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E200 Sorbic acid, or 2,4-hexadienoic acid, is a natural organic compound used as a food preservative.
E200 Sorbic acid has the chemical formula CH3(CH)4CO2H and the structure H3C−CH=CH−CH=CH−C(=O)OH.
E200 Sorbic acid is a colourless solid that is slightly soluble in water and sublimes readily.
CAS: 110-44-1
MF: C6H8O2
MW: 112.13
EINECS: 203-768-7
Synonyms
(e,e)-4-hexadienoicacid;(E,E)-Sorbic acid;2,4-Hexadienoicacid,(E,E)-;2e,4e-hexadienoicacid;4-Hexadienoicacid,(E,E)-2;2-PROPENYL ACRYLIC ACID;1,3-Pentadiene-1-carboxylic acid;2,4-HEXANEDIENOIC ACID
E200 Sorbic acid was first isolated from the unripe berries of the Sorbus aucuparia (rowan tree), hence its name.
E200 Sorbic acid, also known as herbal tea acid, 2,4-hexadienoic acid, 2-propenyl acrylic acid, with molecular formula C6H8O2, is a food additive that has inhibitory effects on many fungi such as yeast and mold.
E200 Sorbic acid is also used in animal feed, cosmetics, pharmaceuticals, packaging materials and rubber additives.
E200 Sorbic acid having trans-double bonds at positions 2 and 4; a food preservative that can induce cutaneous vasodilation and stinging upon topical application to humans.
E200 Sorbic acid is the most thermodynamically stable of the four possible geometri isomers possible, as well as the one with the highest antimicrobial activity.
White powder or crystals.
Melting point 134.5°C.
Slightly acidic and astringent taste with a faint odor.
E200 Sorbic acid, also known by the chemical name E200, is a natural preservative used in the food industry to extend the shelf life of food.
E200 Sorbic acid is an organic compound, belonging to the group of unsaturated acids, obtained both by synthetic methods and from natural sources, such as berries and grains of certain plants.
E200 Sorbic acid is characterized by a faint, peculiar odor and bitter taste, which makes it hardly noticeable when added to food.
E200 Sorbic acid is valued for its bacteriostatic and fungistatic properties, meaning that it inhibits the growth of bacteria and molds without fully destroying them.
E200 Sorbic acid, also known as sorbic acid is a food additive widely used across various industries.
E200 Sorbic acid's applications range from food preservation and use in nutritional supplements to large-scale industrial uses.
E200 Sorbic acid, has the chemical formula CH₃(CH)₄CO₂H.
E200 Sorbic acid is water-soluble and naturally is found in the fruits of the shrub Sorbus aucupari.
E200 Sorbic acid appears as a white to slightly yellow crystalline powder.
E200 Sorbic acid is a good preservative, particularly against molds and yeasts, but it is not effective against bacteria.
E200 Sorbic acid has optimal activity at a pH below 6.5 (acidic and slightly acidic products).
E200 Sorbic acid is a food-grade preservative used to extend the shelf life of food products by inhibiting mould and yeast growth.
E200 Sorbic acid ensures the freshness and safety of products, making it ideal for use in baked goods, dairy products, and beverages.
E200 Sorbic acid is essential for maintaining product quality and safety.
E200 Sorbic acid is the European Union designation for sorbic acid (chemical name: hexa-2,4-dienoic acid), an organic acid used as a food preservative.
E200 Sorbic acid occurs naturally in the berries of the rowan tree (Sorbus aucuparia), but is produced synthetically for commercial use.
E200 Sorbic acid is one of the most widely used food preservatives in the world.
History
E200 Sorbic acid is a white crystalline solid first isolated in 1859 by hydrolysis of the oil distilled from unripened mountain-ash berries.
The name is derived from the scientific term for the rowan tree, Sorbus aucuparia Linne, which is the parent plant of the mountain ash.
E200 Sorbic acid was first synthesized in 1900.
Interest in this compound was minimal until independent researchers, E. Mueller of Germany and C.M. Gooding of the United States, discovered its antimicrobial effect in 1939 and 1940, respectively.
Early interest in manufacturing sorbic acid centered around its use as a tung oil replacement when tung oil supplies were curtailed in the United States during World War II.
High manufacturing costs prohibited expanded use until its approval as a food preservative in 1953.
E200 Sorbic acid is widely used in foods having a pH of 6.5 or below, where control of bacteria, molds, and yeasts is essential for obtaining safe and economical storage life.
E200 Sorbic acid Chemical Properties
Melting point: 132-135 °C (lit.)
Boiling point: 228°C
density: 1.2 g/cm3 at 20 °C
vapor pressure: 0.01 mm Hg ( 20 °C)
refractive index: 1.4600 (estimate)
FEMA: 3921 | 2,4-HEXADIENOIC ACID, (E,E)-
Fp: 127 °C
storage temp.: 2-8°C
solubility: ethanol: 0.1 g/mL, clear
form: Crystalline Powder
pka: 4.76(at 25℃)
color: White or cream-white
Odor: bland
PH: 3.3 (1.6g/l, H2O, 20°C)
biological source: synthetic
Water Solubility: 1.6 g/L (20 ºC)
Merck: 14,8721
JECFA Number: 1176
BRN: 1741831
Henry's Law Constant: 3.3×101 mol/(m3Pa) at 25℃, Abraham and Jr. (2019)
Stability: Material saturated with this acid may ignite spontaneously. Incompatible with strong oxidizing agents. May be light sensitive.
Major Application: cleaning products
cosmetics
flavors and fragrances
food and beverages
personal care
Cosmetics Ingredients Functions: PRESERVATIVE FRAGRANCE
InChI: 1S/C6H8O2/c1-2-3-4-5-6(7)8/h2-5H,1H3,(H,7,8)/b3-2+,5-4+
InChIKey: WSWCOQWTEOXDQX-MQQKCMAXSA-N
LogP: 1.32 at 20℃
CAS DataBase Reference: 110-44-1(CAS DataBase Reference)
NIST Chemistry Reference: 2,4-Hexadienoic acid, (E,E)-(110-44-1)
EPA Substance Registry System: E200 Sorbic acid (110-44-1)
White, crystalline solid.
Slightly soluble in water and many organic solvents. Combustible.
(E,E)-2,4-Hexadienoic acid has a characteristic odor.
With a pKa of 4.76, sorbic acid is about as acidic as acetic acid.
E200 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.
E200 Sorbic acid 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.
E200 Sorbic acid exhibits a number of beneficial properties, thanks to which it is widely used in the food industry.
E200 Sorbic acid is safe for human health, as confirmed by studies and recommendations of organizations such as the World Health Organization (WHO) and the European Food Safety Authority (EFSA).
E200 Sorbic acid's preservative action allows it to effectively inhibit the growth of microorganisms, which contributes to extending the shelf life of food products, while preserving their taste, aroma and nutritional value.
Uses
E200 Sorbic acid is a preservative that is effective against yeasts and molds.
E200 Sorbic acid is effective over a broad ph range up to ph 6.5, being ineffective above ph 7.0.
E200 Sorbic acid is a white, free-flowing powder which is slightly soluble in water with a solubility of 0.16 g in 100 ml of water at 20°c.
E200 Sorbic acid's solubility in water increases with increasing temperatures, although it is not recommended in foods that are pasteurized because it breaks down at high temperatures.
the salts are potas- sium, calcium, and sodium sorbate.
E200 Sorbic acid is used in cheese, jelly, bever- ages, syrup, and pickles.
typical usage levels range from 0.05 to 0.10%.
E200 Sorbic acid is a broad-spectrum, non-toxic preservative against molds and yeasts with moderate sensitizing potential in leave-on cosmetics.
E200 Sorbic acid is used in concentrations of 0.1 to 0.3 percent, and its activity is dependent on the formulation’s pH.
E200 Sorbic acid is used as a replacement for glycerin in emulsions, ointments, and various cosmetic creams.
E200 Sorbic acid is obtained from the berries of the tree commonly known as mountain ash and rowan, and can also be produced synthetically.
E200 Sorbic acid can cause irritation.
E200 Sorbic acid is an naturally occurring organic compound first isolated from unripe berries.
E200 Sorbic acid has been used as a food preservative and as an inhibitor of Clostridium Botulinum bacteria in meat products in order to reduce the amount of nitrites which produce carcinogenic nitroamines.
Mold and yeast inhibitor.
Fungistatic agent for foods, especially cheeses.
To improve the characteristics of drying oils.
In alkyd type coatings to improve gloss.
To improve milling characteristics of cold rubber.
E200 Sorbic acid is used in many food industries.
E200 Sorbic acid is most commonly added to products such as cheeses, cured meats, bakery products, fruit and vegetable preparations, beverages, as well as some types of confectionery.
E200 Sorbic acid is also used in the cosmetics industry as a preservative in products such as creams and shampoos, as well as in the pharmaceutical industry for preserving certain drugs.
Reactions
The chemical reactivity of E200 Sorbic acid is determined by the conjugated double bonds and the carboxyl group.
E200 Sorbic acid is brominated faster than other olefinic acids.
Reaction with hydrogen chloride gives predominately 5-chloro-3-hexenoic acid.
Reactions with amines at high temperatures under pressure lead to mixtures of dehydro-2-piperidinones.
A yellow crystalline complex is formed from sorbic acid and iron tricarbonyl.
Similar coordination occurs also in the presence of other di- and trivalent metals.
Reduction of the double bonds can produce various hexenoic acid mixtures.
Production
The traditional route to sorbic acid involves condensation of malonic acid and crotonaldehyde.
E200 Sorbic acid can also be prepared from isomeric hexadienoic acids, which are available via a nickel-catalyzed reaction of allyl chloride, acetylene, and carbon monoxide.
The route used commercially, however, is from crotonaldehyde and ketene.
An estimated 30,000 tonnes are produced annually.
Biotechnological Production
Today, E200 Sorbic acid is produced solely by chemical synthesis.
However, fermentation and chemical synthesis might be combined to develop a new production route for sorbic acid.
In a first step, glucose would be converted to triacetic acid lactone by fermentation.
E200 Sorbic acid has been shown that triacetic acid lactone can be produced by genetically modified E. coli and S. cerevisiae strains.
After a separation from the fermentation broth, triacetic acid lactone would be transformed into butyl sorbate in a multistage catalyst system (catalysis-hydrogenation and solid acid catalysis).
Then, butyl sorbate would be purified and hydrolyzed to E200 Sorbic acid.
Different scenarios are analyzed to evaluate the economic feasibility of such a production process.
Synthesis
Crotonaldehyde and malonic acid condensation, decarboxylation to get E200 Sorbic acid, crotonaldehyde and malonic acid with pyridine as a solvent at 90-100 reaction for 4-5 hours, and then add dilute sulfuric acid so that the solution is weakly acidic (pH value of about 4-5) freezing, filtration, crystallization to get crude E200 Sorbic acid.
Biochem/physiol Actions
E200 Sorbic acid can be used to inhibit bacterial, yeast and fungal sulfhydryl enzymes by inhibiting amino acid uptake.
Reactivity Profile
E200 Sorbic acid may discolor on exposure to light.
Can react with oxidizing agents.
Also incompatible with bases and reducing agents.
The dust may become explosive, particularly when mixed with free-radical initiators or oxidizing agents.
Toxicology
E200 Sorbic acid and its salts have broad-spectrum activity against yeast and molds, but are less active against bacteria.
The antimicrobial action of E200 Sorbic acid was discovered independently in the United States and Germany in 1939, and since the mid-1950s sorbates have been increasingly used as preservatives.
Sorbates generally have been found superior to benzoate for preservation of margarine, fish, cheese, bread, and cake.
E200 Sorbic acid and its potassium salts are used in low concentrations to control mold and yeast growth in cheese products, some fish and meat products, fresh fruits, vegetables, fruit beverages, baked foods, pickles, and wines.
E200 Sorbic acid is practically nontoxic.
Table 10.4 shows acute toxicity of E200 Sorbic acid and its potassium salt.
Animal studies have not shown obvious problems in tests performed with large doses for longer time periods.
When E200 Sorbic acid (40 mg/kg/day) was injected directly into the stomach of male and female mice for 20 months, no differences were observed in survival rates, growth rates, or appetite between the injected mice and the control.
When the dose was increased to 80 mg/kg/day for three additional months, however, some growth inhibition was observed.
When potassium sorbate (1 and 2% in feed) was fed to dogs for three months, no pathological abnormalities were observed.
This evidence indicates that the subacute toxicity of E200 Sorbic acid is negligible.
As a relatively new food additive, sorbate has been subject to stringent toxicity-testing requirements.
E200 Sorbic acid may well be the most intensively studied of all chemical food preservatives.
In 90-day feeding studies in rats and dogs and a lifetime feeding study in rats, a 5% dietary level of sorbates procured no observable adverse effects.
However, at a 10% dietary level in a 120- day feeding study, rats showed increased growth and increased liver weight.
E200 Sorbic acid has been attributed to the caloric value of sorbate at these high dietary levels since it can act as a substrate for normal catabolic metabolism in mammals.
Sorbates are not mutagenic or tumorigenic, and as noted previously, no reproductive toxicity has been observed.
