800814P

14:0 DG

1,2-dimyristoyl-sn-glycerol, powder

• Synonym(s): 1,2-ditetradecanoyl-sn-glycerol; DG(14:0/14:0/0:0)
• Empirical Formula (Hill Notation): C₃₁H₆₀O₅
• CAS Number: 60562-16-5
• Molecular Weight: 512.81
• MDL number: MFCD00048454
• UNSPSC Code: 12352211
• NACRES: NA.25

Properties

• Assay: >99% (TLC)
• form: powder
• packaging: pkg of 1 × 10 mg (800814P-10mg); pkg of 1 × 25 mg (800814P-25mg)
• manufacturer/tradename: Avanti Research^™ - A Croda Brand 800814P
• lipid type: neutral glycerides; neutral lipids
• shipped in: dry ice
• storage temp.: −20°C
• SMILES string: O([C@H](COC(=O)CCCCCCCCCCCCC)CO)C(=O)CCCCCCCCCCCCC
• InChI: 1S/C31H60O5/c1-3-5-7-9-11-13-15-17-19-21-23-25-30(33)35-28-29(27-32)36-31(34)26-24-22-20-18-16-14-12-10-8-6-4-2/h29,32H,3-28H2,1-2H3/t29-/m0/s1
• InChI key: JFBCSFJKETUREV-LJAQVGFWSA-N

Description

General description

1,2-dimyristoyl-sn-glycerol (14:0 DG) with small polar headgroup and two fatty acid, is an E coli membrane lipid.[1]

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.[2][3][4][5]
Diacylglycerol mimicks the effects of the tumor-promoting compounds phorbol esters.

Application

14:0 DG may be used:

• in the reconstitution of dry lipids for thin layer chromatography[6]
• in lipid nanoparticles for RNA delivery studies[7]
• as a standard in gas chromatography–mass spectrometry (GC-MS) analysis for the quantification of lipid A diacylglycerols[8]

Biochem/physiol Actions

Diacylglycerol (DAG) displays a flip-flop motion. This movement of DAG is inhibited by membrane protein integrase (mini-MPIase-3).It also forms nonlamellar phase.[1]

Packaging

5 mL Amber Glass Screw Cap Vial (800814P-10mg)

5 mL Amber Glass Screw Cap Vial (800814P-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: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable