SORBIC ACID

Table of Contents

SORBIC ACID

(2E,4E)-hexa-2,4-dienoic acid

Cas no: 110-44-1  

Sorbic acid, or 2,4-hexadienoic acid, is a natural organic compound used as a food preservative. It has the chemical formula C6H8O2. 

 

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 and the structure H3C−CH=CH−CH=CH−C(=O)OH. 

Sorbic acid, CH3–CH=CH–CH=CH–COOH, is a di-unsaturated, six carbon-atom fatty acid

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 is  highly effective at inhibiting the growth of mold, which can spoil food and spread fatal diseases. 

For example, when sorbic acid is sprayed on the exterior of a country ham, there won’t be any mold growth for 30 days. 

This allows for food to be shipped and stored all over the globe.

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. 

Calcium sorbate is tasteless and flavourless. Sorbates are mainly used as fungistats in products such as cheese, bakery products, fruit juices, beverages and salad dressing. 

In meat products they can function as antibotulinal agents, reducing the need for nitrite. 

Sorbates are primarily effective against yeasts and moulds, but can also be used against a range of bacteria, especially catalase-positive cocci, spore-forming bacteria and aerobes. Sorbic acid works best below pH 6.0 and is generally ineffective above pH 6.5. Between pH 4.0 and 6.0 sorbates are generally more effective than benzoates. The pK of sorbic acid is 4.80 

Sorbic acid is a preferred preservative compared to nitrates, which can form carcinogenic byproducts. SORBIC ACID is applied to food by either spraying or dipping the food with a solution of sorbic acid and water.

Sorbic acid is only weakly water-soluble; therefore, the form most commonly utilized is the water-soluble potassium sorbate

As a Food Preservative

Sorbic acid is most commonly found in foods, animal feeds, pharmaceutical drugs, and cosmetics.

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 earliest use was against one of the deadliest toxins known to mankind, the bacteria Clostridium botulinum, which can cause botulism. 

The use of Sorbic Acid saved countless lives by preventing bacterial growth while allowing meats to be transported and stored safely.

Thanks to its anti-fungal properties, sorbic acid is also used in canned goods, including pickles, prunes, maraschino cherries, figs, and 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. 

The major food groups contributing to dietary intake of sorbic acid constitute a wide variety permitted at the following levels: various foods 200–2000 mg/kg (liquid egg 5000 mg/kg, cooked seafood 6000 mg/kg) and soft drinks, wine etc. 200–300 mg/ kg (Sacramental grape juice 2000 mg/kg, liquid tea concentrates 600 mg/kg). The acceptable daily intake (ADI) for sorbic acid is 25 mg/kg body weight.

Production

The traditional route to sorbic acid involves condensation of malonic acid and crotonaldehyde.

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.

History

Sorbic acid was isolated in 1859 by distillation of rowanberry oil by A. W. von Hofmann.

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.

Properties and uses

With a pKa 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.

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. 

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 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

Investigation of its antimicrobial activity found it to be an effective inhibitor of molds, yeasts, and fungi. 

Sodium and potassium salts of sorbic acid (i.e., sodium sorbate and potassium sorbate) are not as effective. 

The free acid form is more effective as an antimicrobial. Antimicrobial activity of sorbic acid increases as the pH of the media decreases. 

Enhanced activity at low pH results from the acid being fully protonated (unionized) and thus readily taken up by the microorganism. 

Combination of sorbic acid and lactic acid have also been shown to inhibit the growth of the pathogen Salmonella. 

Sorbic acid is widely used to inhibit yeast and molds in processed cheese, wine, fruit juices, and some baked goods (pastries). 

Sorbic Acid is also used in processed meats as an alternative to preservation using nitrites.

Safety

Sorbic acid and sorbate salts have a very low mammalian toxicity and carcinogenicity.

Its LD50 is estimated to be between 7.4 and 10 g/kg.

SYNONYMS OF SORBIC ACID: 

sorbic acid

110-44-1

2,4-Hexadienoic acid

(2E,4E)-hexa-2,4-dienoic acid

2E,4E-Hexadienoic acid

Panosorb

Sorbistat

2-Propenylacrylic acid

Hexadienoic acid

trans,trans-Sorbic acid

(E,E)-2,4-Hexadienoic acid

2,4-Hexadienoic acid, (2E,4E)-

Hexa-2,4-dienoic acid

2,4-Hexadienoic acid, (E,E)-

alpha-trans-gamma-trans-Sorbic acid

Preservastat

(E,E)-Sorbic acid

trans,trans-2,4-Hexadienoic acid

Crotylidene acetic acid

Kyselina sorbova

Acetic acid, crotylidene-

(2E,4E)-2,4-Hexadienoic acid

(E,E)-1,3-pentadiene-1-carboxylic acid

22500-92-1

Acetic acid, (2-butenylidene)-

trans-trans-2,4-Hexadienoic acid

Hexadienoic acid, (E,E)

(2-Butenylidene)acetic acid

C6:2n-2,4

Sorbic acid (NF)

Sorbic acid [NF]

1,3-Pentadiene-1-carboxylic acid

1,3-Pentadiene-1-carboxylic acid, (E,E)-

E 200

Kyselina 1,3-pentadien-1-karboxylova

(2-butenylidene) acetic acid

FEMA NO. 3921

CHEBI:38358

INS-200

X045WJ989B

NSC-35405

NSC-49103

NSC-50268

5309-56-8

NCGC00091737-01

.alpha.-trans-.gamma.-trans-Sorbic acid

DSSTox_CID_1277

2,4-Hexadienoic acid, (2E,4E)-, homopolymer

DSSTox_RID_76053

DSSTox_GSID_21277

Hexadienic acid

Caswell No. 801

Sorbic Acid [USAN]

Acidum sorbicum

Kyselina sorbova [Czech]

34344-66-6

CAS-110-44-1

Sorbic acid solution

CCRIS 5748

HSDB 590

(2E)-2,4-Hexadienoic acid

EINECS 203-768-7

Sorbic acid, (E,E)-

EPA Pesticide Chemical Code 075901

Sorbinsaeure

Sorbinsaure

sorbic-acid

NSC49103

UNII-X045WJ989B

AI3-14851

E-sorbic acid

trans,trans-SA

Kyselina 1,3-pentadien-1-karboxylova [Czech]

(E,E)-Sorbic acid; Sorbic acid

Sorbic Acid FCC

Hexa-2,4-dienoic acid, (E,E)-

2,4-Hexadiensaeure

MFCD00002703

Crotylidene-Acetic acid

starbld0040592

SORBIC ACID [II]

SORBIC ACID [MI]

SORBIC ACID [FCC]

EC 203-768-7

SCHEMBL1647

SORBIC ACID [HSDB]

SORBIC ACID [INCI]

SORBIC ACID [VANDF]

SORBIC ACID [MART.]

Sorbic acid, >=99.0%

MLS002152937

(2-butenylidene)-Acetic acid

SORBIC ACID [USP-RS]

SORBIC ACID [WHO-DD]

(E,E)-SA

CHEMBL250212

(e,e)-hexa-2,4-dienoic acid

DTXSID3021277

Sorbic acid, analytical standard

CHEBI:35962

FEMA 3921

HMS3039E13

SORBIC ACID [EP MONOGRAPH]

Sorbic acid, potassium salt (van)

HY-N0626

STR09707

ZINC1558385

Tox21_111164

Tox21_201719

Tox21_300182

2,4-SA

LMFA01030100

s4983

(2E,4E)-2,4-Hexadienoic acid #

2, 4-Hexadienoic acid potassium salt

AKOS000119456

CCG-266056

2,4-Hexadienoic acid, (trans,trans)-

2,4-Hexadienoic acid, >=99%, FCC

NCGC00091737-02

NCGC00091737-03

NCGC00091737-05

NCGC00253957-01

NCGC00259268-01

E200

SMR001224532

Sorbic acid, tested according to Ph.Eur.

Sorbic acid, SAJ first grade, >=98.5%

CS-0009618

S0053

Sorbic acid 1000 microg/mL in Acetonitrile

Sorbic acid, Vetec(TM) reagent grade, 98%

(E,E)-2,4-HEXADIENOIC ACID [FHFI]

Sorbic acid, for synthesis, 99.0-101.0%

alpha-trans-Laquo gammaRaquo -trans-sorbic acid

D05892

E80726

Hexadienoic acid1,3-pentadiene-1-carboxylic acid

A829400

AN-651/40229308

Q407131

J-002425

J-524281

F8886-8255 

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