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.

Chemical names: Sorbic acid, 2,4-hexadienoic acid, 2-propenylacrylic acid

Sorbic acid is a reliable preservative that is highly effective at providing a strong protection against numerous molds, yeast and many bacteria.
Sorbic acid is only sparingly soluble in water, making it ideal for low water applications like baked goods or in fatty media.
Upon request, Sorbic Acid is available in pharmaceutical grade.

EC / List no.: 203-768-7
CAS no.: 110-44-1
Mol. formula: C6H8O2

IUPAC name: (2E,4E)-hexa-2,4-dienoic acid
CAS Number: 110-44-1
C.A.S. number 110-44-1
Chemical formula C6H8O2

Properties
Chemical formula: C6H8O2
Molar mass: 112.128 g·mol−1
Density: 1.204 g/cm3
Melting point: 135 °C
Boiling point: 228 °C
Solubility in water: 1.6 g/L at 20 °C
Acidity (pKa): 4.76 at 25 °C

FUNCTIONAL USES: Antimicrobial preservative, fungistatic agent

Sorbic Acid is an organic compound primarily used as a food preservative.
Sorbic Acid is also effective in a wide variety of applications such as animal feed, and personal care products.

When used as a food preservative, sorbic acid inhibits the growth of mold, yeast and other microorganisms for shelf life stability.
Sorbic acid is often used in foods such as cheese, dried fruit, yogurt, pet foods, dried meats, soft drinks, and baked goods.

Sorbic acid (C6H8O2) is a natural preservative that comes from the rowan berries, Sorbus aucuparia (family Rosaceae). It is also prepared synthetically. It inhibits growth of fungi, yeast, mold and some bacteria and is nearly nontoxic to humans. Sorbic acid is safe to use in a wide range of foods, drugs, and cosmetic products. Sorbic acid and its salts, sodium sorbate, potassium sorbate and calcium sorbate are often used in food products as preservatives.

Sorbic Acid is a natural product that is one of the most commonly used food preservatives in the bakery market. It is a highly effective antimicrobial agent that inhibits the growth of mould, yeast and fungi, thereby prolonging shelf life.

Sorbic acid
INCI: Sorbic acid.
CAS-No .: 110-44-1
EINECS-No .: 203-768-7

Synonyms: 2,4-hexadienoic acid. E-200.
Molecular formula: C6H8O2
Molecular weight: 112.13
Crystal powder, white or almost white. Slightly soluble in water, easily soluble in 96 percent ethanol. Melting point: 134.5 ° C.
Wealth: 99.0-101.0%

They have antibacterial and antifungal properties, particularly against molds and yeasts. Its activity decreases to pH> 6.0 – 6.5, with an optimum of 4.5.
They are used as a preservative in pharmaceutical and cosmetic preparations. It has the advantage over sorbic acid of having a greater solubility in water.
Efficacy increases when combined with other antimicrobials or with glycols such as propylene glycol.

In emulsions it is better to use equal parts of the acid and salt of potassium by reason of the partition coefficient.

Product Benefits:
• Antimicrobial agent that inhibits the growth of mould, yeast and fungi.
• Colourless, odourless and tasteless.
• Less is needed by weight compared to other preservatives.

Product Applications:
• Used as a preservative in food and drinks.
• Used to preserve meats because of its natural antibiotic capabilities.

Sorbic acid has physiological inertness and their effectiveness even in the weakly acid pH range and their neutral taste, sorbic acid and its salts have become the leading preservatives in the food sector throughout the world over the past 30 years. Sorbic Acid is widely used as preservative in food production especially in meat, aquatic products, vegetables and fruits to inhibit microbial growth. It is also widely used as preservative in beverage in carbonated drinks, fruit drinks, dairy drinks to inhibit microbial growth.

Sorbic acid is often used as a preservative in food and drinks to prevent the growth of mould, 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 many other foods, such as cheeses and breads.

Sorbic acid, or 2,4-hexadienoic acid, is a natural organic compound used as a food preservative. It has the chemical formula C6H8O2. It is a colourless solid that is slightly soluble in water and sublimes readily. It was first isolated from the unripe berries of the rowan tree (Sorbus aucuparia), hence its name.

SORBIC ACID
INCI: Sorbic Acid

Extraction: This acid is present in various fruits, but it is extracted from sorbellano fruit (sorbus aucuparia).

Benefits: Sorbic acid helps to preserve cosmetics, they are used as antimicrobial agents in the food and cosmetic industry. Specifically reduce the development of yeast and fungi.

Other names: 2,4-Hexadienoic acid, (E,E)-; Sorbic acid, (E,E)-; α-trans-γ-trans-Sorbic acid; trans,trans-Sorbic acid; trans,trans-2,4-Hexadienoic acid; Sorbistat; 1,3-Pentadiene-1-carboxylic acid, (E,E)-; 2-Propenylacrylic acid; 2,4-Hexadienoic acid, (trans,trans)-; Acetic acid, (2-butenylidene)-; Acetic acid, crotylidene-; Kyselina 1,3-pentadien-1-karboxylova; Kyselina sorbova; (E,E)-Sorbic acid; (2-Butenylidene)acetic acid; (E,E)-2,4-hexadienoic acid; Crotylidene acetic acid; Hexa-2,4-dienoic acid, (E,E)-; Hexadienoic acid, (E,E); Panosorb; Preservastat; 2,4-Hexadienoic acid, (2E,4E)-; 2E,4E-Hexadienoic acid; E 200; 2,4-Hexadienoic acid; hexa-2,4-dienoic acid

SORBIC ACID
CAS number: 110-44-1 – Sorbic acid
Origin(s): Natural, Synthetic
Other languages: Acide sorbique, Acido sorbico, Sorbinsäure, Ácido sórbico
INCI name: SORBIC ACID
EINECS/ELINCS number: 203-768-7
Food additive: E200
Classification: Regulated, Preservative
Bio-compatible (COSMOS Reference)
Sorbic acid is a preservative used in cosmetics and food (under the name E200). It is present in its natural state in the bays of the Sorbier des oiseaux (Sorbus aucuparia L., hence its name), from which it was isolated. It is authorized in organic.
Restriction in Europe: The maximum concentration allowed in ready-to-use cosmetic preparations is 0.6%.

Its functions (INCI)
Preservative : Inhibits the development of microorganisms in cosmetic products.
Masking : Reduces or inhibits the odor or basic taste of the product

Sorbic acid is a naturally occurring compound that’s the most commonly used food preservative in the world. It’s highly effective at inhibiting the growth of mold, which can spoil food. When Sorbic acid is sprayed on the exterior of food, mold is inhibited for a period of time that allows the food to be shipped and stored all over the globe. When it comes to human foods, Sorbic acid is most commonly used in wines, cheeses, baked goods, fresh produce and refrigerated meats and shellfish. Because of its anti-fungal properties, Sorbic acid is also used in canned goods, including pickles, prunes, maraschino cherries, figs and prepared salads.

Sorbic acid is a straight-chain monocarboxylic acid used in cosmetic formulations as a preservative at concentrations up to 1.0%.
Sorbic acid and potassium sorbate were practically nontoxic to rats and mice in acute oral toxicity studies.
In subchronic studies no significant adverse effects were observed in rats, mice, or dogs when 10% sorbic acid was included in the diet.
Sorbic acid and potassium sorbate at concentrations up to 10% were practically nonirritating to the rabbit eye.
Both ingredients at concentrations up to 10% were at most only slightly irritating.
Sorbic acid and potassium sorbate have been tested for mutagenic effects using the Ames test, genetic recombination tests, reversion assays, rec assays, tests for chromosomal aberrations, sister chromatid exchanges, and gene mutations.
Results have been both positive and negative. Potassium sorbate at 0.1% in the diet or 0.3% in drinking water of rats for up to 100 weeks produced no neoplasms.
In other chronic studies, no carcinogenic effect was demonstrated by sorbic acid in rats or mice fed diets containing up to 10% sorbic acid.
No teratogenic effects have been observed in pregnant mice and rats ad ministered potassi um sorbate.
In three repeat insult patch tests, sorbic acid had overall sensitization rates of 0, 0.33, and 0.8%.
All of the subjects sensitized were inducted with 20% sorbic acid and challenged with 5% sorbic acid.
Formulations containing up to 0.5% sorbic acid and or potassium sorbate were not significant primary or cumulative irritants and not sensitizers at this test concentration.
A formulation containing 0.01% sorbic acid was not a photosensitizer.
On the basis of the available data, it is concluded that sorbic acid and potassium sorbate are safe as cosmetic ingredients in the present practices of use (and concentration.

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 is a preferred preservative compared to nitrates.
It’s applied to food by either spraying or dipping the food with a solution of sorbic acid and water.

As a Food Preservative
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.

The sorbic acid and its salts have been widely used in the food industries for many years as important food preservatives in order to inhibit the growth of various bacteria, yeasts, and fungi in acidic media. The health effects have led to limitation on the concentrations that can be used in food

CAS No.: 110-44-1

Synonyms: (2E,4E)-hexa-2,4-dienoic acid, 2,4-hexadienoic acid

Sorbic acid is used as a preservative in food and drinks to prevent the growth of mold, yeast and fungi.

Use: Preservative, Cosmetics, Feed, Tobacco, Mold Inhibitor, Yeast Inhibitor, Bactericide, Antimicrobial, Beverages, Beverage Powder, Soft Drink, Cakes, Cheese, Fish, Fruit Juice, Margarine, Pickled Goods, Salad Dressings, Fresh Salad, Wine, Puddings, Sauces, Baking Food, Sauage, Food Colors, Milk, Wine, Flavoring Agent.

General description
Sorbic acid is used as a food preservative and has antimicrobial property.

Biochem/physiol Actions
Sorbic acid can be used to inhibit bacterial, yeast and fungal sulfhydryl enzymes by inhibiting amino acid uptake.

In fact, its earliest use was against one of the deadliest toxins known to mankind, the bacteria Clostridium botulinum, which can cause botulism.
Its 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, and prepared salads.

Sorbic acid appears as white powder or crystals. Melting point 134.5°C. Slightly acidic and astringent taste with a faint odor.

Sorbic acid is a hexadienoic acid with double bonds at C-2 and C-4; it has four geometrical isomers, of which the trans,trans-form is naturally occurring.
It is a hexadienoic acid, a polyunsaturated fatty acid, a medium-chain fatty acid and an alpha,beta-unsaturated monocarboxylic acid.
It is a conjugate acid of a sorbate.

Is It Safe?
The U.S. Food and Drug Administration considers sorbic acid to be safe for regular use, as it’s not linked to cancer or other major health problems.
Some people can be allergic to sorbic acid, but reactions are typically mild and consist of light skin itching.

The Takeaway
Sorbic acid has proven vital to our ability to store food and transport it across long distances.
Allergies are rare and usually very mild, but exposure to undiluted sorbic acid might carry some risks.

Because of their physiological inertness, their effectiveness even in the weakly acid pH range and their neutral taste, sorbic acid and its salts have become the leading preservatives in the food sector throughout the world over the past 30 years.
The most commonly used products are sorbic acid itself (E200) and potassium sorbate (E202).
In many countries sodium sorbate (E201) and calcium sorbate (E203) are also permitted.
Sorbic acid is sparingly soluble in water, sodium sorbate has better solubility, and potassium sorbate is very freely soluble and can be used to produce 50% stock solutions.
The soluble sorbates are preferred when it is desired to use the preservative in liquid form, or when aqueous systems are to be preserved.
Sodium sorbate in solid form is unstable and very rapidly undergoes oxidation on exposure to atmospheric oxygen.
It is therefore not produced on the industrial scale.
Aqueous solutions of sodium sorbate remain stable for some time.
Calcium sorbate is used in the manufacture of fungistatic wrappers because it is highly stable to oxidation, but this use is very limited.
Sorbic acid and sorbates can be directly added into the product. The products can be dipped or sprayed with aqueous solutions of sorbates.
Dusting of food with dry sorbic acid is also possible but less recommended because sorbic acid irritates the skin and mucous membranes.
Sorbic acid and particularly calcium sorbate can be used as active substances in fungistatic wrappers.
A general survey of the numerous uses of sorbic acid in the food sector will be given

Sorbic acid is a short-chained unsaturated (has double bonds) fatty acid. Its iupac name is 2,4 hexadienoic acid and its chemical formula is C6H8O2. It has a carboxylic tail which has a pKa of 4.76. Its melting and boiling points are 136 and 228 degrees Celsius, respectively. It is commonly used by the food industry as a preservative because its mineral salts have antimicrobial properties in acidic solutions. Its undissociated form is several degrees more antimicrobial then its dissociated form and is a function of pH, yet both have antimicrobial properties. It is particularly effective against fungi and has the advantage of not diminishing overtime. Generally, a fungistatic dose in the presence of ethanol and sulfur is roughly 200 mg/L. It can also be used to remove mineral deposits. Sorbic acid by itself has subtle sensory characteristics, but a portion of the population finds it particularly offensive.

Application in Wine Microbiology:
Sorbic acid is often applied prevent off-dry wines from fermenting in the bottle. It is generally used to inhibit Saccharomyces, which it is fairly good at doing. An issue with this is that lactic acid bacteria, specifically Oenococcus can esterify it into an alcohol (sorbyl alcohol) and then it has the tendency to rearrange and become 2ethoxyhexa-3,5-diene, which has a potent, geranium-like odor that is unpleasant. Its sensory threshold has been reported to be around 100ng/L, which is a relatively small amount. Other geneses within lactic acid bacteria have not been reported to be able to metabolize Sorbic acid. To minimize the potential for this off odor in sweet reserves and when blended back, wines should have the solids removed, be filtered, properly sulfited and kept at low temperature.

Sorbic acid is of low-toxicity. It is allowed to be used in many foods, such as fruit/vegetable juices, ready-to-eat soups and broths, fried fish ball, dried apricots and raisins

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

Sorbic acid has been used extensively as a preservative in a vast array of food.
The benefits of sorbates as food preservatives are two-fold: sorbates inhibit a wide spectrum of bacteria yeasts and molds and they have extremely low toxicity.
Several protocols for producing sorbic acid and sorbates are known.
However the most common method of producing commercial quantities requires a decomposition step that yields unwanted colored byproducts.
Multiple purification steps are required to yield product that is food grade or better.

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, 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.

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

Safety

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The LD50 value of sorbic acid is estimated to be between 7.4 and 10 g/kg.
Sorbic acid and sorbates therefore have a very low mammalian toxicity – hence their extensive use in food and beverage preservation.
Sorbic acid occurs naturally in wild berries, is relatively unstable and rapidly degraded in soil, hence it is considered environmentally friendly.
In the body it is generally metabolized by the same oxidation pathway as the 5-carbon saturated fatty acid caproic acid.

See also
Sorbitol
Polysorbate
Acids in wine
Parasorbic acid

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
2,4-Hexadienoic acid, (2E,4E)-
2-Propenylacrylic acid
trans,trans-Sorbic acid
Hexadienoic acid
(E,E)-2,4-Hexadienoic acid
alpha-trans-gamma-trans-Sorbic acid
Preservastat
(E,E)-Sorbic acid
trans,trans-2,4-Hexadienoic acid
2,4-Hexadienoic acid, (E,E)-
Crotylidene acetic acid
Kyselina sorbova
Acetic acid, crotylidene-
Caswell No. 801
Sorbic Acid [USAN]
Acidum sorbicum
Acetic acid, (2-butenylidene)-
Kyselina sorbova [Czech]
trans-trans-2,4-Hexadienoic acid
(E,E)-1,3-pentadiene-1-carboxylic acid
(2E,4E)-2,4-Hexadienoic acid
Hexadienoic acid, (E,E)
(2-Butenylidene)acetic acid
C6:2n-2,4
Sorbic acid (NF)
Sorbic acid [NF]
UNII-X045WJ989B
CCRIS 5748
HSDB 590
1,3-Pentadiene-1-carboxylic acid
1,3-Pentadiene-1-carboxylic acid, (E,E)-
E 200
EINECS 203-768-7
MFCD00002703
5309-56-8
Kyselina 1,3-pentadien-1-karboxylova
EPA Pesticide Chemical Code 075901
(2-butenylidene) acetic acid
AI3-14851
CHEBI:38358
Kyselina 1,3-pentadien-1-karboxylova [Czech]
(E,E)-Sorbic acid; Sorbic acid
X045WJ989B
22500-92-1
NCGC00091737-01
DSSTox_CID_1277
DSSTox_RID_76053
DSSTox_GSID_21277
Hexadienic acid
2,4-Hexadienoic acid, 99%
(2E,4E)hexa-2,4-dienoic acid
CAS-110-44-1
Sorbic acid solution
(2E)-2,4-Hexadienoic acid
Sorbic acid, (E,E)-
Sorbinsaeure
Sorbinsaure
NSC49103
E-sorbic acid
trans,trans-SA
sorbic acid group
Sorbic Acid FCC
Hexa-2,4-dienoic acid, (E,E)-
2,4-Hexadiensaeure
NSC 35405
NSC 49103
NSC 50268
Crotylidene-Acetic acid
EC 203-768-7
SCHEMBL1647
Sorbic acid, >=99.0%
91751-55-2
MLS002152937
(2-butenylidene)-Acetic acid
(E,E)-SA
CHEMBL250212
(e,e)-hexa-2,4-dienoic acid
DTXSID3021277
Sorbic acid, analytical standard
CHEBI:35962
FEMA 3921
HMS3039E13
Sorbic acid, potassium salt (van)
HY-N0626
STR09707
ZINC1558385
Tox21_111164
Tox21_201719
Tox21_300182
2,4-SA
LMFA01030100
LS-504
s4983
SBB060282
(2E,4E)-2,4-Hexadienoic acid #
2, 4-Hexadienoic acid potassium salt
AKOS000119456
CCG-266056
NE10215
2,4-Hexadienoic acid, (trans,trans)-
2,4-Hexadienoic acid, >=99%, FCC
.alpha.-trans-.gamma.-trans-Sorbic acid
NCGC00091737-02
NCGC00091737-03
NCGC00091737-05
NCGC00253957-01
NCGC00259268-01
E200
P891
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%
ST51046499
Sorbic acid, for synthesis, 99.0-101.0%
alpha-trans-Laquo gammaRaquo -trans-sorbic acid
D05892
Hexadienoic acid1,3-pentadiene-1-carboxylic acid
A829400
AN-651/40229308
Q407131
J-002425
J-524281
2,4-Hexadienoic acid, (E,E)-; 2,4-Hexadienoic acid
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

Sorbic Acid
Sorbic acid inhibits the growth of C. botulinum and further reduces nitrosamine formation.
To counter the use of nitrite at high concentrations in meat curing, fractional replacement of nitrite by sorbic acid has been put forth

Sorbic Acid
Sorbic acid, potassium sorbate, and calcium sorbate are novel, highly efficient, safe, and nonpoisonous food preservatives.
They are the substitute for the benzoic acid as a traditional preservative. Sorbic acid, potassium sorbate, and calcium sorbate approved worldwide are often now successfully used as standard products in many branches of the food industry. As they are acidic preservatives, it is better to use them at pH 5–6.

Sorbic acid, potassium sorbate, and calcium sorbate are unsaturated fatty acids and salts of unsaturated fatty acids, which participate in the normal fat metabolism in human body and are oxidized into carbon dioxide and finally water. They do not accumulate in the human body

PRESERVATIVES | Permitted Preservatives – Sorbic Acid
Linda V. Thomas, in Encyclopedia of Food Microbiology, 1999

Introduction
Sorbic acid derives its name from Sorbus aucuparia, because it was from berries of this tree that it was first isolated (Table 1).
Seventy years later its potential as an antimicrobial agent was discovered, and sorbic acid and its salts (generally called sorbate) are now used as preservatives in a variety of foods in many countries.

Table 1. History of the use of sorbate as a food preservative

1859   Isolated from the oil of berries of the rowan (mountain ash) tree
1870–1890   Chemical structure formulated
1900   First synthesized by condensation of crotonaldehyde and malonic acid
1926   Synthesis of sorbic acid by oxidation of sorbaldehyde
1939–1940   Recognition of antimicrobial properties
1945   US patent for use as antifungal agent in foods
1940–1960   Industrial production. Use in dairy, fruit and vegetable products
1974   Potassium sorbate discovered to inhibit growth of bacteria

Sorbic acid is an unsaturated aliphatic straight-chain monocarboxylic fatty acid, 2,4-hexadienoic acid.
Salts and esters form by reaction with the carboxyl group; reactions also occur via its conjugated double bond.
The acid and its sodium, calcium and potassium salts are used in food.
The potassium salt is commonly used because it is more stable and easier to produce.
Furthermore, its greater solubility extends the use of sorbate to solutions appropriate for dipping and spraying.
Other derivatives with antimicrobial capabilities (sorboyl palmitate, sorbamide, ethyl sorbate, sorbic anhydride) have limited use because they are more insoluble, toxic and unpalatable.

Sorbic acid and its calcium, potassium, and sodium salts are used as preservatives in a wide range of food, including dairy, meat, fish, vegetables, fruit, bakery, emulsions, beverages, and so on.
Their advantages include broad antimycotic and antibacterial spectrum of activity; lack of effect on organoleptic properties of the foods; good activity in less acidic conditions (compared with propionate or benzoate) and safety.
Sorbate has been granted generally recommended as safe status and has an acceptable daily intake of 25 mg kg−1 body weight that is higher than most other preservatives.

Sorbic acid is active against yeasts, molds, and many bacteria.
Microbial inhibition by sorbate is variable and depends on species, strains, composition of food, pH, aw, food-processing treatments, temperature of storage, and concentration of sorbate.
The antimicrobial action of sorbate depends on pH and is most effective approaching its dissociation constant (pKa = 4.76); however, it is possible that it has a good inhibitory effect at pH as high as 6.5–7.0, which is an advantage over other preservatives such as benzoic and propionic acids that loss their effectiveness at pH 4.5–5.5.
The most commonly used forms include sorbic acid and its potassium salt.
Sorbates have found wide application in various foods, including dairy products, bakery products, fruit and vegetables products, meat and fish products, beverages, food emulsions, and sugar and confectionery products. The maximum permitted concentration of sorbates for most foods is between 0.1% and 0.3%.

Sorbic acid is nontoxic and is metabolized by fatty acid oxidation, pathways common to both laboratory mammals and humans.

Sorbate is used as a preservative in a wide range of products (Table 3).
It can be mixed with dry ingredients (e.g., flour, salt) or applied to surfaces by dipping, spraying, or dusting.
It can be incorporated within packaging material using organic carriers, such as ethanol, vegetable oil, or propylene glycol.
Permitted levels depend on the product type and country of origin, but the maximum is generally 0.2%. Higher concentrations can be used in packaging or surface treatments.
Sorbate use in the UK is covered by Schedule 2, Part A of the Miscellaneous Food Additives Regulations 1995 (Statutory Instrument 3187).

Sorbic Acid and Sorbates
2,4-Hexadienoic acid and 2-propenylacrylic acid are the chemical names of sorbic acid.
FAO/WHO describes it as colorless needles or white free-flowing powder, having a slight characteristic odor with a purity not less than 99.0% and molar mass of 112.12 g mol− 1, with a melting point between 132 and 135 °C, and being slightly soluble in water and soluble in ethanol.

Sorbic acid is active against yeasts, molds, and many bacteria.
Microbial inhibition by sorbate is variable and depends on species, strains, composition of food, pH, aw, food-processing treatments, temperature of storage, and concentration of sorbate. The antimicrobial action of sorbate depends on pH and is most effective approaching its dissociation constant (pKa = 4.76); however, it is possible that it has a good inhibitory effect at pH as high as 6.5–7.0, which is an advantage over other preservatives such as benzoic and propionic acids that loss their effectiveness at pH 4.5–5.5. The most commonly used forms include sorbic acid and its potassium salt. Sorbates have found wide application in various foods, including dairy products, bakery products, fruit and vegetables products, meat and fish products, beverages, food emulsions, and sugar and confectionery products. The maximum permitted concentration of sorbates for most foods is between 0.1% and 0.3%.

Application: Sorbic acid is a naturally occurring weak acid that is the most common food preservative in the world. Sorbic acid is an antimicrobial agent used to prevent mold, yeast, and fungi growth, particularly in cheese, yogurt, meat, wine, soft drinks, and more. It can also be found in animal feeds, pharmaceutical drugs, and cosmetics.

Preservatives have been commonly used as additives in food, cosmetics, and pharmaceutical products.
Addition of preservatives prevents the alteration and degradation of the product formulation.
Nowadays, this type of preservation is often performed with the use of chemical preservatives, such as sorbic acid and its respective sodium, potassium, and calcium salts due to its high solubility.
Practical usage of sorbates includes the protection of human food, animal nutrition, pharmaceuticals, cosmetic products, and packaging materials.
Sorbates are used as a food preservative in the application areas of cheese and cheese products, yogurt, and sour cream.

These compounds are generally used to inhibit yeast and mold growth.
Additionally, they are effective against a wide range of bacteria.
The highest activity of these compounds is recorded in foods with low pH value, while they are noneffective in foods at neutral pH value.
Their solubility in water varies depending on the pH and temperature of the environment.
As the concentration of soluble food components such as sucrose, glucose, and NaCl increases, the solubility of sorbic acid in water decreases.
While the solubility of sorbic acid in water at 25°C is 0.16%, the solubility of potassium sorbate under the same conditions is above 50%.
Potassium sorbate with a chemical structure of CH3CH = CHCH = CHCOOK is a white crystalline powder.
Its solubility in water is very high, and it has a solubility capacity of 139.2 g in 100 ml of water. 20 g dissolves in 1 ml of alcohol at 20°C.
Sorbates are more soluble in alcohol compared to water.

Sorbic acid can be differently applied in foodstuffs.
It can be added directly to the product or sprayed onto the surface, sprinkled in powder form, dipped into food-grade sorbate solutions prepared in certain concentrations, or coated with sorbate packaging materials.
High concentration solutions are required for dipping and spray applications.

Food additives such as preservatives may cause an allergic or intolerance reaction.
As a preservative, sorbic acid is regarded as safe and nontoxic, but using especially in large amounts can potentially lead to allergies.
Migraine, a common type of headache, is one of the possible adverse health effects of potassium sorbate. Higher than normal levels of potassium in the blood may lead to hyperkalemia .

The use of sorbic acid and its salts in processed foods is extremely important. Not using this antimicrobial agent may cause microbial activities that lead to food poisoning.
However, there are some limitations in using these preservatives.
Fermented products are the foremost food group that have limitations for food additives because of their importance in healthy nutrition, prevention, and curing effects.

The use of sorbic acid and its salts in processed foods is extremely important.
Not using this antimicrobial agent may cause microbial activities that lead to food poisoning.
However, there are some limitations. Fermented products are the foremost food group that have limitations for food additives because of their importance in healthy nutrition, prevention, and curing effects.

Sorbic acid and potassium sorbate are already authorised for use in food and feed as preservatives.
Sorbic acid and its potassium salt are safe when used at the maximum proposed dose in feed for dogs and cats (2 500 (sorbic acid) and 3 400 (potassium sorbate) mg/kg) and young ruminants (6 700 (sorbic acid) and 9 000 (potassium sorbate) mg/kg).
This conclusion is extended to all animal species.
The contribution of potassium sorbate to the potassium supply of animals should be considered when formulating diets or when it is included in water for drinking.
As no measurable residues of sorbic acid or potassium ion are expected in edible products of food-producing animals, sorbic acid and potassium sorbate are considered safe for the consumers when used up to the maximum proposed level.
Sorbic acid and potassium sorbate are skin, eye and respiratory tract irritants.
The use of sorbic acid and its potassium salt in animal nutrition would not pose a risk to the environment.
As sorbic acid and potassium sorbate are authorised food additives within the EU for use as preservatives, it is reasonable to expect that the effect in food will be observed in feed when it is used at comparable concentrations and under similar conditions.
The FEEDAP Panel has reservations about the effectiveness of sorbic acid and its potassium salt as preservatives in complete feedingstuffs with a moisture content of ≤ 12 %.
Equivalent concentrations for sorbic acid and potassium sorbate when used as preservatives in water for drinking should be specified.

Keywords:sorbic acid, E 200, calcium sorbate, E 202, potassium sorbate, E 203, food additives

A. W. Van Hoffman was the first to isolate sorbic acid from the berries of the mountain ash tree in the year 1859. The antimicrobial (preservative) properties of sorbic acid were recognized in the 1940’s. In the late 1940’s and 1950’s it became commercially available. Since then, sorbic acid has been extensively tested and used as a preservative in many foods. In wine, its use was legalized in France in 1959 and in Germany in 1971. Sorbic acid and its potassium salt are now used in many countries in the production of sweet white wines. In the United States, BATF permits the use of sorbic acid and potassium sorbate to preserve wine. The maximum concentration of sorbic acid allowed in finished wine is 300 mg/L, (300 ppm).

Sorbic acid (2,4-hexadienoic acid) is a straight chain unsaturated fatty acid with a molecular weight of 112.13 and the formula: CH3 – CH = CH – CH = CH – COOH. Sorbic acid is commercially produced as a powder or granules, it has a characteristic acrid odor and acid taste. The carboxyl (COOH) group in sorbic acid is very reactive and can form salts with calcium, sodium, and potassium. The potassium salt of sorbic acid is commercially available as a powder or granules. Its molecular weight is 150.22 and it is very soluble in water

The solubility of sorbic acid in water is low (.16 g/100 ml) and it increases with temperature. The solubility is higher in ethanol, but decreases in the presence of other solutes such as sugar. Potassium sorbate (as compared to sorbic acid) is very soluble in water. The solubility decreases with an increase in ethanol, and/or sugar content in the solvent mixture. This point is important since sweet wines contain both sugar and alcohol.

Antimicrobial Activity

The antimicrobial action of sorbic acid is primarily against yeasts and molds. It’s action against bacteria appears to be selective. At concentrations used in wine it does not seem to prevent spoilage from either acetic or lactic acid bacteria. Must and wine related yeasts inhibited by sorbic acid include species of genera Brettanomyces, Candida, Hansenula, Pichia, Saccharomyces, Torulaspora, and Zygosaccharomyces.

The inhibitory effect of sorbic acid on yeast strains is not uniform. Certain species are more tolerant than others. For example, according to Pitt (1974), Zygosaccharomyces bailii was not inhibited by sorbic acid at 0.06% in 10% glucose. It should be noted that the yeast Zygosaccharomyces bailii is also resistant to sulfur dioxide and diethyl pyrocarbonic acid (DEPC) and it can ferment high sugar musts such as grape juice concentrate containing 55 to 72 percent sugar. If contaminated concentrate is used for sweetening wine, it is likely to cause a refermentation even if a normal concentration of sorbic acid is present.

The inhibitory influence of sorbic acid is greatest when it is in undissociated form. The pka of sorbic acid is 4.75. The antimicrobial action increases as the pH value decreases below 4.75. In other words, the proportion of undissociated form of sorbic acid increases (above 50%) as the pH drops below 4.75, this can lead to increased antimicrobial action.

Sorbic acid also inhibits mold growth. Some of the important species that are suppressed by sorbic acid belong to the genera Alternaria, Botrytis, Cladosporiwn, Fusariwn, Mucor, Penicilliwn, Rhizopus, Trichoderma. Mold can be a problem in wine cellars. To control mold in the wine cellar, sorbic acid could be included in the antimicrobial compounds used for sanitizing.

Several microorganisms can metabolize sorbic acid particularly when it is present in small concentrations. For this reason, it is not a suitable preservative in foods with high microbial counts. To derive the maximum benefit from the antimicrobial action of sorbic acid, it is important to clean the wine well and keep the microbial count low in the bottled wine. It should be emphasized that sorbic acid inhibits yeast and mold, but not acetic and lactic acid bacteria. In fact, lactic acid bacteria can metabolize sorbic acid and produce off flavored compounds.

The antimicrobial action of sorbic acid is due to its inhibitory influence on various enzymes in the microbial cell. The enzymes inhibited by sorbic acid include the following:

1. Enzymes involved in carbohydrate metabolism such as enolase and lactate dehydrogenase.

2. Enzymes of citric acid cycles such as malate dehydrogenase, isocitrate dehydrogenase, ketoglutarate dehydrogenase, succinate dehydrogenase, and fumerase.

3. Several enzymes containing SH group, and other enzymes such as catalase and peroxidase.

Application in the Winery

Potassium sorbate is used in the production of sweet white table wines. Although BATF permits its use in wine, up to 300 ppm, it is important to remember that its taste threshold is well below the legal limit. The taste threshold for experienced tasters has been reported to be about 130 ppm. Addition of sorbic acid often results in the formation of ethyl sorbate, which is said to impart an unpleasant odor when present in a significant level.

As mentioned earlier, lactic acid bacteria can decompose sorbic acid and produce 2-ethoxyhexa-3, 5 diene, and other compounds which give a geranium like off odor.

They suggested that in addition to 2 ethoxyhexa – 3, 5 diene (main compound with geranium like odor) other compounds such as the two dienols and the other ether, (1 – ethoxyhexa 2,4 diene) also contribute to the overall off odors in wines containing sorbic acid and spoiled by lactic acid bacteria.

To prevent bacterial spoilage in sweet wines it is important to add a sufficient amount of sufur dioxide in addition to sorbic acid.

Besides pH, the ethanol content of a wine also influences the antimicrobial action of sorbic acid. For this reason, with a relatively high amount of alcohol in the wine, lower levels of sorbic acid would be needed. Peynaud (1980) recommended the following doses of sorbic acid in clarified wine based on alcohol content

It should be emphasized that a wine must be clarified to reduce the yeast population below 100/ml for sorbic acid to be effective.

The key points in sorbic acid use are summarized below.

1. Potassium sorbate (most soluble form of sorbic acid) should be used. However, this can cause bitartrate precipition problems.

2. The solubility of potassium sorbate is influenced by temperature, therefore, it should not be added to a cold wine.

3. Wine should be mixed well after sorbate addition.
4. Sorbate should be used in conjunction with sulfur dioxide.
5. Certain yeast and bacteria are not inhibited by sorbic acid.
6. Properly clarified wine (low yeast count), low pH, and relatively high alcohol would help in reducing the

amount of sorbic acid needed for effectively controlling yeast.
7. Sorbic acid addition should never be considered as a substitute for poor sanitation.

Calculating Potassium Sorbate Additions

Sorbic acid is added to a wine in the form of the potassium salt. Potassium sorbate contains 73.97% sorbic acid. In order to calculate the amount of potassium sorbate, the following formula should be used.

Formula: ppm = mg/liter
mg/liter of sorbic acid x 1.35 = mg/

liter of potassium sorbate
Example: To obtain 200 ppm sorbic acid in wine, the following steps may be used.

I. 200 ppm = 200 mg/liter
II. 200 mg/liter x 1.35 = 270 mg/liter of potassium sorbate
III. 270 mg/liter x 3.785 = 1021.95 mg/gallon or 1.022 gram/gallon

*Values given in the left column are for sorbic acid, while the values given in other columns are for potassium sorbate. For example, to obtain 150 ppm sorbic acid level, you need to add 150 x 1.35 = 202 mg/L of potassium sorbate and not 150 mg/L of potassium sorbate. This is due to the fact that potassium sorbate on a molecular weight basis contains about 74% sorbic acid.

McCarthy et aI.(l9) found that both temperature and type of container affected the breakdown of sorbic acid. Aqueous solutions of sorbic acid (0.1% w/v) stored for 12 weeks in polypropylene, polyvinyl chloride, polyethylene, and glass containers all had significant loss on storage, except when refrigerated or in the presence of an antioxidant (as occurs in polyethylene-92.2% sorbic acid remaining). The mechanism of decomposition was uncertain and in polyvinyl chloride and glass (at 5OOC) was not linear. Although some solutions became increasingly acidic with time, leading to improved contact killing times, both dilution tests confirmed a loss in potency. These losses were not always proportional to the spectrophotometric results. Gruntova et a1.(20) also studied the stability of sorbic acid in aqueous and polysorbate solutions; sorbic acid was oxidized more readily in the polysorbate solutions, with the rate influenced by the packaging material. Kondrat’eva et a1.(21) found that the amount of sorbic acid in petrolatum and emulsified bases stored at room temperature in metal containers started to decrease within 1 month and reached 60-80% of the initial content of the bases. They concluded that sorbic acid does not react with sodium lauryl sulfate or diethylene glycol stearate. Nielsed2*) found that sorbic acid incorporated in a cough syrup formulation did not decompose after 26 months of storage at room temperature. Sorbic acid formed complexes with various starches by interacting with the amylose fraction of the starch. Sorbic acid complexed with acacia in aqueous solution and was also absorbed by nylon and cellulose acetate. The degree of sorbic acid uptake by nylon increased with both temperature and time and was dependent on the pH of the solution, indicating the undissociated molecule was the preferentially absorbed form

Sorbic acid and potassium sorbate are used in cosmetics and toiletries as preservatives and antimicrobials.
The 1986 U.S. Food and Drug Administration (FDA) data show that sorbic acid was used in a total of 445 products, including primarily makeup (44%), skin care (19%), eye makeup (16%), hair (7%), and bath (4%) preparations. Of these formulations, 62% incorporated sorbic acid at concentrations of 50.1%; 37% incorporated sorbic acid at concentrations of > 0.1-1%. Potassium sorbate was reported in 117 products, prirnarily skin care (including suntan preparations) (44%), hair (34’%), and makeup (8%) preparations. Of the formulations, 56% incorporated potassium sorbate at concentrations of > 0.1-1%; 44% incorporated potassium sorbate at concentrations of I 0.1 %.(44) The FDA cosmetic product formulation data presented in Table 2 are compiled through voluntary filing of such data in accordance with Title 21 Part 720.4 (d)(l) of the Code of Federal Regulations (1979). Ingredients are listed in prescribed concentration ranges under specific product type categories. Since certain cosmetic ingredients are supplied by the manufacturer at less than 100% concentration, the value reported by the cosmetic formulator may not necessarily reflect the actual concentration found in the finished product; the actual concentration is a fraction of that reported to the FDA. Data submitted within the framework of preset concentration ranges provide the opportunity for overestimation of the actual concentration of an ingredient in a particular product. An entry at the lowest end of a concentration range is considered the same as one entered at the highest end of that range, thus introducing the possibility of a 2- to 10-fold error in the assumed ingredient concentration.
The formulation data presented in Table 2 indicate that cosmetic products containing sorbic acid and potassium sorbate may contact all external body surfaces and hair, as well as ocular and vaginal mucosae. Sorbic acid additionally may contact the oral mucosae. These products may be used daily or occasionally over a period of up to several years. The frequency and length of application can result in continuous exposure.

Sorbic acid and potassium sorbate are effective preservatives at low concenitration for the control of mold and yeast in cheese products, based goods, fruit juices, fresh fruits and vegetables, wines, soft drinks, pickles, sauerkraut, and certain fish and meat product.
These ingredients are generally recognized as safe direct food additives when used in accordance with good manufacturing practice.
Results of a survey of food manufacturers indicated that the mean (weighted) level of the addition of sorbic acid to foods ranged from < 0.01 to 0.58%.
The Grocery Manufactures of America has made an independent estimate of 0.5-0.3% for the range of sorbate addition to food.

Expert Committee on food additives has estimated the acceptable daily intake of sorbic acid and its salts (expressed as sorbic acid) as 25 m 8,’kg body weight
Potassium sorbate is also recognized as a GRAS indirect food additive as it migrates to food from paper and paperboard products used in food packaging.
Sorbic acid and potassium sorbate are also used as preservatives in a variety of pharmaceuticals.
The Ophthalmic Advisory Review Panel of the FDA over-the-counter (OTC) drug review program has proposed that sorblic acid used alone in concentrations of 0.1-0.2% is not an effective antimicrobial agent because of its limited bactericidal effects.
They also indicated that more data were required to establish the safety and effectiveness of sorbic acid used as a preservative in combination with other approved preservatives.

Sorbic acid is a straight-chain rnonocarboxylic acid, also known as 2,4- hexadienoic acid.
It is a white crystalline powder soluble in alcohol and ether but (only slightly soluble in water.
Potassium sorbate is the potassium salt sorbic acid and is a white crystalline powder or white granules or pellets freely soluble in alcohol and water.
Sorbic acid occurs naturally as the lactone, parasorbic acid, in berries of the mountain ash, Sorbus aucuparia L., Rosaceae. The sorbic acid used in cosmetics is synthesized by various commercial processes.
Potassium sorbate is prepared by reacting sorbic acid with an equimolar portion of potassium hydroxide.
Solutions of sorbic acid are subject to autoxidation and atmospheric oxidation.
Both the temperature and the type of container have also affected the breakdown of sorbic acid.
Sorbic acid and potassium sorbate are analyzed primarily by chromatographic techniques.
Several analytic studies have been conducted to determine whether sorbic acid was contaminated with its isomer parasorbic acid, a suspected carcinogen.
No traces of parasorbic acid were found (tests sensitive down to a concentration of 0.5 mg/kg).
Sorbic acid and potassium sorbate are used in cosmetics and toiletries as preservatives and antimicrobials generally at concentrations of I 1 %.
According to the data voluntarily reported to the FDA through 1986, sorbic acid and potassium sorbate were used in 445 and 117 cosmetic formulations, respectively.
These ingredients are primarily used in facial and eye makeup and skin care and hair preparations.
Sorbic acid and potassium sorbate are generally recognized as safe (GRAS) direct food additives. They are used as preservatives at low concentrations

(2E,4E)-2,4-Hexadienoic acid [ACD/IUPAC Name]
(2E,4E)-2,4-Hexadiensäure [German] [ACD/IUPAC Name]
(2E,4E)hexa-2,4-dienoic acid
(2E,4E)-hexa-2,4-dienoic acid
(E,E)-1,3-Pentadiene-1-carboxylic acid
(E,E)-2,4-Hexadienoic acid
1098547 [Beilstein]
110-44-1 [RN]
2,4-Hexadienoic acid, (2E,4E)- [ACD/Index Name]
2,4-Hexadienoic acid, (E,E)-
2E,4E-Hexadienoic acid
3921
Acide (2E,4E)-2,4-hexadiénoïque [French] [ACD/IUPAC Name]
Acidum sorbicum
C6:2n-2,4
Sorbic acid [Wiki]
trans,trans-2,4-hexadienoic acid
trans,trans-sorbic acid
trans-trans-2,4-Hexadienoic acid
WG2100000
X045WJ989B
α-trans-γ-trans-sorbic acid
“2,4-HEXADIENOIC ACID”
“HEXA-2,4-DIENOIC ACID”
(2-butenylidene)-Acetic acid
(2-Butenylidene)acetic acid
(2e,4e);-hexa-2,4-dienoic acid
(2E,4E)-Hexa-2,4-dienoate
(4E)-Hexa-2,4-dienoic acid
(E,E)-hexa-2,4-dienoic acid
(E,E)-SORBIC ACID
1,3-Pentadiene-1-carboxylic acid
1,3-Pentadiene-1-carboxylic acid, (E,E)-
2, 4-Hexadienoic acid
2,4-Hexadienic acid
2,4-hexadienoic acid 99%
2,4-Hexadienoic acid, (trans,trans)-
2,4-hexadienoic acid, 99%
2,4-HexadienoicAcid
2,4-Hexadiensaeure
2,4-HEXANEDIENOIC ACID
2-Propenylacrylic acid
91751-55-2 secondary RN [RN]
Acetic acid, (2-butenylidene)-
Acetic acid, crotylidene-
c6h8o2
Crotylidene acetic acid
Crotylidene-Acetic acid
foodpreservative-sorbicacidpurity
Hexa-2,4-dienoic acid
Hexa-2,4-dienoic acid, (E,E)-
Hexadienic acid
Hexadienoic acid
Hexadienoic acid, (E,E)
Hexadienoic acid1,3-pentadiene-1-carboxylic acid
http:////www.amadischem.com/proen/602622/
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:38358
InChI=1/C6H8O2/c1-2-3-4-5-6(7)8/h2-5H,1H3,(H,7,8)/b3-2+,5-4
Kyselina 1,3-pentadien-1-karboxylova [Czech]
Kyselina sorbova [Czech]
Panosorb
Parasorbic Acid
Preservastat
Sorbic acid 1000 Ã‚Âµg/mL in Acetonitrile
Sorbic Acid, (E,E)- [USAN]
sorbic acid-分析标准品
Sorbins??ure
Sorbinsaeure
Sorbistat [Trade name]
UNII-X045WJ989B
α-trans-Laquo γRaquo -trans-sorbic acid
α-trans-γ-trans-Sorbic acid
山梨酸 [Chinese]

(2-Butenylidene)acetic acid
(2E,4E)-2,4-Hexadienoic acid
(E,E)-1,3-pentadiene-1-carboxylic acid
(E,E)-2,4-hexadienoic acid
(E,E)-SA
(E,E)-Sorbic acid
1,3-Pentadiene-1-carboxylic acid
2-Propenylacrylic acid
2, 4-Hexadienoic acid potassium salt
2,4-Hexadienoic acid
2,4-Hexadienoic acid, potassium salt
Acetic acid, (2-butenylidene)-
Acetic acid, crotylidene-
alpha-trans-gamma-trans-sorbic acid
Crotylidene acetic acid
Hexa-2,4-dienoic acid
Hexadienic acid
Hexadienoic acid
Hexadienoic acid, (E,E)
Hexadienoic acid1,3-pentadiene-1-carboxylic acid
Kyselina 1,3-pentadien-1-karboxylova
Kyselina sorbova
Panosorb
Parasorbic acid
Potassium sorbate
Preservastat
SA
Sorbic acid (NF)
Sorbic acid, (E,E)-
Sorbic acid, potassium salt (VAN)
Sorbistat
Sorbistat-K
trans,trans-2,4-Hexadienoic acid
trans,trans-SA
trans,trans-Sorbic acid
(e,e)-1,3-Pentadiene-1-carboxylate
(e,e)-2,4-Hexadienoate
(e,e)-Sorbate
1,3-Pentadiene-1-carboxylate
a-trans-g-trans-Sorbate
a-trans-g-trans-Sorbic acid
alpha-trans-gamma-trans-Sorbate
Α-trans-γ-trans-sorbate
Α-trans-γ-trans-sorbic acid
trans,trans-2,4-Hexadienoate
trans,trans-Sorbate
(2E,4E)-2,4-Hexadienoate
Sorbate
(2-Butenylidene)-acetic acid
(2E,4E)-Hexa-2,4-dienoic acid
2E,4E-Hexadienoic acid
Acidum sorbicum
alpha-trans-Laquo gammaraquo -trans-sorbic acid
Crotylidene-acetic acid
FEMA 3921
Sorbic acid, potassium salt
trans-trans-2,4-Hexadienoic acid
Acid, sorbic
Sorbate, sodium
Sorbate, potassium
Acid, propenylacrylic
Sodium sorbate
Acid, hexadienoic
Propenylacrylic acid

Sorbic Acid is a white crystalline unsaturated carboxylic acid found in berries of the mountain ash and used to inhibit the growth of moulds and as an additive for certain synthetic coatings, as of cheese (E200); 2,4-hexadienoic acid. It exists as cis- and trans- isomers, the latter being the one usually obtained. Formula: CH3CH:CHCH:CHCOOH

Sorbic Acid is a mild, natural preservative that usually comes to the formula together with its other mild preservative friends, such as Benzoic Acid and/or Dehydroacetic Acid. Btw, it’s also used as a food preservative.

Preservatives are defined as chemicals which extend shelf life of foods by preserving them against spoilage caused by microbial, enzymatic and chemical changes. For this purpose widely used preservatives are benzoic acid and sorbic acid and their respective potassium and sodium salts that must be monitored and controlled in dairy products, including cheese, yogurt and ayran1-4 . These preservatives have been used in the food sector throughout the world over the past 30 years for the preservation of pastries, margarine, cheese, in sour soup tins, beverages, fruit, sausages, fishes, sweets and ground beef5 . Preservatives are generally used to inhibit mold and yeast growth and they are also effective against many bacteria. Antimicrobial properties of preservatives depend on some factors such as antimicrobial spectrum, chemical and physical properties, concentration, affect mechanism of substance and composition, pH, water activity, storage temperature of food. Besides these factors, it must also be paid attention to some other subjects for choosing a preservative to be used for foods, such as genus and microorganism load on food, cost of preservative and its effect on quality of food1,6,7 . The effect of sodium benzoate against microorganisms is by inactivating cell wall and some enzymes in the cell8,9. Sorbic acid is often used as sodium, potassium and calcium salts. However, in use as potassium sorbate is more common because its solubility is more than 50 % in foods8,10-12. Sorbic acid becomes effective by inactivating enzymes in cells of microorganisms8 . Of these antimicrobial substances, that have common use, benzoic acid is metabolized rapidly and moved out from body. It doesn’t accumulate in tissues. It’s not harmful to health, when added to foods as sodium benzoate at very low levels. However, as the quantity increases, both the nutritional value of food is reduced and some kind of health problems can occur9 . Very high doses of benzoic acid cause adverse effects such as metabolic acidosis, convulsions and hyperpnoea4 . Several studies have been reported that benzoates cause asthma and various allergic reactions in human being4,7,13,14. Sorbic acid and its salts have less toxic effect than benzoic acid and its salts9 . Sorbic acid is metabolized rapidly like some fatty acids (as butyric acid, caproic acid) in human and animals and this is shown as a reason for less toxic effect9,15. Excessive quantities of these acids cause serious hazards for consumers and they must be strictly controlled

Sorbic Acid is an organic compound primarily used as a preservative. It inhibits the growth of mold, yeast and other microorganisms for shelf life stability. This product is often used in foods such as cheese, dried fruit, yogurt, pet foods, dried meats, soft drinks, and baked goods.

Sorbic acid is used to inhibit molds, yeasts, and fungi in many foods, such as cheese, wine, and baked goods.

It reacts with potassium to make potassium sorbate and with calcium to make calcium sorbate, which are also used as anti-fungals.

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.

How Sorbic Acid works as a Preservative?
The bacteriostatic or bactericidal mechanism of sorbic acid are the same as that of potassium sorbate. When added to water, potassium sorbate dissociates into sorbic acid and potassium ions. It is the sorbic acid that is active as an antimicrobial preservative.

Like benzoic acid, sorbic acid is a lipid-soluble weak acid that enters into the cell of microbial through the cell membrane then accumulates and finally influences the internal PH of microbial eventually disrupts its transport functions and metabolic activity result in the death of the microbial

It is generally used to inhibit the growth of molds (also mycotoxin-forming molds), yeast and some bacteria. The European food additive number for it is E200.

Natural source
It can be naturally found in berries species, such as mountain ash, rowan and magnolia vine. (1)

How is Sorbic Acid made?
It is commercially synthesized from the condensation between ketene and crotonaldehyde instead of extracted from berries. The manufacturing process is described in the first three steps of production of potassium sorbate.

Like benzoic acid, sorbic acid is a lipid-soluble weak acid that:

enters into the cell of microbial through the cell membrane
then accumulates and finally influences the internal PH of microbial
eventually disrupts its transport functions and metabolic activity
result in the death of the microbial
Specification
Other names
2,4-Hexadienoic Acid
2-propenylacrylic acid
Chemical formula   C6H8O2
CAS No.   110-44-1
Molecular weight   112.128
Boiling point   270 °C
Properties
Colorless needles or white free-flowing powder with a slight faint characteristic odor.

Structure
sorbic acid chemical structure
Image Source

Solubility
In water

Slightly soluble in water (solubility 0.16 g/100 mL at 20 °C) so it is not suitable to use it in food with much water content. Generally, it is made into salts form, potassium sorbate, which is the commonly utilized form.

In organic solvent

Soluble in ethanol, ether, propylene glycol, peanut oil, glycerin and glacial acetic acid.

PH
The antimicrobial activity of sorbic acid generates when it is in the form of a molecule, the condition of undissociated.

The PKa of sorbic acid is 4.76. That’s to say, its inhibitory activity rises as pH value (below 4.76) decreases as the percentage of the undissociated sorbic acid goes up, this leads to the enhanced antimicrobial activity.

The optimal pH for the antimicrobial activity is from 3.0 to 6.5.

What’re the Uses of Sorbic Acid?
Sorbic acid and potassium sorbate have become the primary preservatives in food application due to its good antimicrobial activity & effectiveness in the weak acid pH range and their safety over benzoic acid and sodium benzoate.

Mostly, it protects food from yeast and mold spoilage and commonly added with usage from 0.025% to 0.10%.

Sodium sorbate and Calcium sorbate

Another two sorbates, sodium sorbate and calcium sorbate which were also used as food additives in Europe. However, in other countries, they are permitted, for example, in the US.

Sodium sorbate (previously had the E number E201) is not an approved food additive in the EU for its genotoxicity.

Calcium sorbate (previously had the E number E203) was no longer allowed to be used in the European Union since Jan, 2018 as the EFSA was not able to evaluate its safety due to the lack of data, such as genotoxicity data, also, it was unable to set an ADI. Therefore this ingredient was deleted in the list of food additives. (2)

Food
Sorbic acid can prevent the spoilage of yeast, mold, and some bacteria in food and therefore prolong food shelf life. It 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.
While in liquid form/aqueous systems for preservation, potassium sorbate is preferred.

How to use it?
Sorbic acid can be added in food with several methods (3):

directly used
dusted in powder form
sprayed onto the food surface
dipped into sorbate solutions to prepare a certain concentrations
packaging materials
Cosmetics
Sorbic acid can also be used as a preservative (4) in cosmetics and personal care products to inhibit the growth of yeast and mold.

Is Sorbic Acid Safe to Eat?
Yes, it has been approved as a safe ingredient by the U.S. Food and Drug Administration (FDA) and the European Food Safety Authority (EFSA), as well as Joint FAO/WHO Expert Committee on Food Additives (JECFA).

FDA
It is generally recognized as safe (GRAS) that can be used as a chemical preservative in accordance with good manufacturing practice for human consumption. (5)

Uses limit
It is authorized in the following food (6)

Cheeses and cheese related products < 0.2%
cheeses and cheese related products, used alone or combined with potassium or sodium sorbate < 0.3%
Art sw fruit jellies, pres, and jams < 0.1%
Concentrated orange juice < 0.2%
Margarine <0.1% alone or <0.2% in combination with other preservatives
EFSA
Sorbic acid (E200) is listed in Commission Regulation (EU) No 231/2012 as an authorised food additive and categorized in “Additives other than colours and sweeteners” (7).

Approved uses
The same with that of potassium sorbate, at the maximum dosage from 20 to 6,000 mg/kg (10) (11)

UK Food Standards Agency
Categorized in “Others” (12)

Food Standards Australia New Zealand
It is an approved ingredient in Australia and New Zealand with the code number 200. (13)

JECFA
Function Class: food additives, preservative. (14)

Acceptable daily intake: ADI “25 mg/kg bw” in 1973. (15)

What are the possible Side Effects of Sorbic acid?
Although sorbic acid is approved safe by FDA and EFSA, there may be some mild possible side effects, like allergy symptoms in skin or scalp irritation or dermatitis from skin care products; digestive problems such as diarrhea. It is almost no toxicity and not linked to cancer.

Allergy
Allergy symptoms like skin and eye irritation, from some people who’re sensitive to sorbic acid especially from cosmetics and personal products.

A report in 2008 showed that sorbic acid may cause allergic reactions, such as dermatitis. (16)

Frequently Asked Questions
Is it Natural or Synthetic?
It is natural if it comes from the fruits, however, mostly sorbic acid in the market is synthetic as made from chemical production.

Is it Vegan?
Yes, it is vegan and manufactured without the use of animal matter or products derived from animal origin. So it can be used in the food for vegetarians.

Sorbic acid vs Ascorbic acid?
Some people may be mistaken these two different categories of food additives, sorbic acid is a preservative while ascorbic acid (vitamin c) is an antioxidant and also a vitamin c supplement.

Conclusion
Now you may have a good knowledge of the preservative – sorbic acid (E200), from the following aspects:

Production process
Uses
Comparison with potassium sorbate
Safety
Possible side effects

sorbic acid is a α,β-unsaturated monocarboxylic acid (CHEBI:79020)
sorbic acid is a hexadienoic acid (CHEBI:24555)
sorbic acid is a medium-chain fatty acid (CHEBI:59554)
sorbic acid is a polyunsaturated fatty acid (CHEBI:26208)
sorbic acid is conjugate acid of sorbate (CHEBI:36550)

(2E,4Z)-6-(4-chlorophenyl)-2-hydroxy-6-oxohexa-2,4-dienoic acid (CHEBI:28978) has functional parent sorbic acid (CHEBI:35962)
2-hydroxy-6-(2-hydroxyphenoxy)-6-oxo-cis,cis-hexa-2,4-dienoic acid (CHEBI:28990) has functional parent sorbic acid (CHEBI:35962)
2-hydroxy-6-(2-hydroxyphenyl)-6-oxo-cis,cis-hexa-2,4-dienoic acid (CHEBI:1135) has functional parent sorbic acid (CHEBI:35962)
2-Hydroxy-6-oxo-(2′-aminophenyl)-hexa-2,4-dienoate (CHEBI:36537) has functional parent sorbic acid (CHEBI:35962)
2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid (CHEBI:17820) has functional parent sorbic acid (CHEBI:35962)
ethyl sorbate (CHEBI:72819) has functional parent sorbic acid (CHEBI:35962)
(2E,4E)-hexa-2,4-dienoic acid (CHEBI:38358) is a sorbic acid (CHEBI:35962)
(2E,4Z)-hexa-2,4-dienoic acid (CHEBI:38361) is a sorbic acid (CHEBI:35962)
(2Z,4E)-hexa-2,4-dienoic acid (CHEBI:38360) is a sorbic acid (CHEBI:35962)
(2Z,4Z)-hexa-2,4-dienoic acid (CHEBI:38359) is a sorbic acid (CHEBI:35962)
sorbate (CHEBI:36550) is conjugate base of sorbic acid (CHEBI:35962)

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

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

2,4-Hexadienoic acid

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

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

2-Propenylacrylic acid

2E,4E-Hexadienoic acid

Acetic acid, (2-butenylidene)-

Acetic acid, crotylidene-

alpha-trans-gamma-trans-Sorbic acid

Hexa-2,4-dienoic acid
EC Inventory, Other
Hexa-2,4-dienoic acid
Cosmetic Products Regulation, Annex V – Allowed Preservatives, Other
hexa-2,4-dienoic acid

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

Hexadienoic acid
Kyselina 1,3-pentadien-1-karboxylova
Kyselina sorbova
Panosorb
Sorbic acid
sorbic acid
Sorbistat

trans,trans-Sorbic acid
trans-trans-2,4-Hexadienoic acid

Translated names
2,4-hexadién sav (Szorbinsav) (hu)

Acid hexa-2,4-dienoic (Acid sorbic) (ro)

Acide hexa-2,4-diénoïque (acide sorbique) (fr)

Acido esa-2,4-dienoico (Acido sorbico) (it)

Aċidu eża-2,4-dienoiku (Aċidu sorbiku) (mt)

Heksa-2,4-dieenhape (sorbiinhape) (et)

Heksa-2,4-dieenihappo (sorbiinihappo) (fi)

Heksa-2,4-dieno rūgštis (sorbo rūgštis) (lt)

Heksa-2,4-dienoična kiselina (sorbinska kiselina) (hr)

Heksa-2,4-dienojska kislina (sorbinska kislina) (sl)

Heksa-2,4-diēnskābe (sorbīnskābe) (lv)

Hexa-2,4-dieenzuur (sorbinezuur) (nl)

Hexa-2,4-dienoic acid (Sorbic acid) (no)

hexa-2,4-dienová kyselina (kyselina sorbová) (cs)

Hexa-2,4-diensyra (Sorbinsyra) (sv)

hexa-2,4-diensyre (sorbinsyre) (da)

Hexa-2,4-diensäure (Sorbinsäure) (de)

Kwas (2E,4E)-heksa-2,4-dienowy (kwas sorbinowy) (pl)

kyselina hexa-2,4-diénová (kyselina sorbová) (sk)

Ácido hexa-2,4-dienoico (ácido sórbico) (es)

Ácido hexa-2,4-dienóico (ácido sórbico) (pt)

Εξα-2,4-διενοϊκό οξύ (σορβικό οξύ) (el)

Хекса-2,4-диенова киселина (сорбинова киселина) (bg)

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

IUPAC names
(2E,4E)-hexa-2,4-dienoic acid
(E,E)-2,4-Hexadienoic acid
(E,E)-2,4-Hexadienoic acid.
(E,E)-hexa-2,4-dienoic acid
2,4 Hexadienoic acid
2,4-HEXADIENOIC ACID
2,4-Hexadienoic acid, (2E,4E)-
2E,4E)-hexa-2,4-dienoic acid
Hexa-2,4-dienoic acid
hexa-2,4-dienoic acid
Hexa-2,4-dienoic acid
SORBIC ACID
Sorbic Acid
Sorbic acid
sorbic acid
Sorbic Acid
Szorbinsav

SORBIC ACID

SORBIC ACID

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