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

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.[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]

References

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Calcium propanoate

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Calcium propanoate, also known as calcium propionate, is the calcium salt of propanoic acid with the molecular formula C₆H₁₀CaO₄ and a molecular weight of 186.22 g/mol.[1] It appears as a white crystalline powder that is soluble in water, with solubility increasing from 49 g/100 mL at 0 °C to 55.8 g/100 mL at 100 °C.[1] As a common food additive designated E282 in the European Union, calcium propanoate functions primarily as an antimicrobial preservative by interfering with the reproduction of molds, bacteria, and other microorganisms. It is widely used in baked goods such as bread and pastries to inhibit mold growth and extend shelf life to weeks or months at most, depending on packaging and storage conditions. No chemical preservative alone enables bread or similar products to remain mold-free for years; achieving multi-year shelf life typically requires low water activity, special packaging (e.g., vacuum sealing), dehydration, or other processing methods beyond simple chemical addition. It is also used in dairy products like cheese and yogurt, processed meats, beverages, and even animal feed to prevent spoilage.[2][3] Beyond food applications, it serves as a preservative in cosmetics and an antifungal agent in pharmaceuticals.[1] Calcium propanoate is recognized as generally recognized as safe (GRAS) by the U.S. Food and Drug Administration under 21 CFR 184.1221, with approvals also from the World Health Organization and the Food and Agriculture Organization, and no specific acceptable daily intake limit established.[4] Toxicity studies indicate low risk, with oral LD50 values of 3,920 mg/kg in rats and 2,350 mg/kg in mice, though it can cause serious eye damage upon direct contact.[1] Rare side effects in humans may include headaches or migraines, but it is metabolized and excreted by the body without accumulation.[2]

Chemical properties

Molecular formula and structure

Calcium propanoate, also known as calcium propionate, has the molecular formula CX6HX10CaOX4\ce{C6H10CaO4}, which can be represented as (CHX3CHX2COO)2Ca(\ce{CH3CH2COO})2\ce{Ca} or Ca(CX2HX5COO)X2\ce{Ca(C2H5COO)2}.[1][5] The preferred IUPAC name is calcium propanoate, while the common name is calcium propionate.[6][7] Its molecular weight is 186.22 g/mol.[1][5] As an ionic compound, calcium propanoate consists of a calcium cation (CaX2+\ce{Ca^2+}) and two propanoate anions (CHX3CHX2COOX−\ce{CH3CH2COO^-}).[1][5] The propanoate anion is derived from propanoic acid (CHX3CHX2COOH\ce{CH3CH2COOH}), forming the salt through neutralization.[8][9] In its solid form, it exists as a crystalline lattice stabilized by electrostatic interactions between the ions.[1] The monohydrate form crystallizes in the monoclinic space group P21/cP2_1/c.[10]

Physical characteristics

Calcium propanoate appears as a white to off-white crystalline powder or granules. It is typically odorless, though some preparations may exhibit a faint acidic smell. The compound does not have a distinct melting point; instead, it decomposes above 300–350°C, releasing acrid smoke and irritating fumes.[11] Its density is approximately 1.4 g/cm³ at 20°C. Calcium propanoate is slightly hygroscopic, meaning it can absorb moisture from the air, which may affect its handling and storage. This behavior stems from its ionic nature as a calcium salt of propanoic acid, contributing to its solid state at room temperature.

Solubility and stability

Calcium propanoate exhibits high solubility in water, with reported values of approximately 49 g/100 mL at 0°C and 55.8 g/100 mL at 100°C for the hydrate form.[1] It is slightly soluble in polar organic solvents such as ethanol and methanol, but insoluble in non-polar solvents like ether, acetone, and benzene.[1] The ionic structure of calcium propanoate, consisting of Ca²⁺ cations and propanoate anions, facilitates its affinity for water through ion-dipole interactions.[1] Aqueous solutions of calcium propanoate are neutral to slightly alkaline, with a pH range of 6.0 to 9.0 in a 10% solution.[1] This pH profile arises from minimal hydrolysis of the propanoate ion under neutral conditions, as the conjugate base of the weak propanoic acid does not significantly affect the solution's acidity.[8] Under normal storage and environmental conditions, calcium propanoate remains stable, showing no significant degradation at room temperature.[1] However, it decomposes upon heating above 300°C, yielding calcium carbonate and organic byproducts such as 3-pentanone in inert atmospheres, or additional species like carbon oxides and acetaldehyde in oxidative environments.[12] The compound is also sensitive to strong acids, which protonate the propanoate ion to liberate propanoic acid, thereby reducing its ionic stability.[8]

Production

Laboratory synthesis

Calcium propanoate, also known as calcium propionate, is commonly synthesized in the laboratory through the neutralization of propanoic acid with calcium hydroxide. The balanced chemical equation for this reaction is:
2CHX3CHX2COOH+Ca(OH)X2→(CHX3CHX2COO)X2Ca+2HX2O 2 \ce{CH3CH2COOH} + \ce{Ca(OH)2} \rightarrow \ce{(CH3CH2COO)2Ca} + 2 \ce{H2O}
This method involves dissolving propanoic acid in distilled water to form an aqueous solution, followed by the gradual addition of a calcium hydroxide slurry while stirring continuously. The mixture is heated to 70–100 °C and maintained for 2–3 hours until the pH reaches neutrality (approximately 7–8), indicating complete reaction. The resulting solution is then filtered to remove any unreacted solids, concentrated by evaporation, cooled to induce crystallization, and the crystals are collected, washed, and dried.[13] An alternative laboratory approach utilizes calcium oxide instead of calcium hydroxide, following the reaction:
CaO+2CHX3CHX2COOH→(CHX3CHX2COO)X2Ca+HX2O \ce{CaO} + 2 \ce{CH3CH2COOH} \rightarrow \ce{(CH3CH2COO)2Ca} + \ce{H2O}
Here, calcium oxide is added directly to the propanoic acid solution under similar heating and stirring conditions, with monitoring for pH neutrality. The procedure proceeds with filtration, evaporation, and crystallization as described above. This variant is noted for its simplicity, as calcium oxide reacts exothermically with the acid.[13] Both methods typically achieve high yields exceeding 90%, with the eggshell-derived calcium carbonate variant reporting up to 96.12% under optimized conditions of 85 °C, 1:16 solid-liquid ratio, and ultrasonic assistance. Purity is enhanced through recrystallization from hot water or ethanol, yielding products with ≥99% purity confirmed by techniques such as infrared spectroscopy. These small-scale techniques allow precise control over reaction parameters, contrasting with larger industrial processes that prioritize efficiency.[14]

Industrial manufacturing

Calcium propanoate is manufactured on an industrial scale primarily through the neutralization reaction of propionic acid with calcium hydroxide in an aqueous medium. This process occurs in large stirred tank reactors where calcium hydroxide is first dispersed in deionized water to form a slurry, and propionic acid is added gradually to manage the exothermic reaction and ensure complete conversion. The resulting calcium propanoate precipitates as a fine white solid, which is then isolated via filtration or centrifugation, washed to remove impurities, and dried using methods such as spray drying or fluidized bed drying to achieve low moisture content and uniform particle size suitable for end-use applications. The dried product is subsequently milled, screened, and packaged under controlled conditions to maintain quality.[15][16] Propionic acid, the key raw material, is obtained from two main sources: biotechnological fermentation using bacteria such as Propionibacterium species on carbohydrate substrates like glucose or glycerol, or petrochemical synthesis via the oxidation of propanal derived from ethylene hydroformylation. Fermentation routes are favored for food-grade production due to their natural origin and alignment with clean-label preferences, while synthetic methods provide scalability for high-volume needs. Calcium hydroxide is typically sourced from industrial lime production.[17][18] As of 2024, global production of calcium propanoate was approximately 300,000 metric tons annually, with the majority produced in dedicated food-grade facilities in regions like North America, Europe, and Asia. Quality control measures throughout the process ensure compliance with standards such as the Food Chemicals Codex, requiring a minimum purity of 98% on a dry basis, low levels of heavy metals and arsenic, and specific pH and solubility parameters.[19][9]

Applications

Food preservation

Calcium propanoate serves as an effective antimicrobial preservative in the food industry, primarily targeting fungal and bacterial spoilage to extend the usability of perishable products. Introduced in the 1930s as a mold inhibitor for bread, it quickly gained adoption due to its ability to combat common bread spoilage issues without significantly altering product quality.[20][21] By the mid-20th century, its use had expanded to various bakery items and dairy products, reflecting its reliability in maintaining freshness amid growing demand for longer-shelf-life foods.[22] It is also used in processed meats and beverages to prevent spoilage.[2][21] The preservative works by releasing propionic acid, which in its undissociated form penetrates the cell membranes of microorganisms, causing physical damage and denaturing proteins essential for metabolism. This disrupts enzyme activity and inhibits the reproduction of molds such as Rhizopus and Penicillium, as well as certain bacteria like those causing rope spoilage in bread. Its efficacy is pH-dependent, performing optimally in acidic environments between pH 4 and 6, where the undissociated acid predominates and maximizes antimicrobial penetration.[23][22][24] In practice, calcium propanoate is commonly incorporated into bread, cakes, cheese, and packaged baked goods at concentrations of 0.1–0.4% by weight of flour, effectively delaying visible mold growth and extending shelf life. For instance, in bakery products, addition at 0.2% can prevent mold for over 8 days under typical storage conditions, representing an extension of 2–7 days compared to untreated controls depending on environmental factors like humidity.[22] In fast food, calcium propanoate is commonly added to hamburger buns and sandwich buns to prevent mold growth and maintain freshness during storage and distribution. Recent trends show some major chains, such as McDonald's and In-N-Out Burger, removing it from buns and replacing it with cultured wheat flour or other natural methods.[25][26] However, calcium propanoate, like other chemical preservatives, has limitations in its preservative effect on bread. No chemical preservative enables bread to remain mold-free for years. Common preservatives such as calcium propanoate inhibit mold growth and extend shelf life to weeks or months at most, depending on packaging and storage conditions. Achieving multi-year shelf life for bread-like products typically requires low water activity, special packaging (e.g., vacuum sealing), dehydration, or processing methods beyond simple chemical addition.[27][28] This application is particularly valuable in commercial baking, where it constitutes about 80% of preservative use to inhibit molds and rope bacteria without impacting yeast fermentation.[22] Compared to sodium propionate, calcium propanoate offers nutritional benefits by supplying bioavailable calcium, which supports bone health, while containing less sodium to align with dietary guidelines reducing salt intake. It also exhibits less interference with chemical leavening agents in certain formulations, making it preferable for yeast-leavened breads.[29][22]

Non-food uses

Calcium propanoate serves as a preservative in pharmaceutical formulations, where it inhibits the growth of molds and other microorganisms to extend shelf life, particularly in oral suspensions and syrups.[1] In the tobacco industry, it is employed to prevent mold growth during storage and processing, helping maintain product quality by targeting fungal contamination.[1] Calcium propanoate is incorporated into butyl rubber compounds to improve processability and scorching resistance, enhancing the material's handling during manufacturing and its tolerance to heat buildup.[1] As a preservative in animal feed, it suppresses mold and bacterial development, preserving nutritional value and preventing spoilage in grains and silage, with typical inclusion levels of 0.1–1% of feed weight.[1][30][31] In cosmetics, calcium propanoate functions as a preservative to inhibit microbial growth, though its use as a stabilizer is relatively uncommon, generally at concentrations up to 2%.[32][1] Across these non-food applications, dosage levels typically range from 0.5–2% in formulations, adjusted based on the specific product and environmental conditions to optimize efficacy without altering functionality.[32][33]

Safety and regulation

Health effects and toxicity

Calcium propanoate exhibits low acute toxicity, with an oral LD50 value of 3,920 mg/kg in rats, indicating it is not highly hazardous in single exposures.[1] It is classified as generally recognized as safe (GRAS) for use in food by regulatory bodies, supporting its non-toxic profile at typical dietary levels.[1] In terms of chronic effects, calcium propanoate shows no evidence of carcinogenicity or mutagenicity based on available toxicological data.[34] Genotoxicity assessments, including tests in bacterial strains, have confirmed the absence of DNA-damaging potential for calcium propanoate and related propionates. At high doses, however, it may cause mild gastrointestinal irritation, such as stomach discomfort, though this is uncommon in standard consumption scenarios.[2] Allergic reactions to calcium propanoate are rare, but some sensitive individuals have reported symptoms including migraines and, in children, hyperactivity or behavioral changes like irritability.[2] These associations remain debated, with limited clinical evidence linking propionate additives directly to such effects, and further research is needed to substantiate causality.[35] Nutritionally, calcium propanoate provides a source of dietary calcium, comprising approximately 21% calcium by weight, which can contribute to daily intake when used in fortified foods.[36]

Regulatory approvals

Calcium propanoate is affirmed as generally recognized as safe (GRAS) by the United States Food and Drug Administration (FDA) for use as a direct food ingredient at levels conforming to current good manufacturing practice, with typical levels up to 0.32% (calculated as propionic acid) in baked goods, while usage in other categories such as cheeses, confections, gelatins, and jams is limited to good manufacturing practice to ensure safety and functionality as an antimicrobial agent.[9] In the European Union, calcium propanoate is approved as a food additive under the designation E 282, authorized for use as a preservative in various categories including baked products and cheeses at maximum levels up to 3,000 mg/kg (expressed as propionic acid).[37] The European Food Safety Authority (EFSA) re-evaluated propionates in 2014 and did not allocate an acceptable daily intake (ADI) for propionic acid and its salts, based on the available database, while concluding no safety concern at authorized levels.[37] The Joint FAO/WHO Expert Committee on Food Additives (JECFA) has evaluated calcium propanoate as part of the group of propionic acid and its salts, assigning an ADI "not limited" since 1973, reaffirmed in 1997, indicating low toxicity and broad safety margins for dietary exposure.[38] Health Canada permits calcium propanoate as a preservative in the List of Permitted Preservatives, allowing up to 0.2% (2,000 p.p.m. as propionic acid) in bread and good manufacturing practice levels in flour and whole wheat flour, with mandatory labeling when used.[39] In Australia and New Zealand, Food Standards Australia New Zealand (FSANZ) approves it under the Food Standards Code (Schedule 15) for use in flour products and baked goods at maximum levels of 3,000 mg/kg (0.3%, as propionic acid), including extensions to processed meats since 2017, subject to labeling requirements as a preservative. As of 2025, no major regulatory changes have been implemented globally for calcium propanoate in general food applications, though routine monitoring continues, including considerations for use in specialized categories like infant foods under frameworks such as EFSA and FDA reviews.[40]

References

  1. Calcium propionate | C6H10O4Ca | CID 19999 - PubChem
  2. Calcium Propionate: Uses and Safety - Healthline
  3. The effect of sourdough and calcium propionate on the microbial shelf-life of salt reduced bread
  4. https://www.ecfr.gov/current/title-21/section-184.1221
  5. Calcium propionate
  6. Calcium propanoate | C6H10CaO4 - ChemSpider
  7. Calcium propionate, 98+% 5 kg - Chemicals - Thermo Fisher Scientific
  8. Calcium Propionate | 4075-81-4 - ChemicalBook
  9. 21 CFR 184.1221 -- Calcium propionate. - eCFR
  10. Crystal data for two salts of propionic acid: Ca(C2H5CO2)2.H2O and ...
  11. [PDF] SAFETY DATA SHEET - Fisher Scientific
  12. Thermal decomposition of calcium propionate: films and powders
  13. How to prepare calcium propionate
  14. [PDF] Optimization of preparation of calcium propionate from eggshell by ...
  15. How to Start a Calcium Propionate Manufacturing Business - NPCS
  16. Method for preparing calcium propionate - Google Patents
  17. Propionic Acid: Method of Production, Current State and Perspectives
  18. https://link.springer.com/article/10.1134/S0965544117060159
  19. https://prismaneconsulting.com/index.php/report-details/calcium-propionate-market
  20. Calcium Propionate - American Society of Baking
  21. [PDF] Calcium Propionate - Kemin
  22. None
  23. A Comprehensive Review on Bio-Preservation of Bread - NIH
  24. EFFECT OF CONCENTRATION AND pH ON THE PRESERVATIVE ...
  25. https://www.bakingbusiness.com/articles/47135-mcdonalds-removes-calcium-propionate-from-buns
  26. https://restaurantbusinessonline.com/food/n-out-burger-moves-away-artificial-ingredients-following-make-america-healthy-again-push
  27. Shelf Life Extension
  28. How Long Does Bread Last?
  29. Calcium (or sodium) propionate
  30. Propionic acid and its salts for all animal species - EFSA
  31. Calcium Propionate - Animal Nutrition - Titan Biotech Ltd.
  32. https://www.cosmeticsinfo.org/ingredient/calcium-propionate
  33. CALCIUM PROPIONATE- Feed Grade - Nipro
  34. evaluation of propionic acid (E 280), sodium ... - EFSA Journal
  35. Harm from bread preservative confirmed - Food Intolerance Network
  36. Calcium Propionate | Baking Ingredients - BAKERpedia
  37. Re-evaluation of propionic acid – propionates (E 280-283) - EFSA
  38. WHO | JECFA
  39. 11. List of Permitted Preservatives (Lists of Permitted Food Additives)
  40. [PDF] Agency Response Letter GRAS Notice No. GRN 000786 - FDA
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