Calcium propanoate
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 442834022
| Reference = Merck Index, 11th Edition, 1705.
| ImageFile = Calcium propanoate.png
| PIN = Calcium dipropanoate
| OtherNames = Calcium propionate
Calcium dipropionate
Mycoban
| Section1 = {{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo=4075-81-4
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 8AI80040KW
| PubChem=19999
| EINECS =223-795-8
| KEGG = D09875
| SMILES=CCC(=O)[O-].CCC(=O)[O-].[Ca+2]
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 18840
| InChI = 1/2C3H6O2.Ca/c2*1-2-3(4)5;/h2*2H2,1H3,(H,4,5);/q;;+2/p-2
| InChIKey = BCZXFFBUYPCTSJ-NUQVWONBAE
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/2C3H6O2.Ca/c2*1-2-3(4)5;/h2*2H2,1H3,(H,4,5);/q;;+2/p-2
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = BCZXFFBUYPCTSJ-UHFFFAOYSA-L
}}
| Section2 = {{Chembox Properties
| Formula=C6H10CaO4
| MolarMass=186.2192 g/mol
| Appearance =White crystalline solid
| Density=
| MeltingPt=300 °C
| BoilingPt=
| Solubility= 49 g/100 mL (0 °C)
55.8 g/100 mL (100 °C)
| SolubleOther = slightly soluble in methanol, ethanol
insoluble in acetone, benzene
}}
| Section3 = {{Chembox Structure
| CrystalStruct = monoclinic
}}
| Section4 = {{Chembox Hazards
| MainHazards=
| FlashPt=
| AutoignitionPt =
| NFPA-H = 2
| NFPA-F = 1
| NFPA-R = 0
}}
}}
Calcium propanoate or calcium propionate has the formula Ca(C2H5COO)2. It is the calcium salt of propanoic acid.
Uses
As a food additive, it is listed as E number 282 in the Codex Alimentarius. Calcium propionate is used as a preservative in a wide variety of products, including: bread, other baked goods, processed meat, whey, and other dairy products.[http://www.codexalimentarius.net/gsfaonline/additives/details.html?id=306 Codex Alimentarius data for calcium propanoate] {{webarchive|url=https://web.archive.org/web/20061021214228/http://www.codexalimentarius.net/gsfaonline/additives/details.html?id=306 |date=2006-10-21 }} In agriculture, it is used, amongst other things, to prevent milk fever in cows and as a feed supplement.[http://www.ams.usda.gov/NOP/NationalList/TAPReviews/CalciumPropionate.pdf Center for Food and Nutrition Policy review of use of calcium propanoate as an organic agent in cow feed and as milk fever prevention] Propionates prevent microbes from producing the energy they need, like benzoates do. However, unlike benzoates, propionates do not require an acidic environment.{{cite web | title=Ingredients -- Calcium propionate| url=http://sci-toys.com/ingredients/calcium_propionate.html| access-date=2007-03-10}}
Calcium propionate is used in bakery products as a mold inhibitor, typically at 0.1–0.4%{{cite web |url=http://www.nysaes.cornell.edu/necfe/pubs/pdf/Venture/venture3_chemical.html |title=NYSAES|FST|FVC|Venture 3| Chemical Food Preservatives |access-date=2010-02-28 |url-status=dead |archive-url=https://web.archive.org/web/20100412155551/http://www.nysaes.cornell.edu/necfe/pubs/pdf/Venture/venture3_chemical.html |archive-date=2010-04-12 }} (though animal feed may contain up to 1%). Mold contamination is considered a serious problem amongst bakers, and conditions commonly found in baking present near-optimal conditions for mold growth.{{cite web |title=Keeping molds, bacteria at bay |url=http://bakingmanagement.bakery-net.com/article/7448 |archive-url=https://web.archive.org/web/20080320010015/http://bakingmanagement.bakery-net.com/article/7448 |archive-date=2008-03-20 |access-date=2007-03-24}}
A few decades ago, Bacillus mesentericus (rope), was a serious problem,Furia, T. E. (1973). CRC Handbook of Food Additives. CRC Handbook of Food Additives. CRC Press. but today's improved sanitary practices in the bakery, combined with rapid turnover of the finished product, have virtually eliminated this form of spoilage.{{Cite journal |last1=Thompson |first1=Jackie M. |last2=Dodd |first2=Christine E.R. |last3=Waites |first3=Will M. |date=1993 |title=Spoilage of bread by bacillus |url=https://linkinghub.elsevier.com/retrieve/pii/0964830593900395 |journal=International Biodeterioration & Biodegradation |language=en |volume=32 |issue=1–3 |pages=55–66 |doi=10.1016/0964-8305(93)90039-5|bibcode=1993IBiBi..32...55T |url-access=subscription }} Calcium propionate and sodium propionate are effective against both B. mesentericus rope and mold.Furia, T. E. (1973). CRC Handbook of Food Additives. CRC Handbook of Food Additives. CRC Press.
Metabolism of propionate begins with its conversion to propionyl coenzyme A (propionyl-CoA), the usual first step in the metabolism of carboxylic acids. Since propanoic acid has three carbons, propionyl-CoA cannot directly enter the beta oxidation or the citric acid cycles. In most vertebrates, propionyl-CoA is carboxylated to D-methylmalonyl-CoA, which is isomerised to L-methylmalonyl-CoA. A vitamin B12–dependent enzyme catalyzes rearrangement of L-methylmalonyl-CoA to succinyl-CoA, which is an intermediate of the citric acid cycle and can be readily incorporated there.
Children were challenged with calcium propionate or placebo through daily bread in a double-blind placebo-controlled crossover trial. Although there was no significant difference by two measures, a statistically significant difference was found in the proportion of children whose behaviours "worsened" with challenge (52%), compared to the proportion whose behaviour "improved" with challenge (19%).{{cite journal
|author1=S. Dengate |author2=A. Rubin | journal = Journal of Paediatrics and Child Health
| title = Controlled trial of cumulative behavioural effects of a common bread preservative
| year = 2002
| volume = 38
| issue = 4
| pages = 373–376
| doi = 10.1046/j.1440-1754.2002.00009.x
|pmid=12173999 |s2cid=24898218 }} When propanoic acid was infused directly into rodents' brains, it produced reversible behavior changes (e.g. hyperactivity, dystonia, social impairment, perseveration) and brain changes (e.g. innate neuroinflammation, glutathione depletion) partially mimicking human autism.{{cite journal
|author1=D. F. MacFabe |author2=D. P. Cain |author3=K. Rodriguez-Capote |author4=A. E. Franklin |author5=J. E. Hoffman |author6=F. Boon |author7=A. R. Taylor |author8=M. Kavaliers |author9=K.-P. Ossenkopp | journal = Behavioural Brain Research
| title = Neurobiological effects of intraventricular propionic acid in rats: Possible role of short-chain fatty acids on the pathogenesis and characteristics of autism spectrum disorders
| year = 2007
| volume = 176
| issue = 1
| pages = 149–169
| doi = 10.1016/j.bbr.2006.07.025
| pmid=16950524 |s2cid=3054752 }}
Calcium propionate can be used as a fungicide on fruit.{{cite journal | last1 = Biggs | first1 = A. R. | last2 = El-Kholi | first2 = M. M. | last3 = El-Neshawy | first3 = S. | last4 = Nickerson | first4 = R. | title = Effects of Calcium Salts on Growth, Polygalacturonase Activity, and Infection of Peach Fruit by Monilinia fructicola | journal = Plant Disease | volume = 81 | pages = 399–403 | year = 1997 | doi = 10.1094/PDIS.1997.81.4.399 | issue = 4| pmid = 30861823 | doi-access = }}
In a 1973 study reported by the EPA, the waterborne administration of 180 ppm of calcium propionate was found to be slightly toxic to bluegill sunfish.{{cite web|url=http://www.ipmcenters.org/Ecotox/Details.cfm?RecordID=18447|title=OPP PESTICIDE ECOTOXICITY DATABASE - Details - Pesticide: Calcium propionate|publisher=EPA / USDA / NIFA|access-date=2019-01-22|archive-url=https://web.archive.org/web/20190123010651/http://www.ipmcenters.org/Ecotox/Details.cfm?RecordID=18447|archive-date=2019-01-23|url-status=dead}}
In a recent well-designed translational study, human subjects fed 500 mg of calcium propionate twice daily demonstrated a modest decrease in LDL and total cholesterol, without a change in HDL. The study, only eight weeks in length, requires additional studies of both verification and longer duration to demonstrate the clinical value of this chemical. The study identified a novel regulatory circuit that links the gut microbiota metabolite propionic acid (PA), a short-chain fatty acid, with the gut immune system to control intestinal cholesterol homeostasis .{{cite journal |last1=Haghikia |first1=Arash |last2=Zimmermann |first2=Friederike |last3=Schumann |first3=Paul |title=Propionate attenuates atherosclerosis by immune-dependent regulation of intestinal cholesterol metabolism |journal=European Heart Journal |date=7 Feb 2022 |volume=43 |issue=6 |pages=518–533 |doi=10.1093/eurheartj/ehab644 |pmid=34597388 |pmc=9097250 }}
References
{{Reflist}}
External links
- [https://www.cspinet.org/page/chemical-cuisine-food-additive-safety-ratings Center for Science in the Public Interest list of food additives]
{{Calcium compounds}}