Quick Search
Sorbic Acid (C6H8O2), or 2,4-hexadienoic acid, is a natural organic compound used as a food preservative.
Sorbic Acid (C6H8O2) has the chemical formula CH3(CH)4CO2H and the structure H3C−CH=CH−CH=CH−C(=O)OH.
Sorbic Acid (C6H8O2) 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
Sorbic Acid (C6H8O2) was first isolated from the unripe berries of the Sorbus aucuparia (rowan tree), hence its name.
Sorbic Acid (C6H8O2), 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.
Sorbic Acid (C6H8O2) is also used in animal feed, cosmetics, pharmaceuticals, packaging materials and rubber additives.
A Sorbic Acid (C6H8O2) having trans-double bonds at positions 2 and 4; a food preservative that can induce cutaneous vasodilation and stinging upon topical application to humans.
Sorbic Acid (C6H8O2) is the most thermodynamically stable of the four possible geometri isomers possible, as well as the one with the highest antimicrobial activity.
Sorbic Acid (C6H8O2) is an organic acid that is used as a food preservative and antimicrobial agent.
Sorbic Acid (C6H8O2) is effective against yeasts and molds, which are the main causes of food spoilage.
Sorbic Acid (C6H8O2) has been shown to be non-genotoxic in biological studies, but it has been found to be genotoxic at high concentrations.
Sorbic Acid (C6H8O2) has also been found to have cardioprotective properties.
The optimum concentration for sorbic acid is 0.1% and it does not require refrigeration. Sorbic Acid (C6H8O2) can be made by reacting p-hydroxybenzoic acid with potassium hydroxide or sodium hydroxide in aqueous solution.
This process can be analyzed by gas chromatography, which separates compounds based on their boiling points, or by liquid chromatography, which separates compounds based on their solubility in an organic solvent like benzyl alcohol or methanol.
Sorbic Acid (C6H8O2) is a natural preservative that comes from the rowan berries, Sorbus aucuparia (family Rosaceae).
Sorbic Acid (C6H8O2) is also prepared synthetically.
Sorbic Acid (C6H8O2) inhibits growth of fungi, yeast, mold and some bacteria and is nearly nontoxic to humans.
Sorbic Acid (C6H8O2) 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 (C6H8O2) or 2,4-hexadienoic acid, is a natural organic compound used as a food preservative.
Sorbic Acid (C6H8O2) has the chemical formula C6H8O2.
Sorbic Acid (C6H8O2) is a colourless solid that is slightly soluble in water and sublimes readily.
Sorbic Acid (C6H8O2) was first isolated from the unripe berries of the rowan tree (Sorbus aucuparia), hence its name.
History
Sorbic Acid (C6H8O2) 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.
Sorbic Acid (C6H8O2) was first synthesized in 1900.
Interest in Sorbic Acid (C6H8O2) 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 (C6H8O2) 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.
Sorbic Acid (C6H8O2) 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.
Sorbic Acid (C6H8O2) 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
Stability: Material saturated with this acid may ignite spontaneously. Incompatible with strong oxidizing agents. May be light sensitive.
InChIKey: WSWCOQWTEOXDQX-MQQKCMAXSA-N
LogP: 1.32 at 20℃
CAS DataBase Reference: 110-44-1(CAS DataBase Reference)
NIST Chemistry Reference: Sorbic Acid (C6H8O2) (110-44-1)
EPA Substance Registry System: Sorbic Acid (C6H8O2) (110-44-1)
Uses
Sorbic Acid (C6H8O2) is a preservative that is effective against yeasts and molds.
Sorbic Acid (C6H8O2) is effective over a broad ph range up to ph 6.5, being ineffective above ph 7.0.
Sorbic Acid (C6H8O2) 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.
Sorbic Acid (C6H8O2)'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.
Sorbic Acid (C6H8O2) is used in cheese, jelly, bever- ages, syrup, and pickles.
typical usage levels range from 0.05 to 0.10%.
Sorbic Acid (C6H8O2) is a broad-spectrum, non-toxic preservative against molds and yeasts with moderate sensitizing potential in leave-on cosmetics.
Sorbic Acid (C6H8O2) is used in concentrations of 0.1 to 0.3 percent, and its activity is dependent on the formulation’s pH.
Sorbic Acid (C6H8O2) is used as a replacement for glycerin in emulsions, ointments, and various cosmetic creams.
Sorbic Acid (C6H8O2) is obtained from the berries of the tree commonly known as mountain ash and rowan, and can also be produced synthetically.
Sorbic Acid (C6H8O2) can cause irritation.
Sorbic Acid (C6H8O2) is an naturally occurring organic compound first isolated from unripe berries.
Sorbic Acid (C6H8O2) has been used as a food preservative and as an inhibitor of Clostridium Botulinum bacteria in mea t 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.
With a pKa of 4.76, Sorbic Acid (C6H8O2) is about as acidic as acetic acid.
Sorbic Acid (C6H8O2) 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.
Sorbic Acid (C6H8O2) 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.
Reactions
The chemical reactivity of Sorbic Acid (C6H8O2) is determined by the conjugated double bonds and the carboxyl group.
Sorbic Acid (C6H8O2) 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 (C6H8O2) 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 (C6H8O2) involves condensation of malonic acid and crotonaldehyde.
Sorbic Acid (C6H8O2) 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.
Biotechnological Production
Today, Sorbic Acid (C6H8O2) 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.
Sorbic Acid (C6H8O2) 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 Sorbic Acid (C6H8O2).
Different scenarios are analyzed to evaluate the economic feasibility of such a production process.
Toxicology
Sorbic Acid (C6H8O2) and its salts have broad-spectrum activity against yeast and molds, but are less active against bacteria.
The antimicrobial action of Sorbic Acid (C6H8O2) 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.
Sorbic Acid (C6H8O2) 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.
Sorbic Acid (C6H8O2) is practically nontoxic.
Table 10.4 shows acute toxicity of Sorbic Acid (C6H8O2) and its potassium salt.
Animal studies have not shown obvious problems in tests performed with large doses for longer time periods.
When Sorbic Acid (C6H8O2) 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 Sorbic Acid (C6H8O2) is negligible.
As a relatively new food additive, sorbate has been subject to stringent toxicity-testing requirements.
Sorbic Acid (C6H8O2) 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.
This has been attributed to the caloric value of sorbate at these high dietary levels since Sorbic Acid (C6H8O2) 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.
