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Wikipedia

Calcium propanoate

January 01, 1970

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

Calcium propanoate[1]
Names
Preferred IUPAC name
Calcium dipropanoate
Other names
Calcium propionate
Calcium dipropionate
Mycoban
Identifiers
  • 4075-81-4 Y
3D model (JSmol)
  • Interactive image
ChemSpider
  • 18840 N
ECHA InfoCard 100.021.633
EC Number
  • 223-795-8
E number E282 (preservatives)
KEGG
  • D09875
  • 19999
UNII
  • 8AI80040KW Y
  • DTXSID1027556
  • 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)
Health 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 YN ?)

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.[citation needed] Calcium propionate and 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%).[9] 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.[10]

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

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.[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 edit

  1. ^ Merck Index, 11th Edition, 1705.
  2. ^ Codex Alimentarius data for calcium propanoate 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. ^ . 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. ^ 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.
  10. ^ 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.
  11. ^ 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.
  12. ^ . EPA / USDA / NIFA. Archived from the original on 2019-01-23. Retrieved 2019-01-22.
  13. ^ 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

  • Center for Science in the Public Interest list of food additives

January 01, 1970
calcium, propanoate, calcium, propionate, formula, c2h5coo, calcium, salt, propanoic, acid, names, preferred, iupac, name, calcium, dipropanoate, other, names, calcium, propionatecalcium, dipropionatemycoban, identifiers, number, 4075, model, jsmol, interactiv. Calcium propanoate or calcium propionate has the formula Ca C2H5COO 2 It is the calcium salt of propanoic acid Calcium propanoate 1 Names Preferred IUPAC name Calcium dipropanoate Other names Calcium propionateCalcium dipropionateMycoban Identifiers CAS Number 4075 81 4 Y 3D model JSmol Interactive image ChemSpider 18840 N ECHA InfoCard 100 021 633 EC Number 223 795 8 E number E282 preservatives KEGG D09875 PubChem CID 19999 UNII 8AI80040KW Y CompTox Dashboard EPA DTXSID1027556 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 210 Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox referencesUses editAs 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 citation needed Calcium propionate and 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 9 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 10 Calcium propionate can be used as a fungicide on fruit 11 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 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 edit Merck Index 11th Edition 1705 Codex Alimentarius data for calcium propanoate Archived 2006 10 21 at the Wayback Machine Center for Food and Nutrition Policy review of use of calcium propanoate as an organic agent in cow feed and as milk fever prevention Ingredients Calcium propionate Retrieved 2007 03 10 NYSAES FST FVC Venture 3 Chemical Food Preservatives Archived from the original on 2010 04 12 Retrieved 2010 02 28 Keeping molds bacteria at bay Retrieved 2007 03 24 Furia T E 1973 CRC Handbook of Food Additives CRC Handbook of Food Additives CRC Press Furia T E 1973 CRC Handbook of Food Additives CRC Handbook of Food Additives CRC Press 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 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 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 OPP PESTICIDE ECOTOXICITY DATABASE Details Pesticide Calcium propionate EPA USDA NIFA Archived from the original on 2019 01 23 Retrieved 2019 01 22 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 editCenter for Science in the Public Interest list of food additives Retrieved from https en wikipedia org w index php title Calcium propanoate amp oldid 1218942834, wikipedia, wiki, book, books, library,

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