DICETYL PHOSPHATE

Uses

Dihexadecyl phosphate is a lipid used for research purposes.

Uses

dicetyl phosphate is used in cosmetic preparations as an emulsifier and surfactant.

Definition

ChEBI: The dihexadecyl ester of phosphoric acid.

Biochem/physiol Actions

Dihexadecyl phosphate (DHP) is a negatively charged lipid that is used for the formation of model membranes.

Synthesis

The general procedure for the synthesis of bishexadecyl phosphate from 1-hexadecanol is as follows: 1. Phosphorus trichloride (2.5 ml, 26.8 mmol) was added slowly and dropwise to a mixture of 1-hexadecanol (19.50 g, 80.4 mmol) and benzene (100 ml) at 80 °C (solvent reflux temperature) and the reaction was continued with stirring for 12 hrs at this temperature. 2. Upon completion of the reaction, the solvent in the reaction solution was removed by distillation under reduced pressure. 3. benzene (50 ml) was added to the residue obtained after decompression distillation and the mixture was cooled overnight to promote crystallization. 4. The cooled mixture was filtered and the resulting white precipitate, i.e., bishexadecyl phosphate (1.64 g, 3.0 mmol, yield: 11%) was collected. The product characterization data were as follows: 1H-NMR (ppm) δ: 0.87-0.89 (t, 6H), 1.25-1.37 (br, s, 52H), 1.65-1.72 (m, 4H), 4.00-4.06 (m, 4H), 7.05 (br, s, 1H). 13C-NMR (ppm) δ: 14.11, 22.69, 25.44, 29.18, 29.36, 29.54, 29.61, 29.66, 29.67, 29.70, 29.71, 30.16, 30.21, 31.93, 67.69, 67.73. 31P-NMR (ppm) δ: 2.15. SIMS mass analysis: measured value 547.85, theoretical value 547.83, corresponding to (C32H68O4P)+.

Purification Methods

Recrystallise it from MeOH [Lukac J Am Chem Soc 106 4387 1984]. [Beilstein 1 IV 1880.]

References

[1] Patent: US2010/94020, 2010, A1. Location in patent: Page/Page column 18
[2] Bulletin of the Chemical Society of Japan, 1978, vol. 51, p. 1877 - 1879
[3] Chemical and Pharmaceutical Bulletin, 1995, vol. 43, # 10, p. 1751 - 1754
[4] Bioconjugate Chemistry, 2010, vol. 21, # 5, p. 844 - 852