Density 972 kg/m³ Appearance White solid | Boiling point 527 °C | |
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Docosanedioic acid is a dicarboxylic acid with the linear formula HOOC(CH2)20COOH.
Contents
Uses
Docosanedioic acid finds uses in organic chemistry and is a starting material for ultrasound contrast agents. It is also used to produce the fluffy white solid 1,22-docosanediol, which in turn is a precursor to 1,22-bis-2-(trimethylammonium)ethylphospatyldocosane, a phosphocholine derivative with antifungal activity.
Synthesis
Disodium 7,16-diketodocosanedioate is reacted with triethanolamine, hydrazine hydrate, potassium hydroxide and a little hydrochloric acid to afford docosanedioic acid via a Wolff–Kishner reduction.
Alternately, 2,5-bis(ω-carboyoctyl)thiophene is desulfurized with Raney nickel to afford docosanedioic acid.
It can also be produced through oxidative coupling of 10-undecynoic acid to docosa-10,12-diynedoic acid and reduction of this intermediate with a palladium catalyst.