SORBIC ACID

Synonyms:
sorbic acid; 110-44-1; 2,4-Hexadienoic acid; (2E,4E)-hexa-2,4-dienoic acid; 2E,4E-Hexadienoic acid; Panosorb; Sorbistat; 2,4-Hexadienoic acid, (2E,4E)-; 2-Propenylacrylic acid; trans,trans-Sorbic acid; Hexadienoic acid; (E,E)-2,4-Hexadienoic acid; Hexa-2,4-dienoic 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-; (2E,4E)-2,4-Hexadienoic acid; 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; Hexadienoic acid, (E,E); (2-Butenylidene)acetic acid; C6:2n-2,4; Sorbic acid (NF); Sorbic acid [NF]; 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; L'acide sorbique; 1,3-PENTADIEN-1-CARBOXYLIC ACID; 1,3-PENTADIENE-1-CARBOXYLIC ACID; 2,4-HEXADIENOIC ACID; 2,4-HEXADIENOIC ACID, (E,E)-; 2-PROPENYL-ACRYLIC ACID; 2-PROPENYLACRYLIC ACID; ACETIC ACID, (2-BUTENYLIDENE)-; ACETIC ACID, CROTYLIDENE-; ACIDE HEXADIENOIQUE-2,4 (TRANS-, TRANS-);  ACIDE PROPENYL-2 ACRYLIQUE; Acide sorbique; ALPHA-TRANS-GAMMA-TRANS-SORBIC ACID; E,E-2,4-HEXADIENOIC ACID; SORBIC ACID COARSE MESH GRADE; TRANS, TRANS-SORBIC ACID; TRANS-TRANS-2,4-HEXADIENOIC ACID; HEXADIENIC ACID; HEXADIENOIC ACID; Sorbic acid;  sorbik asit; acide sorbique; sorbik acit; acide sorbicque; sorbik aside; acide sorbique; sorbik acide

SORBIC ACID

Sorbic acid

Not to be confused with Ascorbic acid.
Sorbic acid
Sorbic acid
Sorbic acid (ball-and-stick model)
Names
IUPAC name
(2E,4E)-hexa-2,4-dienoic acid
Identifiers
CAS Number    
110-44-1 check
3D model (JSmol)    
Interactive image
ChEBI    
CHEBI:38358 ☒
ChEMBL    
ChEMBL250212 ☒
ChemSpider    
558605 check
ECHA InfoCard    100.003.427 
E number    E200 (preservatives)
PubChem CID    
643460
UNII    
X045WJ989B check
CompTox Dashboard (EPA)    
DTXSID3021277 
InChI[show]
SMILES[show]
Properties
Chemical formula    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)
Solubility in water    1.6 g/L at 20 °C
Acidity (pKa)    4.76 at 25 °C
Hazards
NFPA 704 (fire diamond)    
NFPA 704 four-colored diamond
120
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
Sorbic acid, or 2,4-hexadienoic acid, is a natural organic compound used as a food preservative.[1] It has the chemical formula CH3(CH)4CO2H. 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.

Production
The traditional route to sorbic acid involves condensation of malonic acid and trans-butenal.[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.[4]

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.[5]

Properties and uses of Sorbic acid
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.[6]

Sorbic acid can also be used as an additive for cold rubber, and as an intermediate in the manufacture of some plasticizers and lubricants.[7]

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. There is a general consensus that sorbic acid and sorbates are intrinsically devoid of carcinogenic activity. However they have been shown to have the potential to undergo conversion to potential mutagens either through oxidation, or through a chemical reaction with nitrites at pH of 2-4.2 – the latter conditions being ones that mimic the gastric environment. In living yeast cells sorbic acid enhances oxygen free radical formation by the mitochondrial electron transport chain, leading to damage to the mitochondrial DNA.

See also
Sorbitol
Polysorbate
Acids in wine
Parasorbic acid

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

DryPowder

Colourless needles or white free flowing powder, having a slight characteristic odour and showing no change in colour after heating for 90 minutes at 105 °C

Sorbic acid is a preferred preservative compared to nitrates, which can form carcinogenic byproducts. It’s applied to food by either spraying or dipping the food with a solution of sorbic acid and water.

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. 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.

Is Sorbic acid 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.

While rare, allergic contact dermatitis may occur, but, ironically, over-the-counter corticosteroid creams that contain sorbic acid are often the culprit. People with eczema should avoid sorbic acid in cosmetics because of possible irritation, but avoiding it in foods is unnecessary.

If your skin reacts badly to sorbic acid, you can treat it by rinsing the affected area with water, and applying anti-itch cream. If it’s causing you problems internally, drinking eight ounces of water typically reduces symptoms.

While extremely rare, toxic reactions to sorbic acid can occur when handling it in its pure, undiluted form. In these cases, the National Library of Medicine’s Toxicology Data Network recommends washing your skin and clothes. If inhaled, moving the person to fresh air is recommended. While extremely rare, you may require hospitalization if you experience anaphylaxis. This is a severe allergic reaction that can cause you to go into shock, go pale, get a rash, and experience nausea and vomiting.

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.

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.

Molecular Weight of Sorbic acid:    112.13 g/mol    Computed by PubChem 2.1 (PubChem release 2019.06.18)
XLogP3 of Sorbic acid:    1.3    Computed by XLogP3 3.0 (PubChem release 2019.06.18)
Hydrogen Bond Donor Count of Sorbic acid:    1    Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Hydrogen Bond Acceptor Count of Sorbic acid:    2    Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Rotatable Bond Count of Sorbic acid:    2    Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Exact Mass of Sorbic acid:    112.052429 g/mol    Computed by PubChem 2.1 (PubChem release 2019.06.18)
Monoisotopic Mass of Sorbic acid:    112.052429 g/mol    Computed by PubChem 2.1 (PubChem release 2019.06.18)
Topological Polar Surface Area of Sorbic acid:    37.3 Ų    Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Heavy Atom Count of Sorbic acid:    8    Computed by PubChem
Formal Charge of Sorbic acid:    0    Computed by PubChem
Complexity of Sorbic acid:    123    Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Isotope Atom Count of Sorbic acid:    0    Computed by PubChem
Defined Atom Stereocenter Count of Sorbic acid:    0    Computed by PubChem
Undefined Atom Stereocenter Count of Sorbic acid:    0    Computed by PubChem
Defined Bond Stereocenter Count of Sorbic acid:    2    Computed by PubChem
Undefined Bond Stereocenter Count of Sorbic acid:    0    Computed by PubChem
Covalently-Bonded Unit Count of Sorbic acid:    1    Computed by PubChem
Compound  of Sorbic acid Is Canonicalized?    Yes

Sorbic Acid
What is Sorbic Acid?
Sorbic acid is a food preservative which protects many food varieties from yeast and mold spoilage. It is an organic compound, with naturally strong antimicrobial capabilities. This additive is one of the most popular food preservatives, acting as a protectant to many food varieties from yeast and mold spoilage. It is most often found in:

Baked goods
Cheeses
Wines
Fresh produce
Refrigerated meat
Sorbic acid does not create carcinogenic byproducts, as some preservatives such as nitrates do. It also has no noticeable taste or odor when used in baked goods. Its salts – sodium sorbate, calcium sorbate, and potassium sorbate – are more soluble in water than the original form. Potassium sorbate has the highest solubility and is the most commonly used form in the food industry.1

Origin
Sorbic acid was first discovered in 1859 from unripe berries of the rowan tree (Sorbus aucuparia), which is where the name originated. However, it was not until the late 1930s that its antimicrobial properties were revealed. It was discovered first in Germany by E. Muller and then a few months later by C. S. Gooding in the U.S.

By the 1950s, it was being produced industrially. The early uses of the this acid’s salts were to defend meat against the botulism-causing bacteria Clostridium botulinum. Its popularity grew for its organoleptic neutrality and over the last 30 years has become one of the most-used preservatives.2

Commercial Production
Sorbic acid is produced synthetically for commercial use. The main method is creating a condensation reaction of ketene and crotonaldehyde. It is purified with a treatment of sodium hydroxide, hydrochloric acid and activated carbon. For food uses and increased solubility in water, it is granulated by extrusion and pelletization.3

Function
Sorbic acid is a carboxylic acid, virtually odorless and tasteless when used in food processing. It is available in powder, granule and solution form or it can be encapsulated. When adding any sorbate form to food products, methods range from treating packaging materials, dipping and spraying foods, or dusting with a dry form.4 It may also be blended with dry ingredients first, such as flour, salt, or cornstarch, before being added into a formula.

Encapsulation allows this acid to be added directly to the dough, preserving the product from the inside out without killing baker’s yeast. The coating of encapsulates are mainly comprised of lipids (fats), and melt away at temperatures above 145oF. This releases the sorbic acid after yeast kill temperatures (140oF) in the oven. Sometimes, the encapsulated form is used in conjunction with calcium propionate. The combined use of these preservatives can inhibit a broad range of different spoilage microorganisms, extending mold-free shelf life. Encapsulated sorbic acid can also be used in frozen products without affecting its antimicrobial properties.

The advantage of sorbic acid over other food preservatives, such as propionic or benzoic acid, is that it does not impair the final product’s flavor. This is because  less is needed by weight over other preservatives. Sorbic acid, as well as its salts, functions best in products with pH between 4.0 and  7.0.

Sorbic acid has a water solubility of around 0.16g/100 ml, and increases with temperature.5 Its solubility is higher in ethanol, but slows with added sugar. Sorbic acid inhibits yeasts strains differently, as some strains are more tolerant to its effects than others.6

FDA
Sorbic acid and its salts are classified as GRAS by the FDA, as a chemical preservative. Production and use guidelines fall under standard procedures for food additives.

Sorbic Acid

What Is Sorbic Acid?
Sorbic Acid is a white, free-flowing, crystalline powder. Potassium Sorbate, the potassium salt of Sorbic Acid, occurs as a white crystalline powder, white granules, or pellets. In cosmetics and personal care products, Sorbic Acid and Potassium Sorbate are used primarily in the formulation of facial and eye makeup and skin care and hair products.

Why is Sorbic Acid used in cosmetics and personal care products?
Sorbic Acid and Potassium Sorbate kill microorganisms, or prevent or retard their growth and reproduction, and thus protect cosmetics and personal care products from spoilage.

Scientific Facts: 
Sorbic Acid occurs naturally as para-sorbic acid in berries of the mountain ash tree, Sorbus aucuparia, Rosaceae. It can also be synthesized by various processes. Sorbic Acid and Potassium Sorbate have a broad spectrum of fungistatic activity but are less active against bacteria. Optimum antimicrobial activity is attained at pH values up to 6.5.