2-Ethylhexanoic acid is the organic compound

Organic compound

An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...

 with the formula

Chemical formula

A chemical formula or molecular formula is a way of expressing information about the atoms that constitute a particular chemical compound....

 CH₃(CH₂)₃CH(C₂H₅)CO₂H. This carboxylic acid

Carboxylic acid

Carboxylic acids are organic acids characterized by the presence of at least one carboxyl group. The general formula of a carboxylic acid is R-COOH, where R is some monovalent functional group...

 is widely used to prepare metal derivatives that are soluble in nonpolar organic solvents. These lipophilic metal-containing derivatives are used as catalysts in polymer

Polymer

A polymer is a large molecule composed of repeating structural units. These subunits are typically connected by covalent chemical bonds...

izations. For example, tin 2-ethylhexanoate is used in the production of poly(lactic-co-glycolic acid)

PLGA

PLGA or poly is a copolymer which is used in a host of Food and Drug Administration approved therapeutic devices, owing to its biodegradability and biocompatibility. PLGA is synthesized by means of random ring-opening co-polymerization of two different monomers, the cyclic dimers of glycolic...

. The high solubility of these metal complexes is attributable to the long hydrocarbon chain and the presence of a chiral

Chirality (chemistry)

A chiral molecule is a type of molecule that lacks an internal plane of symmetry and thus has a non-superimposable mirror image. The feature that is most often the cause of chirality in molecules is the presence of an asymmetric carbon atom....

 center which leads to mixtures of diastereoisomeric complexes. These metal complexes are often described as salts, when in fact they are not ionic but charge-neutral coordination complexes akin to the better defined, more crystalline acetate

Acetate

An acetate is a derivative of acetic acid. This term includes salts and esters, as well as the anion found in solution. Most of the approximately 5 billion kilograms of acetic acid produced annually in industry are used in the production of acetates, which usually take the form of polymers. In...

s.

Examples of metal ethylhexanoates

• Hydroxyl aluminium bis(2-ethylhexanoate)
  Hydroxyl aluminium bis(2-ethylhexanoate)
  Hydroxyl aluminium bis is a chemical substance derived from 2-ethylhexanoic acid and aluminium. Nominally it is the coordination complex with the formula Al2 where Et = ethyl. The composition is not a homogeneous compound. It is used as a thickening agent in various products, including in napalm....
  
  , used as a thickener
• Tin(II) ethylhexanoate (CAS# 301-10-0), a catalyst for polylactide polymerization
• Cobalt(II) ethylhexanoate (CAS# 136-52-7), a drier for alkyd resins
• Nickel(II) ethylhexanoate (CAS# 4454-16-4)

Health aspects

Some studies showed now subchronic oral

Mouth

The mouth is the first portion of the alimentary canal that receives food andsaliva. The oral mucosa is the mucous membrane epithelium lining the inside of the mouth....

 toxicity. but as a study indicated the teratogenicity of the compound the sources for exposure where evaluated. One major source are the metal derivatives of 2-ethylhexanoic acid

2-Ethylhexanoic acid

2-Ethylhexanoic acid is the organic compound with the formula CH33CHCO2H. This carboxylic acid is widely used to prepare metal derivatives that are soluble in nonpolar organic solvents. These lipophilic metal-containing derivatives are used as catalysts in polymerizations. For example, tin...

, which are widely used as stabilizers for polyvinyl chloride

Polyvinyl chloride

Polyvinyl chloride, commonly abbreviated PVC, is a thermoplastic polymer. It is a vinyl polymer constructed of repeating vinyl groups having one hydrogen replaced by chloride. Polyvinyl chloride is the third most widely produced plastic, after polyethylene and polypropylene. PVC is widely used in...

 PVC

PVC

Polyvinyl chloride is a plastic.PVC may also refer to:*Param Vir Chakra, India's highest military honor*Peripheral venous catheter, a small, flexible tube placed into a peripheral vein in order to administer medication or fluids...

. The other source is the metabolism of bis(2-ethylhexyl) phthalate

Bis(2-ethylhexyl) phthalate

Bisphthalate, commonly abbreviated DEHP, is an organic compound with the formula C6H42. It is sometimes called dioctyl phthalate and abbreviated DOP. It is the most important "phthalate," being the diester of phthalic acid and the branched-chain 2-ethylhexanol. This colourless viscous liquid is...

 (DEHP) the two ester bonds are hydrolysed and the resulting 2-ethylhexanol

2-Ethylhexanol

2-Ethylhexanol is a fatty alcohol, an organic compound is a branched, eight-carbon chiral alcohol. It is a colorless liquid that is nearly insoluble in water but soluble in most organic solvents...

 is oxidized in the organism to 2-ethylhexanoic acid. The elevated levels of the compound even in glass jars was due to the diffusion of the compound from the PVC cap into the food.