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Revision as of 11:28, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 477108233 of page EDDHA for the Chem/Drugbox validation project (updated: 'CASNo').  Latest revision as of 16:02, 21 October 2024 edit JWBE (talk | contribs)Extended confirmed users10,126 edits removed Category:Phenols; added Category:2-Hydroxyphenyl compounds using HotCat 
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
{{chembox {{chembox
| Verifiedfields = changed
| verifiedrevid = 411399870 | verifiedrevid = 477166938
|ImageFile=EDDHA.png | ImageFile=EDDHA.png
|ImageSize=200px | ImageSize=200px
|IUPACName=2-amino]ethylamino]-2-(2-hydroxyphenyl)acetic acid | IUPACName=2-amino]ethylamino]-2-(2-hydroxyphenyl)acetic acid
|OtherNames=Ethylenediamine-''N,N'''-bis(2-hydroxyphenylacetic acid | OtherNames=Ethylenediamine-''N'',''N'''-bis(2-hydroxyphenylacetic acid
|Section1= {{Chembox Identifiers |Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 13782 | ChemSpiderID = 13782
| InChI = 1/C18H20N2O6/c21-13-7-3-1-5-11(13)15(17(23)24)19-9-10-20-16(18(25)26)12-6-2-4-8-14(12)22/h1-8,15-16,19-22H,9-10H2,(H,23,24)(H,25,26) | InChI = 1/C18H20N2O6/c21-13-7-3-1-5-11(13)15(17(23)24)19-9-10-20-16(18(25)26)12-6-2-4-8-14(12)22/h1-8,15-16,19-22H,9-10H2,(H,23,24)(H,25,26)
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = PZZHMLOHNYWKIK-UHFFFAOYSA-N | StdInChIKey = PZZHMLOHNYWKIK-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|??}} | CASNo_Ref = {{cascite|changed|??}}
| CASNo = <!-- blanked - oldvalue: 1170-02-1 --> | CASNo=1170-02-1
| PubChem=14432 | PubChem=14432
| SMILES=C1=CC=C(C(=C1)C(C(=O)O)NCCNC(C2=CC=CC=C2O)C(=O)O)O | SMILES=C1=CC=C(C(=C1)C(C(=O)O)NCCNC(C2=CC=CC=C2O)C(=O)O)O
}} }}
|Section2= {{Chembox Properties |Section2={{Chembox Properties
| C=18 | H=20 | N=2 | O=6
| Formula=C<sub>18</sub>H<sub>20</sub>N<sub>2</sub>O<sub>6</sub>
| Appearance= White solid
| MolarMass=360.3612
| Appearance= | Density=
| Density= | MeltingPt=
| MeltingPt= | BoilingPt=
| BoilingPt= | Solubility=
| Solubility=
}} }}
|Section3= {{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards= | MainHazards=
| FlashPt= | FlashPt=
| AutoignitionPt =
| Autoignition=
}} }}
}} }}

'''EDDHA''' or '''ethylenediamine-''N'',''{{prime|N}}''-bis(2-hydroxyphenylacetic acid)''' is a ]. Like ], it binds metal ions as a ], using two amines, two phenolate centers, and two carboxylates as the six binding sites. The complexes are typically anionic. The ligand itself is a white, water-soluble powder. Both the free ligand and its tetraanionic chelating agent are abbreviated EDDHA. In contrast to EDDHA, most related ] chelating agents feature tertiary amines and few have phenolate groups.

:<sup>−</sup>, which is representative of related C<sub>2</sub>-symmetric complexes.<ref>{{cite journal|author1=Bihari, S. |author2=Smith, P. A. |author3=Parsons, S. |author4=Sadler, P. J. |title=Stereoisomers of Mn(III) Complexes of Ethylenebis|journal=Inorganica Chimica Acta|year=2002|volume=331|pages=310–317|doi=10.1016/S0020-1693(02)00690-4}}</ref>]]{{clear-left}}

==Preparation==
It is produced by the multicomponent reaction of ], ], and ]. In this process, the initial Schiff base condensate alkylates the phenol.<ref>{{cite journal|title=Structure and Fertilizer Properties of Byproducts Formed in the Synthesis of EDDHA|author1=Hernandez-Apaolaza, Lourdes |author2=Garcia-Marco, Sonia |author3=Nadal, Paloma |author4=Lucena, Juan J. |author5=Sierra, Miguel A. |author6=Gomez-Gallego, Mar |author7=Ramirez-Lopez, Pedro |author8=Escudero, Rosa |journal=Journal of Agricultural and Food Chemistry|year=2006|volume=54|issue=12|pages=4355–4363|doi=10.1021/jf0605749|pmid=16756367 }}</ref> Related ligands can be prepared more efficiently using ].<ref>{{cite journal|title=Chelating Agents Related to Ethylenediamine Bis(2-hydroxyphenyl)acetic Acid (EDDHA): Synthesis, Characterization, and Equilibrium Studies of the Free Ligands and Their Mg<sup>2+</sup>, Ca<sup>2+</sup>, Cu<sup>2+</sup>, and Fe<sup>3+</sup> Chelates|author1=Yunta, Felipe |author2=Garcia-Marco, Sonia |author3=Lucena, Juan J. |author4=Gomez-Gallego, Mar |author5=Alcazar, Roberto |author6=Sierra, Miguel A. |journal=Inorganic Chemistry|year=2003|volume=42|issue=17 |pages=5412–5421|doi=10.1021/ic034333j|pmid=12924915}}</ref>

==Uses==
It is used to mobilize metal ions analogously to the use of EDTA.<ref>{{cite journal |vauthors=Diarra MS, Petitclerc D, Lacasse P |title=Response of ''Staphylococcus aureus'' isolates from bovine mastitis to exogenous iron sources |journal=J. Dairy Sci. |volume=85 |issue=9 |pages=2141–8 |year=2002 |pmid=12362445 |doi=10.3168/jds.S0022-0302(02)74292-6|doi-access=free }}</ref><ref>{{cite journal |vauthors=Sritharan M, Asuthkar S |title=Iron-regulated proteins (IRPS) of leptospira biflexa serovar Patoc strain Patoc I |journal=Indian Journal of Medical Microbiology |volume=22 |issue=2 |pages=92–6 |year=2004 |doi=10.1016/S0255-0857(21)02887-5 |pmid=17642703 |doi-access= }}</ref>

EDDHA has been used in ] of lead from contaminated soils.<ref>{{cite journal|title=Phytoremediation of Lead-Contaminated Soils: Role of Synthetic Chelates in Lead Phytoextraction |author1=Huang, Jianwei W. |author2=Chen, Jianjun |author3=Berti, William R. |author4=Cunningham, Scott D. |journal=Environmental Science and Technology|year=1997|volume=31|issue=3|pages=800–805|doi=10.1021/ES9604828|bibcode=1997EnST...31..800H}}</ref> It degrades with release of ].<ref>{{cite journal|title=Is flowering in Lemnaceae stress-induced? A review|author=Pieterse, Arnold H.|journal=Aquatic Botany|year=2013|volume=104|pages=1–4|doi=10.1016/j.aquabot.2012.08.002}}</ref>

==References==
<references/>

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