810811P

18:1 DGPP

dioleoylglycerol pyrophosphate (ammonium salt), powder

• Synonym(s): 110744
• Empirical Formula (Hill Notation): C₃₉H₈₀N₂O₁₁P₂
• CAS Number: 474943-14-1
• Molecular Weight: 815.01
• UNSPSC Code: 12352211
• NACRES: NA.25

Properties

• Assay: >99% (TLC)
• form: powder
• packaging: pkg of 1 × 5 mg (810811P-5mg)
• manufacturer/tradename: Avanti Research^™ - A Croda Brand 810811P
• lipid type: bioactive lipids
• shipped in: dry ice
• storage temp.: −20°C
• SMILES string: [O-]P(OC[C@]([H])(OC(CCCCCCC/C=C\CCCCCCCC)=O)COC(CCCCCCC/C=C\CCCCCCCC)=O)(OP([O-])(O)=O)=O.[NH4+].[NH4+]
• InChI: 1S/C39H74O11P2.2H3N/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-38(40)47-35-37(36-48-52(45,46)50-51(42,43)44)49-39(41)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2;;/h17-20,37H,3-16,21-36H2,1-2H3,(H,45,46)(H2,42,43,44);2*1H3/b19-17-,20-18-;;/t37-;;/m1../s1
• InChI key: SIWIEYLZDXPRIY-AXQFFRRZSA-N

Description

General description

Diacylglycerol pyrophosphate (DGPP), involved in a novel signaling pathway, has been found in plants, Saccharomyces cerevisiae, and Escherichia coli and macrophage-activating factor, and suggests a potential role for this compound in triggering homeostatic cellular responses.Biological Applications: Short chain DGPP (DiC8) DiC8 DGPP is added to a test tube as a chloroform solution and the solvent is removed. Add water or buffer to the dry lipid residue followed by sonication. The solution is added to cells directly. The short chain DGPP is taken up by mammalian cells and by yeast. Long chain DGPP (DiC18:1) DiC18:1 DGPP is added to a test tube as a chloroform solution and the solvent is removed. Add 0.5% Tergitol (detergent) solution and add this to cells.Notes:Biological Application — "I am not sure how well the long chain DGPP is taken up in yeast cells, that is why we synthesized the DiC8 compound. We only use the long chain compound as a standard for TLC, HPLC and for DGPP phosphatase assays".Storage Conditions — "Store concentrated, ~25mg/ml in chloroform. Concentrations below 10mg/ml are not as stable".Personal communication, George M. Carman, Sept. 1999

Dioleoylglycerophosphate (DGPP) is mainly present in plants and yeast. It carries two phosphate groups in its headgroup. DGPP 18:1 (dioleoylglycerol pyrophosphate) has two oleyl chains and is a bioactive lipid.

Application

DGPP 18:1 (dioleoylglycerol pyrophosphate) may be used in biochemical assays to study its effects on transient receptor potential 1 (TRPV1) function. It may also be used in liposome binding studies.

Biochem/physiol Actions

Dioleoylglycerophosphate (DGPP) is capable of stimulating stress-related responses in plants. It may also play a role in abscisic acid (ABA) signaling.

Packaging

5 mL Clear Glass Sealed Ampule (810811P-5mg)

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): No data available
• Flash Point(C): No data available