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Merck

860532P

Avanti

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

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

Sinónimos:

Ammonium (2S,3R,4E)-3-hydroxy-2-(octanoylamino)octadec-4-en-1-yl hydrogen phosphate

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About This Item

Fórmula empírica (notación de Hill):
C26H55N2O6P
Número de CAS:
Peso molecular:
522.70
Código UNSPSC:
12352211
NACRES:
NA.25

formulario

powder

envase

pkg of 1 × 1 mg (860532P-1mg)

fabricante / nombre comercial

Avanti Research - A Croda Brand 860532P

tipo de lípido

sphingolipids

Condiciones de envío

dry ice

temp. de almacenamiento

−20°C

cadena SMILES

[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

Clave InChI

WDZBNEWCUHJJDF-AAMXSQEYSA-N

Categorías relacionadas

Descripción general

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).

Aplicación

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

Acciones bioquímicas o fisiológicas

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).

Envase

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

Información legal

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3


Certificados de análisis (COA)

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Visite la Librería de documentos

Ceramide-1-phosphate in cell survival and inflammatory signaling
Gomez-Munoz, A, et al.
Sphingolipids as Signaling and Regulatory Molecules, 118-130 (2010)
Metabolomic insights into system-wide coordination of vertebrate metamorphosis
Ichu T, et al.
BMC Developmental Biology, 14(1), 5-5 (2014)
Hebe Agustina Mena et al.
Arteriosclerosis, thrombosis, and vascular biology, 39(10), e219-e232 (2019-08-23)
Ceramide 1-phosphate (C1P) is a bioactive sphingolipid highly augmented in damaged tissues. Because of its abilities to stimulate migration of murine bone marrow-derived progenitor cells, it has been suggested that C1P might be involved in tissue regeneration. In the present
Ceramide and ceramide 1-phosphate in health and disease
Arana L, et al.
Lipids in Health and Disease, 9(1), 15-15 (2010)
V T Hinkovska-Galcheva et al.
The Journal of biological chemistry, 273(50), 33203-33209 (1998-12-05)
Ceramide, a product of agonist-stimulated sphingomyelinase activation, is known to be generated during the phagocytosis of antibody-coated erythrocytes by polymorphonuclear leukocytes. Agonist-stimulated formation of ceramide-1-phosphate is now shown to occur in 32PO4-labeled neutrophils. Ceramide-1-phosphate is formed by a calcium-dependent ceramide

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