Acidul sorbic

A nu se confunda cu Acidul ascorbic.

Acid sorbic
Denumirea IUPAC (2E,4E)-hexa-2,4-dienoic acid

CAS

Numar de identificare 110-44-1 Proprietati C6H8O2 112.13 g mol1 135 C, 408 K, 275 F 228 C (dec) 4.76 la 25 C

Formula moleculara Masa moleculara Punct de topire Punct de fierbere Aciditate (pKa)

Acidul sorbic, sau 2,4- acid hexadienoic, este un compus organic natural folosit ca si conservant alimentar. Este solid, incolor, usor solubil in apa. It was first isolated from the unripe berries of Rowan (Sorbus aucuparia), hence its name.

Productie
The traditional route to sorbic acid involves condensation of malonic acid and transbutenal. It can also be prepared from isomeric hexadienoic acids, which are available via a nickel-catalyzed reaction of allyl chloride, acetylene, and carbon monoxide. An estimated 30,000 tons are produced annually.[1]

Istorie
Sorbic acid was isolated in 1859 by distillation of rowanberry oil by A.W von Hofmann. This affords 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 in order to reduce the amount of nitrites, which produce carcinogenic nitrosamines.[2]

Proprietati si utilizari
With a pKa of 4.76, it is about 10x more acidic than 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 it is the acid form that is active. 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. 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-hexanoic acid.[3]

Siguranta
The LD50 value of sorbic acid is estimated between 10-7.4 g/kg, which is quite low. The compound is relatively unstable and is rapidly degraded in soil, hence it is often considered enviromentally friendly.