800800C
Avanti
08:0 DG
1,2-dioctanoyl-sn-glycerol, chloroform solution
Synonym(s):
DG(8:0/8:0/0:0)
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About This Item
Empirical Formula (Hill Notation):
C19H36O5
CAS Number:
Molecular Weight:
344.49
UNSPSC Code:
12352211
NACRES:
NA.25
Recommended Products
Assay
>99% (TLC)
form
liquid
packaging
pkg of 1 × 5 mL (800800C-10mg)
pkg of 1 × 5 mL (800800C-25mg)
manufacturer/tradename
Avanti Research™ - A Croda Brand 800800C
concentration
2 mg/mL (800800C-10mg)
5 mg/mL (800800C-25mg)
lipid type
neutral lipids
neutral glycerides
shipped in
dry ice
storage temp.
−20°C
InChI
1S/C19H36O5/c1-3-5-7-9-11-13-18(21)23-16-17(15-20)24-19(22)14-12-10-8-6-4-2/h17,20H,3-16H2,1-2H3/t17-/m0/s1
InChI key
ZQBULZYTDGUSSK-KRWDZBQOSA-N
General description
08:0 DG (1,2-dioctanoyl-sn-glycerol), also called as di-C8, is a cell-permeable and a short-chain diacyl glycerol.
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.
Diacylglycerol mimicks the effects of the tumor-promoting compounds phorbol esters.
Application
08:0 DG may be used as a component of phosphatidylinositol 3-phosphate (PI3P) liposomes for vacuolar morphogenesis protein 7 (Vam7-6A) binding studies. It has been used in T-cell lymphoma invasion and metastasis–inducing protein 1 (TIAM1) transfection studies.
Biochem/physiol Actions
08:0 DG (1,2-dioctanoyl-sn-glycerol) binds to the epidermal growth factor (EGF) receptor similar to 4β-phorbol 12β-myristate 13α-acetate (PMA). It also elevates the phosphoserine and phosphothreonine levels. DAG DiC8 activates protein kinase C (PKC). DiC8 stimulates the release of superoxide in neutrophils. It also inhibits the nicotine and clothianidin induced currents in neurosecretory cells and downregulates nicotinic acetylcholine receptor α1 subunit 1 (nAChR1).
Packaging
30 mL Amber Narrow Mouth Glass Bottle with Screw Cap (800800C-10mg)
30 mL Amber Narrow Mouth Glass Bottle with Screw Cap (800800C-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.
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.
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
Signal Word
Danger
Hazard Statements
Precautionary Statements
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
Certificates of Analysis (COA)
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Find documentation for the products that you have recently purchased in the Document Library.
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)
The Central Polybasic Region of the Soluble SNARE Vam7 Affects Binding to Phosphatidylinositol 3-phosphate by the PX domain
Miner GE, et al.
Test, jbc-M116 (2016)
Phosphatidic acid is required for the constitutive ruffling and macropinocytosis of phagocytes
Bohdanowicz M, et al.
Molecular Biology of the Cell, 24(11), 1700-1712 (2013)
The Central Polybasic Region of the Soluble SNARE Vam7 Affects Binding to Phosphatidylinositol 3-phosphate by the PX domain
Miner GE, et al.
The Journal of Biological Chemistry, jbc-M116 (2016)
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(3), 1562-1566 (1985)
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