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经验公式（希尔记法）:
C39H72O5
化学文摘社编号:
分子量:
620.99
MDL number:
UNSPSC Code:
12352211
NACRES:
NA.25
产品名称
18:0-18:2 DG, 1-stearoyl-2-linoleoyl-sn-glycerol, chloroform
SMILES string
O([C@H](COC(=O)CCCCCCCCCCCCCCCCC)CO)C(=O)CCCCCCC\C=C/C\C=C/CCCCC
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
assay
>99% (TLC)
form
liquid
packaging
pkg of 1 × 5 mL (800817C-10mg)
manufacturer/tradename
Avanti Research™ - A Croda Brand 800817C
concentration
2 mg/mL (800817C-10mg)
lipid type
neutral lipids
neutral glycerides
shipped in
dry ice
storage temp.
−20°C
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
Other Notes
Effective concentration:
Most biological responses saturate at 20 to 250 μM sn-1,2-dioctanoylglycerol. Only sn-1,2 isomers appear to be active.
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.
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.
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.
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.
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.
Packaging
30 mL Amber Narrow Mouth Glass Bottle with Screw Cap (800817C-10mg)
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
法规信息
易制毒化学品（2类）
危险化学品
此项目有
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
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)
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)
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
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