Calcium citrate: Difference between revisions

Calcium citrate
	; 2D structure of calcium citrate
	; Calcium citrate tetrahydrate
	; Calcium citrate tetrahydrate
Names
	IUPAC name 2-hydroxy-1,2,3-propane-tricarboxylic acid calcium salt (2:3)
	Other names E333, tricalcium dicitrate
Identifiers
CAS Number	813-94-5 [PubChem]; 5785-44-4 (tetrahydrate) ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:190513;
ChEMBL	ChEMBL2106123;
ChemSpider	12584 ;
DrugBank	DB11093;
ECHA InfoCard	100.011.265
EC Number	212-391-7;
E number	E333 (antioxidants, ...)
PubChem CID	13136;
UNII	86117BWO7P ; MLM29U2X85 (tetrahydrate) ;
CompTox Dashboard (EPA)	DTXSID7061148 ;
	InChI InChI=1S/2C6H8O7.3Ca/c27-3(8)1-6(13,5(11)12)2-4(9)10;;;/h213H,1-2H2,(H,7,8)(H,9,10)(H,11,12);;;/q;;3+2/p-6 Key: FNAQSUUGMSOBHW-UHFFFAOYSA-H ; InChI=1/2C6H8O7.3Ca/c27-3(8)1-6(13,5(11)12)2-4(9)10;;;/h213H,1-2H2,(H,7,8)(H,9,10)(H,11,12);;;/q;;3+2/p-6 Key: FNAQSUUGMSOBHW-CYFPFDDLAZ;
	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;
Properties
Chemical formula	Ca3(C6H5O7)2
Molar mass	498.4334 g/mol (anhydrous) ; 570.4945 g/mol (tetrahydrate)
Appearance	White powder
Odor	odorless
Density	1.63 g/cm3 (anhydrous); 2.00 g/cm3 (tetrahydrate)
Melting point	Decomposes
Boiling point	Decomposes
Solubility in water	0.85 g/L (18 °C) ; 0.95 g/L (25 °C)
Solubility	insoluble in alcohol
Structure
Crystal structure	Triclinic (tetrahydrate)
Space group	P1, No. 2
Lattice constant	a = 0.59466(4) nm, b = 1.02247(8) nm, c = 1.66496(13) nm α = 72.213(7)°, β = 79.718(7)°, γ = 89.791(6)°
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Irritant
NFPA 704 (fire diamond)	1 1 0
Related compounds
Other cations	Magnesium citrate; Strontium citrate
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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Calcium citrate is the calcium salt of citric acid. It is commonly used as a food additive (E333), usually as a preservative, but sometimes for flavor. In this sense, it is similar to 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.^[1]

Production

Calcium citrate is an intermediate in the isolation of citric acid from the fungal fermentation process by which citric acid is produced industrially.^[2] 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).^[3] However, alterations to the digestive tract may change how calcium is digested and absorbed. Unlike calcium carbonate, which is basic and neutralizes stomach acid, calcium citrate has no effect on stomach acid.^[4]^{[better source needed]} Calcium carbonate is harder to digest than calcium citrate,^[4] and calcium carbonate carries a risk of "acid rebound" (the stomach overcompensates by producing more acid),^[4] 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,^[5] 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.

References

^ ^a ^b ^c ^d Herdtweck E, Kornprobst T, Sieber R, Straver L, Plank J (2011). "Crystal Structure, Synthesis, and Properties of tri-Calcium di-Citrate tetra-Hydrate [Ca₃(C₆H₅O₇)₂(H₂O)₂]·2H₂O". Zeitschrift für anorganische und allgemeine Chemie. 637 (6): 655–659. doi:10.1002/zaac.201100088.
^ "Use of Lime in the Chemical Industry". National Lime Association. Archived from the original on 2006-09-29. Retrieved 2006-11-25.
^ Heaney RP, Dowell MS, Bierman J, Hale CA, Bendich A (2001). "Absorbability and cost-effectiveness in calcium supplementation". Journal of the American College of Nutrition. 20 (3): 239–46. doi:10.1080/07315724.2001.10719038. PMID 11444420. S2CID 206488.
^ ^a ^b ^c "What you need to know about calcium". Harvard Health Publications. 9 June 2009. Retrieved 4 August 2014.
^ Tondapu P, Provost D, Adams-Huet B, Sims T, Chang C, Sakhaee K (June 2009). "Comparison of the Absorption of Calcium Carbonate and Calcium Citrate after Roux-en-Y Gastric Bypass". Obesity Surgery. 19 (9): 1256–1261. doi:10.1007/s11695-009-9850-6. PMC 4469176. PMID 19437082.

External links

National Cancer Institute

[str-1] Herdtweck E, Kornprobst T, Sieber R, Straver L, Plank J (2011). "Crystal Structure, Synthesis, and Properties of tri-Calcium di-Citrate tetra-Hydrate [Ca₃(C₆H₅O₇)₂(H₂O)₂]·2H₂O". Zeitschrift für anorganische und allgemeine Chemie. 637 (6): 655–659. doi:10.1002/zaac.201100088.

[2] "Use of Lime in the Chemical Industry". National Lime Association. Archived from the original on 2006-09-29. Retrieved 2006-11-25.

[3] Heaney RP, Dowell MS, Bierman J, Hale CA, Bendich A (2001). "Absorbability and cost-effectiveness in calcium supplementation". Journal of the American College of Nutrition. 20 (3): 239–46. doi:10.1080/07315724.2001.10719038. PMID 11444420. S2CID 206488.

[hhp-4] "What you need to know about calcium". Harvard Health Publications. 9 June 2009. Retrieved 4 August 2014.

[5] Tondapu P, Provost D, Adams-Huet B, Sims T, Chang C, Sakhaee K (June 2009). "Comparison of the Absorption of Calcium Carbonate and Calcium Citrate after Roux-en-Y Gastric Bypass". Obesity Surgery. 19 (9): 1256–1261. doi:10.1007/s11695-009-9850-6. PMC 4469176. PMID 19437082.

[1]

[2]

[3]

[4]

[5]

@@ Line 1: / Line 1: @@
+{{cs1 config|name-list-style=vanc}}
 {{chembox
 | Verifiedfields = changed
@@ Line 4: / Line 5: @@
 | verifiedrevid = 476999632
 | Name = Calcium citrate
+| ImageFile1 = Calciumcitrat V2.svg
-| ImageFile = Ca-citrate-tetrahydrate.png
-| ImageSize = 261px
+| ImageSize1 = 300px
+| ImageCaption1 = 2D structure of calcium citrate
-| ImageCaption = Calcium citrate tetrahydrate<ref name=str/>
+| 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
@@ Line 13: / Line 20: @@
 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
 | 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
 | InChIKey = FNAQSUUGMSOBHW-CYFPFDDLAZ
@@ Line 19: / Line 35: @@
 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
 | StdInChIKey = FNAQSUUGMSOBHW-UHFFFAOYSA-H
-| CASNo_Ref = {{cascite|changed|??}}
+| CASNo_Ref = {{cascite|correct|PubChem}}
 | CASNo = 813-94-5
-| CASNo2_Ref = {{cascite|changed|??}}
+| CASNo2_Ref = {{cascite|correct|CAS}}
 | CASNo2 = 5785-44-4
 | CASNo2_Comment = (tetrahydrate)
-| EINECS = 212-391-7
 | PubChem = 13136
   }}
@@ Line 34: / Line 49: @@
 | Density = 1.63 g/cm<sup>3</sup> (anhydrous)<br> 2.00 g/cm<sup>3</sup> (tetrahydrate)<ref name=str/>
 | Solubility = 0.85 g/L (18&nbsp;°C) <br> 0.95 g/L (25&nbsp;°C)
-| SolubleOther = insoluble in [[alcohol]]
+| SolubleOther = insoluble in [[ethanol|alcohol]]
 | MeltingPt = Decomposes
 | BoilingPt = Decomposes
@@ Line 51: / Line 66: @@
 }}
 |Section7={{Chembox Hazards
-| ExternalSDS = [http://physchem.ox.ac.uk/MSDS/CA/calcium_citrate.html External MSDS]
 | MainHazards = Irritant
 | NFPA-H = 1
@@ Line 58: / Line 72: @@
   }}
 |Section8={{Chembox Related
-| OtherCations = [[Sodium citrate]]
+| 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 [[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). 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]].
+'''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 [Ca<sub>3</sub>(C<sub>6</sub>H<sub>5</sub>O<sub>7</sub>)<sub>2</sub>(H<sub>2</sub>O)<sub>2</sub>]·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>
+Calcium citrate is sparingly soluble in water. Needle-shaped crystals of tricalcium dicitrate tetrahydrate [Ca<sub>3</sub>(C<sub>6</sub>H<sub>5</sub>O<sub>7</sub>)<sub>2</sub>(H<sub>2</sub>O)<sub>2</sub>]·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
-| first= Eberhardt | last= Herdtweck
+| first1= Eberhardt | last1= Herdtweck
 | first2= Tobias | last2= Kornprobst
 | first3 =Roland | last3=Sieber
@@ Line 78: / Line 92: @@
 ==Production==
-Calcium citrate is an intermediate in the isolation of [[citric acid]] from the [[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|accessdate=2006-11-25|publisher=National Lime Association |archiveurl = https://web.archive.org/web/20060929115254/http://www.lime.org/ENV02/Other802.htm |archivedate = 2006-09-29}}</ref> The citric acid in the broth solution is neutralized by [[calcium hydroxide]], precipitating insoluble calcium citrate. This is then filtered off from the rest of the broth and washed to give clean calcium citrate.
+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)<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 ==
-==Biological role==
+It's primarily sold as a [[food supplement]] of calcium.
-In many individuals, [[bioavailability]] of calcium citrate is found to be equal to that of the cheaper [[calcium carbonate]].<ref>
+=== Bioavailability ===
+In many individuals, [[bioavailability]] of calcium citrate is found to be equal to that of the cheaper [[calcium carbonate]] (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
+|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
@@ Line 94: / Line 111: @@
 | doi =10.1080/07315724.2001.10719038
 | pmid =11444420
+| s2cid = 206488
-}}| {{PMID|11444420}}</ref> However, alterations to the digestive tract may change how calcium is digested and absorbed. Unlike calcium carbonate, which is basic and neutralizes stomach acid, calcium citrate has no effect on stomach acid.<ref name=hhp>{{cite web|title=What you need to know about calcium|url=http://www.health.harvard.edu/newsweek/What_you_need_to_know_about_calcium.htm|publisher=Harvard Health Publications|accessdate=4 August 2014}}</ref> 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 recent research into calcium absorption after gastric bypass surgery,<ref>
+}}</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
@@ Line 105: / Line 125: @@
 | 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==
@@ Line 119: / Line 145: @@
 [[Category:Citrates]]
 [[Category:Calcium compounds]]
+[[Category:E-number additives]]

v t e Calcium compounds
Hydrogen & halogens	CaH₂ CaF₂ CaCl₂ Ca(ClO)₂ Ca(ClO₃)₂ Ca(ClO₄)₂ CaBr₂ Ca(BrO₃)₂ CaI₂ Ca(IO₃)₂ Ca^ICl
Chalcogens	CaO CaO₂ Ca(OH)₂ CaS CaSO₃ CaH₂S₂O₆ CaSO₄ CaSe
Pnictogens	Ca₃N₂ CaN₆ Ca(NO₂)₂ Ca(NO₃)₂ Ca₃P₂ CaP Ca₄(PO₄)₂O Ca₃(PO₄)₂ CaHPO₄ Ca(H₂PO₄)₂ Ca₂P₂O₇ CaAs Ca₃(AsO₄)₂
Group 13 & 14	CaC₂ Ca(CN)₂ CaCN₂ CaCO₃ Ca(HCO₃)₂ CaSi CaSi₂ Ca₂SiO₄ Ca₃(BO₃)₂ CaAl₂O₄ Ca₃Al₂O₆
Trans metals	Ca(MnO₄)₂ CaCrO₄ CaTiO₃
Organics	CaC₂O₄ Ca(HCO₂)₂ Ca(CH₃CO₂)₂ Ca(C₃H₅O₂)₂ CaC₄H₂O₄ Ca₃(C₆H₅O₇)₂ C₃H₇CaO₆P Ca(C₆H₅O₅S)₂ Ca(C₆H₇O₆)₂ C₁₀H₁₁CaN₄O₈P CaC₁₀H₁₂O₄N₅PO₄ C₁₀H₁₆CaN₂O₈ C₁₂H₂₂CaO₁₄ C₁₄H₂₆CaO₁₆ C₁₈H₃₂CaO₁₉ C₃₆H₇₀CaO₄ C₂₄H₄₀B₂CaO₂₄