800800C

08:0 DG

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

• Synonym(s): DG(8:0/8:0/0:0)
• Empirical Formula (Hill Notation): C₁₉H₃₆O₅
• CAS Number: 60514-48-9
• Molecular Weight: 344.49
• UNSPSC Code: 12352211
• NACRES: NA.25

Properties

• 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

Description

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.

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Safety Information

• Pictograms: GHS06,GHS08
• Signal Word: Danger
• Hazard Statements: H302 - H315 - H319 - H331 - H336 - H351 - H361d - H372 - H412
• Precautionary Statements: P201 - P273 - P301 + P312 + P330 - P302 + P352 - P304 + P340 + P311 - P308 + P313
• 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