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About This Item
Empirical Formula (Hill Notation):
C23H42O5
CAS Number:
Molecular Weight:
398.58
MDL number:
UNSPSC Code:
12352211
NACRES:
NA.25
Product Name
18:1-2:0 DG, 1-oleoyl-2-acetyl-sn-glycerol, chloroform
SMILES string
O([C@H](COC(=O)CCCCCCC\C=C/CCCCCCCC)CO)C(=O)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
assay
>99% (TLC)
form
liquid
packaging
pkg of 1 × 5 mL (800100C-10mg)
pkg of 1 × 5 mL (800100C-25mg)
manufacturer/tradename
Avanti Research™ - A Croda Brand 800100C
concentration
2 mg/mL (800100C-10mg)
5 mg/mL (800100C-25mg)
lipid type
neutral lipids
neutral glycerides
shipped in
dry ice
storage temp.
−20°C
Application
18:1-2:0 DG (1-oleoyl-2-acetyl-sn-glycerol) has been used as a diacyl glycerol (DAG) analog to test its impact on DAG-sensitive channels in thalamocortical (TC) neurons. It may be used as an internal standard for retention time calibration in ultra-high performance liquid chromatography-quadrupole time-of-flight mass spectrometry (UPLC-QTOF MS) for blood sample lipid quantification. It may also be used as a protein kinase C (PKC) activator in adrenal glands.
Biochem/physiol Actions
1-oleoyl-2-acetyl-sn-glycerol (OAG) has ability to activate protein kinase C (PKC) . 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). It also inhibits mitochondrial permeability transition pore (MPTP) formation and prevents fatty acid release and necrosis in lung fibroblasts.
General description
18:1-2:0 DG, also called 1-oleoyl-2-acetyl-sn-glycerol (OADG), is a synthetic analog of diacyl glycerol (DAG) and is membrane permeable.
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.
Packaging
30 mL Amber Narrow Mouth Glass Bottle with Screw Cap (800100C-10mg)
30 mL Amber Narrow Mouth Glass Bottle with Screw Cap (800100C-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.
Legal Information
Avanti Research is a trademark of Avanti Polar Lipids, LLC
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
Regulatory Information
易制毒化学品（2类）
危险化学品
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Specificity and Mechanism of Protein Kinase C Activation by sn-1,2-diacylglycerols.
Ganong, B.R, et. al.
Proceedings of the National Academy of Sciences of the USA, 83, 1184-1188 (1986)
Exogenous sn-1,2-diacylglycerols Containing Saturated Fatty Acids Functions as Bioregulators of Protein Kinase C in Human Platelets.
Lapetina, E.G, et. al.
The Journal of Biological Chemistry, 260, 1358-1361 (1985)
sn-1,2-dioctanoylglycerol: a Cell Permeable Diacylglycerol That Mimics Phorbol Diester Action on the Epidermal Growth Factor Receptor and Mitogenesis
Davis, R.J, et.al.
The Journal of Biological Chemistry, 260, 1562-1566 (1985)
Diacylglycerols and Phorbol Diesters Induce Leukemic Cell Differentiation via a Common Mechanism.
Ebeling, J.G, 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.
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