Sorbic acid, or 2,4-hexadienoic acid, is a natural

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon- hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. Th ...

used as a food

preservative A preservative is a substance or a chemical that is added to products such as food products, beverages, pharmaceutical drugs, paints, biological samples, cosmetics, wood, and many other products to prevent decomposition by microbial growth or ...

. It has the

chemical formula In chemistry, a chemical formula is a way of presenting information about the chemical proportions of atoms that constitute a particular chemical compound or molecule, using chemical element symbols, numbers, and sometimes also other symbols, ...

and the structure . It is a colourless solid that is slightly

soluble In chemistry, solubility is the ability of a substance, the solute, to form a solution with another substance, the solvent. Insolubility is the opposite property, the inability of the solute to form such a solution. The extent of the solub ...

in water and

sublimes Sublimation is the transition of a substance directly from the solid to the gas state, without passing through the liquid state. Sublimation is an endothermic process that occurs at temperatures and pressures below a substance's triple point i ...

readily. It was first isolated from the unripe berries of the ''Sorbus aucuparia'' (

rowan The rowans ( or ) or mountain-ashes are shrubs or trees in the genus ''Sorbus'' of the rose family, Rosaceae. They are native throughout the cool temperate regions of the Northern Hemisphere, with the highest species diversity in the Himalaya ...

tree), hence its name.

Production

The traditional route to sorbic acid involves condensation of

malonic acid Malonic acid (IUPAC systematic name: propanedioic acid) is a dicarboxylic acid with structure CH2(COOH)2. The ionized form of malonic acid, as well as its esters and salts, are known as malonates. For example, diethyl malonate is malonic aci ...

and

crotonaldehyde Crotonaldehyde is a chemical compound with the formula CH3CH=CHCHO. The compound is usually sold as a mixture of the ''E''- and ''Z''-isomers, which differ with respect to the relative position of the methyl and formyl groups. The ''E''-isome ...

. It can also be prepared from isomeric hexadienoic acids, which are available via a nickel-catalyzed reaction of

allyl chloride Allyl chloride is the organic compound with the formula C H2=CHCH2 Cl. This colorless liquid is insoluble in water but soluble in common organic solvents. It is mainly converted to epichlorohydrin, used in the production of plastics. It is a ch ...

acetylene Acetylene ( systematic name: ethyne) is the chemical compound with the formula and structure . It is a hydrocarbon and the simplest alkyne. This colorless gas is widely used as a fuel and a chemical building block. It is unstable in its pur ...

, and

carbon monoxide Carbon monoxide ( chemical formula CO) is a colorless, poisonous, odorless, tasteless, flammable gas that is slightly less dense than air. Carbon monoxide consists of one carbon atom and one oxygen atom connected by a triple bond. It is the si ...

. The route used commercially, however, is from

and

ketene In organic chemistry, a ketene is an organic compound of the form , where R and R' are two arbitrary monovalent chemical groups (or two separate substitution sites in the same molecule). The name may also refer to the specific compound eth ...

. An estimated 30,000 tons are produced annually.

History

Sorbic acid was isolated in 1859 by

distillation Distillation, or classical distillation, is the process of separating the components or substances from a liquid mixture by using selective boiling and condensation, usually inside an apparatus known as a still. Dry distillation is the he ...

berry oil by A. W. von Hofmann. This affords parasorbic acid, the

lactone Lactones are cyclic carboxylic esters, containing a 1-oxacycloalkan-2-one structure (), or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. Lactones are formed by intramolecular esterification of the co ...

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 ''Clostridium botulinum'' is a Gram-positive, rod-shaped, anaerobic, spore-forming, motile bacterium with the ability to produce the neurotoxin botulinum. The botulinum toxin can cause botulism, a severe flaccid paralytic disease in humans ...

'' in meat products to replace the use of

nitrites The nitrite ion has the chemical formula . Nitrite (mostly sodium nitrite) is widely used throughout chemical and pharmaceutical industries. The nitrite anion is a pervasive intermediate in the nitrogen cycle in nature. The name nitrite also r ...

, which can produce carcinogenic

nitrosamines In organic chemistry, nitrosamines (or more formally ''N''-Nitrosamines) are organic compounds with the chemical structure , where R is usually an alkyl group. They feature a nitroso group () bonded to a deprotonated amine. Most nitrosamines a ...

Properties and uses

With a p''K''_a of 4.76, sorbic acid is about as acidic as acetic acid. Sorbic acid and its salts, especially

potassium sorbate Potassium sorbate is the potassium salt of sorbic acid, chemical 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). Potassium sor ...

and

calcium sorbate Calcium sorbate is the calcium salt of sorbic acid. Calcium sorbate is a polyunsaturated fatty acid salt. It is a commonly used food preservative Food preservation includes processes that make food more resistant to microorganism growth a ...

, are antimicrobial agents often used as preservatives in food and drinks to prevent the growth of

mold A mold () or mould () is one of the structures certain fungi can form. The dust-like, colored appearance of molds is due to the formation of spores containing fungal secondary metabolites. The spores are the dispersal units of the fungi. Not ...

yeast Yeasts are eukaryotic, single-celled microorganisms classified as members of the fungus kingdom. The first yeast originated hundreds of millions of years ago, and at least 1,500 species are currently recognized. They are estimated to consti ...

, and

fungi A fungus (plural, : fungi or funguses) is any member of the group of Eukaryote, eukaryotic organisms that includes microorganisms such as yeasts and Mold (fungus), molds, as well as the more familiar mushrooms. These organisms are classified ...

. 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. The E numbers are: * E200 Sorbic acid * E201

Sodium sorbate Sodium sorbate is the sodium salt of sorbic acid. It is an unstable white solid. Unlike other sorbic acid salts such as potassium sorbate (E202) and calcium sorbate (E203), the use of sodium sorbate as a food additive Food additives are subs ...

* E202

Potassium sorbate Potassium sorbate is the potassium salt of sorbic acid, chemical 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). Potassium sor ...

* E203

Calcium sorbate Calcium sorbate is the calcium salt of sorbic acid. Calcium sorbate is a polyunsaturated fatty acid salt. It is a commonly used food preservative Food preservation includes processes that make food more resistant to microorganism growth a ...

Some molds (notably some ''

Trichoderma ''Trichoderma'' is a genus of fungi in the family Hypocreaceae that is present in all soils, where they are the most prevalent culturable fungi. Many species in this genus can be characterized as opportunistic avirulent plant symbionts. This ...

'' and ''

Penicillium ''Penicillium'' () is a genus of ascomycetous fungi that is part of the mycobiome of many species and is of major importance in the natural environment, in food spoilage, and in food and drug production. Some members of the genus produce ...

'' strains) and

s are able to detoxify sorbates by

decarboxylation Decarboxylation is a chemical reaction that removes a carboxyl group and releases carbon dioxide (CO2). Usually, decarboxylation refers to a reaction of carboxylic acids, removing a carbon atom from a carbon chain. The reverse process, which is ...

, producing ''trans''-1,3-pentadiene. The pentadiene manifests as a typical odor of

kerosene Kerosene, paraffin, or lamp oil is a combustible hydrocarbon liquid which is derived from petroleum. It is widely used as a fuel in aviation as well as households. Its name derives from el, κηρός (''keros'') meaning " wax", and was reg ...

petroleum Petroleum, also known as crude oil, or simply oil, is a naturally occurring yellowish-black liquid mixture of mainly hydrocarbons, and is found in geological formations. The name ''petroleum'' covers both naturally occurring unprocessed crude ...

. Other detoxification reactions include reduction to 4-

hexenol ''cis''-3-Hexen-1-ol, also known as (''Z'')-3-hexen-1-ol and leaf alcohol, is a colorless oily liquid with an intense grassy-green odor of freshly cut green grass and Leaf, leaves. It is produced in small amounts by most plants and it acts as an ...

and 4-hexenoic acid. Sorbic acid can also be used as an

additive Additive may refer to: Mathematics * Additive function, a function in number theory * Additive map, a function that preserves the addition operation * Additive set-functionn see Sigma additivity * Additive category, a preadditive category with f ...

for cold rubber, and as an intermediate in the manufacture of some

plasticizers A plasticizer ( UK: plasticiser) is a substance that is added to a material to make it softer and more flexible, to increase its plasticity, to decrease its viscosity, and/or to decrease friction during its handling in manufacture. Plasticiz ...

and

lubricants A lubricant (sometimes shortened to lube) is a substance that helps to reduce friction between surfaces in mutual contact, which ultimately reduces the heat generated when the surfaces move. It may also have the function of transmitting forces, t ...

Safety

Sorbic acid and sorbate salts have a very low mammalian toxicity and carcinogenicity. Its is estimated to be between 7.4 and 10 g/kg.

References

External links