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Calcium citrate

From Wikipedia, the free encyclopedia

Calcium citrate
2D structure of calcium citrate
Calcium citrate tetrahydrate[1]
Calcium citrate tetrahydrate
Names
IUPAC name
2-hydroxy-1,2,3-propane-tricarboxylic acid calcium salt (2:3)
Other names
E333, tricalcium dicitrate
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard100.011.265Edit this at Wikidata
EC Number
  • 212-391-7
E numberE333(antioxidants, ...)
UNII
  • InChI=1S/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 checkY
    Key: FNAQSUUGMSOBHW-UHFFFAOYSA-H checkY
  • 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
    Key: FNAQSUUGMSOBHW-CYFPFDDLAZ
  • [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
Ca3(C6H5O7)2
Molar mass498.4334 g/mol (anhydrous)
570.4945 g/mol (tetrahydrate)
AppearanceWhite powder
Odorodorless
Density1.63 g/cm3 (anhydrous)
2.00 g/cm3 (tetrahydrate)[1]
Melting pointDecomposes
Boiling pointDecomposes
0.85 g/L (18 °C)
0.95 g/L (25 °C)
Solubilityinsoluble inalcohol
Structure
Triclinic (tetrahydrate)
P1, No. 2
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)°[1]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Irritant
NFPA 704 (fire diamond)
Related compounds
Othercations
Magnesium citrate
Strontium citrate
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Calcium citrate is thecalcium salt ofcitric acid. It is commonly used as afood additive (E333), usually as apreservative, but sometimes forflavor. In this sense, it is similar tosodium citrate. Calcium citrate is also found in some dietary calcium supplements (e.g.Citracal orCaltrate). 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 mineralEarlandite.

Chemical properties

[edit]

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

[edit]

Calcium citrate is an intermediate in the isolation ofcitric acid from the fungalfermentation process by which citric acid is produced industrially.[2] The citric acid in the broth solution is neutralized bylimewater, 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 C6H8O7(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.[citation needed]

Medical uses

[edit]

It's primarily sold as afood supplement of calcium.[citation needed]

Bioavailability

[edit]

In many individuals,bioavailability of calcium citrate is found to be equal to that of the cheapercalcium carbonate (CaCO3).[3] However, alterations to the digestive tract may change how calcium is digested and absorbed. Unlike calcium carbonate, which is basic and neutralizesstomach 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 adietary 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

[edit]

References

[edit]
  1. ^abcdHerdtweck 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 fromthe original on 2006-09-29. Retrieved2006-11-25.
  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.
  4. ^abc"What you need to know about calcium". Harvard Health Publications. 9 June 2009. Retrieved4 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.

External links

[edit]
Hydrogen & halogens
Chalcogens
Pnictogens
Group 13 & 14
Trans metals
Organics
Truespecies
Majorhybrids
True and hybrid
cultivars
Citrons
Mandarin oranges
Papedas
Pomelos
Kumquats group
Kumquat species
Kumquat hybrids
(×Citrofortunella)
Australian
and Papuan
wild limes group
Eromocitrus
(former genera)
Microcitrus
(former genera)
Clymenia
(former genera)
Oxanthera
(former genera)
Related genera
(perhaps
properlyCitrus)
Drinks
Products
Diseases
Citrus botanists
Citrus production
Related topics
Salts of thecitrate ion
C6H8O7He
Li3C6H5O7BeBC(NH4)3C6H5O7OFNe
Na3C6H5O7
Na2C6H6O7
NaC6H7O7
Mg3(C6H5O7)2
MgC6H6O7
AlC6H5O7SiPSClAr
K3C6H5O7Ca3(C6H5O7)2
CaC6H6O7
Ca(C6H7O7)2
ScTiVCrMnFeC6H6O7
FeC6H5O7
CoNiCu2C6H4O7ZnGaGeAsSeBrKr
RbSrYZrNbMoTcRuRhPdAgCdInSnSbTeIXe
CsBa*LuHfTaWReOsIrPtAuHgTlPb3(C6H5O7)2BiPoAtRn
FrRa**LrRfDbSgBhHsMtDsRgCnNhFlMcLvTsOg
 
*LaCePrNdPmSmEuGdTbDyHoErTmYb
**AcThPaUNpPuAmCmBkCfEsFmMdNo
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