DICETYL PHOSPHATE Chemical Properties

Melting point:

74-75 °C(lit.)

Boiling point:

600.4±38.0 °C(Predicted)

Density 

0.925±0.06 g/cm3(Predicted)

storage temp. 

-20°C

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Solid

pka

1.50±0.50(Predicted)

color 

White

Odor

at 100.00?%. bland

BRN 

1717117

InChIKey

RNPXCFINMKSQPQ-UHFFFAOYSA-N

LogP

14.679 (est)

CAS DataBase Reference

2197-63-9

EPA Substance Registry System

1-Hexadecanol, hydrogen phosphate (2197-63-9)

Safety Information

WGK Germany 

3

RTECS 

MM0225450

MSDS

• Language:English Provider:SigmaAldrich

DICETYL PHOSPHATE Usage And Synthesis

Uses

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

Uses

Dihexadecyl phosphate is a lipid used for research purposes.

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

DICETYL PHOSPHATE(2197-63-9)Related Product Information

• DICETYL PHOSPHATE
• DIETHYL PHOSPHATE
• AMPHISOL A
• DI-N-OCTADECYL PHOSPHATE
• DIPROPYL PHOSPHITE
• Dibutyl phosphate
• PHOSPHORIC ACID DI-N-DECYL ESTER
• MONO-N-DODECYL PHOSPHATE
• DI-N-DECYL PHOSPHITE
• DILAURYL HYDROGEN PHOSPHITE
• DI-N-AMYLPHOSPHATE
• Dibutyl phosphite
• Pentyl dihydrogen phosphate
• DIMETHYL PHOSPHATE
• Diethyl phosphite
• ALUMINUM DICETYL PHOSPHATE
• N-BUTYL PHOSPHATE
• DI-N-PROPYLPHOSPHATE (1:1 MIXTURE OF MONO AND DI)
• Dihexadecyl Phosphate