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800815O

Avanti

16:0-18:1 DG

1-palmitoyl-2-oleoyl-sn-glycerol, neat oil

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:
29541-66-0
Molecular Weight:
594.95
UNSPSC Code:
12352211
NACRES:
NA.25

Assay

>99% (TLC)

form

liquid

packaging

pkg of 1 × 10 mg (with screw cap (800815O-10mg))
pkg of 2 × 100 mg (with screw cap 800815O-20)0mg)
pkg of 1 × 25 mg (with screw cap (800815O-25mg))

manufacturer/tradename

Avanti Research™ - A Croda Brand 800815O

lipid type

neutral lipids
neutral glycerides

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.

Application

16:0-18:1 DG may be used:
  • in the lipid vesicle preparation for protein kinase C (PKC) activity studies
  • in aqueous phospholipid dispersions for differential scanning calorimetry (DSC) analysis
  • in in vitro diacylglycerol kinase assay

Packaging

5 mL PTFE Vial with Screw Cap (800815O-10mg)
5 mL PTFE Vial with Screw Cap (800815O-200mg)
5 mL PTFE Vial with Screw Cap (800815O-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.
Effective concentration:
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 Code

10 - Combustible liquids

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

800815O-BULK:
800815O-200MG:
800815O-10MG:
800815O-VAR:
800815O-25MG:

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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The phase behavior of aqueous dispersions of unsaturated mixtures of diacylglycerols and phospholipids
Jimenez-Monreal AM, et al.
Biochimica et Biophysica Acta - Biomembranes, 1373(1), 209-219 (1998)
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)
Acyl chain dependence of diacylglycerol activation of protein kinase C activity in vitro
Marignani PA, et al.
Biochemical and Biophysical Research Communications, 225(2), 469-473 (1996)
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
Xinxing Zhang et al.
Journal of the American Chemical Society (2018-11-22)
Nature carefully designs the components of amphiphile-composed monolayer and bilayer membranes to deliver specific functions. The compositions of these interfacial layered structures are so delicate that minute modifications can result in huge changes in function. Great efforts have been expended
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