12/22/2018 Calcium propanoate - Wikipedia

Calcium propanoate
Calcium propanoate or calcium propionate has the formula
Ca(C2H5COO)2. It is the calcium salt of propanoic acid. Calcium propanoate[1]

Uses
As a food additive, it is listed as E number 282 in the Codex Alimentarius. Names
Calcium propionate is used as a preservative in a wide variety of products, IUPAC name
including but not limited to: bread, other baked goods, processed meat, whey, Calcium propanoate
and other dairy products.[2] In agriculture, it is used, amongst other things, to
[3]
Other names
prevent milk fever in cows and as a feed supplement Propionates prevent
Calcium propionate
microbes from producing the energy they need, like benzoates do. However,
Calcium dipropionate
unlike benzoates, propionates do not require an acidic environment.[4]
Mycoban
Calcium propionates is used in bakery products as a mold inhibitor, typically at Identifiers
0.1-0.4% [5] (though animal feed may contain up to 1%). Mold contamination is CAS Number 4075-81-4 (http://ww
considered a serious problem amongst bakers, and conditions commonly
w.commonchemistry.
found in baking present near-optimal conditions for mold growth.[6]
org/ChemicalDetail.a
A few decades ago, Bacillus mesentericus (rope), was a serious problem,[7] but spx?ref=4075-81-4)
today's improved sanitary practices in the bakery, combined with rapid
turnover of the finished product, have virtually eliminated this form of 3D model Interactive image (htt
spoilage. Calcium propionate and sodium propionate are effective against both (JSmol)
ps://chemapps.stola
B. mesentericus rope and mold.[8] f.edu/jmol/jmol.php?
model=CCC%28%3
Metabolism of propionate begins with its conversion to propionyl coenzyme A
DO%29%5BO-%5D.
(propionyl-CoA), the usual first step in the metabolism of carboxylic acids.
CCC%28%3DO%2
Since propanoic acid has three carbons, propionyl-CoA can directly enter
9%5BO-%5D.%5BC
neither beta oxidation nor the citric acid cycles. In most vertebrates, propionyl-
a%2B2%5D)
CoA is carboxylated to D-methylmalonyl-CoA, which is isomerised to L-
methylmalonyl-CoA. A vitamin B12-dependent enzyme catalyzes ChemSpider 18840 (http://www.ch
rearrangement of L-methylmalonyl-CoA to succinyl-CoA, which is an emspider.com/Chem
intermediate of the citric acid cycle and can be readily incorporated there. ical-Structure.18840.
html)
When propanoic acid is infused directly into rodents' brains, it produces
reversible behavior changes (e.g. hyperactivity, dystonia, social impairment,
ECHA 100.021.633 (https://
perseveration) and brain changes (e.g. innate neuroinflammation, glutathione
InfoCard echa.europa.eu/subs
depletion) that may be used as a model of human autism in rats.[9]
tance-information/-/s
ubstanceinfo/100.02
According to the Pesticide Action Network North America, calcium propionate 1.633)
is slightly toxic.[10] Calcium propionate can be used as a fungicide on fruit.[11] EC Number 223-795-8
E number E282 (preservatives)
References KEGG D09875 (http://www.
kegg.jp/entry/D0987
https://en.wikipedia.org/wiki/Calcium_propanoate 1/2
12/22/2018 Calcium propanoate - Wikipedia

1. Merck Index, 11th Edition, 1705. 5)

2. Codex Alimentarius data for calcium propanoate (http://www.codexaliment
PubChem 19999 (https://pubch
arius.net/gsfaonline/additives/details.html?id=306) Archived (https://web.ar CID
chive.org/web/20061021214228/http://www.codexalimentarius.net/gsfaonli em.ncbi.nlm.nih.gov/
ne/additives/details.html?id=306) 2006-10-21 at the Wayback Machine. compound/19999)
3. Center for Food and Nutrition Policy review of use of calcium propanoate InChI
as an organic agent in cow feed and as milk fever prevention (http://www.a
ms.usda.gov/NOP/NationalList/TAPReviews/CalciumPropionate.pdf) SMILES
4. "Ingredients -- Calcium propionate" (http://sci-toys.com/ingredients/calcium Properties
_propionate.html). Retrieved 2007-03-10.
Chemical C6H10CaO4
5. "Archived copy" (https://web.archive.org/web/20100412155551/http://www. formula
nysaes.cornell.edu/necfe/pubs/pdf/Venture/venture3_chemical.html).
Molar mass 186.2192 g/mol
Archived from the original (http://www.nysaes.cornell.edu/necfe/pubs/pdf/V
enture/venture3_chemical.html) on 2010-04-12. Retrieved 2010-02-28. Appearance White crystalline
6. "Keeping molds, bacteria at bay" (http://bakingmanagement.bakery-net.co solid
m/article/7448). Retrieved 2007-03-24. Solubility in 49 g/100 mL (0 °C)
7. Furia, T. E. (1973). CRC Handbook of Food Additives. CRC Handbook of water 55.8 g/100 mL (100
Food Additives. CRC Press.
°C)
8. Furia, T. E. (1973). CRC Handbook of Food Additives. CRC Handbook of
Food Additives. CRC Press.
Solubility slightly soluble in
methanol, ethanol
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). insoluble in acetone,
"Neurobiological effects of intraventricular propionic acid in rats: Possible benzene
role of short-chain fatty acids on the pathogenesis and characteristics of Structure
autism spectrum disorders". Behavioural Brain Research. 176 (1): 149–
169. doi:10.1016/j.bbr.2006.07.025 (https://doi.org/10.1016%2Fj.bbr.2006. Crystal monoclinic
07.025).
structure

10. Pesticide Action Network data on calcium propanoate (http://www.pesticid Hazards

einfo.org/Detail_Chemical.jsp?Rec_Id=PC33679) NFPA 704
11. Biggs, A. R.; El-Kholi, M. M.; El-Neshawy, S.; Nickerson, R. (1997). 1
"Effects of Calcium Salts on Growth, Polygalacturonase Activity, and 2 0
Infection of Peach Fruit by Monilinia fructicola". Plant Disease. 81 (4): 399.
doi:10.1094/PDIS.1997.81.4.399 (https://doi.org/10.1094%2FPDIS.1997.8
1.4.399). Except where otherwise noted, data
are given for materials in their
standard state (at 25 °C [77 °F],
100 kPa).
External links verify (what is ?)
Center for Science in the Public Interest list of food additives (http://www.c Infobox references
spinet.org/reports/chemcuisine.htm)

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