Arsenobetaine

Last updated
Arsenobetaine
ArsenobetainePIC.svg
Arsenobetaine-zwitterion-3D-balls.png
Names
Preferred IUPAC name
(Trimethylarsaniumyl)acetate
Identifiers
3D model (JSmol)
3933180
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.162.654 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 634-697-3
KEGG
MeSH Arsenobetaine
PubChem CID
RTECS number
  • CH9750000
UNII
  • InChI=1S/C5H11AsO2/c1-6(2,3)4-5(7)8/h4H2,1-3H3 X mark.svgN
    Key: SPTHHTGLGVZZRH-UHFFFAOYSA-N X mark.svgN
  • InChI=1/C5H11AsO2/c1-6(2,3)4-5(7)8/h4H2,1-3H3
    Key: SPTHHTGLGVZZRH-UHFFFAOYAQ
  • C[As+](C)(C)CC(=O)[O-]
  • C[As+](C)(C)CC([O-])=O
Properties
C5H11AsO2
Molar mass 177.99/ g.mol−1
Hazards
GHS labelling:
GHS-pictogram-skull.svg GHS-pictogram-pollu.svg
Danger
H301, H331, H410
P261, P264, P270, P271, P273, P301+P310, P304+P340, P311, P321, P330, P391, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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.

Contents

Arsenobetaine is a common substance in marine biological systems and unlike many other organoarsenic compounds, such as trimethylarsine, it is relatively non-toxic. [5] [6] The compound may play a similar role as urea does for nitrogen, as a non-toxic waste compound made in the bodies of animals to dispose of the relevant element.

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. [7]

Safety

Whereas arsenous acid (As(OH)3) has an LD50 (mice) of 34.5 mg/kg (mice), the LD50 for the arsenobetaine exceeds 10 g/kg. [8]

Related Research Articles

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4
ions in the mineral skutterudite. In the +3 oxidation state, arsenic is typically pyramidal owing to the influence of the lone pair of electrons.

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. Gaion A, Sartori D, Scuderi A, Fattorini D (2014). "Bioaccumulation and biotransformation of arsenic compounds in Hediste diversicolor (Muller 1776) after exposure to spiked sediments". Environmental Science and Pollution Research. 21 (9): 5952–5959. doi:10.1007/s11356-014-2538-z. PMID   24458939. S2CID   12568097.
  6. 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. Bibcode:2007ScTEn.379..109B. doi:10.1016/j.scitotenv.2007.02.037. PMID   17434206.
  7. 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.
  8. Cullen, William R.; Reimer, Kenneth J. (1989). "Arsenic speciation in the environment". Chemical Reviews. 89 (4): 713–764. doi:10.1021/cr00094a002. hdl: 10214/2162 .

Further reading