SORBIC ACID

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

CAS Number: 110-44-1
EC Number: 203-768-7
IUPAC Name: (2E,4E)-hexa-2,4-dienoic acid
Chemical Formula: C6H8O2

Other names: Sorbic acid, 110-44-1, (2E,4E)-hexa-2,4-dienoic acid, 2,4-Hexadienoic acid, 2E,4E-Hexadienoic acid, Hexa-2,4-dienoic acid, Panosorb, Sorbistat, 2-Propenylacrylic acid, Hexadienoic acid, trans,trans-Sorbic acid, (2E,4E)-2,4-Hexadienoic acid, (E,E)-2,4-Hexadienoic acid, 2,4-Hexadienoic acid, (2E,4E)-, 2,4-Hexadienoic acid, (E,E)-, alpha-trans-gamma-trans-Sorbic acid, Preservastat, Kyselina sorbova, (E,E)-Sorbic acid, Crotylidene acetic acid, trans,trans-2,4-Hexadienoic acid, Acetic acid, crotylidene-, Caswell No. 801, (E,E)-1,3-pentadiene-1-carboxylic acid, 22500-92-1, Acetic acid, (2-butenylidene)-, Hexadienoic acid, (E,E), trans-trans-2,4-Hexadienoic acid, (2-Butenylidene)acetic acid, Sorbinsaeure, CCRIS 5748, HSDB 590, Acidum sorbicum, Hexadienic acid, trans,trans-SA, 1,3-Pentadiene-1-carboxylic acid, E 200, EINECS 203-768-7, 1,3-Pentadiene-1-carboxylic acid, (E,E)-, Kyselina 1,3-pentadien-1-karboxylova, (2-butenylidene) acetic acid, C6:2n-2,4, EPA Pesticide Chemical Code 075901, Sorbic acid (NF), Sorbic acid [NF], UNII-X045WJ989B, 2,4-Hexadiensaeure, C6H8O2, FEMA NO. 3921, CHEBI:38358, AI3-14851, INS-200, (E,E)-Sorbic acid; Sorbic acid, X045WJ989B, 5309-56-8, Acid, Hexadienoic, MFCD00002703, NSC-35405, NSC-49103, NSC-50268, (E,E)-SA, DTXSID3021277, CHEBI:35962, EC 203-768-7, 2,4-SA, NCGC00091737-01, .alpha.-trans-.gamma.-trans-Sorbic acid, SORBIC ACID (II), SORBIC ACID [II], SORBIC ACID (MART.), SORBIC ACID [MART.], SORBIC ACID (USP-RS), SORBIC ACID [USP-RS], DTXCID401277, Sorbic Acid [USAN], SORBIC ACID (EP MONOGRAPH), SORBIC ACID [EP MONOGRAPH], Kyselina sorbova [Czech], Acid, Sorbic, CAS-110-44-1, Acid, Propenylacrylic, Sorbic acid, (E,E)-, Sorbinsaure, sorbic-acid, NSC49103, E-sorbic acid, Kyselina 1,3-pentadien-1-karboxylova [Czech], Hexa-2,4-dienoic acid, (E,E)-, NSC 35405, NSC 49103, NSC 50268, Sorbic Acid (SA), Crotylidene-Acetic acid, starbld0040592, trans, trans-Sorbic acid, Sorbic acid 1000 microg/mL in Acetonitrile, SORBIC ACID [MI], SORBIC ACID [FCC], SCHEMBL1647, SORBIC ACID [HSDB], SORBIC ACID [VANDF], Sorbic acid, >=99.0%, MLS002152937, (2-butenylidene)-Acetic acid, SORBIC ACID [WHO-DD], CHEMBL250212, (e,e)-hexa-2,4-dienoic acid, Sorbic acid, analytical standard, FEMA 3921, (2E,4E)-2,4-Hexenoic acid, HMS3039E13, Sorbic acid, potassium salt (van), 161814-42-2, HY-N0626, STR09707, Tox21_111164, Tox21_201719, Tox21_300182, HB8334, LMFA01030100, s4983, (2E,4E)-2,4-Hexadienoic acid #, 2, 4-Hexadienoic acid potassium salt, AKOS000119456, 1ST2503, CCG-266056, 2,4-Hexadienoic acid, (trans,trans)-, 2,4-Hexadienoic acid, >=99%, FCC, NCGC00091737-02, NCGC00091737-03, NCGC00091737-05, NCGC00253957-01, NCGC00259268-01, 91751-55-2, DA-58006, E200, SMR001224532, Sorbic acid, tested according to Ph.Eur., DB-309726, Sorbic acid, SAJ first grade, >=98.5%, CS-0009618, NS00002145, S0053, Sorbic acid, Vetec(TM) reagent grade, 98%, (E,E)-2,4-HEXADIENOIC ACID [FHFI], EN300-17945, Sorbic acid, for synthesis, 99.0-101.0%, alpha-trans-Laquo gammaRaquo -trans-sorbic acid, D05892, E80726, EN300-332923, SBI-0653859.0001, Hexadienoic acid1,3-pentadiene-1-carboxylic acid, AN-651/40229308, Q407131, J-002425, J-524281, BRD-K55892330-001-01-8, Z57127888, F8886-8255, Sorbic acid, European Pharmacopoeia (EP) Reference Standard, Sorbic acid, United States Pharmacopeia (USP) Reference Standard, Sorbic acid, Pharmaceutical Secondary Standard; Certified Reference Material, InChI=1/C6H8O2/c1-2-3-4-5-6(7)8/h2-5H,1H3,(H,7,8)/b3-2+,5-4

Sorbic Acid's Production:
The traditional route to Sorbic Acid involves condensation of malonic acid and trans-butenal.
Sorbic Acid 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.
An estimated 30,000 tons are produced annually.

Properties and Uses:
With a pKa of 4.76, it is about as acidic as acetic acid.

Sorbic Acid and its salts, such as sodium sorbate, 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 cheeses and breads.
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. 

Other detoxification reactions include reduction to 4-hexenol and 4-hexenoic acid.
Sorbic Acid can also be used as an additive for cold rubber, and as an intermediate in the manufacture of some plasticizers and lubricants.

Sorbic Acid is a naturally occurring compound that’s become the most commonly used food preservative in the world, and it makes the global food chain possible. 
Sorbic Acid’s highly effective at inhibiting the growth of mold, which can spoil food and spread fatal diseases

Sorbic Acid is most commonly found in foods, animal feeds, pharmaceutical drugs, and cosmetics.
When it comes to human foods, Sorbic Acid is most commonly used in:
wines
cheeses
baked goods
fresh produce
refrigerated meat and shellfish

Sorbic Acid is used to preserve meats because of its natural antibiotic capabilities.
Sorbic Acid's use saved countless lives by preventing bacterial growth while allowing meats to be transported and stored safely.

Because of its anti-fungal properties, Sorbic Acid is also used in: 
canned goods
including pickles
prunes
maraschino cherries
figs
prepared salads

Sorbic Acid is used as a preservative in a wide variety of foods. 
Sorbic Acid retards the growth of yeast and moulds and is usually added to foods as a salt.

Sorbic Acid is a natural preservative first isolated in 1859 from the berries of an ash tree. 
Sorbic Acid is unsaturated fatty acid containing two carbon-carbon double bonds and both are in the trans configuration 

Sorbic Acids are used as preservatives in various meat products to retard the growth of yeasts and molds.
Sorbic Acid inhibits the growth of C. botulinum and further reduces nitrosamine formation. 

Sorbic Acid and its salts have broad-spectrum activity against yeast and molds, but are less active against bacteria. 
Sorbic Acid is mainly used in foods in the forms of calcium, sodium or potassium sorbates.

Sorbic Acid is the most common food preservative against molds, bacteria, fungi, and yeasts. 
Sorbic Acid is favored for its organoleptic neutrality, safety, and efficacy in low moisture foods such as cheeses, and bakery.

Sorbic Acid is a carboxylic acid that is slightly soluble in water and is available as a powder, granules, or microcapsules. 
Sorbic Acid can be applied to foods using various methods:

Dipping and spraying finished products with solutions.
Dusting with powdered Sorbic Acid
Mixing into formula dry ingredients
Treatment of packaging material

Sorbic Acid's Functions:
Microbial inhibition by Sorbic Acid is variable and depends on species, strains, composition of food, pH, aw, processing, temperature, and concentration of sorbate. 
In baking, it is used in sliced and packaged bread, bagels and pita as well as in par-baked, baked goods and frozen doughs.

Optimal antimicrobial activity is at pH below 6.5 (maximum activity at pH 4.76), an advantage compared to benzoic and propionic acids which lose their activities at pH 4.5 – 5.5
Practical considerations when using this acid in baking:

Sorbic Acid has a water solubility of around 0.16g/100 ml which increases with temperature but is reduced in the presence of sugars.

This acid inhibits yeasts strains differently, as some strains are more tolerant to its effects than others.

Sodium sorbate, calcium sorbate, and potassium sorbates are more soluble in water than Sorbic Acid. 
So, they are more commonly used in foods. However, they may raise the pH slightly, therefore some medium adjustments may be necessary.

Sorbic Acid appears as white powder or crystals. 
Sorbic Acid's Melting point 134.5°C. 

Sorbic Acid is slightly acidic and astringent taste with a faint odor.
Sorbic Acid is a hexadienoic acid with double bonds at C-2 and C-4

Sorbic Acid has four geometrical isomers, of which the trans,trans-form is naturally occurring. 
Sorbic Acid is a hexadienoic acid, a polyunsaturated fatty acid, a medium-chain fatty acid and an alpha,beta-unsaturated monocarboxylic acid. 

Sorbic Acid is a conjugate acid of a sorbate.
Sorbic Acid is a natural product found in Prunus domestica and Schisandra chinensis 

Sorbic Acid, an unsaturated six-carbon fatty acid, is a naturally occurring preservative that is used less in food compared to its potassium salt – potassium sorbate (E202) due to the slight solubility in water. 
This ingredient can be used in low water content food such as baked goods, cheese, dried fruits, meat and fatty media.

Sorbic Acid is generally used to inhibit the growth of molds yeast and some bacteria. 
The European food additive number for it is E200. 

Sorbic Acid can be naturally found in berries species, such as mountain ash, rowan and magnolia vine
Sorbic Acid is commercially synthesized from the condensation between ketene and crotonaldehyde instead of extracted from berries.

Sorbic Acid can prevent the spoilage of yeast, mold, and some bacteria in food and therefore prolong food shelf life. 
Sorbic Acid can be used to preserve foods with low water content and the following food may contain it:
cheese
dried fruit
yogurt
pet foods
dried meats
baked goods

Sorbic Acid appears as white powder or crystals. 
Sorbic Acid's Melting point 134.5°C. 
Sorbic Acid is used as a preservative in a wide variety of foods. 

Sorbic Acid retards the growth of yeast and moulds and is usually added to foods as a salt.
Sorbic Acid can also be used as an additive for cold rubber, and as an intermediate in the manufacture of some plasticizers and lubricants.

Hydrogen Bond Donor Count: 1    
Hydrogen Bond Acceptor Count: 2    
Rotatable Bond Count: 2
Heavy Atom Count: 8    
Complexity: 123    
Defined Bond Stereocenter Count: 2    
Covalently-Bonded Unit Count: 1    
Compound Is Canonicalized: Yes

Sorbic Acid, or 2,4-hexadienoic acid, is a natural organic compound used as a food preservative.
Sorbic Acid has the chemical formula CH3(CH)4CO2H. 
Sorbic Acid is a colourless solid that is slightly soluble in water and sublimes readily. 

Sorbic Acid was first isolated from the unripe berries of the Sorbus aucuparia (rowan tree), hence its name.
Sorbic Acid is a naturally occurring compound that’s become the most commonly used food preservative in the world, and it makes the global food chain possible. 

Sorbic Acid’s highly effective at inhibiting the growth of mold, which can spoil food and spread fatal diseases
Sorbic Acid is most commonly found in foods, animal feeds, pharmaceutical drugs, and cosmetics.
Sorbic Acid is a natural preservative first isolated in 1859 from the berries of an ash tree. 

Sorbic Acid is unsaturated fatty acid containing two carbon-carbon double bonds and both are in the trans configuration 
Sorbic Acids are used as preservatives in various meat products to retard the growth of yeasts and molds.

Sorbic Acid inhibits the growth of C. botulinum and further reduces nitrosamine formation. 
Sorbic Acid and its salts have broad-spectrum activity against yeast and molds, but are less active against bacteria. 
Sorbic Acid is mainly used in foods in the forms of calcium, sodium or potassium sorbates.

Sorbic Acid is the most common food preservative against molds, bacteria, fungi, and yeasts. 
Sorbic Acid is favored for its organoleptic neutrality, safety, and efficacy in low moisture foods such as cheeses, and bakery.

Sorbic Acid is a carboxylic acid that is slightly soluble in water and is available as a powder, granules, or microcapsules. 
Sorbic Acid is slightly acidic and astringent taste with a faint odor.
Sorbic Acid is a hexadienoic acid with double bonds at C-2 and C-4

Sorbic Acid has four geometrical isomers, of which the trans,trans-form is naturally occurring. 
Sorbic Acid is a hexadienoic acid, a polyunsaturated fatty acid, a medium-chain fatty acid and an alpha,beta-unsaturated monocarboxylic acid. 

Sorbic Acid is a conjugate acid of a sorbate.
Sorbic Acid is a natural product found in Prunus domestica and Schisandra chinensis.