Calcium oxalate

Calcium oxalate
Names
IUPAC name
Calcium oxalate
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.008.419
EC Number
  • 209-260-1
KEGG
UNII
  • InChI=1S/C2H2O4.Ca/c3-1(4)2(5)6;/h(H,3,4)(H,5,6);/q;+2/p-2 Y
    Key: QXDMQSPYEZFLGF-UHFFFAOYSA-L Y
  • InChI=1/C2H2O4.Ca/c3-1(4)2(5)6;/h(H,3,4)(H,5,6);/q;+2/p-2
    Key: QXDMQSPYEZFLGF-NUQVWONBAM
  • C(=O)(C(=O)[O-])[O-].[Ca+2]
Properties
CaC2H2O5 (monohydrate)
CaC2O4 (anhydrous)
Molar mass 128.097 g/mol
Appearance white solid
Density 2.20 g/cm3, monohydrate[1]
Melting point 200 °C (392 °F; 473 K) decomposes (monohydrate)
0.61 mg/100 g H2O (20 °C)[2]
2.7 × 10−9 for CaC
2O
4[3]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Harmful, Irritant
GHS labelling:
Warning
H302, H312
P280
NFPA 704 (fire diamond)
2
1
0
Related compounds
Other anions
 Calcium carbonate
Calcium acetate
Calcium formate
Other cations
 Sodium oxalate
Beryllium oxalate
Magnesium oxalate
Strontium oxalate
Barium oxalate
Radium oxalate
Iron(II) oxalate
Iron(III) oxalate
Related compounds
 Oxalic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references
Scanning electron micrograph of the surface of a kidney stone showing tetragonal crystals of Weddellite (calcium oxalate dihydrate) emerging from the amorphous central part of the stone (the horizontal length of the picture represents 0.5 mm of the figured original)

Calcium oxalate (in archaic terminology, oxalate of lime) is a calcium salt of oxalate with the chemical formula CaC2O4·(H2O)x, where x varies from 1 to 3. All forms are colorless or white. The monohydrate occurs naturally as the mineral whewellite, forming envelope-shaped crystals, known in plants as raphides. The rarer dihydrate (mineral: weddellite) and trihydrate (mineral: caoxite) are also recognized. Some foods have high quantities of calcium oxalates and can produce sores and numbing on ingestion and may even be fatal. Tribes with diets that depend highly on fruits and vegetables high in calcium oxalate, such as in Micronesia, reduce the level of it by boiling and cooking them.[4][5] They are a constituent in 76% of human kidney stones.[6] Calcium oxalate is also found in beerstone, a scale that forms on containers used in breweries.

Occurrence

Many plants accumulate calcium oxalate as it has been reported in more than 1000 different genera of plants.[7] The calcium oxalate accumulation is linked to the detoxification of calcium (Ca2+) in the plant.[8]

The poisonous plant dumb cane (Dieffenbachia) contains the substance and on ingestion can prevent speech and be suffocating. It is also found in sorrel, rhubarb (in large quantities in the leaves), cinnamon, turmeric and in species of Oxalis, Araceae, Arum italicum, taro, kiwifruit, tea leaves, agaves, Virginia creeper (Parthenocissus quinquefolia), and Alocasia and in spinach in varying amounts. Plants of the genus Philodendron contain enough calcium oxalate that consumption of parts of the plant can result in uncomfortable symptoms. Insoluble calcium oxalate crystals are found in plant stems, roots, and leaves and produced in idioblasts. Vanilla plants exude calcium oxalates upon harvest of the orchid seed pods and may cause contact contact dermatitis.

Calcium oxalate, as ‘beerstone’, is a brownish precipitate that tends to accumulate within vats, barrels, and other containers used in the brewing of beer. If not removed in a cleaning process, beerstone will leave an unsanitary surface that can harbour microorganisms.[9] Beerstone is composed of calcium and magnesium salts and various organic compounds left over from the brewing process; it promotes the growth of unwanted microorganisms that can adversely affect or even ruin the flavour of a batch of beer.

Calcium oxalate crystals in the urine are the most common constituent of human kidney stones, and calcium oxalate crystal formation is also one of the toxic effects of ethylene glycol poisoning.

Chemical properties

Calcium oxalate is a combination of calcium ions and the conjugate base of oxalic acid, the oxalate anion. Its aqueous solutions are slightly basic because of the basicity of the oxalate ion. The basicity of calcium oxalate is weaker than that of sodium oxalate, due to its lower solubility in water. Solid calcium oxalate hydrate has been characterized by X-ray crystallography. It is a coordination polymer. featuring planar oxalate anions linked to calcium, which also has water ligands.[1]

Medical significance

Calcium oxalate can produce sores and numbing on ingestion and may even be fatal.

Morphology and diagnosis

The monohydrate and dihydrate can be distinguished by the shape of the respective crystals.

  • Calcium oxalate dihydrate crystals are octahedral. A large portion of the crystals in a urine sediment will have this type of morphology, as they can grow at any pH and naturally occur in normal urine.
  • Calcium oxalate monohydrate crystals vary in shape, and can be shaped like dumbbells, spindles, ovals, or picket fences, the last of which is most commonly seen due to ethylene glycol poisoning.[10]
  • Urine microscopy showing calcium oxalate crystals in the urine. The octahedral crystal morphology is clearly visible.
  • Urine microscopy showing a calcium oxalate monohydrate crystal (dumbbell shaped) and a calcium oxalate dihydrate crystal (envelope shaped) along with several erythrocytes.
  • Urine microscopy showing several calcium oxalate monohydrate crystals (dumbbell shaped, some of them clumped) and a calcium oxalate dihydrate crystal (envelope shaped) along with several erythrocytes.
  • Urinary sediment showing several calcium oxalate crystals. 40X

Kidney stones
Calcium oxalate monohydrate stones can be spiculated, resembling the head of a morning star.
Main article: Kidney stone disease § Diagnosis

About 76% of kidney stones are partially or entirely of the calcium oxalate type.[6] They form when urine is persistently saturated with calcium and oxalate. Between 1% and 15% of people globally are affected by kidney stones at some point.[11][12] In 2015, they caused about 16,000 deaths worldwide.[13]

Some of the oxalate in urine is produced by the body. Calcium and oxalate in the diet play a part but are not the only factors that affect the formation of calcium oxalate stones. Dietary oxalate is an organic ion found in many vegetables, fruits, and nuts. Calcium from bone may also play a role in kidney stone formation.

Industrial applications

Calcium oxalate is used in the manufacture of ceramic glazes.[14]

See also

References
  1. S. Deganello (1981). "The Structure of Whewellite, CaC2O4.H2O, at 328 K". Acta Crystallogr. B. 37 (4): 826–829. doi:10.1107/S056774088100441X.
  2. Haynes, W., ed. (2015–2016). Handbook of Chemistry and Physics (96th ed.). CRC Press. p. 4-55.
  3. Euler. "Ksp Table: Solubility product constants near 25 °C". chm.uri.edu. Retrieved 10 June 2021.
  4. Arnold, Michael A. (2014). "Pandanus tectorius S. Parkinson" (PDF). Aggie Horticulture. Texas A&M University. Retrieved 30 September 2020.
  5. Contributors, WebMD Editorial. "Foods High in Oxalates". WebMD. Retrieved 30 January 2022. {{cite web}}: |last= has generic name (help)
  6. Singh, Prince; Enders, Felicity T.; Vaughan, Lisa E.; Bergstralh, Eric J.; Knoedler, John J.; Krambeck, Amy E.; Lieske, John C.; Rule, Andrew D. (October 2015). "Stone Composition Among First-Time Symptomatic Kidney Stone Formers in the Community". Mayo Clinic Proceedings. 90 (10): 1356–1365. doi:10.1016/j.mayocp.2015.07.016. PMC 4593754. PMID 26349951.
  7. Francesci, V.R.; Nakata (2005). "Calcium oxalate in plants: formation and function". Annu Rev Plant Biol. 56 (56): 41–71. doi:10.1146/annurev.arplant.56.032604.144106. PMID 15862089.
  8. Martin, G; Matteo Guggiari; Daniel Bravo; Jakob Zopfi; Guillaume Cailleau; Michel Aragno; Daniel Job; Eric Verrecchia; Pilar Junier (2012). "Fungi, bacteria and soil pH: the oxalate–carbonate pathway as a model for metabolic interaction". Environmental Microbiology. 14 (11): 2960–2970. doi:10.1111/j.1462-2920.2012.02862.x. PMID 22928486.
  9. Ryan, James (27 May 2018). "What is beerstone (and how to remove it)". Retrieved 28 May 2018.
  10. "Urine Crystals". ahdc.vet.cornell.edu/. Cornell University. Retrieved 12 July 2014.
  11. Morgan, Monica S C; Pearle, Margaret S (2016). "Medical management of renal stones". BMJ. 352: i52. doi:10.1136/bmj.i52. ISSN 1756-1833. PMID 26977089. S2CID 28313474.
  12. Abufaraj, Mohammad; Xu, Tianlin; Cao, Chao; Waldhoer, Thomas; Seitz, Christian; d'Andrea, David; Siyam, Abdelmuez; Tarawneh, Rand; Fajkovic, Harun; Schernhammer, Eva; Yang, Lin; Shariat, Shahrokh F. (6 September 2020). "Prevalence and Trends in Kidney Stone Among Adults in the USA: Analyses of National Health and Nutrition Examination Survey 2007–2018 Data". European Urology Focus. doi:10.1016/j.euf.2020.08.011. ISSN 2405-4569. PMID 32900675. S2CID 221572651.
  13. Vos T, Allen C, Arora M, Barber RM, Bhutta ZA, Brown A, et al. (GBD 2015 Disease and Injury Incidence and Prevalence Collaborators) (October 2016). "Global, regional, and national life expectancy, all-cause mortality, and cause-specific mortality for 249 causes of death, 1980–2015: a systematic analysis for the Global Burden of Disease Study 2015". Lancet. 388 (10053): 1459–1544. doi:10.1016/s0140-6736(16)31012-1. PMC 5388903. PMID 27733281.
  14. "Calcium Oxalate Data Sheet". Hummel Croton Inc. Retrieved 23 April 2017.
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