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Calcium propanoate - Wikipedia Jump to content

Calcium propanoate

From Wikipedia, the free encyclopedia
Calcium propanoate [1]
Names
Preferred IUPAC name
Calcium dipropanoate
Other names
Calcium propionate
Calcium dipropionate
Mycoban
Identifiers
3D model ( JSmol )
ChemSpider
ECHA InfoCard 100.021.633 Edit this at Wikidata
EC Number
  • 223-795-8
E number E282 (preservatives)
KEGG
UNII
  • InChI=1S/2C3H6O2.Ca/c2*1-2-3(4)5;/h2*2H2,1H3,(H,4,5);/q;;+2/p-2   ☒N
    Key: BCZXFFBUYPCTSJ-UHFFFAOYSA-L   ☒N
  • InChI=1/2C3H6O2.Ca/c2*1-2-3(4)5;/h2*2H2,1H3,(H,4,5);/q;;+2/p-2
    Key: BCZXFFBUYPCTSJ-NUQVWONBAE
  • CCC(=O)[O-].CCC(=O)[O-].[Ca+2]
Properties
C 6 H 10 CaO 4
Molar mass 186.2192 g/mol
Appearance White crystalline solid
Melting point 300 °C
49 g/100 mL (0 °C)
55.8 g/100 mL (100 °C)
Solubility slightly soluble in methanol , ethanol
insoluble in acetone , benzene
Structure
monoclinic
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
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  ?)

Calcium propanoate or calcium propionate has the formula Ca ( C 2 H 5 C O O ) 2 . It is the calcium salt of propanoic acid .

Uses [ edit ]

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 B 12 ?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]

References [ edit ]

  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. 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 .


External links [ edit ]

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