Docosanedioic acid: Difference between revisions
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Revision as of 16:15, 15 June 2020
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| Names | |
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| IUPAC name
Docosanedioic acid
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| Other names
Felogenic acid; Phelogenic acid; Phellogenic acid; 1,22-Docosanedoic acid; 1,20-Eicosanedicarboxylic acid
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.127.871 |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| 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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Docosanedioic acid is a dicarboxylic acid with the linear formula HOOC(CH2)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.