800100O
Avanti
18:1-2:0 DG
1-oleoyl-2-acetyl-sn-glycerol, neat oil
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Synonym(s):
1--(9Z-octadecenoyl)-2-acetoyl-sn-glycerol; DG(18:1(9Z)/2:0/0:0); OAG
Empirical Formula (Hill Notation):
C23H42O5
Recommended Products
Assay
>99% (TLC)
form
liquid
packaging
pkg of 1 × 10 mg (with screw cap (800100O-10mg))
pkg of 1 × 25 mg (with screw cap (800100O-25mg))
manufacturer/tradename
Avanti Polar Lipids 800100O
lipid type
neutral glycerides
neutral lipids
shipped in
dry ice
storage temp.
−20°C
InChI
1S/C23H42O5/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-23(26)27-20-22(19-24)28-21(2)25/h10-11,22,24H,3-9,12-20H2,1-2H3/b11-10-/t22-/m0/s1
InChI key
PWTCCMJTPHCGMS-YRBAHSOBSA-N
General description
18:1-2:0 DG, also called 1-oleoyl-2-acetyl-sn-glycerol (OADG), is a membrane permeable and synthetic analog of diacyl glycerol (DAG).
Application
18:1-2:0 DG (1-oleoyl-2-acetyl-sn-glycerol) may be used:
- in the induction of superoxide generation in neutrophils
- as a substrate for platelet-activating factor acetyl hydrolases
- as a protein kinase C (PKC) activator in adrenal glands
Biochem/physiol Actions
18:1-2:0 DG (OAG) halts the inhibition of glucose uptake by the phospholipase C (PLC) inhibitor, U73122. It also inhibits mitochondrial permeability transition pore (MPTP) formation and prevents fatty acid release and necrosis in lung fibroblasts. OAG is a protein kinase C (PKC) activator. It also inhibits TWIK-related acid-sensitive (TASK)-like potassium channels in peripheral arterial chemoreceptors. OAG stimulates 5-lipooxygenase (5-LO) in human polymorphonuclear leukocytes (PMNL).
Packaging
5 mL PTFE Vial with Screw Cap (800100O-10mg)
5 mL PTFE Vial with Screw Cap (800100O-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.
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
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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sn-1,2-dioctanoylglycerol: a Cell Permeable Diacylglycerol That Mimics Phorbol Diester Action on the Epidermal Growth Factor Receptor and Mitogenesis.
Davis RJ, et al.
The Journal of Biological Chemistry, 260, 1562-1566 (1985)
J H Min et al.
Biochemistry, 38(39), 12935-12942 (1999-10-03)
Human plasma platelet activating factor acetylhydrolase (pPAF-AH) is a phospholipase A(2) that specifically hydrolyzes the sn-2 ester of platelet activating factor (PAF) and of phospholipids with oxidatively truncated sn-2 fatty acyl chains. pPAF-AH is bound to lipoproteins in vivo, and
Diacylglycerols and Phorbol Diesters Induce Leukemic Cell Differentiation via a Common Mechanism.
Ebeling JG, et al.
Proceedings of the National Academy of Sciences of the USA, 82, 815-819 (1985)
Insulin activates phospholipase C-gamma1 via a PI-3 kinase dependent mechanism in 3T3-L1 adipocytes.
J Eichhorn et al.
Biochemical and biophysical research communications, 282(2), 615-620 (2001-06-13)
Previously we have shown that the insulin receptor and phospholipase C-gamma1 physically interact in the 3T3-L1 adipocyte cell line. In this study, we investigated the ability of insulin and PDGF to stimulate PLC-gamma1 enzyme activity as measured by PI-(4,5)P(2) hydrolysis.
Christina Hörnig et al.
The Journal of biological chemistry, 280(29), 26913-26921 (2005-06-01)
5-Lipoxygenase (5-LO) catalysis is positively regulated by Ca2+ ions and phospholipids that both act via the N-terminal C2-like domain of 5-LO. Previously, we have shown that 1-oleoyl-2-acetylglycerol (OAG) functions as an agonist for human polymorphonuclear leukocytes (PMNL) in stimulating 5-LO
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