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About This Item
Empirical Formula (Hill Notation):
C19H36O5
CAS Number:
Molecular Weight:
344.49
MDL number:
UNSPSC Code:
12352211
NACRES:
NA.25
Product Name
08:0 DG, Avanti Research™ - A Croda Brand
description
1,2-dioctanoyl-sn-glycerol, neat oil
assay
>99% (TLC)
form
oil
packaging
pkg of 1 × 10 mg (with screw cap (800800O-10mg)), pkg of 1 × 25 mg (with screw cap (800800O-25mg))
manufacturer/tradename
Avanti Research™ - A Croda Brand
lipid type
neutral lipids
neutral glycerides
shipped in
dry ice
storage temp.
−20°C
SMILES string
O([C@H](COC(=O)CCCCCCC)CO)C(=O)CCCCCCC
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
InChI key
ZQBULZYTDGUSSK-KRWDZBQOSA-N
General description
In biochemical signaling, diacylglycerol (DAG) functions as a second messenger signaling lipid, and is a product of the hydrolysis of the phospholipid PIP2 (phosphatidylinositolbisphosphate) by the enzyme phospholipase C (PLC) (a membrane-bound enzyme) that, through the same reaction, produces inositol trisphosphate (IP3). Although inositol trisphosphate (IP3) diffuses into the cytosol, DAG remains within the plasma membrane due to its hydrophobic properties. IP3 stimulates the release of calcium ions from the smooth endoplasmic reticulum, whereas DAG is a physiological activator of protein kinase C (PKC). The production of DAG in the membrane facilitates translocation of PKC from the cytosol to the plasma membrane.
Diacylglycerol mimicks the effects of the tumor-promoting compounds phorbol esters.
Diacylglycerol mimicks the effects of the tumor-promoting compounds phorbol esters.
08:0 DG (1,2-dioctanoyl-sn-glycerol), also referred as di-C8, is a short-chain cell-permeable diacyl glycerol.
Application
08:0 DG may be used:
- to study its stimulatory effect on protein kinase C (PKC) in human cell lines
- as a lipid cofactor in PKC activity assay
- in vesicular-fusion protein Sec-18 binding studies
Biochem/physiol Actions
08:0 DG (1,2-dioctanoyl-sn-glycerol) mimics endogenous diacylglycerol andis a active phorbol compund. It activates protein kinase C (PKC). It binds to the epidermal growth factor (EGF) receptor similar to 4β-phorbol 12β-myristate 13α-acetate (PMA). DiC8 elevates the phosphoserine and phosphothreonine levels. DiC8 stimulates the release of superoxide in neutrophils. It downregulates nicotinic acetylcholine receptor α1 subunit 1 (nAChR1).
Packaging
5 mL PTFE Vial with Screw Cap (800800O-10mg)
5 mL PTFE Vial with Screw Cap (800800O-25mg)
Preparation Note
Diacylglycerols are conveniently stored in chloroform solutions in glass vials with PTFE-lined caps at -20°C. Under these conditions acyl migration is minimal. Avoid plastic when handling chloroform solutions.
Other Notes
Delivery to cells:
Dry samples of diacylglycerol in chloroform, using a stream of nitrogen. Dissolve the residue in an appropriate volume of ethanol or DMSO, then dilute to the desired aqueous medium.
Dry samples of diacylglycerol in chloroform, using a stream of nitrogen. Dissolve the residue in an appropriate volume of ethanol or DMSO, then dilute to the desired aqueous medium.
Effective concentration:
Most biological responses saturate at 20 to 250 μM sn-1,2-dioctanoylglycerol. Only sn-1,2 isomers appear to be active.
Most biological responses saturate at 20 to 250 μM sn-1,2-dioctanoylglycerol. Only sn-1,2 isomers appear to be active.
Precaution: Since short chain Diacylglycerols mimic effects of the tumor-promoting phorbol diesters in a number of biological systems, extra care should be employed in their handling. Treatment of solutions, vessels and other articles with 1N NaOH before washing or discarding will destroy diacylglycerols.
Legal Information
Avanti Research is a trademark of Avanti Polar Lipids, LLC
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Storage Class
10 - Combustible liquids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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Rottlerin is a mitochondrial uncoupler that decreases cellular ATP
Soltoff SP
Test, 276(41), 37986-37992 (1986)
Regulation of human monocyte surface antigen expression. I. Up-modulation of Mo3e antigen expression on U-937 and HL-60 cells stimulated by pharmacologic activators of protein kinase C
Todd RF, et al.
Blood, 68(5), 1154-1161 (1986)
Protein Kinase Calpha (PKCalpha) Is Resistant to Long Term Desensitization/Down-regulation by Prolonged Diacylglycerol Stimulation
Lum MA, et al.
The Journal of biological chemistry, 291(12), 6331-6346 (2016)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 800800O-10MG | 04061835533756 |
| 800800O-25MG | 04061835533763 |