Potassium sorbate

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Potassium sorbate[1][2]
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Names
Preferred IUPAC name
Potassium (2E,4E)-hexa-2,4-dienoate
Other names
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  • E202
  • Sorbistat-K
  • Sorbistat potassium
Identifiers
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3D model (JSmol)
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  • InChI=1S/C6H8O2.K/c1-2-3-4-5-6(7)8;/h2-5H,1H3,(H,7,8);/q;+1/p-1/b3-2+,5-4+; checkY
    Key: CHHHXKFHOYLYRE-STWYSWDKSA-M checkY
  • InChI=1/C6H8O2.K/c1-2-3-4-5-6(7)8;/h2-5H,1H3,(H,7,8);/q;+1/p-1/b3-2+,5-4+;
    Key: CHHHXKFHOYLYRE-ZCSOUONQBI
  • [K+].[O-]C(=O)\C=C\C=C\C
Properties
C6H7KO2
Molar mass 150.218 g·mol−1
Appearance White crystals
Odor Yes
Density 1.363 g/cm3
Melting point 270 °C (518 °F; 543 K) decomposes
58.5 g/100Template:NnbspmL (100 °C)
Solubility in other solvents Template:Ubli
Hazards
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2
1
0
Lethal dose or concentration (LD, LC):
4920 mg/kg (oral, rat)[3]
Safety data sheet (SDS) Fisher Scientific
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Template:Chembox Footer/trackingTemplate:Short description

Potassium sorbate is the potassium salt of sorbic acid, structural formula CH3CH=CH−CH=CH−CO2K. It is a white salt that is very soluble in water (58.2% at 20 °C). It is primarily used as a food preservative (E number 202).[4] Potassium sorbate is effective in a variety of applications including food, wine, and personal care products. While sorbic acid occurs naturally in rowan and hippophae berries, virtually all of the world's supply of sorbic acid, from which potassium sorbate is derived, is manufactured synthetically.

Production

Potassium sorbate is produced industrially by neutralizing sorbic acid with potassium hydroxide. The precursor sorbic acid is produced in a two-step process via the condensation of crotonaldehyde and ketene.[5][6][7]

Uses

Potassium sorbate is used to inhibit molds and yeasts in many foods, such as cheese, wine, yogurt, dried meats, apple cider, dried fruits, soft drinks and fruit drinks, and baked goods.[8] It can also be found in the ingredients list of many dried fruit products. In addition, herbal dietary supplement products generally contain potassium sorbate, which acts to prevent mold and microbes and to increase shelf life. It is used in quantities at which no adverse health effects are known, over short periods of time.[9] Labeling of this preservative on ingredient statements reads as "potassium sorbate" or "E202".

Also, it is used in many personal care products to inhibit the development of microorganisms to increase shelf stability. Some manufacturers use this preservative as a replacement for parabens.

Also known as "wine stabilizer", potassium sorbate produces sorbic acid when added to wine. It serves two purposes:

  • When active fermentation has ceased and the wine is racked for the final time after clearing, potassium sorbate renders any surviving yeast incapable of multiplying. Yeast living at that moment can continue fermenting any residual sugar into CO2 and alcohol, but when they die, no new yeast will be present to cause future fermentation. When a wine is sweetened before bottling, potassium sorbate is used to prevent refermentation when used in conjunction with potassium metabisulfite. It is primarily used with sweet wines, sparkling wines, and some hard ciders, but may be added to table wines, which may not maintain their clarity after fining.

Some molds (notably some Trichoderma and Penicillium strains) and yeasts are able to detoxify sorbates by decarboxylation, producing piperylene (1,3-pentadiene). The pentadiene manifests as a typical odor of kerosene or petroleum.[12]

Toxicology

In pure form, potassium sorbate is a skin, eye, and respiratory irritant.[13][14] Concentrations up to 0.5% are not significant skin irritants.[15]

As a food additive, potassium sorbate is used as a preservative in concentrations of 0.025%–0.1%,[16] which in a 100 g serving yields an intake of 25–100 mg. In the United States, no more than 0.1% is allowed in fruit butters, jellies, preserves, and related products.[17] Up to 0.4% has been studied in low-salt, naturally-fermented pickles, and when combined with calcium chloride, 0.2% made "good quality pickles."[18] Potassium sorbate has about 74% of sorbic acid's anti-microbial activity.[16] When calculated as sorbic acid, 0.3% is allowed in "cold pack cheese food."[19] The upper pH limit for effectiveness is 6.5.[16]

The maximum acceptable daily intake for human consumption is 25 mg/kg, or 1.75 g daily for an average adult (70 kg).[9][20] Under some conditions, particularly at high concentrations or when combined with nitrites, potassium sorbate has shown genotoxic activity in vitro.[20]

Three studies conducted in the 1970s did not find it to have any carcinogenic effects in rats.[21][22][23] However, a 2009-2023 cohort study of 105,260 participants in France found a 14% increase in overall cancer risk and 26% increase in breast cancer risk associated with high consumption of potassium sorbate.[24]

See also

References

  1. ^ Merck Index, 11th Edition, 7661.
  2. ^ |SIAL&N5=SEARCH_CONCAT_PNO|BRAND_KEY&F=SPEC Potassium sorbate at Sigma-Aldrich.
  3. ^ Page Module:Citation/CS1/styles.css has no content.Lewis, Richard J., ed. (2004-10-15). Sax's Dangerous Properties of Industrial Materials. Wiley. p. 3043. doi:10.1002/0471701343. ISBN 978-0-471-47662-7.
  4. ^ Nordic Food Additive Database Script error: No such module "webarchive". Nordic Working Group on Food Toxicology and Risk Assessment.
  5. ^ Erich Lück, Martin Jager and Nico Raczek "Sorbic Acid" in Ullmann's Encyclopedia of Industrial Chemistry, 2011, Wiley-VCH, Weinheim. Script error: No such module "CS1 identifiers".
  6. ^ patent process for commercial potassium sorbate Script error: No such module "webarchive".
  7. ^ Page Module:Citation/CS1/styles.css has no content."Agricultural Marketing Service". www.ams.usda.gov. Archived from the original on 2014-06-11. Retrieved 2012-09-21.
  8. ^ Erich Lück, Martin Jager and Nico Raczek "Sorbic Acid" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2000.Script error: No such module "CS1 identifiers".
  9. ^ a b Page Module:Citation/CS1/styles.css has no content."036. Sorbate, potassium (FAO Nutrition Meetings Report Series 40abc)". Inchem.org. Retrieved 2013-02-22.
  10. ^ Page Module:Citation/CS1/styles.css has no content.Sofos JN, Busta FF, Bhothipaksa K, Allen CE, Robach MC, Paquette MW (September 1980). "Effects of various concentrations of sodium nitrite and potassium sorbate on Clostridium botulinum toxin production in commercially prepared bacon". Journal of Food Science. 45 (5): 1285–1292. doi:10.1111/j.1365-2621.1980.tb06539.x.
  11. ^ Page Module:Citation/CS1/styles.css has no content.Tulamait, Aiman; Laghi, Franco; Mikrut, Kathleen; et al. (2005). "Potassium sorbate reduces gastric colonization in patients receiving mechanical ventilization". J. Crit. Care. 20 (3): 281–287. doi:10.1016/j.jcrc.2005.03.002. PMID 16253799.
  12. ^ The Soft Drinks Companion – A technical handbook for the beverage industry, Chapter 10.
  13. ^ Page Module:Citation/CS1/styles.css has no content."Potassium Sorbate" (PDF). Chem One, Ltd. 2010-06-14. Archived from the original (PDF) on 2023-10-08. Retrieved 2015-05-04.
  14. ^ Page Module:Citation/CS1/styles.css has no content."Sorbic Acid - National Library of Medicine HSDB Database". National Institute of Health.
  15. ^ Page Module:Citation/CS1/styles.css has no content.Elder, R. E. (1988). "Final report on the safety assessment of sorbic acid and potassium sorbate" (PDF). J Am Coll Toxicol. 7 (6): 837–880. doi:10.3109/10915818809078711. S2CID 5998542. Archived from the original (PDF) on May 27, 2018. Retrieved May 26, 2018.
  16. ^ a b c Page Module:Citation/CS1/styles.css has no content."Potassium sorbate - Agricultural Marketing Service - USDA" (PDF). U.S. government. Retrieved May 26, 2018. Potassium sorbate is effective against yeasts, molds, and select bacteria, and is widely used at 0.025 to 0.10 % levels in cheeses, dips, yogurt, sour cream, bread, cakes, pies and fillings, baking mixes, doughs, icings, fudges, toppings, beverages, margarine, salads, fermented and acidified vegetables, olives, fruit products, dressings, smoked and salted fish, confections and mayonnaise.
  17. ^ Page Module:Citation/CS1/styles.css has no content."21 CFR 150 - Fruit butters, jellies, preserves, and related products" (PDF). Government Printing Office. April 1, 2011. Retrieved May 25, 2018.
  18. ^ Page Module:Citation/CS1/styles.css has no content.Guillou, A.A.; Floros, J.D.; Cousin, M.A. (1992). "Calcium Chloride and Potassium Sorbate Reduce Sodium Chloride used during Natural Cucumber Fermentation and Storage". Journal of Food Science. 57 (6): 1364–1368. doi:10.1111/j.1365-2621.1992.tb06859.x. ISSN 0022-1147.
  19. ^ Page Module:Citation/CS1/styles.css has no content."21 CFR 133 - Cheeses and related cheese products" (PDF). Government Printing Office. April 1, 2011. Retrieved May 25, 2018.
  20. ^ a b Page Module:Citation/CS1/styles.css has no content.Carocho, Márcio; Barreiro, Maria Filomena; Morales, Patricia; Ferreira, Isabel C. F. R. (2014). "Adding Molecules to Food, Pros and Cons: A Review on Synthetic and Natural Food Additives". Comprehensive Reviews in Food Science and Food Safety. 13 (4): 377–399. doi:10.1111/1541-4337.12065. hdl:10198/12042. PMID 33412697.
  21. ^ Page Module:Citation/CS1/styles.css has no content.Hendy, R. J.; Hardy, J.; Gaunt, I. F.; Kiss, I. S.; Butterworth, K. R. (1976). "Long-term toxicity studies of sorbic acid in mice". Food and Cosmetics Toxicology. 14 (5): 381–386. doi:10.1016/S0015-6264(76)80173-3. PMID 1010505.
  22. ^ Page Module:Citation/CS1/styles.css has no content.Gaunt, I. F.; Butterworth, K. R.; Hardy, J.; Gangolli, S. D. (1975). "Long-term toxicity of sorbic acid in the rat". Food and Cosmetics Toxicology. 13 (1): 31–45. doi:10.1016/0015-6264(75)90080-2. PMID 1123201.
  23. ^ Page Module:Citation/CS1/styles.css has no content.Mason, P. L.; Gaunt, I. F.; Hardy, J.; Kiss, I. S.; Butterworth, K. R.; Gangolli, S. D. (1976). "Long-term toxicity of parasorbic acid in rats". Food and Cosmetics Toxicology. 14 (5): 387–394. doi:10.1016/S0015-6264(76)80174-5. PMID 1010506.
  24. ^ Page Module:Citation/CS1/styles.css has no content.Hasenböhler, Anaïs; Javaux, Guillaume; de la Garanderie, Marie Payen de; de Edelenyi, Fabien Szabo; Yvroud-Hoyos, Paola; Agaësse, Cédric; De Sa, Alexandre; Huybrechts, Inge; Pierre, Fabrice; Audebert, Marc; Coumoul, Xavier; Julia, Chantal; Kesse-Guyot, Emmanuelle; Allès, Benjamin; Deschamps, Valérie; Hercberg, Serge; Chassaing, Benoit; Srour, Bernard; Deschasaux-Tanguy, Mélanie; Touvier, Mathilde (2026). "Intake of food additive preservatives and incidence of cancer: results from the NutriNet-Santé prospective cohort". BMJ. 392 (8479). doi:10.1136/bmj-2025-084917.
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