800815C
Avanti
16:0-18:1 DG
1-palmitoyl-2-oleoyl-sn-glycerol, chloroform
Synonym(s):
1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycerol; DG(16:0/18:1(9Z)/0:0)
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About This Item
Empirical Formula (Hill Notation):
C37H70O5
CAS Number:
Molecular Weight:
594.95
UNSPSC Code:
12352211
NACRES:
NA.25
Recommended Products
Assay
>99% (TLC)
form
liquid
packaging
pkg of 1 × 5 mL (800815C-10mg)
pkg of 1 × 5 mL (800815C-25mg)
pkg of 1 × 8 mL (800815C-200mg)
manufacturer/tradename
Avanti Research™ - A Croda Brand 800815C
concentration
2 mg/mL (800815C-10mg)
25 mg/mL (800815C-200mg)
5 mg/mL (800815C-25mg)
lipid type
neutral glycerides
neutral lipids
shipped in
dry ice
storage temp.
−20°C
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.
Application
16:0-18:1 DG has been used to spike brain samples for mass spectrometric analysis. It may be used as benchmark dataset lipid in collision induced dissociation tandem mass spectrometry (CID-MS/MS) experiments and in in vitro diacylglycerol kinase assay.
Packaging
30 mL Amber Narrow Mouth Glass Bottle with Screw Cap (800815C-10mg)
30 mL Amber Narrow Mouth Glass Bottle with Screw Cap (800815C-200mg)
30 mL Amber Narrow Mouth Glass Bottle with Screw Cap (800815C-25mg)
Storage and Stability
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
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Acute Tox. 3 Inhalation - Acute Tox. 4 Oral - Aquatic Chronic 3 - Carc. 2 - Eye Irrit. 2 - Repr. 2 - Skin Irrit. 2 - STOT RE 1 - STOT SE 3
Target Organs
Central nervous system, Liver,Kidney
WGK
WGK 3
Certificates of Analysis (COA)
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CD1a-autoreactive T cells recognize natural skin oils that function as headless antigens
De Jong A, et al.
Nature Immunology, 15(2), 177-177 (2014)
Diacylglycerol kinase delta and sphingomyelin synthase-related protein functionally interact via their sterile alpha motif domains
Murakami C, et al.
The Journal of Biological Chemistry, 295(10), 2932-2947 (2020)
Quantification of signaling lipids by nano-electrospray ionization tandem mass spectrometry (Nano-ESI MS/MS)
Haag M, et al.
Metabolites, 2(1), 57-76 (2012)
Chiaki Murakami et al.
The Journal of biological chemistry, 295(10), 2932-2947 (2020-01-26)
The δ isozyme of diacylglycerol kinase (DGKδ) plays critical roles in lipid signaling by converting diacylglycerol (DG) to phosphatidic acid (PA). We previously demonstrated that DGKδ preferably phosphorylates palmitic acid (16:0)- and/or palmitoleic acid (16:1)-containing DG molecular species, but not
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
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