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Revision as of 11:43, 7 August 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChEBI').← Previous edit		Latest revision as of 18:37, 15 December 2024 edit undoEsculenta (talk | contribs)Autopatrolled, Extended confirmed users58,667 edits added a paragraph about function of calcium oxalate in lichens
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			{{Short description|Calcium salt of oxalic acid}}
			{{Use dmy dates|date=April 2022}}
	{{chembox		{{chembox
	| Watchedfields = changed		|Verifiedfields = changed
			|Watchedfields = changed
	| verifiedrevid = 399703063
			|verifiedrevid = 443496090
	| Name = Calcium oxalate
	| ImageFile = Calcium oxalate resonance.png		|PIN = Calcium oxalate
			|SystematicName = Calcium ethanedioate
	| ImageSize = 200px
			|IUPACName =
	| ImageName = Calcium oxalate
			|OtherNames = Oxalate of lime
	| IUPACName = calcium ethanedioate
			|ImageFile = Calcium oxalate resonance.png
	| Section1 = {{Chembox Identifiers
			|ImageSize = 150px
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
			|ImageName = Calcium oxalate
	| ChemSpiderID = 30549
			|ImageFile1 = 246802-ICSDox.png
	| InChI = 1/C2H2O4.Ca/c3-1(4)2(5)6;/h(H,3,4)(H,5,6);/q;+2/p-2
			|ImageSize1 = 150px
	| InChIKey = QXDMQSPYEZFLGF-NUQVWONBAM
			|ImageName1 = structure of calcium oxalate dihydrate
	| ChEBI = 60579
			|ImageCaption1 = Structure of calcium oxalate dihydrate{{legend|mediumspringgreen|], Ca}}{{legend|grey|], C}}{{legend|red|], O}}{{legend|white|], H}}
	| SMILES = C(=O)(C(=O)).
			|Section1 = {{Chembox Identifiers
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
			|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| StdInChI = 1S/C2H2O4.Ca/c3-1(4)2(5)6;/h(H,3,4)(H,5,6);/q;+2/p-2
			|ChemSpiderID = 30549
	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
			|InChI = 1/C2H2O4.Ca/c3-1(4)2(5)6;/h(H,3,4)(H,5,6);/q;+2/p-2
	| StdInChIKey = QXDMQSPYEZFLGF-UHFFFAOYSA-L
			|InChIKey = QXDMQSPYEZFLGF-NUQVWONBAM
	| CASNo = 25454-23-3
			|ChEBI_Ref = {{ebicite|correct|EBI}}
	| CASOther = (anhydrous)<br>5794-28-5 (monohydrate)
			|ChEMBL = 3184709
	| PubChem = 16212978
			|ChEBI = 60579
			|EINECS = 209-260-1
			|KEGG = C17478
			|SMILES = C(=O)(C(=O)).
			|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
			|StdInChI = 1S/C2H2O4.Ca/c3-1(4)2(5)6;/h(H,3,4)(H,5,6);/q;+2/p-2
			|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
			|StdInChIKey = QXDMQSPYEZFLGF-UHFFFAOYSA-L
			|CASNo_Ref = {{cascite|correct|??}}
			|CASNo = 5794-28-5
			|CASNo_Comment = (monohydrate)
			|CASNo2 = 25454-23-3
			|CASNo2_Comment = (dihydrate)
			|CASNo3 = 192389-49-4
			|CASNo3_Comment = (trihydrate)
			|CASNo2_Ref = {{cascite|changed|??}}
			|UNII_Ref = {{fdacite|correct|FDA}}
			|UNII = 4PP86KK527
			|UNII_Comment = (monohydrate)
			|PubChem = 16212978
	}}		}}
	| Section2 = {{Chembox Properties		|Section2 = {{Chembox Properties
	| Formula = CaC<sub>2</sub>O<sub>4</sub>		|Formula = {{chem2|CaC2O4}}
			|Ca=1|C=2|O=4
	| MolarMass = 128.097 g/mol, anhydrous<br />146.112 g/mol, monohydrate
	| Appearance = white solid		|Appearance = colourless or white crystals (anhydrous and hydrated forms)
	| Density = 2.12 g/cm³, anhydrous<br />2.12 g/cm³, monohydrate		|Density = 2.20 g/cm<sup>3</sup>, monohydrate<ref name=Acta/>
			|Solubility = 0.61 mg/(100 g) {{chem2|H2O}} (20&nbsp;°C)<ref>{{cite book |editor1-last=Haynes |editor1-first=W. |title=Handbook of Chemistry and Physics |date=2015–2016 |publisher=CRC Press |page=4-55 |edition=96th}}</ref>
	| Solubility = 0.00067 g/100 ml (20 °C)
			|SolubilityProduct = 2.7 × 10<sup>−9</sup> for {{chem2|CaC2O4}}<ref name="Euler_Ksp">{{Cite web |title=K<sub>sp</sub> Table: Solubility product constants near 25 °C |author=Euler |work=chm.uri.edu |access-date=10 June 2021 |url= https://www.chm.uri.edu/weuler/chm112/refmater/KspTable.html |language=English}}</ref>
	| MeltingPt = 200°C, decomposes (monohydrate)
			|MeltingPtC = 200
	}}
			|MeltingPt_notes = decomposes (monohydrate)
	}}		}}
			|Section3 = {{Chembox Hazards
	'''Calcium oxalate''' (in archaic terminology, '''oxalate of lime''') is a chemical compound that forms needle-shaped crystals, known in plants as ]. A major constituent of human ], the chemical is also found in beerstone, a scale that forms on containers used in ]. Its chemical formula is CaC<sub>2</sub>O<sub>4</sub> or Ca (COO)<sub>2</sub>.
			|MainHazards = Harmful, Irritant
			|GHSPictograms = {{GHS07}}
			|GHSSignalWord = Warning
			|HPhrases = {{H-phrases|302|312}}
			|PPhrases = {{P-phrases|280}}
			|NFPA-H = 2
			|NFPA-F = 1
			|NFPA-R = 1
			|ExternalSDS =
			}}
			|Section4 = {{Chembox Related
			|OtherCations = ]<br />]<br/>]<br/>]<br/>]<br/>]<br />]<br />]
			|OtherAnions = ]<br />]<br />]
			|OtherCompounds = ]
			}}
			}}
			] (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 ] ] of ] with the chemical formula {{chem2|CaC2O4}} or {{chem2|Ca(COO)2}}. It forms hydrates {{chem2|CaC2O4*''n''H2O}}, where ''n'' varies from 1 to 3. Anhydrous and all hydrated forms are colorless or white. The monohydrate {{chem2|CaC2O4*H2O}} occurs naturally as the mineral ], forming envelope-shaped crystals, known in plants as ]s. The two rarer hydrates are dihydrate {{chem2|CaC2O4*2H2O}}, which occurs naturally as the mineral ], and trihydrate {{chem2|CaC2O4*3H2O}}, which occurs naturally as the mineral ], are also recognized. Some foods have high quantities of calcium oxalates and can produce sores and numbing on ingestion and may even be fatal. Cultural groups with diets that depend highly on fruits and vegetables high in calcium oxalate, such as those in ], reduce the level of it by boiling and cooking them.<ref name=Arno14>{{Citation |mode=cs1 |last1=Arnold |first1=Michael A. |year=2014 |title=''Pandanus tectorius'' S. Parkinson |website=Aggie Horticulture |publisher=Texas A&M University |url=https://aggie-horticulture.tamu.edu/syllabi/206/Lists/Fourth%20Edition/Pandanustectorius.pdf |access-date=30 September 2020 |archive-date=31 August 2021 |archive-url=https://web.archive.org/web/20210831185729/https://aggie-horticulture.tamu.edu/syllabi/206/Lists/Fourth%20Edition/Pandanustectorius.pdf |url-status=dead}}</ref><ref>{{Cite web|author=WebMD Editorial|title=Foods High in Oxalates|url=https://www.webmd.com/diet/foods-high-in-oxalates|access-date=30 January 2022|website=WebMD|language=en}}</ref> They are a constituent in 76% of human ].<ref name="Singh">{{cite journal |last1=Singh |first1=Prince |last2=Enders |first2=Felicity T. |last3=Vaughan |first3=Lisa E. |last4=Bergstralh |first4=Eric J. |last5=Knoedler |first5=John J. |last6=Krambeck |first6=Amy E. |last7=Lieske |first7=John C. |last8=Rule |first8=Andrew D. |title=Stone Composition Among First-Time Symptomatic Kidney Stone Formers in the Community |journal=Mayo Clinic Proceedings |date=October 2015 |volume=90 |issue=10 |pages=1356–1365 |doi=10.1016/j.mayocp.2015.07.016|pmid=26349951 |pmc=4593754}}</ref> Calcium oxalate is also found in beerstone, a scale that forms on containers used in ].
	==Occurrence==		==Occurrence==
			Many plants accumulate calcium oxalate as it has been reported in more than 1000 different genera of plants.<ref>{{cite journal|last=Francesci|first=V.R.|author2=Nakata|title=Calcium oxalate in plants: formation and function|journal=Annu Rev Plant Biol|volume=56|year=2005|issue=56|pages=41–71|doi=10.1146/annurev.arplant.56.032604.144106|pmid=15862089}}</ref> The calcium oxalate accumulation is linked to the detoxification of calcium ({{chem2|Ca(2+)}}) in the plant.<ref>{{cite journal|last=Martin|first=G|author2=Matteo Guggiari|author3=Daniel Bravo|author4=Jakob Zopfi|author5=Guillaume Cailleau|author6=Michel Aragno|author7=Daniel Job|author8=Eric Verrecchia|author9=Pilar Junier|title=Fungi, bacteria and soil pH: the oxalate–carbonate pathway as a model for metabolic interaction|journal=Environmental Microbiology|year=2012|volume=14|issue=11|pages=2960–2970|doi=10.1111/j.1462-2920.2012.02862.x|pmid=22928486|url=https://zenodo.org/record/3436719}}{{Dead link|date=February 2022 |bot=InternetArchiveBot |fix-attempted=yes}}</ref> Upon decomposition, the calcium oxalate is oxidised by bacteria, fungi, or wildfire to produce the soil nutrient ].<ref>{{cite journal |last1=Parsons |first1=Robert F. |last2=Attiwill |first2=Peter M. |last3=Uren |first3=Nicholas C. |last4=Kopittke |first4=Peter M. |title=Calcium oxalate and calcium cycling in forest ecosystems |journal=Trees |date=1 April 2022 |volume=36 |issue=2 |pages=531–536 |doi=10.1007/s00468-021-02226-4 |s2cid=239543937}}</ref>
	Quantities of calcium oxalate are found in many tropical house plants. Calcium oxalate is a poisonous substance that can produce sores and numbing on ingestion and could even be fatal.
	The ]ous plant dumb cane ('']'') contains the substance and on ingestion can prevent speech and be suffocating. It is also found in ] (in large quantities in the leaves) and in species of '']'', '']'', ], ], ] leaves, ]s, and '']'' and in ] in varying amounts. Insoluble calcium oxalate crystals are found in plant stems, roots, and leaves and produced in ]. Kidney stone sufferers should not eat plants high in oxalates.
	]
			The ]ous plant dumb cane ('']'') contains the substance and on ingestion can prevent speech and be suffocating. It is also found in ], ] (in large quantities in the leaves), ], ] and in species of '']'', ], '']'', ], ], tea leaves, ]s, Virginia creeper ('']''), and '']'' and in ] in varying amounts. Plants of the genus '']'' 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 ]s. ] plants exude calcium oxalates upon harvest of the orchid seed pods and may cause ].
	Calcium oxalate, as 'beerstone', is a brownish precipitate that tends to accumulate within vats, barrels and other containers used in the ] of ]. If not completely removed in a cleaning process, beerstone will leave an unsanitary surface that can harbour microorganisms.<ref>{{cite web|url=http://www.birkocorp.com/Brewing/beerstone.html|title=Removing Beerstone|accessdate=2007-08-06|last=Johnson|first=Dana|date=23 March 1998|work=Modern Brewery Age|publisher=Birko Corporation R&D}}</ref> 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 flavor of a batch of beer.
			Calcium oxalate crystals are commonly found in ]s, where they occur in two mineral forms: weddellite (CaC<sub>2</sub>O<sub>4</sub>·(2+x)H<sub>2</sub>O) and whewellite (CaC<sub>2</sub>O<sub>4</sub>·H<sub>2</sub>O). These crystals can form both on the surface of the lichen as a powdery coating called {{lichengloss|pruina}} and within the internal structures of the lichen ]. The type and distribution of these crystals often correlates with environmental conditions: weddellite typically forms in dry environments and can serve as a water source for the lichen, while whewellite is more common in moist habitats. In addition to water regulation, calcium oxalate crystals in lichens serve several protective functions, including shielding against excessive sunlight and potentially helping to neutralize pollutants such as ]. The formation of these crystals is linked to the lichen's ability to dissolve calcium from rocky ] through the production of oxalic acid, with the amount of calcium oxalate often correlating with the calcium content of the substrate on which the lichen grows.<ref name="Wilk & Osyczka 2024">{{cite journal |last1=Wilk |first1=Karina |last2=Osyczka |first2=Piotr |title=Crystalline deposit in lichens: Determination of crystals with regard to practical application in standard taxonomic studies |journal=Acta Mycologica |volume=59 |date=2024-11-14 |doi=10.5586/am/193965 |doi-access=free |pages=1–11}}</ref>
			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.<ref>{{cite web|url=https://www.howtohomebrewbeers.com/2018/05/beerstone-removal.html|title=What is beerstone (and how to remove it)|access-date=28 May 2018|last=Ryan|first=James|date=27 May 2018}}</ref> 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 ], and calcium oxalate crystal formation is also one of the toxic effects of ].		Calcium oxalate crystals in the urine are the most common constituent of human ], and calcium oxalate crystal formation is also one of the toxic effects of ].
			== Chemical properties ==
	Hydrated forms of the compound occur naturally as three mineral species: ] (monohydrate, known from some coal beds), ] (dihydrate) and a very rare trihydrate called caoxite.
			Calcium oxalate is a combination of calcium ions and the conjugate base of ], 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 ], due to its lower solubility in water. Solid calcium oxalate hydrate has been characterized by ]. It is a ] featuring planar oxalate anions linked to calcium, which also has water ]s.<ref name=Acta>{{cite journal|journal=Acta Crystallogr. B|year=1981|volume=37|issue=4|pages=826–829|title=The Structure of Whewellite, CaC<sub>2</sub>O<sub>4</sub><sup>.</sup>H<sub>2</sub>O, at 328 K|author=S. Deganello|doi=10.1107/S056774088100441X|doi-access=}}</ref>
	==Effects of Ingestion==		==Medical significance==
			Calcium oxalate can produce sores and numbing on ingestion and may even be fatal.
	Even a small dose of calcium oxalate is enough to cause intense sensations of burning in the mouth and throat, swelling, and choking that could last for up to two weeks.<ref>. Informa Healthcare.</ref> In greater doses it can cause severe digestive upset, breathing difficulties, coma or even death. Recovery from severe oxalate poisoning is possible, but permanent liver and kidney damage may have occurred.
			===Morphology and diagnosis===
	The stalks of plants in the '']'' genus produce the most severe oxalate reactions. The needle-like oxalate crystals produce pain and swelling when they contact lips, tongue, oral mucosa, conjunctiva, or skin. ] primarily is due to direct trauma from the needle-like crystals and, to a lesser extent, by other plant toxins (e.g., ]s, enzymes).
			The monohydrate and dihydrate can be distinguished by the shape of the respective crystals.
			* Calcium oxalate ''dihydrate'' crystals are ]. 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 ].<ref>{{cite web|title=Urine Crystals|url=https://ahdc.vet.cornell.edu/clinpath/modules/UA-ROUT/crystsed.htm|website=ahdc.vet.cornell.edu/|publisher=Cornell University|access-date=12 July 2014}}</ref>
			<gallery>
			File:Calcium oxalate crystals in urine.jpg|Urine microscopy showing calcium oxalate crystals in the urine. The ] crystal morphology is clearly visible.
			File:Calcium oxalate crystals (urine) - kalsiyum oksalat kristalleri (idrar) - 01.png|Urine microscopy showing a ''calcium oxalate monohydrate'' crystal (dumbbell shaped) and a ''calcium oxalate dihydrate'' crystal (envelope shaped) along with several erythrocytes.
			File:Calcium oxalate crystals (urine) - kalsiyum oksalat kristalleri (idrar) - 02.png|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.
			File:Calcium Oxalate Detail.png|Urinary sediment showing several calcium oxalate crystals. 40X
			File:Urine crystals comparison.png|Comparison of different types of urinary stones.
			File:Histopathology of a breast cyst with calcium oxalate crystals, annotated.jpg|Histopathology of calcium oxalate crystals in a benign breast cyst, H&E stain. In the breast, they can be seen on ] and are usually benign, but can be associated with ].<ref>Image by Mikael Häggström, MD.<br>- Reference for benign/LCIS association: {{cite web|url=https://www.pathologyoutlines.com/topic/breastcalcification.html|title=Microcalcifications|author=Hind Warzecha, M.D.|website=Pathology Outlines}} Last author update: 1 June 2010</ref>
			</gallery>
			===Kidney stones===
	Depending on the plant ingested, mild (Elephant Ear '']'') to more severe (], '']'') can cause compromised airways. One bite on the ''Arisaema'' seed pod will result in immediate swelling and burning. It will take over 12 hours for the swelling to subside.{{Citation needed|date=September 2010}}
			{{multiple image
			| direction = horizontal
			| total_width = 250
			| footer = Calcium oxalate monohydrate stones can be spiculated, resembling the head of a ].
			| image1 = Spiculated kidney stone.jpg
			| image2 = Head of a morning star.jpg
			}}
			{{Main|Kidney stone disease#Diagnosis}}
			About 76% of kidney stones are partially or entirely of the calcium oxalate type.<ref name="Singh"/> 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.<ref name=BMJ2016>{{cite journal|last1=Morgan|first1=Monica S C|last2=Pearle|first2=Margaret S|title=Medical management of renal stones|journal=BMJ|year=2016|volume=352|pages=i52|issn=1756-1833|doi=10.1136/bmj.i52|pmid=26977089|s2cid=28313474}}</ref><ref name=":3">{{Cite journal|date=6 September 2020|title=Prevalence and Trends in Kidney Stone Among Adults in the USA: Analyses of National Health and Nutrition Examination Survey 2007–2018 Data|url=https://www.sciencedirect.com/science/article/abs/pii/S2405456920302248|journal=European Urology Focus|language=en|doi=10.1016/j.euf.2020.08.011|issn=2405-4569|last1=Abufaraj|first1=Mohammad|last2=Xu|first2=Tianlin|last3=Cao|first3=Chao|last4=Waldhoer|first4=Thomas|last5=Seitz|first5=Christian|last6=d'Andrea|first6=David|last7=Siyam|first7=Abdelmuez|last8=Tarawneh|first8=Rand|last9=Fajkovic|first9=Harun|last10=Schernhammer|first10=Eva|last11=Yang|first11=Lin|last12=Shariat|first12=Shahrokh F.|volume=7 |issue=6 |pages=1468–1475 |pmid=32900675|s2cid=221572651|doi-access=free}}</ref> In 2015, they caused about 16,000 deaths worldwide.<ref name=GBD2015De>{{cite journal | vauthors = Vos T, Allen C, Arora M, Barber RM, Bhutta ZA, Brown A, etal | collaboration = GBD 2015 Disease and Injury Incidence and Prevalence Collaborators | title = 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 | journal = Lancet | volume = 388 | issue = 10053 | pages = 1459–1544 | date = October 2016 | pmid = 27733281 | pmc = 5388903 | doi = 10.1016/s0140-6736(16)31012-1}}</ref>
			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.
	===Treatment===
			In one study of modulators of calcium oxalate crystallization in urine, magnesium-] was shown to inhibit CaO{{sub|{{mvar|x}}}} (calcium oxalate) crystallization, “probably via actions of the citrate, but not the Mg.” This was in comparison to magnesium, citrate, and magnesium citrate. Currently the preparation of magnesium-potassium citrate that was used in one positive study is not available in the United States. <ref>{{Cite journal |last1=Schwille |first1=P. O. |last2=Schmiedl |first2=A. |last3=Herrmann |first3=U. |last4=Fan |first4=J. |last5=Gottlieb |first5=D. |last6=Manoharan |first6=M. |last7=Wipplinger |first7=J. |date=1999-05-01 |title=Magnesium, citrate, magnesium citrate and magnesium-alkali citrate as modulators of calcium oxalate crystallization in urine: observations in patients with recurrent idiopathic calcium urolithiasis. |url=https://doi.org/10.1007/s002400050097 |journal=Urological Research |language=en |volume=27 |issue=2 |pages=117–126 |doi=10.1007/s002400050097 |pmid=10424393 |s2cid=1506052 |issn=1434-0879}}</ref>
	Medication administered at the ER may include ], ], or ], all intravenously. Although this most likely will be a localized reaction, it will be treated by the ER as an ] reaction.{{Citation needed|date=September 2010}}
			==Industrial applications==
	==References==
			Calcium oxalate is used in the manufacture of ].<ref name="HummelCrotonDataSheet">{{cite web |url=http://www.hummelcroton.com/datasheet/caox.html |title=Calcium Oxalate Data Sheet|publisher=Hummel Croton Inc. |access-date=23 April 2017}}</ref>
	<references />
	==See also==		==See also==
	*]		* ]
			* ]
			* ]
			==References==
			{{reflist}}
	{{Calcium compounds}}		{{Calcium compounds}}
			{{Oxalates}}
	{{Use dmy dates|date=September 2010}}
			{{Authority control}}
	{{DEFAULTSORT:Calcium Oxalate}}
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