| Revision as of 10:55, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 477162758 of page Potassium_sorbate for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 15:59, 29 October 2024 edit 165.189.255.59 (talk) →Uses: copyedits |
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{{short description|Chemical compound}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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|Reference=<ref>'']'', 11th Edition, '''7661'''.</ref><ref> at ]</ref> |
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| verifiedrevid = 477163963 |
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|ImageFile=Sorbato_de_Potássio-2D.png |
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| Reference =<ref>'']'', 11th Edition, '''7661'''.</ref><ref> at ].</ref> |
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|ImageSize=200px |
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|ImageName=The structure of potassium sorbate |
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| ImageFile =Potassium sorbate.svg |
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|IUPACName=Potassium (2''E'',4''E'')-hexa-2,4-dienoate |
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| ImageName = The structure of potassium sorbate |
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|OtherNames=E202<br>Sorbistat-K<br>Sorbistat potassium |
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| ImageFile1 = Potassium sorbate ball-and-stick.png |
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|Section1= {{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| PIN = Potassium (2''E'',4''E'')-hexa-2,4-dienoate |
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| OtherNames = {{Unbulleted list|E202|Sorbistat-K|Sorbistat potassium}} |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 4445644 |
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| ChemSpiderID = 4445644 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| StdInChIKey = CHHHXKFHOYLYRE-STWYSWDKSA-M |
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| StdInChIKey = CHHHXKFHOYLYRE-STWYSWDKSA-M |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo=24634-61-5 |
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| CASNo = 24634-61-5 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| PubChem = 5282505 |
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| UNII = 1VPU26JZZ4 |
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| SMILES = .C(=O)\C=C\C=C\C |
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| PubChem = 23676745 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI = 77868 |
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| SMILES = .C(=O)\C=C\C=C\C |
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|Section2= {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=6 | H=7 | K=1 | O=2 |
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| Formula=C<sub>6</sub>H<sub>7</sub>KO<sub>2</sub> |
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| Appearance = White crystals |
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| MolarMass=150.22 g/mol |
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| Odor = Yes |
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| Appearance= |
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| Density=1.363 g/cm<sup>3</sup> |
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| Density = 1.363 g/cm<sup>3</sup> |
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| MeltingPtC = 270 |
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| MeltingPt=270 °C (decomposition) |
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| MeltingPt_notes = decomposes |
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| Solubility=58.2% at 20 °C |
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| Solubility = 58.5{{nbsp}}g/100{{nnbsp}}mL (100{{nbsp}}°C) |
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| SolubleOther = soluble in ], ] <hr> slightly soluble in ] <hr> very slightly soluble in ], ], ] <hr> insoluble in ] |
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| SolubleOther = {{ubli |
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| Soluble in ], ] |
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| Slightly soluble in ] |
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| Very slightly soluble in ], ], ] |
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| Insoluble in ] |
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| Solvent = other solvents |
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|Section3= {{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| NFPA-H = 2 |
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| FlashPt= |
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| NFPA-F = 1 |
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| NFPA-R = 0 |
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| LD50 = 4920 mg/kg (rat, oral) |
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| FlashPt = |
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| LD50 = 4920{{nbsp}}mg/kg (oral, rat)<ref>{{cite book | title=Sax's Dangerous Properties of Industrial Materials | publisher=Wiley | date=2004-10-15 | isbn=978-0-471-47662-7 | doi=10.1002/0471701343 | page=3043 | editor-last1=Lewis | editor-first1=Richard J. }}</ref> |
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'''Potassium sorbate''' is the ] ] of ], chemical formula CH<sub>3</sub>CH=CH−CH=CH−CO<sub>2</sub>K. It is a white salt that is very soluble in water (58.2% at 20 °C). It is primarily used as a ] (] 202).<ref> {{webarchive|url=https://web.archive.org/web/20080502102138/http://www.norfad.dk/FoodAddDetails.asp?ENumber=E+202 |date=2008-05-02 }} Nordic Working Group on Food Toxicology and Risk Assessment.</ref> Potassium sorbate is effective in a variety of applications including ], ], and ]. While sorbic acid occurs naturally in ] and ] berries, virtually all of the world's supply of sorbic acid, from which potassium sorbate is derived, is manufactured synthetically. |
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==Production== |
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Potassium sorbate is produced industrially by ] ] with ]. The precursor sorbic acid is produced in a two-step process via the condensation of ] and ].<ref>Erich Lück, Martin Jager and Nico Raczek "Sorbic Acid" in Ullmann's Encyclopedia of Industrial Chemistry, 2011, Wiley-VCH, Weinheim. {{doi|10.1002/14356007.a24_507.pub2}}</ref><ref> {{webarchive|url=https://web.archive.org/web/20120131004448/http://www.patentstorm.us/patents/6512142/description.html |date=2012-01-31 }}</ref><ref>{{cite web|url=http://www.ams.usda.gov/AMSv1.0/getfile?dDocName=STELPRDC5067082|title=Agricultural Marketing Service|website=www.ams.usda.gov|access-date=2012-09-21|archive-date=2014-06-11|archive-url=https://web.archive.org/web/20140611194224/http://www.ams.usda.gov/AMSv1.0/getfile?dDocName=STELPRDC5067082|url-status=dead}}</ref> |
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==Uses== |
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Potassium sorbate is used to inhibit ]s and ]s in many foods, such as ], ], ], ]s, ], ], soft drinks and fruit drinks, and baked goods.<ref name=Ullmann>Erich Lück, Martin Jager and Nico Raczek "Sorbic Acid" in ''Ullmann's Encyclopedia of Industrial Chemistry'', Wiley-VCH, Weinheim, 2000.{{doi|10.1002/14356007.a24_507}}</ref> 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.<ref name="expert"/> Labeling of this preservative on ingredient statements reads as "potassium sorbate" or "E202". Also, it is used in many ] to inhibit the development of ]s for shelf stability. Some manufacturers are using this preservative as a replacement for ]s. Tube feeding of potassium sorbate reduces the gastric burden of pathogenic bacteria.<ref>{{cite journal |doi= 10.1016/j.jcrc.2005.03.002 |title= Potassium sorbate reduces gastric colonization in patients receiving mechanical ventilization |first5= G. R. Scott |last5= Budinger |first4= Roberta B. |last4= Carey |first3= Kathleen |last3= Mikrut |journal= J. Crit. Care |first2= Franco |year= 2005 |volume= 20 |last2= Laghi |issue= 3 |pages= 281–287 |last1= Tulamait |first1= Aiman |pmid= 16253799 |display-authors= 3 }}</ref> |
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Also known as "wine stabilizer", potassium sorbate produces ] when added to ]. It serves two purposes. When active ] 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 ] into ] and ], 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 ]. It is primarily used with ]s, ]s, and some ]s, but may be added to ]s, which exhibit difficulty in maintaining clarity after ]. |
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Some ]s (notably some '']'' and '']'' ]) and ]s are able to detoxify sorbates by ], producing ] (1,3-pentadiene). The pentadiene manifests as a typical odor of ] or ].<ref>''The Soft Drinks Companion – A technical handbook for the beverage industry'', Chapter 10.</ref> |
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== Toxicology == |
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In pure form, potassium sorbate is a skin, eye, and respiratory ].<ref name="Material Data Safety Sheet for potassium sorbate">{{cite web|url= http://www.chemone.com/default/msds/Potassium%20sorbate.pdf|title= Potassium Sorbate|publisher= Chem One, Ltd.|date= 2010-06-14|access-date= 2015-05-04}}{{dead link|date=March 2018 |bot=InternetArchiveBot |fix-attempted=yes }}</ref><ref>{{cite web |publisher=National Institute of Health |title=Sorbic Acid - National Library of Medicine HSDB Database |url=https://toxnet.nlm.nih.gov/cgi-bin/sis/search/a?dbs+hsdb:@term+@DOCNO+590}}</ref> Concentrations up to 0.5% are not significant skin irritants.<ref>{{cite journal|author=Elder, R. E. |year=1988 |title=Final report on the safety assessment of sorbic acid and potassium sorbate. |journal=J Am Coll Toxicol |volume=7 |issue=6 |pages=837–880 |url=https://pdfs.semanticscholar.org/bbbe/1de833dfb7ebaf3959eaace0762e9b9ffb9b.pdf |archive-url=https://web.archive.org/web/20180527201422/https://pdfs.semanticscholar.org/bbbe/1de833dfb7ebaf3959eaace0762e9b9ffb9b.pdf |url-status=dead |archive-date=May 27, 2018 |access-date=May 26, 2018|doi=10.3109/10915818809078711 |s2cid=5998542 }}</ref> |
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As a food additive, potassium sorbate is ] in concentrations of 0.025–0.100%,<ref name="potassium sorbate AMS USDA">{{cite web |title=Potassium sorbate - Agricultural Marketing Service - USDA |url=https://www.ams.usda.gov/sites/default/files/media/P%20Sor%20technical%20advisory%20panel%20report.pdf |publisher=U.S. government |quote=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. |access-date=May 26, 2018}}</ref> 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 ]s, jellies, preserves, and related products.<ref>{{cite web|title=21 CFR 150 - Fruit butters, jellies, preserves, and related products |publisher=Government Printing Office |date=April 1, 2011 |url=https://www.gpo.gov/fdsys/pkg/CFR-2011-title21-vol2/pdf/CFR-2011-title21-vol2-part150.pdf |access-date=May 25, 2018}}</ref> 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."<ref name="GuillouFloros1992">{{cite journal |last1=Guillou |first1=A.A. |last2=Floros |first2=J.D. |last3=Cousin|first3=M.A. |title=Calcium Chloride and Potassium Sorbate Reduce Sodium Chloride used during Natural Cucumber Fermentation and Storage |journal=Journal of Food Science |volume=57 |issue=6|year=1992 |pages=1364–1368 |issn=0022-1147 |doi=10.1111/j.1365-2621.1992.tb06859.x}}</ref> Potassium sorbate has about 74% of sorbic acid's anti-microbial activity.<ref name="potassium sorbate AMS USDA" /> When calculated as sorbic acid, 0.3% is allowed in "cold pack cheese food."<ref>{{cite web|title=21 CFR 133 - Cheeses and related cheese products |publisher=Government Printing Office |date=April 1, 2011 |url=https://www.gpo.gov/fdsys/pkg/CFR-2011-title21-vol2/pdf/CFR-2011-title21-vol2-part133.pdf |access-date=May 25, 2018}}</ref> The upper pH limit for effectiveness is 6.5.<ref name="potassium sorbate AMS USDA" /> |
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The maximum acceptable daily intake for human consumption is 25 mg/kg, or 1750 mg daily for an average adult (70 kg).<ref name="expert">{{cite web|url=http://www.inchem.org/documents/jecfa/jecmono/40abcj15.htm |title=036. Sorbate, potassium (FAO Nutrition Meetings Report Series 40abc) |publisher=Inchem.org |access-date=2013-02-22}}</ref><ref name="CarochoBarreiro2014">{{cite journal | last1=Carocho | first1=Márcio | last2=Barreiro | first2=Maria Filomena | last3=Morales | first3=Patricia | last4=Ferreira | first4=Isabel C. F. R. | title=Adding Molecules to Food, Pros and Cons: A Review on Synthetic and Natural Food Additives | journal=Comprehensive Reviews in Food Science and Food Safety | volume=13 | issue=4 | year=2014 | pages=377–399 | doi=10.1111/1541-4337.12065| pmid=33412697 | hdl=10198/12042 | hdl-access=free }}</ref> Under some conditions, particularly at high concentrations or when combined with ]s, potassium sorbate has shown ] in vitro.<ref name="CarochoBarreiro2014"/> |
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Three studies conducted in the 1970s did not find it to have any carcinogenic effects in ]s.<ref>{{Cite journal | doi = 10.1016/S0015-6264(76)80173-3 | title = Long-term toxicity studies of sorbic acid in mice | year = 1976 | last1 = Hendy | first1 = R. J. | last2 = Hardy | first2 = J. | last3 = Gaunt | first3 = I. F. | last4 = Kiss | first4 = I. S. | last5 = Butterworth | first5 = K. R. | journal = Food and Cosmetics Toxicology | volume = 14 | issue = 5 | pages = 381–386 | pmid = 1010505 }}</ref><ref>{{Cite journal | doi = 10.1016/0015-6264(75)90080-2 | title = Long-term toxicity of sorbic acid in the rat | year = 1975 | last1 = Gaunt | first1 = I. F. | last2 = Butterworth | first2 = K. R. | last3 = Hardy | first3 = J. | last4 = Gangolli | first4 = S. D. | journal = Food and Cosmetics Toxicology | volume = 13 | issue = 1 | pages = 31–45 | pmid = 1123201 }}</ref><ref>{{Cite journal | doi = 10.1016/S0015-6264(76)80174-5 | title = Long-term toxicity of parasorbic acid in rats | year = 1976 | last1 = Mason | first1 = P. L. | last2 = Gaunt | first2 = I. F. | last3 = Hardy | first3 = J. | last4 = Kiss | first4 = I. S. | last5 = Butterworth | first5 = K. R. | last6 = Gangolli | first6 = S. D. | journal = Food and Cosmetics Toxicology | volume = 14 | issue = 5 | pages = 387–394| pmid = 1010506 }}</ref> |
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==See also== |
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*]<ref>{{Cite journal|last=Saltmarsh|first=Mike|date=2015-03-15|title=Recent trends in the use of food additives in the United Kingdom|journal=Journal of the Science of Food and Agriculture|volume=95|issue=4|pages=649–652|doi=10.1002/jsfa.6715|issn=1097-0010|pmid=24789520|bibcode=2015JSFA...95..649S |quote=... the preservative used in the study, sodium benzoate, has been replaced by potassium sorbate in the majority of soft drinks.}}</ref> |
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== References == |
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<references/> |
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