860532P

C8 Ceramide-1-Phosphate (d18:1/8:0)

N-octanoyl-ceramide-1-phosphate (ammonium salt), powder

• Synonym(s): Ammonium (2S,3R,4E)-3-hydroxy-2-(octanoylamino)octadec-4-en-1-yl hydrogen phosphate
• Empirical Formula (Hill Notation): C₂₆H₅₅N₂O₆P
• CAS Number: 474943-70-9
• Molecular Weight: 522.70
• UNSPSC Code: 12352211
• NACRES: NA.25

Properties

• form: powder
• packaging: pkg of 1 × 1 mg (860532P-1mg)
• manufacturer/tradename: Avanti Research^™ - A Croda Brand 860532P
• lipid type: sphingolipids
• shipped in: dry ice
• storage temp.: −20°C
• SMILES string: [H][C@](/C=C/CCCCCCCCCCCCC)(O)[C@@]([H])(NC(CCCCCCC)=O)COP([O-])(O)=O.[NH4+]
• InChI: 1S/C26H52NO6P.H3N/c1-3-5-7-9-10-11-12-13-14-15-16-18-19-21-25(28)24(23-33-34(30,31)32)27-26(29)22-20-17-8-6-4-2;/h19,21,24-25,28H,3-18,20,22-23H2,1-2H3,(H,27,29)(H2,30,31,32);1H3/b21-19+;/t24-,25+;/m0./s1
• InChI key: WDZBNEWCUHJJDF-AAMXSQEYSA-N

Description

General description

C8 Ceramide-1-Phosphate (d18:1/8:0) or N-octanoyl-ceramide-1-phosphate is a synthetic short-chain ceramide.

Ceramide-1-phosphate is synthesized from ceramide by the phosphorylation reaction catalyzed by ceramide kinase (CerK).

Application

C8 Ceramide-1-Phosphate (d18:1/8:0) has been used as one of the authentic standards to validate selected metabolites in metabolomic study of vertebrate metamorphosis.

C8 Ceramide-1-Phosphate (d18:1/8:0) or N-octanoyl-ceramide-1-phosphate has been used:

• in lipid preparation to treat endothelial colony-forming cells (ECFCs) for nuclear morphology analysis
• for the validation of C8 ceramide-1-phosphate metabolite to study its effects on the metabolic pathways of Rana catesbeiana during metamorphosis
• to screen lipids that rapidly and reversibly alter transepithelial electrical resistance (TER) or tight junction (TJ) permeability in epithelial tissue

Biochem/physiol Actions

Ceramide-1-phosphate (C1P), as a lipid derived secondary messenger plays a vital role in various cellular processes such as inflammation, cell proliferation, differentiation and apoptosis. It is mitogenic for fibroblasts. C1P is also implicated in the modulation of macrophage chemotaxis. It promotes cell-survival by inhibiting the enzyme acid sphingomyelinase (SMase).

Packaging

5 mL Amber Glass Screw Cap Vial (860532P-1mg)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3