Calcium propanoate (original) (raw)

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Calcium propanoate[1]
Names
Preferred IUPAC name Calcium dipropanoate
Other namesCalcium propionateCalcium dipropionateMycoban
Identifiers
CAS Number 4075-81-4 checkY
3D model (JSmol) Interactive image
ChemSpider 18840 ☒N
ECHA InfoCard 100.021.633 Edit this at Wikidata
EC Number 223-795-8
E number E282 (preservatives)
KEGG D09875
PubChem CID 19999
UNII 8AI80040KW checkY
CompTox Dashboard (EPA) DTXSID90904548 DTXSID1027556, DTXSID90904548 Edit this at Wikidata
InChI InChI=1S/2C3H6O2.Ca/c2*1-2-3(4)5;/h2*2H2,1H3,(H,4,5);/q;;+2/p-2 ☒NKey: BCZXFFBUYPCTSJ-UHFFFAOYSA-L ☒NInChI=1/2C3H6O2.Ca/c2*1-2-3(4)5;/h2*2H2,1H3,(H,4,5);/q;;+2/p-2Key: BCZXFFBUYPCTSJ-NUQVWONBAE
SMILES CCC(=O)[O-].CCC(=O)[O-].[Ca+2]
Properties
Chemical formula C6H10CaO4
Molar mass 186.2192 g/mol
Appearance White crystalline solid
Melting point 300 °C
Solubility in water 49 g/100 mL (0 °C) 55.8 g/100 mL (100 °C)
Solubility slightly soluble in methanol, ethanol insoluble in acetone, benzene
Structure
Crystal structure monoclinic
Hazards
NFPA 704 (fire diamond) NFPA 704 four-colored diamond 2 1 0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). ☒N verify (what is checkY☒N ?) Infobox references

Chemical compound

Calcium propanoate or calcium propionate has the formula Ca(C2H5COO)2. It is the calcium salt of propanoic acid.

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.[2] In agriculture, it is used, amongst other things, to prevent milk fever in cows and as a feed supplement.[3] Propionates prevent microbes from producing the energy they need, like benzoates do. However, unlike benzoates, propionates do not require an acidic environment.[4]

Calcium propionate is used in bakery products as a mold inhibitor, typically at 0.1–0.4%[5] (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.[6]

A few decades ago, Bacillus mesentericus (rope), was a serious problem,[7] but today's improved sanitary practices in the bakery, combined with rapid turnover of the finished product, have virtually eliminated this form of spoilage.[8] Calcium propionate and sodium propionate are effective against both B. mesentericus rope and mold.[9]

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%).[10] 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.[11]

Calcium propionate can be used as a fungicide on fruit.[12]

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.[13]

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 .[14]

  1. ^ Merck Index, 11th Edition, 1705.
  2. ^ Codex Alimentarius data for calcium propanoate Archived 2006-10-21 at the Wayback Machine
  3. ^ Center for Food and Nutrition Policy review of use of calcium propanoate as an organic agent in cow feed and as milk fever prevention
  4. ^ "Ingredients -- Calcium propionate". Retrieved 2007-03-10.
  5. ^ "NYSAES|FST|FVC|Venture 3| Chemical Food Preservatives". Archived from the original on 2010-04-12. Retrieved 2010-02-28.
  6. ^ "Keeping molds, bacteria at bay". Archived from the original on 2008-03-20. Retrieved 2007-03-24.
  7. ^ Furia, T. E. (1973). CRC Handbook of Food Additives. CRC Handbook of Food Additives. CRC Press.
  8. ^ Thompson, Jackie M.; Dodd, Christine E.R.; Waites, Will M. (1993). "Spoilage of bread by bacillus". International Biodeterioration & Biodegradation. 32 (1–3): 55–66. Bibcode:1993IBiBi..32...55T. doi:10.1016/0964-8305(93)90039-5.
  9. ^ Furia, T. E. (1973). CRC Handbook of Food Additives. CRC Handbook of Food Additives. CRC Press.
  10. ^ S. Dengate; A. Rubin (2002). "Controlled trial of cumulative behavioural effects of a common bread preservative". Journal of Paediatrics and Child Health. 38 (4): 373–376. doi:10.1046/j.1440-1754.2002.00009.x. PMID 12173999. S2CID 24898218.
  11. ^ D. F. MacFabe; D. P. Cain; K. Rodriguez-Capote; A. E. Franklin; J. E. Hoffman; F. Boon; A. R. Taylor; M. Kavaliers; K.-P. Ossenkopp (2007). "Neurobiological effects of intraventricular propionic acid in rats: Possible role of short-chain fatty acids on the pathogenesis and characteristics of autism spectrum disorders". Behavioural Brain Research. 176 (1): 149–169. doi:10.1016/j.bbr.2006.07.025. PMID 16950524. S2CID 3054752.
  12. ^ Biggs, A. R.; El-Kholi, M. M.; El-Neshawy, S.; Nickerson, R. (1997). "Effects of Calcium Salts on Growth, Polygalacturonase Activity, and Infection of Peach Fruit by Monilinia fructicola". Plant Disease. 81 (4): 399–403. doi:10.1094/PDIS.1997.81.4.399. PMID 30861823.
  13. ^ "OPP PESTICIDE ECOTOXICITY DATABASE - Details - Pesticide: Calcium propionate". EPA / USDA / NIFA. Archived from the original on 2019-01-23. Retrieved 2019-01-22.
  14. ^ Haghikia, Arash; Zimmermann, Friederike; Schumann, Paul (7 Feb 2022). "Propionate attenuates atherosclerosis by immune-dependent regulation of intestinal cholesterol metabolism". European Heart Journal. 43 (6): 518–533. doi:10.1093/eurheartj/ehab644. PMC 9097250. PMID 34597388.