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860521P

Avanti

C16 Galactosyl(β) Ceramide (d18:1/16:0)

Avanti Research™ - A Croda Brand 860521P, powder

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C40H77NO8
CAS Number:
34324-89-5
Molecular Weight:
700.04
UNSPSC Code:
12352211
NACRES:
NA.25

form

powder

packaging

pkg of 1 × 5 mg (860521P-5mg)

manufacturer/tradename

Avanti Research™ - A Croda Brand 860521P

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

InChI

1S/C40H77NO8/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-34(43)33(32-48-40-39(47)38(46)37(45)35(31-42)49-40)41-36(44)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h27,29,33-35,37-40,42-43,45-47H,3-26,28,30-32H2,1-2H3,(H,41,44)/b29-27+/t33?,34-,35-,37+,38+,39-,40+/m1/s1

InChI key

VJLLLMIZEJJZTE-BUDJNAOESA-N

General description

D-galactosyl-β-1,1′N-palmitoyl-D-erythro-sphingosine or C16 Galactosyl(β) ceramide consists of a cer(d18:1/16:0) core structure to which a sugar molecule and galactose, is linked through β-glycosidic linkage. Galactosyl ceramide is a complex glycosphingolipid, which contains a single galactose residue linked to ceramide. It is a major constituent of the myelin sheath. Galactosyl ceramide is found majorly on the surface of colonic epithelial cells, vaginal epithelium and primary mammary epithelial cells.

Application

C16 Galactosyl(β) ceramide (d18:1/16:0) has been used as a lipid standard for its quantification using differential ion mobility spectrometry (DMS) coupled with liquid chromatography in electrospray ionization tandem mass spectrometry (LC-ESI-DMS-MS/MS) in human plasma. It has also been used for the preparation of lipid dispersions. It may be used as a glycosphingolipid (GSL) standard to optimize its characteristic fragmentation using electrospray ionization (ESI) triple quadrupole tandem mass spectrometry (MS/MS). It may also be used to study the structural changes caused by ultraviolet (UVA)?induced photooxidation of galactosyl (GalCer) by electrospray ionization mass spectrometry (ESI?MS) analysis.

Biochem/physiol Actions

Galactosyl ceramide is crucial for normal myelin function and stability. It prevents epithelial cell-human immunodeficiency virus 1 (HIV-1) virion binding.

Packaging

5 mL Amber Glass Screw Cap Vial (860521P-5mg)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Joseph R Mazzulli et al.
Cell, 146(1), 37-52 (2011-06-28)
Parkinson's disease (PD), an adult neurodegenerative disorder, has been clinically linked to the lysosomal storage disorder Gaucher disease (GD), but the mechanistic connection is not known. Here, we show that functional loss of GD-linked glucocerebrosidase (GCase) in primary cultures or
K M Koshy et al.
Biophysical journal, 77(1), 306-318 (1999-07-02)
Divalent cations mediate a carbohydrate-carbohydrate association between the two major glycolipids, galactosylceramide (GalCer) and its sulfated form, cerebroside sulfate (CBS), of the myelin sheath. We have suggested that interaction between these glycolipids on apposed extracellular surfaces of myelin may be
Deolinda Santinha et al.
Rapid communications in mass spectrometry : RCM, 28(21), 2275-2284 (2014-10-04)
Glycosphingolipids are important lipid molecules namely as constituents of the plasma membrane organized in lipid rafts, in signal transduction, and cell-cell communication. Although many human diseases are associated with oxidative stress and lipid oxidation, a link between oxidative stress and
Gangliosides in Health and Disease
Gangliosides in Health and Disease, 77(1), 306-318 (2018)
Differential mobility spectrometry as an orthogonal separation to LC-ESI-MS/MS for quantification of isomeric cerebrosides in plasma and cerebrospinal fluid
Xu H, et al.
Journal of Lipid Research, 88(16), jlr-D089797 (2018)
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