Names | |
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Preferred IUPAC name (2E,4E)-Hexa-2,4-dienoic acid | |
Identifiers | |
3D model (JSmol) | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.003.427 |
E number | E200 (preservatives) |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
| |
| |
Properties | |
C6H8O2 | |
Molar mass | 112.128 g·mol−1 |
Density | 1.204 g/cm3 |
Melting point | 135 °C (275 °F; 408 K) |
Boiling point | 228 °C (442 °F; 501 K) |
1.6 g/L at 20 °C | |
Acidity (pKa) | 4.76 at 25 °C |
Hazards | |
NFPA 704 (fire diamond) | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Sorbic acid, or 2,4-hexadienoic acid, is a natural organic compound used as a food preservative. It has the chemical formula CH3(CH)4CO2H and the structure H3C−CH=CH−CH=CH−C(=O)OH . It is a colourless solid that is slightly soluble in water and sublimes readily. It was first isolated from the unripe berries of the Sorbus aucuparia (rowan tree), hence its name. [1]
The traditional route to sorbic acid involves condensation of malonic acid and crotonaldehyde. [2] 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. [3] An estimated 30,000 tons are produced annually. [1]
Sorbic acid was isolated in 1859 by distillation of rowanberry oil by A. W. von Hofmann. [4] 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. [5]
With a pKa of 4.76, sorbic acid is about as acidic as acetic acid.
Sorbic acid and its salts, especially potassium sorbate and calcium sorbate, are antimicrobial agents often used as preservatives in food and drinks to prevent the growth of mold, yeast, and fungi. In general the salts are preferred over the acid form because they are more soluble in water, but the active form is the acid. The optimal pH for the antimicrobial activity is below pH 6.5. Sorbates are generally used at concentrations of 0.025% to 0.10%. Adding sorbate salts to food will, however, raise the pH of the food slightly so the pH may need to be adjusted to assure safety. It is found in foods such as various kinds of cheese, bread, muffins, donuts, pies, cookies, protein bars, syrups, lemonades, fruit juices, dried meats, sausages, nuggets, burgers, sandwiches, tacos, pizzas, smoked fish, margarine, sauces, soups, and more. [6]
The E numbers are:
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. [7]
Sorbic acid can also be used as an additive for cold rubber, and as an intermediate in the manufacture of some plasticizers and lubricants. [8]
Sorbic acid and sorbate salts have a very low mammalian toxicity and carcinogenicity. [9] Its LD50 is estimated to be between 7.4 and 10 g/kg. [1]
Benzoic acid is a white solid organic compound with the formula C6H5COOH, whose structure consists of a benzene ring with a carboxyl substituent. The benzoyl group is often abbreviated "Bz", thus benzoic acid is also denoted as BzOH, since the benzoyl group has the formula –C6H5CO. It is the simplest aromatic carboxylic acid. The name is derived from gum benzoin, which was for a long time its only source.
A preservative is a substance or a chemical that is added to products such as food products, beverages, pharmaceutical drugs, paints, biological samples, cosmetics, wood, and many other products to prevent decomposition by microbial growth or by undesirable chemical changes. In general, preservation is implemented in two modes, chemical and physical. Chemical preservation entails adding chemical compounds to the product. Physical preservation entails processes such as refrigeration or drying. Preservative food additives reduce the risk of foodborne infections, decrease microbial spoilage, and preserve fresh attributes and nutritional quality. Some physical techniques for food preservation include dehydration, UV-C radiation, freeze-drying, and refrigeration. Chemical preservation and physical preservation techniques are sometimes combined.
An organic acid is an organic compound with acidic properties. The most common organic acids are the carboxylic acids, whose acidity is associated with their carboxyl group –COOH. Sulfonic acids, containing the group –SO2OH, are relatively stronger acids. Alcohols, with –OH, can act as acids but they are usually very weak. The relative stability of the conjugate base of the acid determines its acidity. Other groups can also confer acidity, usually weakly: the thiol group –SH, the enol group, and the phenol group. In biological systems, organic compounds containing these groups are generally referred to as organic acids.
Potassium benzoate (E212), the potassium salt of benzoic acid, is a food preservative that inhibits the growth of mold, yeast and some bacteria. It works best in low-pH products, below 4.5, where it exists as benzoic acid.
Sodium benzoate also known as benzoate of soda is the sodium salt of benzoic acid, widely used as a food preservative (with an E number of E211) and a pickling agent. It appears as a white crystalline chemical with the formula C6H5COONa.
Nutrinova is a global manufacturer of food constituents. It was formerly a division of Hoechst until 1997 when it was taken over by Celanese and adopted its current name.
Sodium sorbate is the sodium salt of sorbic acid. It is an unstable white solid. Unlike other sorbic acid salts such as potassium sorbate (E202) and calcium sorbate (E203), the use of sodium sorbate as a food additive is not allowed in the EU due to potential genotoxic effects.
Potassium sorbate is the potassium salt of sorbic acid, chemical formula CH3CH=CH−CH=CH−CO2K. It is a white salt that is very soluble in water (58.2% at 20 °C). It is primarily used as a food preservative (E number 202). Potassium sorbate is effective in a variety of applications including food, wine, and personal-care products. While sorbic acid occurs naturally in rowan and hippophae berries, virtually all of the world's supply of sorbic acid, from which potassium sorbate is derived, is manufactured synthetically.
Calcium benzoate refers to the calcium salt of benzoic acid. When used in the food industry as a preservative, its E number is E213 ; it is approved for use as a food additive in the EU, USA and Australia and New Zealand.
Zygosaccharomyces bailii is a species in the genus Zygosaccharomyces. It was initially described as Saccharomyces bailii by Lindner in 1895, but in 1983 it was reclassified as Zygosaccharomyces bailii in the work by Barnett et al.
Crotonaldehyde is a chemical compound with the formula CH3CH=CHCHO. The compound is usually sold as a mixture of the E- and Z-isomers, which differ with respect to the relative position of the methyl and formyl groups. The E-isomer is more common (data given in Table is for the E-isomer). This lachrymatory liquid is moderately soluble in water and miscible in organic solvents. As an unsaturated aldehyde, crotonaldehyde is a versatile intermediate in organic synthesis. It occurs in a variety of foodstuffs, e.g. soybean oils.
Fruit2O, formerly manufactured by Kraft, is a lightly flavored, non-carbonated water beverage introduced in 1999. Fruit2o was introduced to compete not only with the bottled water market but also with the soft drink market. Sunny Delight Beverages purchased the Veryfine Products line from Kraft in 2007.
A dough conditioner, flour treatment agent, improving agent or bread improver is any ingredient or chemical added to bread dough to strengthen its texture or otherwise improve it in some way. Dough conditioners may include enzymes, yeast nutrients, mineral salts, oxidants and reductants, bleaching agents and emulsifiers. They are food additives combined with flour to improve baking functionality. Flour treatment agents are used to increase the speed of dough rising and to improve the strength and workability of the dough.
The acids in wine are an important component in both winemaking and the finished product of wine. They are present in both grapes and wine, having direct influences on the color, balance and taste of the wine as well as the growth and vitality of yeast during fermentation and protecting the wine from bacteria. The measure of the amount of acidity in wine is known as the “titratable acidity” or “total acidity”, which refers to the test that yields the total of all acids present, while strength of acidity is measured according to pH, with most wines having a pH between 2.9 and 3.9. Generally, the lower the pH, the higher the acidity in the wine. There is no direct connection between total acidity and pH. In wine tasting, the term “acidity” refers to the fresh, tart and sour attributes of the wine which are evaluated in relation to how well the acidity balances out the sweetness and bitter components of the wine such as tannins. Three primary acids are found in wine grapes: tartaric, malic, and citric acids. During the course of winemaking and in the finished wines, acetic, butyric, lactic, and succinic acids can play significant roles. Most of the acids involved with wine are fixed acids with the notable exception of acetic acid, mostly found in vinegar, which is volatile and can contribute to the wine fault known as volatile acidity. Sometimes, additional acids, such as ascorbic, sorbic and sulfurous acids, are used in winemaking.
A disulfite, commonly known as metabisulfite or pyrosulfite, is a chemical compound containing the ion S
2O2−
5. It is a colorless dianion that is primarily marketed in the form of sodium metabisulfite or potassium metabisulfite. When dissolved in water, these salts release the hydrogensulfite HSO−
3 anion. These salts act equivalently to sodium hydrogensulfite or potassium hydrogensulfite.
Sting Energy is a carbonated energy drink produced by Rockstar Inc.. Sting is available in flavors such as the original Gold Rush, Gold, Power Pacq, Power Lime (Kiwifruit/Lime), Berry Blast (Strawberry) and blue thunder
Biopreservation is the use of natural or controlled microbiota or antimicrobials as a way of preserving food and extending its shelf life. The biopreservation of food, especially utilizing lactic acid bacteria (LAB) that are inhibitory to food spoilage microbes, has been practiced since early ages, at first unconsciously but eventually with an increasingly robust scientific foundation. Beneficial bacteria or the fermentation products produced by these bacteria are used in biopreservation to control spoilage and render pathogens inactive in food. There are a various modes of action through which microorganisms can interfere with the growth of others such as organic acid production, resulting in a reduction of pH and the antimicrobial activity of the un-dissociated acid molecules, a wide variety of small inhibitory molecules including hydrogen peroxide, etc. It is a benign ecological approach which is gaining increasing attention.
Fungistatics are anti-fungal agents that inhibit the growth of fungus. The term fungistatic may be used as both a noun and an adjective. Fungistatics have applications in agriculture, the food industry, the paint industry, and medicine.
Wine preservatives are used to preserve the quality and shelf life of bottled wine without affecting its taste. Specifically, they are used to prevent oxidation and bacterial spoilage by inhibiting microbial activity.
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