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About This Item
Empirical Formula (Hill Notation):
C23H44O5
CAS Number:
Molecular Weight:
400.59
MDL number:
UNSPSC Code:
12352211
NACRES:
NA.25
Product Name
10:0 DG, 1,2-didecanoyl-sn-glycerol, powder
SMILES string
O([C@H](COC(=O)CCCCCCCCC)CO)C(=O)CCCCCCCCC
InChI
1S/C23H44O5/c1-3-5-7-9-11-13-15-17-22(25)27-20-21(19-24)28-23(26)18-16-14-12-10-8-6-4-2/h21,24H,3-20H2,1-2H3/t21-/m0/s1
InChI key
GNSDEDOVXZDMKM-NRFANRHFSA-N
assay
>99% (TLC)
form
powder
packaging
pkg of 1 × 10 mg (with screw cap (800810P-10mg))
manufacturer/tradename
Avanti Research™ - A Croda Brand 800810P
lipid type
neutral lipids
neutral glycerides
shipped in
dry ice
storage temp.
−20°C
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General description
10:0 DG (DDG), also called 1,2-didecanoyl-sn-glycerol, is a substrate for human pancreatic lipase (HPL).
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.
Application
10:0 DG may be used in the diacylglycerol kinase (DGK) activity in DDT1-MF2 cells and in glomerulus homogenate from diabetic rats. It may be also used in monolayers as substrate for human pancreatic lipase (HPL).
Packaging
5 mL PTFE Vial with Screw Cap (800810P-10mg)
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
Storage Class
11 - Combustible Solids
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Chitosan does not inhibit enzymatic action of human pancreatic lipase in Langmuir monolayers of 1, 2-didecanoyl-glycerol (DDG)
Souza AL, et al.
Colloids and Surfaces, B: Biointerfaces, 123, 870-877 (2014)
Importance of chroman ring and tyrosine phosphorylation in the subtype-specific translocation and activation of diacylglycerol kinase alpha by d-alpha-tocopherol
Fukunaga-Takenaka R, et al.
Genes Cells, 10(4), 311-319 (2005)
Effects of vitamin E and its derivatives on diabetic nephropathy in Rats and identification of diacylglycerol kinase subtype involved in the improvement of diabetic nephropathy
Kakehi T, et al.
Functional Foods in Health and Disease, 7(10), 816-832 (2017)
B R Ganong et al.
Proceedings of the National Academy of Sciences of the United States of America, 83(5), 1184-1188 (1986-03-01)
The specificity of protein kinase C activation by sn-1,2-diacylglycerols and analogues was investigated by using a Triton X-100 mixed micellar assay [Hannun, Y. A., Loomis, C. R. & Bell, R. M. (1985) J. Biol. Chem. 260, 10039-10043]. Analogues containing acyl
Specificity and Mechanism of Protein Kinase C Activation by sn-1,2-diacylglycerols.
Ganong BR, et al.
Proceedings of the National Academy of Sciences of the USA, 83, 1184-1188 (1986)
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