1,2-DIOCTANOYL-SN-GLYCEROL Chemical Properties

Boiling point:

429.1±12.0 °C(Predicted)

Density 

0.992±0.06 g/cm3(Predicted)

storage temp. 

−20°C

solubility 

DMSO: soluble

pka

13.70±0.10(Predicted)

form 

oil

color 

yellow

Stability:

Temperature Sensitive

InChI

1S/C19H36O5/c1-3-5-7-9-11-13-18(21)23-16-17(15-20)24-19(22)14-12-10-8-6-4-2/h17,20H,3-16H2,1-2H3/t17-/m0/s1

InChIKey

ZQBULZYTDGUSSK-KRWDZBQOSA-N

SMILES

O([C@H](COC(=O)CCCCCCC)CO)C(=O)CCCCCCC

CAS DataBase Reference

60514-48-9(CAS DataBase Reference)

Safety Information

Safety Statements 

23-24/25

WGK Germany 

3

RTECS 

RH0764500

F 

10-21

Storage Class

10 - Combustible liquids

MSDS

• Language:English Provider:SigmaAldrich

1,2-DIOCTANOYL-SN-GLYCEROL Usage And Synthesis

Chemical Properties

Off-White Solid

Uses

1,2-Dioctanoyl-sn-glycerol is a cell permeable analog of the PKC-activating second messenger DAG. 1,2-Dioctanoyl-sn-glycerol and 1,2-dioleoyl-sn-glycerol are nearly equipotent in induction of the acrosome reaction in human sperm.[Cayman Chemical]

Uses

Cell permeable lipid shown to mimic the effect of tumor-promoting phorbol diesters on mitogenesis and EGF binding and action in intact cells.

Definition

ChEBI: 1,2-diacyl-sn-glycerol in which both the 1- and 2-acyl groups are specified as octanoyl.

Biological Activity

Cell permeable: yes', 'Primary Target
Protein kinase C', 'Reversible: no

Synthesis

Over ten minutes, octanoyl chloride (8.93 g, 54.87 mmol) was added dropwise to a solution of (R)-(+)-3-benzyloxy-1,2-propanediol (4.0 g, 21.95 mmol) in anhydrous pyridine (40 mL) followed by DMAP (267 mg, 2.19 mmol). The reaction mixture was stirred at 55??C for 48 h. The reaction mixture was diluted with EtOAc (300 mL), washed sequentially with water (100 mL), 1NHCl (2x100 mL) and brine (100 mL), dried (Na2SO4) and concentrated. The residue was purified on a SiO2 column (3% EtOAc/hexane) to give 7.3 g (75%) of colorless slurry product. Yield 7.3 g (75%).
A solution of the above oil (6.8 g,15.66 mmol) dissolved in EtOH:EtOAc:AcOH (9:1:0.1) (30 mL) was hydrogenated in 10% Pd/C (900 mg, 10%) at 40 psi for 3 hours. The catalyst was filtered over a bed of diatomaceous earth and concentrated to give 1,2-octadecanoyl-SN-glycerol in (5.0,93%) yield.

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