Calcium oxalate

Last updated

Contents

Calcium oxalate
Calcium oxalate resonance.png
246802-ICSDox.png
Names
IUPAC name
Calcium oxalate
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.008.419 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 209-260-1
KEGG
PubChem CID
UNII
  • InChI=1S/C2H2O4.Ca/c3-1(4)2(5)6;/h(H,3,4)(H,5,6);/q;+2/p-2 Yes check.svgY
    Key: QXDMQSPYEZFLGF-UHFFFAOYSA-L Yes check.svgY
  • 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
CaC2O4
Molar mass 128.096 g·mol−1
Appearancecolourless or white crystals (anhydrous and hydrated forms)
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 CaC2O4 [3]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Harmful, Irritant
GHS labelling:
GHS-pictogram-exclam.svg GHS-pictogram-skull.svg
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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)
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) Surface of a kidney stone.jpg
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 oxalic acid with the chemical formula CaC2O4. It forms hydrates CaC2O4·nH2O, where n varies from 1 to 3. Anhydrous and all hydrated forms are colorless or white. The monohydrate CaC2O4·H2O occurs naturally as the mineral whewellite, forming envelope-shaped crystals, known in plants as raphides. The two rarer hydrates are dihydrate CaC2O4·2H2O, which occurs naturally as the mineral weddellite, and trihydrate CaC2O4·3H2O, which occurs naturally as the 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] Upon decomposition, the calcium oxalate is oxidised by bacteria, fungi, or wildfire to produce the soil nutrient Calcium carbonate. [9]

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 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. [10] 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.

Kidney stones

Spiculated kidney stone.jpg
Head of a morning star.jpg
Calcium oxalate monohydrate stones can be spiculated, resembling the head of a morning star.

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. [12] [13] In 2015, they caused about 16,000 deaths worldwide. [14]

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. [15]

See also

Related Research Articles

Kidney stone disease Formation of mineral stones in the urinary tract

Kidney stone disease, also known as nephrolithiasis or urolithiasis, is a crystallopathy where a solid piece of material develops in the urinary tract. Kidney stones typically form in the kidney and leave the body in the urine stream. A small stone may pass without causing symptoms. If a stone grows to more than 5 millimeters, it can cause blockage of the ureter, resulting in sharp and severe pain in the lower back or abdomen. A stone may also result in blood in the urine, vomiting, or painful urination. About half of people who have had a kidney stone will have another within ten years.

Bladder stone Concretion of material in the urinary bladder

A bladder stone is a stone found in the urinary bladder.

Oxalic acid Simplest dicarboxylic acid

Oxalic acid is an organic acid with the IUPAC name ethanedioic acid and formula HO2C−CO2H. It is the simplest dicarboxylic acid. It is a white crystalline solid that forms a colorless solution in water. Its name comes from the fact that early investigators isolated oxalic acid from flowering plants of the genus Oxalis, commonly known as wood-sorrels. It occurs naturally in many foods, but excessive ingestion of oxalic acid or prolonged skin contact can be dangerous.

Oxalate Any derivative of oxalic acid; chemical compound containing oxalate moiety

Oxalate (IUPAC: ethanedioate) is an anion with the formula C2O42−. This dianion is colorless. It occurs naturally, including in some foods. It forms a variety of salts, for example sodium oxalate (Na2C2O4), and several esters such as dimethyl oxalate (C2O4(CH3)2). It is a conjugate base of oxalic acid. At neutral pH in aqueous solution, oxalic acid converts completely to oxalate.

Weddellite

Weddellite (CaC2O4·2H2O) is a mineral form of calcium oxalate named for occurrences of millimeter-sized crystals found in bottom sediments of the Weddell Sea, off Antarctica. Occasionally, weddellite partially dehydrates to whewellite, forming excellent pseudomorphs of grainy whewellite after weddellite's short tetragonal dipyramids. It was first described in 1942.

Glyoxylic acid Chemical compound

Glyoxylic acid or oxoacetic acid is an organic compound. Together with acetic acid, glycolic acid, and oxalic acid, glyoxylic acid is one of the C2 carboxylic acids. It is a colourless solid that occurs naturally and is useful industrially.

Dicalcium phosphate Chemical compound

Dicalcium phosphate is the calcium phosphate with the formula CaHPO4 and its dihydrate. The "di" prefix in the common name arises because the formation of the HPO42– anion involves the removal of two protons from phosphoric acid, H3PO4. It is also known as dibasic calcium phosphate or calcium monohydrogen phosphate. Dicalcium phosphate is used as a food additive, it is found in some toothpastes as a polishing agent and is a biomaterial.

Feline lower urinary tract disease Any disorder affecting the bladder or urethra of cats

Feline lower urinary tract disease (FLUTD) is a generic category term to describe any disorder affecting the bladder or urethra of cats.

Raphide

Raphides are needle-shaped crystals of calcium oxalate monohydrate or calcium carbonate as aragonite, found in more than 200 families of plants. Both ends are needle-like, but raphides tend to be blunt at one end and sharp at the other.

<i>Oxalis pes-caprae</i> Species of flowering plant in the wood sorrel family

Oxalis pes-caprae is a species of tristylous yellow-flowering plant in the wood sorrel family Oxalidaceae. Oxalis cernua is a less common synonym for this species. Some of the most common names for the plant reference its sour taste owing to oxalic acid present in its tissues. Indigenous to South Africa, the plant has become a pest plant in different parts of the word that is difficult to eradicate because of how it propagates through underground bulbs.

Bladder stone (animal)

Bladder stones or uroliths are a common occurrence in animals, especially in domestic animals such as dogs and cats. Occurrence in other species, including tortoises, has been reported as well. The stones form in the urinary bladder in varying size and numbers secondary to infection, dietary influences, and genetics. Stones can form in any part of the urinary tract in dogs and cats, but unlike in humans, stones of the kidney are less common and do not often cause significant disease, although they can contribute to pyelonephritis and chronic kidney disease. Types of stones include struvite, calcium oxalate, urate, cystine, calcium phosphate, and silicate. Struvite and calcium oxalate stones are by far the most common.

Ethylene glycol poisoning is poisoning caused by drinking ethylene glycol. Early symptoms include intoxication, vomiting and abdominal pain. Later symptoms may include a decreased level of consciousness, headache, and seizures. Long term outcomes may include kidney failure and brain damage. Toxicity and death may occur after drinking even a small amount.

Crystal arthropathy is a class of joint disorder that is characterized by accumulation of tiny crystals in one or more joints. Polarizing microscopy and application of other crystallographic techniques have improved identification of different microcrystals including monosodium urate, calcium pyrophosphate dihydrate, calcium hydroxyapatite, and calcium oxalate.

Druse (botany)

A druse is a group of crystals of calcium oxalate, silicates, or carbonates present in plants, and are thought to be a defense against herbivory due to their toxicity. Calcium oxalate (Ca(COO)2, CaOx) crystals are found in algae, angiosperms and gymnosperms in a total of more than 215 families. These plants accumulate oxalate in the range of 3–80% (w/w) of their dry weight through a biomineralization process in a variety of shapes. Araceae have numerous druses, multi-crystal druses and needle-shaped raphide crystals of CaOx present in the tissue. Druses are also found in leaves and bud scales of Prunus, Rosa, Allium, Vitis, Morus and Phaseolus.

Hydrogenoxalate Ion

Hydrogenoxalate or hydrogen oxalate is an anion with chemical formula HC
2
O
4
or HO
2
C–CO
2
, derived from oxalic acid by the loss of a single proton; or, alternatively, from the oxalate anion C
2
O2−
4
by addition of a proton. The name is also used for any salt containing this anion. Especially in older literature, hydrogenoxalates may also be referred to as bioxalates, acid oxalates, or monobasic oxalates. Hydrogenoxalate is amphoteric, in that it can react both as an acid or a base.

Ammonium oxalate Chemical compound

Ammonium oxalate, C2H8N2O4 – more commonly written as (NH4)2C2O4 – is an oxalate salt with ammonium (sometimes as a monohydrate). It is a colorless (white) salt under standard conditions and is odorless and non-volatile. It is the ammonium salt of oxalic acid, and occurs in many plants and vegetables.

Magnesium oxalate Magnesium compound

Magnesium oxalate is an organic compound comprising a magnesium cation with a 2+ charge bonded to an oxalate anion. It has the chemical formula MgC2O4. Magnesium oxalate is a white solid that comes in two forms: an anhydrous form and a dihydrate form where two water molecules are complexed with the structure. Both forms are practically insoluble in water and are insoluble in organic solutions.

Sodium hydrogenoxalate Partly deprotonated oxalic acid

Sodium hydrogenoxalate is salt of formula NaHC
2
O
4
, consisting of sodium cations Na+
and hydrogenoxalate anions HC
2
O
4
or -. The anion can be described as the result of removing one hydrogen ion H+
from oxalic acid H
2
C
2
O
4
, or adding one to the oxalate anion C
2
O2−
4
.

Crystallopathy is a harmful state or disease associated with the formation and aggregation of crystals in tissues or cavities, or in other words, a heterogeneous group of diseases caused by intrinsic or environmental microparticles or crystals, promoting tissue inflammation and scarring.

Manganese oxalate is a chemical compound, a salt of manganese and oxalic acid with the chemical formula MnC
2
O
4
. The compound creates light pink crystals, does not dissolve in water, and forms crystalline hydrates. It occurs naturally as the mineral Lindbergite.

References

  1. 1 2 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. 1 2 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.[ permanent dead link ]
  9. Parsons, Robert F.; Attiwill, Peter M.; Uren, Nicholas C.; Kopittke, Peter M. (1 April 2022). "Calcium oxalate and calcium cycling in forest ecosystems". Trees. 36 (2): 531–536. doi:10.1007/s00468-021-02226-4. S2CID   239543937.
  10. Ryan, James (27 May 2018). "What is beerstone (and how to remove it)" . Retrieved 28 May 2018.
  11. "Urine Crystals". ahdc.vet.cornell.edu/. Cornell University. Retrieved 12 July 2014.
  12. 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.
  13. 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. 7 (6): 1468–1475. doi:10.1016/j.euf.2020.08.011. ISSN   2405-4569. PMID   32900675. S2CID   221572651.
  14. 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.
  15. "Calcium Oxalate Data Sheet". Hummel Croton Inc. Retrieved 23 April 2017.