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Revision as of 13:43, 28 October 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,084 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'KEGG', 'StdInChI', 'StdInChIKey', 'CASNo').← Previous edit Latest revision as of 23:07, 31 May 2023 edit undoScyrme (talk | contribs)Extended confirmed users19,963 edits GHS omission rule 
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{{Chembox {{Chembox
|Verifiedfields = changed
⚫ | ImageFile = ArsenobetainePIC.svg
|Watchedfields = changed
⚫ | ImageSize = 244
|verifiedrevid = 457817360
⚫ | ImageName = Structural formula of arsenobetaine
⚫ |ImageFile = ArsenobetainePIC.svg
| PIN = 2-Trimethylarsoniumylacetate
⚫ |ImageSize = 160
⚫ | SystematicName = 2-(Trimethylarsaniumyl)acetate
⚫ |ImageAlt = Structural formula of arsenobetaine
⚫ | Section1 = {{Chembox Identifiers
|ImageFile1 = Arsenobetaine-zwitterion-3D-balls.png
| CASNo = <!-- blanked - oldvalue: 64436-13-1 -->
|ImageSize1 = 160
⚫ | CASNo_Ref = {{cascite|correct|??}}
|ImageAlt1 = Ball-and-stick model of arsenobetaine
⚫ | PubChem = 47364
⚫ |PIN = (Trimethylarsaniumyl)acetate
| PubChem_Ref = {{Pubchemcite|correct|PubChem}}
⚫ |Section1={{Chembox Identifiers
⚫ | MeSHName = Arsenobetaine
|CASNo = 64436-13-1
⚫ | RTECS = CH9750000
⚫ |CASNo_Ref = {{cascite|correct|CAS}}
⚫ | Beilstein = 3933180
⚫ |PubChem = 47364
⚫ | KEGG_Ref = {{keggcite|correct|kegg}}
⚫ |MeSHName = Arsenobetaine
| KEGG = <!-- blanked - oldvalue: C19331 -->
⚫ |RTECS = CH9750000
⚫ | SMILES = C(C)(C)CC(=O)
⚫ |Beilstein = 3933180
⚫ | SMILES1 = C(C)(C)CC()=O
⚫ |KEGG_Ref = {{keggcite|correct|kegg}}
⚫ | StdInChI = <!-- blanked - oldvalue: 1S/C5H11AsO2/c1-6(2,3)4-5(7)8/h4H2,1-3H3 -->
|KEGG = C19331
⚫ | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
|ChEMBL = 2448348
⚫ | StdInChIKey = <!-- blanked - oldvalue: SPTHHTGLGVZZRH-UHFFFAOYSA-N -->
|ChEBI = 82392
}}
|UNII = UWC1LS4V3I
⚫ | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
|EINECS = 634-697-3
⚫ | Section2 = {{Chembox Properties
⚫ |SMILES = C(C)(C)CC(=O)
| C = 5
⚫ |SMILES1 = C(C)(C)CC()=O
| H = 11
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| As = 1
|ChemSpiderID = 43109
| O = 2
|InChI = 1/C5H11AsO2/c1-6(2,3)4-5(7)8/h4H2,1-3H3
⚫ | MolarMass = 177.997501013 g mol<sup>-1</sup>}}
|InChIKey = SPTHHTGLGVZZRH-UHFFFAOYAQ
⚫ |StdInChI_Ref = {{stdinchicite|changed|chemspider}}
⚫ |StdInChI = 1S/C5H11AsO2/c1-6(2,3)4-5(7)8/h4H2,1-3H3
⚫ |StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
⚫ |StdInChIKey = SPTHHTGLGVZZRH-UHFFFAOYSA-N}}
⚫ |Section2={{Chembox Properties
|C=5 | H=11 | As=1 | O=2
⚫ |MolarMass = 177.99/ g.mol<sup>−1</sup>}}
|Section3={{Chembox Hazards |Section3={{Chembox Hazards
|GHSPictograms = {{GHS06}}{{GHS09}}
| EUClass = Toxic (T); Dangerous for the environment (N)
|GHSSignalWord = Danger
| RPhrases ={{R23/25}} {{R50/53}}
|HPhrases = {{H-phrases|301|331|410}}
| SPhrases = {{S20/21}} {{S28}} {{S45}} {{S60}} {{S61}}
|PPhrases = {{P-phrases|261|264|270|271|273|301+310|304+340|311|321|330|391|403+233|405|501}}
| Autoignition=
}} }}
}} }}


'''Arsenobetaine''' is an ] that is the main source of ] found in ].<ref>''Environmental Chemistry'', 2005, Volume 2, Issue 3</ref> It is the arsenic analog of ], commonly known as ]. The biochemistry and its ] are similar to those of ] and betaine. '''Arsenobetaine''' is an ] that is the main source of ] found in ].<ref>{{cite journal | first1 = B. | last1 = Maher | title = Foreword: Research Front — Arsenic Biogeochemistry | journal = Environmental Chemistry | year = 2005 | volume = 2 | issue = 3 | pages= 139–140 | doi = 10.1071/EN05063 | doi-access = free }}</ref><ref>{{cite journal | first1 = K. A. | last1 = Francesconi | title = Current Perspectives in Arsenic Environmental and Biological Research | journal = Environmental Chemistry | year = 2005 | volume = 2 | issue = 3 | pages = 141–145 | doi = 10.1071/EN05042 }}</ref><ref>{{cite journal | first1 = B. M. | last1 = Adair | first2 = S. B. | last2 = Waters | first3 = V. | last3 = Devesa | first4 = Z. | last4 = Drobna | first5 = M. | last5 = Styblo | first6 = D. J. | last6 = Thomas | title = Commonalities in Metabolism of Arsenicals | journal = Environmental Chemistry | year = 2005 | volume = 2 | issue = 3 | pages = 161–166 | doi = 10.1071/EN05054 | url = https://zenodo.org/record/1236044 }}</ref><ref>{{cite journal | first1 = J. C. | last1 = Ng | title = Environmental Contamination of Arsenic and its Toxicological Impact on Humans | journal = Environmental Chemistry | year = 2005 | volume = 2 | issue = 3 | pages = 146–160 | doi = 10.1071/EN05062 }}</ref> It is the arsenic analog of ], commonly known as ]. The biochemistry and its ] are similar to those of ] and betaine.


Arsenobetaine is a common substance in marine biological systems and unlike many other organoarsenic compounds, such as ], it is relatively non-toxic.<ref>{{cite journal |vauthors=Gaion A, Sartori D, Scuderi A, Fattorini D |date=2014 |title=Bioaccumulation and biotransformation of arsenic compounds in Hediste diversicolor (Muller 1776) after exposure to spiked sediments|url=https://link.springer.com/article/10.1007/s11356-014-2538-z|journal=Environmental Science and Pollution Research |volume=21 |issue=9 |pages=5952–5959|doi=10.1007/s11356-014-2538-z|pmid=24458939 |s2cid=12568097 }}</ref><ref>{{cite journal | last1 = Bhattacharya | first1 = P. | last2 = Welch | first2 = A. H. | last3 = Stollenwerk | first3 = K. G. | last4 = McLaughlin | first4 = M. J. | last5 = Bundschuh | first5 = J. | last6 = Panaullah | first6 = G. | title = Arsenic in the Environment: Biology and Chemistry | journal = Science of the Total Environment | year = 2007 | volume = 379 | issue = 2–3 | pages = 109–120 | pmid = 17434206 | doi = 10.1016/j.scitotenv.2007.02.037 | bibcode = 2007ScTEn.379..109B }}</ref> The compound may play a similar role as ] does for nitrogen, as a non-toxic waste compound made in the bodies of animals to dispose of the relevant element.
Arsenobetaine is a common substance in marine biological systems and unlike many other organoarsenic compounds, such as ] and ], it is relatively non-toxic.


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.<ref>{{cite journal | title = Isolation, crystal structure and synthesis of arsenobetaine, the arsenical constituent of the western rock lobster panulirus longipes cygnus George | author = John S. Edmonds, Kevin A. Francesconi, Jack R. Cannon, Colin L. Raston, Brian W. Skelton and Allan H. White | journal = Tetrahedron Letters | volume = 18 | issue = 18 | pages = 1543–1546 | year = 1977 | url = | doi = 10.1016/S0040-4039(01)93098-9 }}</ref> 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.<ref>{{cite journal |author1=Edmonds, J. S. |author2=Francesconi, K. A. |author3=Cannon, J. R. |author4=Raston, C. L. |authorlink4=Colin Raston |author5=Skelton, B. W. |author6=White, A. H. | title = Isolation, Crystal Structure and Synthesis of Arsenobetaine, the Arsenical Constituent of the Western Rock Lobster ''Panulirus longipes cygnus'' George | journal = Tetrahedron Letters | year = 1977 | volume = 18 | issue = 18 | pages = 1543–1546 | doi = 10.1016/S0040-4039(01)93098-9 }}</ref>

==Safety==
Whereas arsenous acid (As(OH)<sub>3</sub>) has an ] (mice) of 34.5 mg/kg (mice), the LD50 for the arsenobetaine exceeds 10 g/kg.<ref name=spec>{{cite journal | title = Arsenic speciation in the environment | first1 = William R. | last1 = Cullen |last2=Reimer|first2=Kenneth J. | journal = Chemical Reviews | year = 1989 | volume = 89 | issue = 4 |pages =713&ndash;764 | doi = 10.1021/cr00094a002| hdl = 10214/2162 | hdl-access = free }}</ref>


==References== ==References==
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==Further reading== ==Further reading==
*{{ cite book | author = Craig, P. J. | title = Organometallic Compounds in the Environment | edition = 2nd | year = 2003 | pages = 415 | isbn = 978-0-471-89993-8 | location = Chichester | publisher = John Wiley and Sons | url = https://books.google.com/books?id=zdjwlDvtzUYC }}
*{{cite journal
| title = Organometallic Compounds in the Environment
| author = P. J. Craig
| publisher = John Wiley and Sons
| pages = 415
| year = 2003
| url = http://books.google.com/?id=zdjwlDvtzUYC
| isbn = 0471899933
| location = Chichester
| unused_data = isbn status = May be invalid - please double check }}



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Latest revision as of 23:07, 31 May 2023

Arsenobetaine
Structural formula of arsenobetaine
Ball-and-stick model of arsenobetaine
Names
Preferred IUPAC name (Trimethylarsaniumyl)acetate
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 3933180
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.162.654 Edit this at Wikidata
EC Number
  • 634-697-3
KEGG
MeSH Arsenobetaine
PubChem CID
RTECS number
  • CH9750000
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C5H11AsO2/c1-6(2,3)4-5(7)8/h4H2,1-3H3Key: SPTHHTGLGVZZRH-UHFFFAOYSA-N
  • InChI=1/C5H11AsO2/c1-6(2,3)4-5(7)8/h4H2,1-3H3Key: SPTHHTGLGVZZRH-UHFFFAOYAQ
SMILES
  • C(C)(C)CC(=O)
  • C(C)(C)CC()=O
Properties
Chemical formula C5H11AsO2
Molar mass 177.99/ g.mol
Hazards
GHS labelling:
Pictograms GHS06: ToxicGHS09: Environmental hazard
Signal word Danger
Hazard statements H301, H331, H410
Precautionary statements 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 , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Arsenobetaine is an organoarsenic compound that is the main source of arsenic found in fish. 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 trimethylarsine, it is relatively non-toxic. 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.

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.

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

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