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.
It’s 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.
It’s 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
