Calcium propanoate

Last updated
Calcium propanoate [1]
Calcium propanoate.png
Names
Preferred IUPAC name
Calcium dipropanoate
Other names
Calcium propionate
Calcium dipropionate
Mycoban
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.021.633 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 223-795-8
E number E282 (preservatives)
KEGG
PubChem CID
UNII
  • InChI=1S/2C3H6O2.Ca/c2*1-2-3(4)5;/h2*2H2,1H3,(H,4,5);/q;;+2/p-2 X mark.svgN
    Key: BCZXFFBUYPCTSJ-UHFFFAOYSA-L X mark.svgN
  • 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
AppearanceWhite 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.svgHealth 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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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.

Contents

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, 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 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%). [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]

Related Research Articles

<span class="mw-page-title-main">Food additive</span> Substances added to food

Food additives are substances added to food to preserve flavor or enhance taste, appearance, or other sensory qualities. Some additives have been used for centuries as part of an effort to preserve food, for example vinegar (pickling), salt (salting), smoke (smoking), sugar (crystallization), etc. This allows for longer-lasting foods such as bacon, sweets or wines. With the advent of ultra-processed foods in the second half of the twentieth century, many additives have been introduced, of both natural and artificial origin. Food additives also include substances that may be introduced to food indirectly in the manufacturing process, through packaging, or during storage or transport.

A preservative is a substance or a chemical that is added to products such as food products, beverages, pharmaceutical drugs, paints, biological samples, cosmetics, wood, and many other products to prevent decomposition by microbial growth or by undesirable chemical changes. In general, preservation is implemented in two modes, chemical and physical. Chemical preservation entails adding chemical compounds to the product. Physical preservation entails processes such as refrigeration or drying. Preservative food additives reduce the risk of foodborne infections, decrease microbial spoilage, and preserve fresh attributes and nutritional quality. Some physical techniques for food preservation include dehydration, UV-C radiation, freeze-drying, and refrigeration. Chemical preservation and physical preservation techniques are sometimes combined.

<span class="mw-page-title-main">Propionic acid</span> Carboxylic acid with chemical formula CH3CH2CO2H

Propionic acid is a naturally occurring carboxylic acid with chemical formula CH
3CH
2CO
2H. It is a liquid with a pungent and unpleasant smell somewhat resembling body odor. The anion CH
3CH
2CO−
2 as well as the salts and esters of propionic acid are known as propionates or propanoates.

<span class="mw-page-title-main">Stearic acid</span> Eighteen-carbon straight-chain fatty acid

Stearic acid is a saturated fatty acid with an 18-carbon chain. The IUPAC name is octadecanoic acid. It is a soft waxy solid with the formula CH3(CH2)16CO2H. The triglyceride derived from three molecules of stearic acid is called stearin. Stearic acid is a prevalent fatty-acid in nature, found in many animal and vegetable fats, but is usually higher in animal fat than vegetable fat. It has a melting point of 69.4 °C (156.9 °F) °C and a pKa of 4.50.

Succinyl-coenzyme A, abbreviated as succinyl-CoA or SucCoA, is a thioester of succinic acid and coenzyme A.

<span class="mw-page-title-main">Sodium benzoate</span> Chemical compound

Sodium benzoate also known as benzoate of soda is the sodium salt of benzoic acid, widely used as a food preservative (with an E number of E211) and a pickling agent. It appears as a white crystalline chemical with the formula C6H5COONa.

<span class="mw-page-title-main">Sorbic acid</span> Organic compound (CH3(CH)4COOH)

Sorbic acid, or 2,4-hexadienoic acid, is a natural organic compound used as a food preservative. It has the chemical formula CH3(CH)4CO2H and the structure H3C−CH=CH−CH=CH−C(=O)OH. It is a colourless solid that is slightly soluble in water and sublimes readily. It was first isolated from the unripe berries of the Sorbus aucuparia, hence its name.

<span class="mw-page-title-main">Sodium propionate</span> Chemical compound

Sodium propanoate or sodium propionate is the sodium salt of propionic acid which has the chemical formula Na(C2H5COO). This white crystalline solid is deliquescent in moist air.

<span class="mw-page-title-main">Potassium propanoate</span> Chemical compound

Potassium propanoate or potassium propionate has formula K(C2H5COO). Its melting point is 410 °C. It is the potassium salt of propanoic acid.

<span class="mw-page-title-main">Calcium benzoate</span> Chemical compound

Calcium benzoate refers to the calcium salt of benzoic acid. When used in the food industry as a preservative, its E number is E213 ; it is approved for use as a food additive in the EU, USA and Australia and New Zealand.

<span class="mw-page-title-main">Methylmalonyl-CoA mutase deficiency</span> Medical condition

Methylmalonyl-CoA mutase is a mitochondrial homodimer apoenzyme that focuses on the catalysis of methylmalonyl CoA to succinyl CoA. The enzyme is bound to adenosylcobalamin, a hormonal derivative of vitamin B12 in order to function. Methylmalonyl-CoA mutase deficiency is caused by genetic defect in the MUT gene responsible for encoding the enzyme. Deficiency in this enzyme accounts for 60% of the cases of methylmalonic acidemia.

<i>Zygosaccharomyces bailii</i> Species of fungus

Zygosaccharomyces bailii is a species in the genus Zygosaccharomyces. It was initially described as Saccharomyces bailii by Lindner in 1895, but in 1983 it was reclassified as Zygosaccharomyces bailii in the work by Barnett et al.

Propionyl-CoA is a coenzyme A derivative of propionic acid. It is composed of a 24 total carbon chain and its production and metabolic fate depend on which organism it is present in. Several different pathways can lead to its production, such as through the catabolism of specific amino acids or the oxidation of odd-chain fatty acids. It later can be broken down by propionyl-CoA carboxylase or through the methylcitrate cycle. In different organisms, however, propionyl-CoA can be sequestered into controlled regions, to alleviate its potential toxicity through accumulation. Genetic deficiencies regarding the production and breakdown of propionyl-CoA also have great clinical and human significance.

<span class="mw-page-title-main">Methylmalonic acid</span> Chemical compound

Methylmalonic acid (MMA) is a chemical compound from the group of dicarboxylic acids. It consists of the basic structure of malonic acid and also carries a methyl group. The salts of methylmalonic acid are called methylmalonates.

<span class="mw-page-title-main">Methylmalonyl-CoA</span> Chemical compound

Methylmalonyl-CoA is the thioester consisting of coenzyme A linked to methylmalonic acid. It is an important intermediate in the biosynthesis of succinyl-CoA, which plays an essential role in the tricarboxylic acid cycle.

α-Ketobutyric acid Chemical compound

α-Ketobutyric acid is an organic compound with the formula CH3CH2C(O)CO2H. It is a colorless solid that melts just above room temperature. Its conjugate base α-ketobutyrate is the predominant form found in nature (near neutral pH). It results from the lysis of cystathionine. It is also one of the degradation products of threonine, produced by the catabolism of the amino acid by threonine dehydratase. It is also produced by the degradation of homocysteine and the metabolism of methionine.

In enzymology, a propionate—CoA ligase is an enzyme that catalyzes the chemical reaction

<span class="mw-page-title-main">Ammonium propionate</span> Chemical compound

Ammonium propionate or ammonium propanoate is the ammonium salt of propionic acid. It has the chemical formula NH4(C2H5COO).

Combined malonic and methylmalonic aciduria (CMAMMA), also called combined malonic and methylmalonic acidemia is an inherited metabolic disease characterized by elevated levels of malonic acid and methylmalonic acid. However, the methylmalonic acid levels exceed those of malonic acid. CMAMMA is not only an organic aciduria but also a defect of mitochondrial fatty acid synthesis (mtFASII). Some researchers have hypothesized that CMAMMA might be one of the most common forms of methylmalonic acidemia, and possibly one of the most common inborn errors of metabolism. Due to being infrequently diagnosed, it most often goes undetected.

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". 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. Bibcode:1993IBiBi..32...55T. 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 . PMID   34597388.
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