Felogenic acid; Phelogenic acid; Phellogenic acid; 1,22-Docosanedoic acid; 1,20-Eicosanedicarboxylic acid
|3D model (Jmol)||Interactive image|
|Molar mass||370.57 g·mol−1|
|Melting point||130 to 131 °C (266 to 268 °F; 403 to 404 K)|
|Boiling point||527 °C (981 °F; 800 K)|
|Insoluble in water|
|Flash point||286.6 °C (547.9 °F; 559.8 K)|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
Docosanedioic acid is a dicarboxylic acid with the linear formula HOOC(CH2)20COOH.
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.
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.
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