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Revision as of 12:37, 29 November 2010 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: InChI1->InChI StdInChI StdInChIKey.← Previous edit Latest revision as of 00:54, 16 November 2024 edit undoGraeme Bartlett (talk | contribs)Administrators249,716 edits more ids; remove pubchemcids with too much hydrogen 
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{{Short description|Highly soluble organic compound, food ingredient}}
{{Use dmy dates|date=June 2023}}
{{chembox {{chembox
| Verifiedfields = changed
| ImageFile = Ferric ammonium citrate.png
| Watchedfields = changed
| ImageSize = 200px
| ImageFile1=Ammoniumeisen(III)-citrat V7.svg
| ImageSize1=260px
| ImageCaption1 = Structure of ammonium ferric citrate
| ImageFile2=Ammonium ferric citrate dihydrate structure.png
| ImageSize2=260px
| ImageCaption2 = Crystal structure of {{chem2|5*2H2O}}<ref name=str/>
| verifiedrevid = 399508653
| IUPACName = 2-Hydroxypropane-1,2,3-tricarboxylate, ammonium iron(3+) salt | IUPACName = 2-Hydroxypropane-1,2,3-tricarboxylate, ammonium iron(3+) salt
| OtherNames = Ferric ammonium citrate; Ammonium Iron(III) Citrate; Ammonium ferric citrate; Iron ammonium citrate; Prothoate+ | OtherNames = Ferric ammonium citrate<br>Ammonium iron(III) citrate<br> Ammonium ferric citrate<br>Iron ammonium citrate<br>FerriSeltz
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 2338386
| ChemSpiderID = 13804
| ChEBI = 31604
| InChI = 1/C6H8O7.Fe.H3N/c7-3(8)1-6(13,5(11)12)2-4(9)10;;/h13H,1-2H2,(H,7,8)(H,9,10)(H,11,12);;1H3/q;+3;/p-2 | InChI = 1/C6H8O7.Fe.H3N/c7-3(8)1-6(13,5(11)12)2-4(9)10;;/h13H,1-2H2,(H,7,8)(H,9,10)(H,11,12);;1H3/q;+3;/p-2
| InChIKey = FRHBOQMZUOWXQL-NUQVWONBAA | InChIKey = FRHBOQMZUOWXQL-NUQVWONBAA
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C6H8O7.Fe.H3N/c7-3(8)1-6(13,5(11)12)2-4(9)10;;/h13H,1-2H2,(H,7,8)(H,9,10)(H,11,12);;1H3/q;+3;/p-2 | StdInChI = 1S/C6H8O7.Fe.H3N/c7-3(8)1-6(13,5(11)12)2-4(9)10;;/h13H,1-2H2,(H,7,8)(H,9,10)(H,11,12);;1H3/q;+3;/p-2
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = FRHBOQMZUOWXQL-UHFFFAOYSA-L | StdInChIKey = FRHBOQMZUOWXQL-UHFFFAOYSA-L
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 1185-57-5
| EINECS = 214-686-6 | CASNo = 1185-57-5
| UNII_Ref = {{fdacite|correct|FDA}}
| PubChem = 3080636
| UNII = UVP74NG1C5
| SMILES = .O=C()CC(O)(C()=O)CC(=O).
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1200460
| EC_number = 214-686-6
| EINECS =
| PubChem = 14457
| SMILES = C(C(=O))C(CC(=O))(C(=O))O.N.
| MeSHName = | MeSHName =
| KEGG_Ref = <ref>{{cite web | url=http://www.genome.jp/dbget-bin/www_bget?drug:D01644 | title=KEGG DRUG: Ferric ammonium citrate}}</ref>
| ChEBI =
| KEGG = | KEGG =D01644
| ATCCode_prefix = V08
| ATCCode_suffix = CA07
| ATC_Supplemental =
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| Formula = C<sub>6</sub>H<sub>5+4y</sub>Fe<sub>x</sub>N<sub>y</sub>O<sub>7</sub> | Formula = C<sub>6</sub>H<sub>8</sub>O<sub>7</sub>⋅''x''Fe<sup>3+</sup>⋅''y''NH<sub>3</sub>
| MolarMass = Variable | MolarMass =
| Appearance = Reddish-brown powder | Appearance = yellow crystals
| Density = | Density =
| MeltingPt = | MeltingPt =
| BoilingPt = | BoilingPt =
| Solubility = }} | Solubility = }}
| Section3 = {{Chembox Hazards |Section7={{Chembox Hazards
| ExternalMSDS = | ExternalSDS =
| FlashPt = | FlashPt =
| Autoignition = }} | AutoignitionPt = }}
| Section5 = {{Chembox Pharmacology |Section6={{Chembox Pharmacology
| AdminRoutes = | ATCCode_prefix = V08
| Bioavail = | ATCCode_suffix = CA07
| Metabolism = | AdminRoutes =
| HalfLife = | Bioavail =
| Metabolism =
| HalfLife =
| ProteinBound = | ProteinBound =
| Excretion = | Excretion =
| Legal_status = | Legal_status =
| Legal_US = | Legal_US =
| Legal_UK = | Legal_UK =
| Legal_AU = | Legal_AU =
| Legal_CA = | Legal_CA =
| Pregnancy_category =
| PregCat =
| PregCat_AU = | Pregnancy_AU =
}}
| PregCat_US = }}
}} }}
'''Ammonium ferric citrate''' (also known as '''ferric ammonium citrate''' or '''ammoniacal ferrous citrate''') has the formula {{chem2|y}}. The ] in this compound is ]. All three ]s and the central ] of ] are ]. A distinguishing feature of this compound is that it is very soluble in water, in contrast to ] which is not very soluble.<ref>{{Cite web |last=PubChem |title=Ammonium ferric citrate |url=https://pubchem.ncbi.nlm.nih.gov/compound/3080636 |access-date=2022-10-04 |website=pubchem.ncbi.nlm.nih.gov |language=en}}</ref>
{{Refimprove|date=July 2009}}


In its crystal structure each ] of ] has lost four protons. The deprotonated ] and two of the carboxylate groups ligate to the ferric center, while the third carboxylate group coordinates with the ammonium.<ref name=str>
'''Ammonium ferric citrate''' is a ] with ] E381 used as an ].{{Citation needed|date=July 2009}} It is a green or reddish-brown powder which is very soluble in water.
{{cite journal
| first1= M. | last1= Matzapetakis
| first2= C. P. | last2= Raptopoulou
| first3 =A. | last3=Tsohos
| first4 = V. | last4= Papaefthymiou
| first5 = N. | last5= Moon
| first6 = A. | last6= Salifoglou
| title= Synthesis, Spectroscopic and Structural Characterization of the First Mononuclear, Water Soluble Iron−Citrate Complex, (NH<sub>4</sub>)<sub>5</sub>Fe(C<sub>6</sub>H<sub>4</sub>O<sub>7</sub>)<sub>2</sub>·2H<sub>2</sub>O
| journal= J. Am. Chem. Soc.| year = 1998| volume= 120| issue= 50| pages= 13266–13267| doi= 10.1021/ja9807035
}}</ref>


==Uses==
The molecular formula of ammonium iron(III) citrate is variable. It can be prepared by adding Fe(OH)<sub>2</sub> to an aqueous solution of citric acid and ammonia.<ref name=patent>{{US patent|src=uspto|2644828}}</ref> The brown form is approximately 9% NH<sub>3</sub>, 16.5-18.5% Fe, and 65% hydrated citric acid; the green form is approximately 7.5% NH<sub>3</sub>, 14.5-16% Fe, and 75% hydrated citric acid. The green type is more readily reduced by light than the brown.<ref name=merck>{{Merck13th}}</ref>
Ammonium ferric citrate has a range of uses, including:


* As a food ingredient, it has an ] number 381, and is used as an ].<ref>{{Cite web |title=AMMONIUM FERRIC CITRATE |url=https://apps.who.int/food-additives-contaminants-jecfa-database/Home/Chemical/40 |access-date=2022-09-21 |publisher=World Health Organization}}</ref> Most notably used in the Scottish beverage ].
Other uses for ammonium ferric citrate include water purification and printing (]). It is used as a reducing agent of metal salts of low activity like gold and silver and is also in a commonly used recipe with ] to make cyanotype prints. Ammonium ferric citrate is also used in Kligler iron deeps to determine ] production in microbial metabolism.
* Water purification<ref name=":0">{{Cite web |title=Ammonium Ferric Citrate Properties, Molecular Formula, Applications – WorldOfChemicals |url=https://www.worldofchemicals.com/chemicals/chemical-properties/ammonium-ferric-citrate.html |access-date=2022-10-17 |website=worldofchemicals.com}}</ref>

* As a reducing agent of metal salts of low activity like gold and ]<ref name=":0" />
Ammonium ferric citrate is present in Scottish carbonated soft drink ].
* With ] as part of the ] photographic process

* Used in ]'s Iron Agar (KIA) test to identify ] bacteria by observing their metabolism of different sugars, producing ]<ref>{{cite web |last1=Aryal |first1=Sagar |title=Kligler's Iron Agar Test – Procedure, Uses and Interpretation |url=https://microbiologyinfo.com/kliglers-iron-agar-test/ |website=MicrobiologyInfo.com |date=28 November 2018 |access-date=5 November 2021}}</ref>
In medicine, ammonium ferric citrate is used as a ]. It is also used as a ]<ref name=merck>{{Merck13th}}</ref> .
* In medical imaging, ammonium ferric citrate is used as a ].

* As a ]<ref name=merck>{{Merck13th}}</ref>
== Compendial status ==
* ] <ref name=cs>{{cite web
| last = ]
| first =
| authorlink =
| coauthors =
| title = Chemical Substances
| work =
| publisher =
| date =
| url = http://www.tga.gov.au/docs/pdf/aan/aanchem.pdf
| format =
| doi =
| accessdate = 27 July 2009
}}</ref> {{Clarify|date=July 2009}}
{{Expand section|date=July 2009}}


== See also == == See also ==
* ] <ref name=rfse>{{cite web
| last = ]
| first =
| authorlink =
| coauthors =
| title = Revisions to FCC Sixth Edition 2S
| work =
| publisher =
| date =
| url = http://www.usp.org/fcc/2009-06-19_Revisions_to_FCC_2S.html
| doi =
| accessdate = 27 July 2009
}}</ref>
* ] * ]
* ]
* ] * ]


== Notes == == References ==
{{reflist}} {{reflist}}


{{Contrast media}} {{Ammonium salts}}
{{iron compounds}}
{{Contrast media |state=collapsed}}


{{DEFAULTSORT:Ammonium Ferric Citrate}} {{DEFAULTSORT:Ammonium Ferric Citrate}}
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] ]
] ]
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