Linoleic Acid Alkyne Chemical Properties

Boiling point:

393.8±37.0 °C(Predicted)

Density 

0.948±0.06 g/cm3(Predicted)

solubility 

0.15 M Tris-HCl pH 8.5: >1 mg/ml; DMF: > 100 mg/ml; DMSO: > 100 mg/ml; Ethanol: > 100 mg/ml; PBS (pH 7.2): <100 μg/ml

pka

4.78±0.10(Predicted)

Linoleic Acid Alkyne Usage And Synthesis

Description

Linoleic acid alkyne is an ω-alkyne derivative of linoleic acid . The ω-alkyne moiety allows Cu(I)-catalyzed cycloaddition chemistry with other molecules containing an azide group.^1,2 Linoleic acid alkyne has been used in experiments focusing on the biological roles of linoleic acid.^3,4 Alternatively, this modified lipid can be used to synthesize other alkyne-containing products, such as glycerophospholipids, for click chemistry.⁵

References

1. Gaebler, A., Penno, A., Kuerschner, L., et al. A highly sensitive protocol for microscopy of alkyne lipids and fluorescently tagged or immunostained proteins J. Lipid. Res. 57(10),1934-1947(2016).
2. Grammel, M., and Hang, H.C. Chemical reporters for biological discovery Nat. Chem. Biol. 9(8),475-484(2013).
3. Beavers, W.N., Serwa, R., Shimozu, Y., et al. ω-Alkynyl lipid surrogates for polyunsaturated fatty acids: Free radical and enzymatic oxidations J. Am. Chem. Soc. 136(32),11529-11539(2014).
4. Windsor, K., Genaro-Mattos, T.C., Kim, H.-Y.H., et al. Probing lipid-protein adduction with alkynyl surrogates: application to Smith-Lemli-Opitz syndrome J. Lipid. Res. 54(10),2842-2850(2013).
5. Milne, S.B., Tallman, K.A., Serwa, R., et al. Capture and release of alkyne-derivatized glycerophospholipids using cobalt chemistry Nat. Chem. Biol. 6(3),205-207(2010).