Calcium propanoate

Calcium propanoate[1]
Names
IUPAC name
Calcium propanoate
Other names
Calcium propionate
Calcium dipropionate
Mycoban
Identifiers
4075-81-4 YesY
3D model (Jmol) Interactive image
ChemSpider 18840 N
ECHA InfoCard 100.021.633
EC Number 223-795-8
E number E282 (preservatives)
PubChem 19999
Properties
C6H10CaO4
Molar mass 186.2192 g/mol
Appearance White crystalline solid
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
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
1
2
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 YesYN ?)
Infobox references

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 propanoate is used as a preservative in a wide variety of products, including but not limited to: 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] Propanoates prevent microbes from producing the energy they need, like benzoates do. However, unlike benzoates, propanoates do not require an acidic environment.[4]

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

Metabolism of propanoate 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 can directly enter neither beta oxidation nor 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.

When propanoic acid is infused directly into rodents' brains, it produces reversible behavior changes (e.g. hyperactivity, dystonia, social impairment, perseveration) and brain changes (e.g. innate neuroinflammation, glutathione depletion) that may be used as a model of human autism in rats.[9]

According to the Pesticide Action Network North America, calcium propionate is slightly toxic.[10] This rating is not uncommon for food products; vitamin C is also rated by the same standards as being slightly toxic.[11] Calcium propanoate can be used as a fungicide on fruit.[12]

References

  1. ↑ Merck Index, 11th Edition, 1705.
  2. ↑ Codex Alimentarius data for calcium propanoate
  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. ↑ http://www.nysaes.cornell.edu/necfe/pubs/pdf/Venture/venture3_chemical.html
  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. ↑ 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". Behavioral Brain Research. 176 (1): 149–169. doi:10.1016/j.bbr.2006.07.025.
  10. ↑ Pesticide Action Network data on calcium propanoate
  11. ↑ Pesticide Action Network data on Vitamin C
  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. doi:10.1094/PDIS.1997.81.4.399.
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