1-O-HEXADECYL-SN-GLYCEROL Chemical Properties

Melting point:

64°

alpha 

D20 +3.0° (c = 1.16 in chloroform)

Boiling point:

bp0.005 120°

Density 

1.0054 (rough estimate)

refractive index 

1.4410 (estimate)

storage temp. 

-15°C

solubility 

DMF: 16 mg/ml; DMSO: 0.16 mg/ml; Ethanol: 5 mg/ml

form 

A crystalline solid

pka

13.68±0.20(Predicted)

InChI

InChI=1S/C19H40O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-22-18-19(21)17-20/h19-21H,2-18H2,1H3/t19-/m0/s1

InChIKey

OOWQBDFWEXAXPB-IBGZPJMESA-N

SMILES

C(O)[C@H](O)COCCCCCCCCCCCCCCCC

LogP

6.702 (est)

1-O-HEXADECYL-SN-GLYCEROL Usage And Synthesis

Description

1-O-Hexadecyl-sn-glycerol is a bioactive alkyl glyceryl ether. It reduces UVB-induced cell death and production of reactive oxygen species (ROS) and prostaglandin E₂ (PGE₂; ) in normal human epidermal keratinocytes (NHEKs). 1-O-Hexadecyl-sn-glycerol (50 μM) increases coronary flow and left ventricular developed pressure and reduces malondialdehyde (MDA) formation ex vivo in a rat heart model of ischemia/reperfusion injury.

Uses

1-O-Hexadecyl-sn-glycerol restores plasmalogen levels in Chinese hamster ovary (CHO) cells and human pulmonary arterial endothelial cells (PAEC). Plasmalogen may play a role in protecting animal cells against photosensitized killing.

Definition

ChEBI: A 1-n-hexadecyl analogue of an optically active alkylglycerol compound.

Purification Methods

Recrystallise it from hexane. [Beilstein 1 III 2322.]

References

[1] MARIKO YOKOTA. Chimyl Alcohol Suppresses PGE2 Synthesis by Human Epidermal Keratinocytes through the Activation of PPAR-γ.[J]. Journal of oleo science, 2018, 67 4: 455-462. DOI: 10.5650/jos.ess17157
[2] N MAULIK. Myocardial salvage by chimyl alcohol: possible role of peroxisomal dysfunction in reperfusion injury.[J]. Annals of the New York Academy of Sciences, 1994, 723: 380-384.

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