Docosanedioic acid

Docosanedioic acid is a dicarboxylic acid with the linear formula HOOC(CH
2)
20COOH.

Docosanedioic acid
Names
Preferred IUPAC name
Docosanedioic acid
Other names
Felogenic acid; Phelogenic acid; Phellogenic acid; 1,22-Docosanedoic acid; 1,20-Eicosanedicarboxylic acid
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.127.871
UNII
  • InChI=1S/C22H42O4/c23-21(24)19-17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-18-20-22(25)26/h1-20H2,(H,23,24)(H,25,26) ☒N
    Key: DGXRZJSPDXZJFG-UHFFFAOYSA-N ☒N
  • C(CCCCCCCCCCC(=O)O)CCCCCCCCCC(=O)O
Properties
C22H42O4
Molar mass 370.574 g·mol−1
Appearance White solid
Density 0.972 g/cm3
Melting point 119–125 °C (246–257 °F; 392–398 K)[1]
Boiling point 527 °C (981 °F; 800 K)
Insoluble in water
Hazards
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).
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Infobox references

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.

References
  1. "Docosanedioic acid".
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