/21 S28 S45 S60 S61
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

Arsenobetaine is an organoarsenic compound that is the main source of arsenic found in fish.[1][2][3][4] It is the arsenic analog of trimethylglycine, commonly known as betaine. The biochemistry and its biosynthesis are similar to those of choline and betaine.

Arsenobetaine is a common substance in marine biological systems and unlike many other organoarsenic compounds, such as dimethylarsine and trimethylarsine, it is relatively non-toxic.[5]

It has been known since 1920 that marine fish contain organoarsenic compounds, but it was not until 1977 that the chemical structure of the most predominant compound arsenobetaine was determined.[6]

References

  1. ↑ Maher, B. (2005). "Foreword: Research Front — Arsenic Biogeochemistry". Environmental Chemistry. 2 (3): 139–140. doi:10.1071/EN05063.
  2. ↑ Francesconi, K. A. (2005). "Current Perspectives in Arsenic Environmental and Biological Research". Environmental Chemistry. 2 (3): 141–145. doi:10.1071/EN05042.
  3. ↑ Adair, B. M.; Waters, S. B.; Devesa, V.; Drobna, Z.; Styblo, M.; Thomas, D. J. (2005). "Commonalities in Metabolism of Arsenicals". Environmental Chemistry. 2 (3): 161–166. doi:10.1071/EN05054.
  4. ↑ Ng, J. C. (2005). "Environmental Contamination of Arsenic and its Toxicological Impact on Humans". Environmental Chemistry. 2 (3): 146–160. doi:10.1071/EN05062.
  5. ↑ Bhattacharya, P.; Welch, A. H.; Stollenwerk, K. G.; McLaughlin, M. J.; Bundschuh, J.; Panaullah, G. (2007). "Arsenic in the Environment: Biology and Chemistry". Science of the Total Environment. 379 (2–3): 109–120. doi:10.1016/j.scitotenv.2007.02.037. PMID 17434206.
  6. ↑ Edmonds, J. S.; Francesconi, K. A.; Cannon, J. R.; Raston, C. L.; Skelton, B. W.; White, A. H. (1977). "Isolation, Crystal Structure and Synthesis of Arsenobetaine, the Arsenical Constituent of the Western Rock Lobster Panulirus longipes cygnus George". Tetrahedron Letters. 18 (18): 1543–1546. doi:10.1016/S0040-4039(01)93098-9.

Further reading

  • Craig, P. J. (2003). Organometallic Compounds in the Environment (2nd ed.). Chichester: John Wiley and Sons. p. 415. ISBN 978-0-471-89993-8.
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