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Merck

800815C

Avanti

16:0-18:1 DG

Avanti Research™ - A Croda Brand

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
MDL number:
MFCD00166985
NACRES:
NA.25
UNSPSC Code:
12352211

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Product Name

16:0-18:1 DG, 1-palmitoyl-2-oleoyl-sn-glycerol, chloroform

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

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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 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)

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.
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

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

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

Storage Class

6.1D - Non-combustible acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects

flash_point_f

does not flash

flash_point_c

does not flash

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.

67-66-3

CAS No.

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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
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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