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800818C

Avanti

18:0-20:4 DG

1-stearoyl-2-arachidonoyl-sn-glycerol, chloroform

Synonym(s):

1-octadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycerol; DG(18:0/18:2(9Z,12Z)/0:0)

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About This Item

Empirical Formula (Hill Notation):
C41H72O5
CAS Number:
65914-84-3
Molecular Weight:
645.01
UNSPSC Code:
12352211
NACRES:
NA.25

Assay

>99% (TLC)

form

liquid

packaging

pkg of 1 × 5 mL (800818C-10mg)

manufacturer/tradename

Avanti Research™ - A Croda Brand 800818C

concentration

2 mg/mL (800818C-10mg)

lipid type

neutral lipids
neutral glycerides

shipped in

dry ice

storage temp.

−20°C

InChI

1S/C41H72O5/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-36-41(44)46-39(37-42)38-45-40(43)35-33-31-29-27-25-23-21-18-16-14-12-10-8-6-4-2/h11,13,17,19,22,24,28,30,39,42H,3-10,12,14-16,18,20-21,23,25-27,29,31-38H2,1-2H3/b13-11-,19-17-,24-22-,30-28-/t39-/m0/s1

InChI key

NSXLMTYRMFVYNT-IUJDHQGTSA-N

General description

18:0-20:4 DG or 1-stearoyl-2-arachidonoyl-sn-glycerol is a diglyceride. Diglycerides contain two fatty acids linked to the glycerol backbone with an ester bond.

Application

18:0-20:4 DG or 1-stearoyl-2-arachidonoyl-sn-glycerol has been used to study its effect on conventional protein kinase C (cPKC) and novel protein kinase C (nPKC) isozymes in vitro. It has also been used as a substrate for the measurement of diacylglycerol kinase δ (DGK#948;) and DGKη1 activity in vitro.

Biochem/physiol Actions

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.

Packaging

30 mL Amber Narrow Mouth Glass Bottle with Screw Cap (800818C-10mg)

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

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

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

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.

PRTR

Class I Designated Chemical Substances

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

800818C-VAR:
800818C-BULK:
800818C-10MG:

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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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)
Mathias Haag et al.
Metabolites, 2(1), 57-76 (2012-01-01)
Lipids, such as phosphoinositides (PIPs) and diacylglycerol (DAG), are important signaling intermediates involved in cellular processes such as T cell receptor (TCR)-mediated signal transduction. Here we report identification and quantification of PIP, PIP2 and DAG from crude lipid extracts. Capitalizing
J G Ebeling et al.
Proceedings of the National Academy of Sciences of the United States of America, 82(3), 815-819 (1985-02-01)
Activation of cellular protein kinase C appears to be involved in the mechanism by which phorbol diesters induce differentiation of human myeloid leukemia cells (HL-60). Protein kinase C is thought to be physiologically activated by diacylglycerol derived from receptor-mediated phosphatidylinositol
R J Davis et al.
The Journal of biological chemistry, 260(3), 1562-1566 (1985-02-10)
The cell-permeable diacylglycerol, sn-1,2-dioctanoylglycerol (DiC8), is shown to mimic the effect of tumor promoting phorbol diesters on epidermal growth factor (EGF) binding and action in intact cells. DiC8 inhibited the binding of [3H]phorbol dibutyrate to A431 cell monolayers indicating that
E G Lapetina et al.
The Journal of biological chemistry, 260(3), 1358-1361 (1985-02-10)
The ability of exogenous sn-1,2-diacylglycerols and analogs to function as bioregulators of protein kinase C in human platelets was investigated. The activation of protein kinase C in platelets is indicated by specific phosphorylation of a 40,000-dalton protein. Dihexanoylglycerol, dioctanoylglycerol (diC8)
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