1-Oleoyl-2-acetyl-rac-glycerol

Names

[ Name ]:
1-Oleoyl-2-acetyl-rac-glycerol

[Synonym ]:
2-Acetoxy-3-hydroxypropyl (9Z)-9-octadecenoate
9-Octadecenoic acid, 2-(acetyloxy)-3-hydroxypropyl ester, (9Z)-
9-Octadecenoic acid, (2S)-2-(acetyloxy)-3-hydroxypropyl ester, (9Z)-
1-oleoyl-2-acetyl-sn-glycerol
(2S)-2-Acetoxy-3-hydroxypropyl (9Z)-9-octadecenoate
2-(acetyloxy)-3-hydroxypropyl (9Z)-octadec-9-enoate
MFCD00166985
1-Oleoyl-2-acetyl-rac-glycerol

Biological Activity

[Description]:

1-Oleoyl-2-acetyl-sn glycerol is a synthetic, cell permeable diacylglycerol analog. 1-Oleoyl-2-acetyl-sn glycerol activates calcium-dependent protein kinase C (PKC) and induces the superoxide-production.

[Related Catalog]:

Signaling Pathways >> Epigenetics >> PKC

Research Areas >> Metabolic Disease

Signaling Pathways >> TGF-beta/Smad >> PKC

[References]

[1]. Fujita I, Irita K, Takeshige K, Minakami S. Diacylglycerol, 1-oleoyl-2-acetyl-glycerol, stimulates superoxide-generation from human neutrophils. Biochem Biophys Res Commun. 1984;120(2):318-324.

[2]. Martin AC, Cooper DM. Capacitative and 1-oleyl-2-acetyl-sn-glycerol-activated Ca(2+) entry distinguished using adenylyl cyclase type 8. Mol Pharmacol. 2006;70(2):769-777.

Chemical & Physical Properties

[ Density]:
1.0±0.1 g/cm3

[ Boiling Point ]:
490.0±15.0 °C at 760 mmHg

[ Molecular Formula ]:
C₂₃H₄₂O₅

[ Molecular Weight ]:
398.577

[ Flash Point ]:
152.3±13.9 °C

[ Exact Mass ]:
398.303223

[ PSA ]:
72.83000

[ LogP ]:
7.45

[ Vapour Pressure ]:
0.0±2.8 mmHg at 25°C

[ Index of Refraction ]:
1.471

[ Storage condition ]:
−20°C

[ Stability ]:
Temperature Sensitive. This compound can rearrange to the 1,3-isomer in solution or during prolonged storage.

[ Water Solubility ]:
ethanol: 20 mg/mL

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves

[ Hazard Codes ]:
F+

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

Synthetic Route

Click to get detail synthetic route

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