Docosanedioic acid

Chemical compound

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
CAS Number	505-56-6^Y
3D model (JSmol)	Interactive image
ChemSpider	214170^N
ECHA InfoCard	100.127.871
PubChem CID	244872
UNII	FR7J081T20^Y
CompTox Dashboard (EPA)	DTXSID20198519
InChI 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
SMILES C(CCCCCCCCCCC(=O)O)CCCCCCCCCC(=O)O
Properties
Chemical formula	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)
Solubility in water	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). N verify (what is ^YN ?) Infobox references

Chemical compound

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

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.^{[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.