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800800C

Avanti

08:0 DG

1,2-dioctanoyl-sn-glycerol, chloroform solution

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Synonym(s):
DG(8:0/8:0/0:0)
Empirical Formula (Hill Notation):
C19H36O5
CAS Number:
Molecular Weight:
344.49
NACRES:
NA.25

Assay

>99% (TLC)

form

liquid

packaging

pkg of 1 × 5 mL (800800C-10mg)
pkg of 1 × 5 mL (800800C-25mg)

manufacturer/tradename

Avanti Polar Lipids 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.

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.
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.

Pictograms

Skull and crossbonesHealth hazard

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

Regulatory Information

危险化学品
易制毒化学品(2类)

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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)
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)
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)

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