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Key Documents

800817C

Avanti

18:0-18:2 DG

1-stearoyl-2-linoleoyl-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):
C39H72O5
CAS Number:
34487-26-8
Molecular Weight:
620.99
UNSPSC Code:
12352211
NACRES:
NA.25

Assay

>99% (TLC)

form

liquid

packaging

pkg of 1 × 5 mL (800817C-10mg)

manufacturer/tradename

Avanti Polar Lipids 800817C

concentration

2 mg/mL (800817C-10mg)

lipid type

neutral lipids
neutral glycerides

shipped in

dry ice

storage temp.

−20°C

InChI

1S/C39H72O5/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-38(41)43-36-37(35-40)44-39(42)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h12,14,18,20,37,40H,3-11,13,15-17,19,21-36H2,1-2H3/b14-12-,20-18-/t37-/m0/s1

InChI key

AJMZUFBKADIAKC-SKTOPKGQSA-N

General description

18:0-18:2 DG (diacylglycerol) is a second messenger signaling lipid in biochemical signaling 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). It possess hydrophobic properties due to which it remains within the plasma membrane.

Biochem/physiol Actions

DAG plays a vital role in the physiological activation 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 (800817C-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

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

does not flash

Flash Point(C)

does not flash

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)
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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