Docosanedioic acid

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Docosanedioic acid
Docosanedioic acid.svg
Identifiers
CAS number 505-56-6 YesY
Jmol-3D images Image 1
Properties
Molecular formula C22H42O4
Molar mass 370.57 g mol−1
Appearance White solid
Density 0.972 g/cm3
Melting point 130 to 131 °C (266 to 268 °F; 403 to 404 K)
Boiling point 527 °C (981 °F; 800 K)
Solubility in water Insoluble in water
Hazards
Flash point 286.6 °C (547.9 °F; 559.8 K)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

Docosanedioic acid is a dicarboxylic acid with the linear formula HOOC(CH2)20COOH.

Uses[edit]

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[edit]

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.[clarification needed]

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.

References[edit]