800800O

08:0 DG

1,2-dioctanoyl-sn-glycerol, neat oil

• Synonym(s): DG(8:0/8:0/0:0)
• Empirical Formula (Hill Notation): C₁₉H₃₆O₅
• CAS Number: 60514-48-9
• Molecular Weight: 344.49
• MDL number: MFCD00036835
• UNSPSC Code: 12352211
• NACRES: NA.25

Properties

• Assay: >99% (TLC)
• form: liquid
• packaging: pkg of 1 × 10 mg (with screw cap (800800O-10mg)); pkg of 1 × 25 mg (with screw cap (800800O-25mg))
• manufacturer/tradename: Avanti Research^™ - A Croda Brand 800800O
• lipid type: neutral lipids; neutral glycerides
• shipped in: dry ice
• storage temp.: −20°C
• SMILES string: O([C@H](COC(=O)CCCCCCC)CO)C(=O)CCCCCCC
• 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 referred as di-C8, is a short-chain[1] cell-permeable diacyl glycerol.[2]

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.[3][4][5][6]
Diacylglycerol mimicks the effects of the tumor-promoting compounds phorbol esters.

Application

08:0 DG may be used:

• to study its stimulatory effect on protein kinase C (PKC) in human cell lines[7]
• as a lipid cofactor in PKC activity assay[8]
• in vesicular-fusion protein Sec-18 binding studies[9]

Biochem/physiol Actions

08:0 DG (1,2-dioctanoyl-sn-glycerol) mimics endogenous diacylglycerol andis a active phorbol compund.[8] It activates protein kinase C (PKC).[1] It binds to the epidermal growth factor (EGF) receptor similar to 4β-phorbol 12β-myristate 13α-acetate (PMA). DiC8 elevates the phosphoserine and phosphothreonine levels.[2] DiC8 stimulates the release of superoxide in neutrophils.[10] It downregulates nicotinic acetylcholine receptor α1 subunit 1 (nAChR1).[2]

Packaging

5 mL PTFE Vial with Screw Cap (800800O-10mg)

5 mL PTFE Vial with Screw Cap (800800O-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

• Storage Class Code: 10 - Combustible liquids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable