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Merck

860539P

Avanti

C16 Glucosyl(β) Ceramide (d18:1/16:0)

Avanti Research - A Croda Brand

Sinónimos:

D-glucosyl-β-1,1′-N-palmitoyl-D-erythro-sphingosine

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About This Item

Fórmula empírica (notación de Hill):
C40H77NO8
Número de CAS:
Peso molecular:
700.04
UNSPSC Code:
12352211
NACRES:
NA.25

form

powder

packaging

pkg of 1 × 25 mg (860539P-25mg)
pkg of 1 × 5 mg (860539P-5mg)

manufacturer/tradename

Avanti Research - A Croda Brand

lipid type

sphingolipids

shipped in

dry ice

storage temp.

−20°C

SMILES string

[H][C@](/C=C/CCCCCCCCCCCCC)(O)[C@@]([H])(NC(CCCCCCCCCCCCCCC)=O)CO[C@H](O1)[C@H](O)[C@@H](O)[C@@H]([C@H]1CO)O

General description

Glucosyl(β) Ceramide (β-GlcCer) is a naturally occurring glycolipid and an ubiquitous intracellular metabolite. It might be present in the endoplasmic reticulum or Golgi apparatus.

Application

C16 Glucosyl(β) Ceramide (d18:1/16:0) or D-glucosyl-β-1,1′-N-palmitoyl-D-erythro-sphingosine has been used as a stock solution for the in vitro treatment of bacteria and to study the role of sphingolipids on pulmonary Pseudomonas aeruginosa infections in cystic fibrosis (CF). It may be used in the quantification of lipid in green fluorescence protein (GFP) and fatty acid transport protein 4 (FATP4) cells using electrospray ionization tandem mass spectrometry (ESI-MS/MS).

Biochem/physiol Actions

Glucosyl(β) Ceramide (β-GlcCer) is an endogenous macrophage inducible C-type lectin (Mincle) ligand, which has immunostimulatory property. It also stimulates inflammatory and acquired immune responses on myeloid cells through Mincle. It is a potential biomarker in Gaucher′s disease. β-GlcCer regulates the function of natural killer T (NKT) lymphocytes and exhibits antimetastatic effects. A balanced level of intracellular β-GlcCer is essential for maintaining tissue homeostasis.

Packaging

5 mL Amber Glass Screw Cap Vial (860539P-25mg)
5 mL Amber Glass Screw Cap Vial (860539P-5mg)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

also commonly purchased with this product

Storage Class

11 - Combustible Solids


Certificados de análisis (COA)

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Marko Jović et al.
Molecular biology of the cell, 23(8), 1533-1545 (2012-02-18)
Gaucher disease is a lysosomal storage disorder caused by a defect in the degradation of glucosylceramide catalyzed by the lysosomal enzyme β-glucocerebrosidase (GBA). GBA reaches lysosomes via association with its receptor, lysosomal integral membrane protein type 2 (LIMP-2). We found
Masashi Inafuku et al.
Lipids, 47(6), 581-591 (2012-03-20)
Natural killer (NK) T cells are well known to play important roles in both tumor rejection and the defense against infectious. Therefore, the antitumor potential of NKT cell-activating antigens have been the focus for the development of NKT cell-based immunotherapies.
Masahiro Nagata et al.
Proceedings of the National Academy of Sciences of the United States of America, 114(16), E3285-E3294 (2017-04-05)
Sensing and reacting to tissue damage is a fundamental function of immune systems. Macrophage inducible C-type lectin (Mincle) is an activating C-type lectin receptor that senses damaged cells. Notably, Mincle also recognizes glycolipid ligands on pathogens. To elucidate endogenous glycolipids
E Zigmond et al.
Gut, 56(1), 82-89 (2006-12-19)
beta-Glucosylceramide, a naturally occurring glycolipid, exerts modulatory effects on natural killer T (NKT) lymphocytes. To determine whether beta-glucosylceramide can alter NKT function in opposite directions, colitis was induced by intracolonic installation of trinitrobenzenesulphonic acid, and hepatocellular carcinoma (HCC) was induced
Barbara Kovacic et al.
Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology, 41(3), 1208-1218 (2017-04-21)
Cystic fibrosis (CF) is the most common autosomal-recessive disorder in western countries. Previous studies have demonstrated an important role of sphingolipids in the pathophysiology of cystic fibrosis. It has been shown that ceramide has a central role in various pulmonary

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