Dehydroacetic acid is an

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

which has several industrial applications. The compound is classified as a

pyrone Pyrones or pyranones are a class of heterocyclic chemical compounds. They contain an unsaturated six-membered ring, which has one oxygen atom and a carbonyl functional group. There are two isomers, denoted as 2-pyrone and 4-pyrone. The 2-pyrone ...

derivative. It presents as an odorless, colorless to white crystalline powder, almost insoluble in water and moderately soluble in most organic solvents.

Preparation

It is prepared by the base-catalysed

dimerization In chemistry, dimerization is the process of joining two identical or similar molecular entities by bonds. The resulting bonds can be either strong or weak. Many symmetrical chemical species are described as dimers, even when the monomer is u ...

diketene Diketene is an organic compound with the molecular formula , and which is sometimes written as . It is formed by dimerization of ketene, . Diketene is a member of the oxetane family. It is used as a reagent in organic chemistry. It is a colorle ...

. Commonly used organic bases include

imidazole Imidazole (ImH) is an organic compound with the formula . It is a white or colourless solid that is soluble in water, producing a mildly alkaline solution. It can be classified as a heterocycle, specifically as a diazole. Many natural products, ...

DABCO DABCO (1,4-diazabicyclo .2.2ctane), also known as triethylenediamine or TEDA, is a bicyclic organic compound with the formula N2(C2H4)3. This colorless solid is a highly nucleophilic tertiary amine base, which is used as a catalyst and reagent in ...

, and

pyridine Pyridine is a basic (chemistry), basic heterocyclic compound, heterocyclic organic compound with the chemical formula . It is structurally related to benzene, with one methine group replaced by a nitrogen atom . It is a highly flammable, weak ...

Uses

Industrially, dehydroacetic acid has several uses which include the following: * as a

fungicide Fungicides are pesticides used to kill parasitic fungi or their spores. Fungi can cause serious damage in agriculture, resulting in losses of yield and quality. Fungicides are used both in agriculture and to fight fungal infections in animals, ...

and

bactericide A bactericide or bacteriocide, sometimes abbreviated Bcidal, is a substance which kills bacteria. Bactericides are disinfectants, antiseptics, or antibiotics. However, material surfaces can also have bactericidal properties based solely on their p ...

. The

sodium Sodium is a chemical element; it has Symbol (chemistry), symbol Na (from Neo-Latin ) and atomic number 11. It is a soft, silvery-white, highly reactive metal. Sodium is an alkali metal, being in group 1 element, group 1 of the peri ...

salt In common usage, salt is a mineral composed primarily of sodium chloride (NaCl). When used in food, especially in granulated form, it is more formally called table salt. In the form of a natural crystalline mineral, salt is also known as r ...

, sodium dehydroacetate, is often used in place of dehydroacetic acid because of its greater solubility in water. * as a food preservative to prevent pickle bloating in squash and

strawberries The garden strawberry (or simply strawberry; ''Fragaria × ananassa'') is a widely grown hybrid plant cultivated worldwide for its fruit. The genus ''Fragaria'', the strawberries, is in the rose family, Rosaceae. The fruit is appreciated f ...

. When used as a food additive, dehydroacetic acid is referred to using the

International Numbering System for Food Additives The International Numbering System for Food Additives (INS) is an international naming system for food additives, aimed at providing a short designation of what may be a lengthy actual name."Class Names and the International Numbering System for Fo ...

E number E numbers, short for Europe numbers, are codes for substances used as food additives, including those found naturally in many foods, such as vitamin C, for use within the European Union (EU) and European Free Trade Association (EFTA). Commonly ...

265. * as a

plasticizer A plasticizer ( UK: plasticiser) is a substance that is added to a material to make it softer and more flexible, to increase its plasticity, to decrease its viscosity, and/or to decrease friction during its handling in manufacture. Plasticizer ...

in synthetic resins. * as an antienzyme in toothpastes. * as a precursor for dimethyl-

4-pyridone 4-Pyridone is an organic compound with the formula . It is a colorless solid. Preparation 4-Pyridone, and its derivatives, are prepared from 4-pyrone and amines in protic solvents. : Tautomerism 4-Pyridone exists a keto-enol tautomerism with ...

s. The compounds are synthesized when dehydroacetic acid is exposed to aqueous solutions containing primary

amine In chemistry, amines (, ) are organic compounds that contain carbon-nitrogen bonds. Amines are formed when one or more hydrogen atoms in ammonia are replaced by alkyl or aryl groups. The nitrogen atom in an amine possesses a lone pair of elec ...

References

{{Reflist Fungicides 4-Pyrones