{{short description|Food preservative - (CH3(CH)4COOH)}} {{distinguish|Sorbitol|Polysorbate|Ascorbic acid}} {{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 439112841 | Name = Sorbic acid | ImageFile = Sorbinsäure.svg | ImageSize = 200px | ImageName = Sorbic acid | ImageFile2 = Sorbic-acid-3D-balls-B.png | ImageSize2 = 200px | ImageName2 = Sorbic acid (ball-and-stick model) | PIN = (2''E'',4''E'')-Hexa-2,4-dienoic acid | Section1 = {{Chembox Identifiers | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 558605 | PubChem = 643460 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = X045WJ989B | InChI = 1/C6H8O2/c1-2-3-4-5-6(7)8/h2-5H,1H3,(H,7,8)/b3-2+,5-4+ | InChIKey = WSWCOQWTEOXDQX-MQQKCMAXBN | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C6H8O2/c1-2-3-4-5-6(7)8/h2-5H,1H3,(H,7,8)/b3-2+,5-4+ | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = WSWCOQWTEOXDQX-MQQKCMAXSA-N | CASNo_Ref = {{cascite|correct|CAS}} | CASNo = 110-44-1 | ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL = 250212 | ChEBI_Ref = {{ebicite|changed|EBI}} | ChEBI = 38358 | SMILES = O=C(O)\C=C\C=C\C }} | Section2 = {{Chembox Properties | C=6|H=8|O=2 | MeltingPtC = 135 | BoilingPtC = 228 | pKa = 4.76 at 25 °C | Solubility = 1.6 g/L at 20 °C | Density = 1.204 g/cm<sup>3</sup> }} |Section3= {{Chembox Hazards | NFPA-H = 2 | NFPA-F = 1 | NFPA-R = 0 }} }}
'''Sorbic acid''', or '''2,4-hexadienoic acid''', is a natural organic compound used as a food preservative. It has the chemical formula {{chem2|CH3(CH)4CO2H}} and the structure {{chem2|H3C\sCH\dCH\sCH\dCH\sC(\dO)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'' (rowan tree), hence its name.<ref name=Ullmann/>
==Production== The traditional route to sorbic acid involves condensation of malonic acid and crotonaldehyde.<ref>{{cite journal|journal=Org. Synth.|year=1944|volume=24|page=92|doi=10.15227/orgsyn.024.0092|title=Sorbic Acid|author=C. F. H. Allen |author2=J. VanAllan }}</ref> It can also be prepared from isomeric hexadienoic acids, which are available via a nickel-catalyzed reaction of allyl chloride, acetylene, and carbon monoxide. The route used commercially, however, is from crotonaldehyde and ketene.<ref>{{cite book|title=Ashford's Dictionary of Industrial Chemicals|edition=3rd|date=2011|page=8482}}</ref> An estimated 30,000 tonnes are produced annually.<ref name=Ullmann>{{cite encyclopedia|author=Erich Lück, Martin Jager, Nico Raczek|title=Sorbic Acid|encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry|publisher=Wiley-VCH|location=Weinheim|year=2000|doi=10.1002/14356007.a24_507|isbn=3-527-30673-0 }}</ref>
==History== Sorbic acid was isolated in 1859 by distillation of rowanberry oil by A. W. von Hofmann.<ref>{{cite journal |last1=Hofmann |first1=A.W. |title=Neue flüchtige Säure der Vogelbeeren |journal=Annalen der Chemie und Pharmacie |date=1859 |volume=110 |issue=2 |pages=129–140 |doi=10.1002/jlac.18591100202 |url=https://babel.hathitrust.org/cgi/pt?id=uc1.c036497389&view=1up&seq=141 |trans-title=New volatile acid of rowan berries |language=German}} Hofmann named sorbic acid on p. 133: ''"Ich schlage für die krystallinische Säure den Namen ''Sorbinsäure'' vor, wodurch ein alter Name der in den Vogelbeeren gefundenen Aepfelsäure neue Bedeutung gewinnt."'' (For the crystalline acid, I suggest the name "sorbic acid", whereby an old name of the malic acid that's found in rowan berries gains new meaning.) </ref> This affords parasorbic acid, the lactone of sorbic acid, which he converted to sorbic acid by hydrolysis. Its antimicrobial activities were discovered in the late 1930s and 1940s, and it became commercially available in the late 1940s and 1950s. Beginning in the 1980s, sorbic acid and its salts were used as inhibitors of ''Clostridium botulinum'' in meat products to replace the use of nitrites, which can produce carcinogenic nitrosamines.<ref name="Naidu">{{cite book|title=Natural food antimicrobial systems |year=2000|isbn=0-8493-2047-X|page=637|publisher=CRC Press |url=https://books.google.com/books?id=_rmdPO9BNBcC&q=%22sorbic+acid%22&pg=PA637|editor= A. S. Naidu}}</ref>
==Properties and uses== With a p''K''<sub>a</sub> of 4.76, sorbic acid is about as acidic as acetic acid.
Sorbic acid and its salts, especially potassium sorbate and calcium sorbate, are antimicrobial agents often used as preservatives in food and drinks to prevent the growth of mold, yeast, and fungi. In general the salts are preferred over the acid form because they are more soluble in water, but the active form is the acid. The optimal pH for the antimicrobial activity is below pH 6.5. Sorbates are generally used at concentrations of 0.025% to 0.10%. Adding sorbate salts to food will, however, raise the pH of the food slightly so the pH may need to be adjusted to assure safety. It is found in foods such as various kinds of cheese, bread, muffins, donuts, pies, cookies, protein bars, syrups, lemonades, fruit juices, dried meats, sausages, nuggets, burgers, sandwiches, tacos, pizzas, smoked fish, margarine, sauces, soups, and more.<ref>{{cite web|url=https://healthknight.com/sorbic-acid-e200-side-effects-benefits |title=Sorbic Acid (E200) – Overview, Uses, Side Effects & More |date=21 May 2022 |publisher=HealthKnight |access-date=2022-08-04}}</ref>
The E numbers are: * E200 Sorbic acid * E201 Sodium sorbate * E202 Potassium sorbate * E203 Calcium sorbate
Some molds (notably some ''Trichoderma'' and ''Penicillium'' strains) and yeasts are able to detoxify sorbates by decarboxylation, producing ''trans''-1,3-pentadiene. The pentadiene manifests as a typical odor of kerosene or petroleum.<!-- The Soft Drinks Companion - A technical handbook for the beverage industry, chapter 10 --> Other detoxification reactions include reduction to 4-hexenol and 4-hexenoic acid.<ref>{{cite journal |vauthors=Kinderlerer JL, Hatton PV |title=Fungal metabolites of sorbic acid |journal=Food Addit Contam |volume=7 |issue=5 |pages=657–669 |year=1990 |pmid=2253810 |doi=10.1080/02652039009373931}}</ref>
Sorbic acid can also be used as an additive for cold rubber, and as an intermediate in the manufacture of some plasticizers and lubricants.<ref name="Patty's Toxicology">{{cite book|vauthors=Bingham E, Cohrssen B|title=Patty's Toxicology|year=2012|publisher=John Wiley & Sons|page=547|url=http://app.knovel.com/hotlink/toc/id:kpPTEV0011/pattys-toxicology-6th}}</ref>
==Safety== Sorbic acid and sorbate salts have a very low mammalian toxicity and carcinogenicity.<ref>{{cite journal|last1=Piper JD|first1=Piper PW|title=Benzoate and Sorbate Salts: A Systematic Review of the Potential Hazards of These Invaluable Preservatives and the Expanding Spectrum of Clinical Uses for Sodium Benzoate.|journal=Comprehensive Reviews in Food Science and Food Safety|date=2017|volume=16|issue=5|pages=868–880|doi=10.1111/1541-4337.12284|pmid=33371618|doi-access=free}}</ref> Its {{LD50}} is estimated to be between 7.4 and 10{{nbsp}}g/kg.<ref name=Ullmann/>
==See also== * Acids in wine * Parasorbic acid
==References== {{reflist}}
==External links== * [http://www.inchem.org/documents/jecfa/jecmono/40abcj14.htm Sorbic inchem.org]
{{Authority control}}
Category:Enoic acids Category:Preservatives Category:E-number additives Category:Conjugated dienes Category:Substances discovered in the 19th century