Calcium propanoate

Source: 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
C6H10CaO4
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

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.[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,

sodium propionate are effective against both B. mesentericus rope and mold.[8]

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%).

autism.[10]

Calcium propionate can be used as a fungicide on fruit.[11]

In a 1973 study reported by the

ppm of calcium propionate was found to be slightly toxic to bluegill sunfish.[12]

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 .[13]

References

  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". Retrieved 2007-03-24.
  7. ^ Furia, T. E. (1973). CRC Handbook of Food Additives. CRC Handbook of Food Additives. CRC Press.
  8. ^ Furia, T. E. (1973). CRC Handbook of Food Additives. CRC Handbook of Food Additives. CRC Press.
  9. S2CID 24898218
    .
  10. S2CID 3054752
    .
  11. PMID 30861823
    .
  12. ^ "OPP PESTICIDE ECOTOXICITY DATABASE - Details - Pesticide: Calcium propionate". EPA / USDA / NIFA. Archived from the original on 2019-01-23. Retrieved 2019-01-22.
  13. PMC 9097250
    .


External links
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