Docosanedioic acid
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Names | |
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Preferred IUPAC name Docosanedioic acid | |
Other names Felogenic acid; Phelogenic acid; Phellogenic acid; 1,22-Docosanedoic acid; 1,20-Eicosanedicarboxylic acid | |
Identifiers | |
CAS Number |
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3D model (JSmol) |
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ChemSpider |
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ECHA InfoCard | 100.127.871 ![]() |
PubChem CID |
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UNII |
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CompTox Dashboard (EPA) |
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InChI
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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). ![]() ![]() ![]() Infobox references |
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.
References
- ^ "Docosanedioic acid".
- v
- t
- e
- Ethanedioic acid (Oxalic acid) (CO2H)
- Propanedioic acid (Malonic acid) CH2(CO2H)
- Butanedioic acid (Succinic acid) C2H4(CO2H)
- Pentanedioic acid (Glutaric acid) C3H6(CO2H)
- Hexanedioic acid (Adipic acid) C4H8(CO2H)
- Heptanedioic acid (Pimelic acid) C7H12O4
- Octanedioic acid (Suberic acid) C8H14O4
- Nonanedioic acid (Azelaic acid) C9H16O4
- Decanedioic acid (Sebacic acid) C10H18O4
- Dodecanedioic acid C12H22O4
- Tredecanedioic acid (Brassylic acid) C13H24O4
- Hexadecanedioic acid (Thapsic acid) C16H30O4
- Docosanedioic acid (Phelogenic acid) C22H42O4