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Revision as of 13:17, 15 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 475618292 of page Calcium_citrate for the Chem/Drugbox validation project (updated: 'CASNo').  Latest revision as of 13:08, 24 January 2024 edit Maxim Masiutin (talk | contribs)Extended confirmed users, IP block exemptions, Pending changes reviewers31,042 edits Used lowercase "cite" template everywhere for consistency. Added the cs1 style template to denote Vancouver ("vanc") citation style, because references contain "vauthors" attribute to specify the list of authors. 
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{{cs1 config|name-list-style=vanc}}
{{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
| Watchedfields = changed | Watchedfields = changed
| verifiedrevid = 442204959 | verifiedrevid = 476999632
| Name = Calcium citrate | Name = Calcium citrate
| ImageFile1 = Calciumcitrat V2.svg
| ImageFile = Calcium citrate.png
| ImageSize1 = 300px
| ImageSize =
| ImageName = Calcium citrate | ImageCaption1 = 2D structure of calcium citrate
| ImageFile2 = Ca-citrate-tetrahydrate.png
| IUPACName = 2-hydroxy-1,2,3-propane- tricarboxylic acid calcium salt (2:3)
| OtherNames = E333 | ImageSize2 = 261
| ImageCaption2 = Calcium citrate tetrahydrate<ref name=str/>
| Section1 = {{Chembox Identifiers
| ImageFile3 = Calcium citrate.jpg
| SMILES = ...O=C()CC(O)(C()=O)CC(=O).C(=O)C(O)(CC()=O)CC()=O
| ImageSize3 = 240
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ImageCaption3 = Calcium citrate tetrahydrate
| IUPACName = 2-hydroxy-1,2,3-propane-tricarboxylic acid calcium salt (2:3)
| OtherNames = E333, tricalcium dicitrate
|Section1={{Chembox Identifiers
| SMILES = ...O=C()CC(O)(C()=O)CC(=O).C(=O)C(O)(CC()=O)CC()=O
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 12584 | ChemSpiderID = 12584
| ChEBI = 190513
| ChEMBL = 2106123
| EC_number = 212-391-7
| DrugBank = DB11093
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 86117BWO7P
| UNII1_Ref = {{fdacite|correct|FDA}}
| UNII1 = MLM29U2X85
| UNII1_Comment = (tetrahydrate)
| InChI = 1/2C6H8O7.3Ca/c2*7-3(8)1-6(13,5(11)12)2-4(9)10;;;/h2*13H,1-2H2,(H,7,8)(H,9,10)(H,11,12);;;/q;;3*+2/p-6 | InChI = 1/2C6H8O7.3Ca/c2*7-3(8)1-6(13,5(11)12)2-4(9)10;;;/h2*13H,1-2H2,(H,7,8)(H,9,10)(H,11,12);;;/q;;3*+2/p-6
| InChIKey = FNAQSUUGMSOBHW-CYFPFDDLAZ | InChIKey = FNAQSUUGMSOBHW-CYFPFDDLAZ
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = FNAQSUUGMSOBHW-UHFFFAOYSA-H | StdInChIKey = FNAQSUUGMSOBHW-UHFFFAOYSA-H
| CASNo_Ref = {{cascite|correct|??}} | CASNo_Ref = {{cascite|correct|PubChem}}
| CASNo = <!-- blanked - oldvalue: 813-94-5 --> | CASNo = 813-94-5
| CASNo2_Ref = {{cascite|correct|CAS}}
| CASOther = 5785-44-4 (tetrahydrate)
| EINECS = 212-391-7 | CASNo2 = 5785-44-4
| CASNo2_Comment = (tetrahydrate)
| PubChem = 13136 | PubChem = 13136
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| Formula = Ca<sub>3</sub>(C<sub>6</sub>H<sub>5</sub>O<sub>7</sub>)<sub>2</sub> | Formula = Ca<sub>3</sub>(C<sub>6</sub>H<sub>5</sub>O<sub>7</sub>)<sub>2</sub>
| MolarMass = 498.46 g/mol (anhydrous) <br> 570.5 g/mol (tetrahydrate) | MolarMass = 498.4334 g/mol (anhydrous) <br> 570.4945 g/mol (tetrahydrate)
| Appearance = White powder | Appearance = White powder
| Odor = odorless | Odor = odorless
| Density = 1.63 g/cm<sup>3</sup>, solid | Density = 1.63 g/cm<sup>3</sup> (anhydrous)<br> 2.00 g/cm<sup>3</sup> (tetrahydrate)<ref name=str/>
| Solubility = 0.085 g/100 mL (18&nbsp;°C) <br> 0.095 g/100 mL (25&nbsp;°C) | Solubility = 0.85 g/L (18&nbsp;°C) <br> 0.95 g/L (25&nbsp;°C)
| SolubleOther = insoluble in ] | SolubleOther = insoluble in ]
| MeltingPt = 120&nbsp;°C (loses water) | MeltingPt = Decomposes
| BoilingPt = Decomposes | BoilingPt = Decomposes
}} }}
| Section7 = {{Chembox Hazards |Section3={{Chembox Structure
| CrystalStruct = Triclinic (tetrahydrate)
| ExternalMSDS =
| SpaceGroup = P{{overline|1}}, No. 2
| MainHazards = Irritant
| PointGroup =
| LattConst_a = 0.59466(4) nm
| LattConst_b = 1.02247(8) nm
| LattConst_c = 1.66496(13) nm
| LattConst_alpha = 72.213(7)
| LattConst_beta =79.718(7)
| LattConst_gamma =89.791(6)
| LattConst_ref =<ref name=str/>
}}
|Section7={{Chembox Hazards
| MainHazards = Irritant
| NFPA-H = 1
| NFPA-F = 1
| NFPA-R = 0
}} }}
| Section8 = {{Chembox Related |Section8={{Chembox Related
| OtherCations = ] | OtherCations = ]<br />]
| OtherCompounds =
| OtherCpds =}}
}}
}} }}

'''Calcium citrate''' is the ] of ]. It is commonly used as a ] (]), usually as a ], but sometimes for ]. In this sense, it is similar to ]. Calcium citrate is also found in some dietary calcium supplements (e.g. ] or ]). Calcium makes up 24.1% of calcium citrate (anhydrous) and 21.1% of calcium citrate (tetrahydrate) by mass. The tetrahydrate occurs in nature as the mineral ].

==Chemical properties==
Calcium citrate is sparingly soluble in water. Needle-shaped crystals of tricalcium dicitrate tetrahydrate ·2H<sub>2</sub>O were obtained by hydrothermal synthesis. The crystal structure comprises a three-dimensional network in which eightfold coordinated Ca<sup>2+</sup> cations are linked by citrate anions and hydrogen bonds between two non-coordinating crystal water molecules and two coordinating water molecules.<ref name=str>
{{cite journal
| first1= Eberhardt | last1= Herdtweck
| first2= Tobias | last2= Kornprobst
| first3 =Roland | last3=Sieber
| first4 = Leo | last4= Straver
| first5 = Johann | last5= Plank
| title= Crystal Structure, Synthesis, and Properties of tri-Calcium di-Citrate tetra-Hydrate ·2H<sub>2</sub>O
| journal= Zeitschrift für anorganische und allgemeine Chemie| year = 2011| volume= 637| issue= 6| pages= 655–659| doi= 10.1002/zaac.201100088
}}</ref>

==Production==
Calcium citrate is an intermediate in the isolation of ] from the fungal ] process by which citric acid is produced industrially.<ref>{{cite web|url=http://www.lime.org/ENV02/Other802.htm|title=Use of Lime in the Chemical Industry|access-date=2006-11-25|publisher=National Lime Association |archive-url = https://web.archive.org/web/20060929115254/http://www.lime.org/ENV02/Other802.htm |archive-date = 2006-09-29}}</ref> The citric acid in the broth solution is neutralized by ], precipitating insoluble calcium citrate. This is then filtered off from the rest of the broth and washed to give clean calcium citrate.
: 3 Ca(OH)<sub>2(s)</sub> + 2 C<sub>6</sub>H<sub>8</sub>O<sub>7(l)</sub> → Ca<sub>3</sub>(C<sub>6</sub>H<sub>5</sub>O<sub>7</sub>)<sub>2(s)</sub> + 6 H<sub>2</sub>O<sub>(l)</sub>

The calcium citrate thus produced may be sold as-is, or it may be converted to citric acid using dilute sulfuric acid.

== Medical uses ==
It's primarily sold as a ] of calcium.

=== Bioavailability ===
In many individuals, ] of calcium citrate is found to be equal to that of the cheaper ] (CaCO<sub>3</sub>).<ref>
{{cite journal
|vauthors=Heaney RP, Dowell MS, Bierman J, Hale CA, Bendich A | title = Absorbability and cost-effectiveness in calcium supplementation
| journal = ]
| volume = 20
| issue = 3
| pages = 239–46
| date =2001
| doi =10.1080/07315724.2001.10719038
| pmid =11444420
| s2cid = 206488
}}</ref> However, alterations to the digestive tract may change how calcium is digested and absorbed. Unlike calcium carbonate, which is basic and neutralizes ], calcium citrate has no effect on stomach acid.<ref name="hhp">{{cite web|title=What you need to know about calcium|date=9 June 2009|url=http://www.health.harvard.edu/newsweek/What_you_need_to_know_about_calcium.htm|publisher=Harvard Health Publications|access-date=4 August 2014}}</ref>{{Better source needed|reason=The current source is insufficiently reliable (]).|date=May 2023}} Calcium carbonate is harder to digest than calcium citrate,{{r|hhp}} and calcium carbonate carries a risk of "acid rebound" (the stomach overcompensates by producing more acid),{{r|hhp}} so individuals who are sensitive to antacids or who have difficulty producing adequate stomach acid may choose calcium citrate over calcium carbonate for supplementation.

According to a 2009 research into calcium absorption after gastric bypass surgery,<ref>
{{cite journal
| vauthors=Tondapu P, Provost D, Adams-Huet B, Sims T, Chang C, Sakhaee K
| title = Comparison of the Absorption of Calcium Carbonate and Calcium Citrate after Roux-en-Y Gastric Bypass
| journal = Obesity Surgery
| volume = 19
| issue = 9
| pages = 1256–1261
| date =June 2009
| doi = 10.1007/s11695-009-9850-6
| pmid =19437082
| pmc =4469176
}}</ref> calcium citrate may have improved bioavailability over calcium carbonate in Roux-en-Y gastric bypass patients who are taking calcium citrate as a ] after surgery. This is mainly due to the changes related to where calcium absorption occurs in the digestive tract of these individuals.

== See also ==

* ]
* ]

==References==
{{Reflist|2}}

==External links==
*

{{Calcium compounds}}
{{citrus}}

{{DEFAULTSORT:Calcium Citrate}}
]
]
]