Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Calcium citrate: Difference between pages

{{cs1 config|name-list-style=vanc}}

| Verifiedfields = changed

| verifiedrevid = 476999632

| Name = Calcium citrate

| ImageFile1 = Calciumcitrat V2.svg

| ImageSize1 = 300px

| ImageCaption1 = 2D structure of calcium citrate

| ImageFile2 = Ca-citrate-tetrahydrate.png

| ImageSize2 = 261

| ImageCaption2 = Calcium citrate tetrahydrate<ref name=str/>

| ImageFile3 = Calcium citrate.jpg

| ImageSize3 = 240

| 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 = [Ca+2].[Ca+2].[Ca+2].O=C([O-])CC(O)(C([O-])=O)CC(=O)[O-].[O-]C(=O)C(O)(CC([O-])=O)CC([O-])=O

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| 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)

| CASNo_Ref = {{cascite|correct|PubChem}}

| CASNo = 813-94-5

| CASNo2_Ref = {{cascite|correct|CAS}}

| CASNo2 = 5785-44-4

| CASNo2_Comment = (tetrahydrate)

|Section2={{Chembox Properties

| Formula = Ca₃(C₆H₅O₇)₂

| MolarMass = 498.4334 g/mol (anhydrous) <br> 570.4945 g/mol (tetrahydrate)

| Appearance = White powder

| Odor = odorless

| Density = 1.63 g/cm³ (anhydrous)<br> 2.00 g/cm³ (tetrahydrate)<ref name=str/>

| Solubility = 0.85 g/L (18&nbsp;°C) <br> 0.95 g/L (25&nbsp;°C)

| SolubleOther = insoluble in [[ethanol|alcohol]]

| MeltingPt = Decomposes

| BoilingPt = Decomposes

|Section3={{Chembox Structure

| CrystalStruct = Triclinic (tetrahydrate)

| SpaceGroup = P{{overline|1}}, No. 2

| 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

| OtherCations = [[Magnesium citrate]]<br />[[Strontium citrate]]

| OtherCompounds =

}}

'''Calcium citrate''' is the [[calcium salt]] of [[citric acid]]. It is commonly used as a [[food additive]] ([[E number|E333]]), usually as a [[preservative]], but sometimes for [[Flavoring|flavor]]. In this sense, it is similar to [[Trisodium citrate|sodium citrate]]. Calcium citrate is also found in some dietary calcium supplements (e.g. [[Citracal]] or [[Caltrate]]). 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 [[Earlandite]].

==Chemical properties==

Calcium citrate is sparingly soluble in water. Needle-shaped crystals of tricalcium dicitrate tetrahydrate [Ca₃(C₆H₅O₇)₂(H₂O)₂]·2H₂O were obtained by hydrothermal synthesis. The crystal structure comprises a three-dimensional network in which eightfold coordinated Ca²⁺ 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 [Ca₃(C₆H₅O₇)₂(H₂O)₂]·2H₂O

| 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 [[citric acid]] from the fungal [[fermentation]] 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 [[limewater]], 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)_2(s) + 2 C₆H₈O_7(l) → Ca₃(C₆H₅O₇)_2(s) + 6 H₂O_(l)

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 [[food supplement]] of calcium.

=== Bioavailability ===

In many individuals, [[bioavailability]] of calcium citrate is found to be equal to that of the cheaper [[calcium carbonate]] (CaCO₃).<ref>

{{cite journal

|vauthors=Heaney RP, Dowell MS, Bierman J, Hale CA, Bendich A | title = Absorbability and cost-effectiveness in calcium supplementation

| journal = [[Journal of the American College of Nutrition]]

| 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 [[Gastric acid|stomach acid]], 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 ([[WP:NOTRS]]).|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 [[dietary supplement]] after surgery. This is mainly due to the changes related to where calcium absorption occurs in the digestive tract of these individuals.

== See also ==

* [[Calcium gluconate]]

* [[Glucono delta-lactone]]

==References==

{{Reflist|2}}

==External links==

*[http://www.cancer.gov/drugdictionary/?CdrID=41817 National Cancer Institute]

{{Calcium compounds}}

{{citrus}}

{{DEFAULTSORT:Calcium Citrate}}

[[Category:Citrates]]

[[Category:Calcium compounds]]

[[Category:E-number additives]]