| Revision as of 13:43, 28 October 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'KEGG', 'StdInChI', 'StdInChIKey', 'CASNo').← Previous edit |
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{{Chembox |
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{{Chembox |
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| ImageFile = ArsenobetainePIC.svg |
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|Watchedfields = changed |
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| ImageSize = 244 |
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|verifiedrevid = 457817360 |
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| ImageName = Structural formula of arsenobetaine |
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|ImageFile = ArsenobetainePIC.svg |
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| PIN = 2-Trimethylarsoniumylacetate |
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|ImageSize = 160 |
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| SystematicName = 2-(Trimethylarsaniumyl)acetate |
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|ImageAlt = Structural formula of arsenobetaine |
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| Section1 = {{Chembox Identifiers |
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|ImageFile1 = Arsenobetaine-zwitterion-3D-balls.png |
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| CASNo = <!-- blanked - oldvalue: 64436-13-1 --> |
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|ImageSize1 = 160 |
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| CASNo_Ref = {{cascite|correct|??}} |
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|ImageAlt1 = Ball-and-stick model of arsenobetaine |
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| PubChem = 47364 |
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|PIN = (Trimethylarsaniumyl)acetate |
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| PubChem_Ref = {{Pubchemcite|correct|PubChem}} |
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|Section1={{Chembox Identifiers |
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| MeSHName = Arsenobetaine |
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|CASNo = 64436-13-1 |
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| RTECS = CH9750000 |
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|CASNo_Ref = {{cascite|correct|CAS}} |
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| Beilstein = 3933180 |
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|PubChem = 47364 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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|MeSHName = Arsenobetaine |
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| KEGG = <!-- blanked - oldvalue: C19331 --> |
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|RTECS = CH9750000 |
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| SMILES = C(C)(C)CC(=O) |
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|Beilstein = 3933180 |
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| SMILES1 = C(C)(C)CC()=O |
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|KEGG_Ref = {{keggcite|correct|kegg}} |
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| StdInChI = <!-- blanked - oldvalue: 1S/C5H11AsO2/c1-6(2,3)4-5(7)8/h4H2,1-3H3 --> |
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|KEGG = C19331 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|ChEMBL = 2448348 |
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| StdInChIKey = <!-- blanked - oldvalue: SPTHHTGLGVZZRH-UHFFFAOYSA-N --> |
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|ChEBI = 82392 |
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|UNII = UWC1LS4V3I |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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|EINECS = 634-697-3 |
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| Section2 = {{Chembox Properties |
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|SMILES = C(C)(C)CC(=O) |
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| C = 5 |
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|SMILES1 = C(C)(C)CC()=O |
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| H = 11 |
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|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| As = 1 |
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|ChemSpiderID = 43109 |
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| O = 2 |
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|InChI = 1/C5H11AsO2/c1-6(2,3)4-5(7)8/h4H2,1-3H3 |
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| MolarMass = 177.997501013 g mol<sup>-1</sup>}} |
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|InChIKey = SPTHHTGLGVZZRH-UHFFFAOYAQ |
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|StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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|StdInChI = 1S/C5H11AsO2/c1-6(2,3)4-5(7)8/h4H2,1-3H3 |
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|StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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|StdInChIKey = SPTHHTGLGVZZRH-UHFFFAOYSA-N}} |
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|Section2={{Chembox Properties |
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|C=5 | H=11 | As=1 | O=2 |
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|MolarMass = 177.99/ g.mol<sup>−1</sup>}} |
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|Section3={{Chembox Hazards |
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|Section3={{Chembox Hazards |
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|GHSPictograms = {{GHS06}}{{GHS09}} |
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| EUClass = Toxic (T); Dangerous for the environment (N) |
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|GHSSignalWord = Danger |
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| RPhrases ={{R23/25}} {{R50/53}} |
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|HPhrases = {{H-phrases|301|331|410}} |
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| SPhrases = {{S20/21}} {{S28}} {{S45}} {{S60}} {{S61}} |
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|PPhrases = {{P-phrases|261|264|270|271|273|301+310|304+340|311|321|330|391|403+233|405|501}} |
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| Autoignition= |
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'''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. |
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'''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. |
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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. |
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Arsenobetaine is a common substance in marine biological systems and unlike many other organoarsenic compounds, such as ] and ], it is relatively non-toxic. |
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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> |
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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> |
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==Safety== |
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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 =713–764 | doi = 10.1021/cr00094a002| hdl = 10214/2162 | hdl-access = free }}</ref> |
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==References== |
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==References== |
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==Further reading== |
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==Further reading== |
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*{{ 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 }} |
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*{{cite journal |
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| title = Organometallic Compounds in the Environment |
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| author = P. J. Craig |
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| publisher = John Wiley and Sons |
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| pages = 415 |
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| year = 2003 |
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| url = http://books.google.com/?id=zdjwlDvtzUYC |
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| isbn = 0471899933 |
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| location = Chichester |
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| unused_data = isbn status = May be invalid - please double check }} |
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