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860537P

Avanti

Galactosyl(β) Sphingosine (d18:1)

Avanti Research™ - A Croda Brand 860537P, powder

Synonym(s):

D-galactosyl-β1-1′-D-erythro-sphingosine

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About This Item

Empirical Formula (Hill Notation):
C24H47NO7
CAS Number:
2238-90-6
Molecular Weight:
461.63
UNSPSC Code:
12352211
NACRES:
NA.25

form

powder

packaging

pkg of 1 × 25 mg (860537P-25mg)
pkg of 1 × 5 mg (860537P-5mg)

manufacturer/tradename

Avanti Research™ - A Croda Brand 860537P

lipid type

sphingolipids

shipped in

dry ice

storage temp.

−20°C

SMILES string

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

InChI

1S/C24H47NO7/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19(27)18(25)17-31-24-23(30)22(29)21(28)20(16-26)32-24/h14-15,18-24,26-30H,2-13,16-17,25H2,1H3/b15-14+/t18-,19+,20+,21-,22-,23+,24+/m0/s1

InChI key

HHJTWTPUPVQKNA-PIIMIWFASA-N

General description

Galactosyl(β) Sphingosine (d18:1) is a substrate for the enzyme endoglycoceramidase I (EGCase I). It has sphingosine backbone with galactose attached to it and is a brain glycospingolipid.

Application

Galactosyl(β) Sphingosine (d18:1) has been used in the liposome preparation for α-synuclein aggregation studies. It is suitable for use to test its inhibitory effect on cytokinesis in cells expressing T-cell death-associated gene 8 (TDAG8). It is also suitable for use as a standard for differential mobility spectrometry (DMS) coupled with liquid chromatography in electrospray ionizatoin tandem mass spectrometry (LC-ESI-DMS-MS/MS) for ceramide quantification and ultra-high resolution ion mobility spectrometry measurments.

Biochem/physiol Actions

Galatosylsphingosine or psychosine is a cytotoxic lipid which accumulates in oligodendrocytes due to dysfunctional lysosomal enzyme galactosylceramidase and is implicated in globoid cell leukodystrophy. Psychosine accumulation induces demyelination, astrocyte dysfunction and pro-inflammatory cytokine release in Krabbe disease.

Packaging

5 mL Amber Glass Screw Cap Vial (860537P-25mg)
5 mL Amber Glass Screw Cap Vial (860537P-5mg)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

also commonly purchased with this product

Product No.
Description
Pricing

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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Normal immune development and glucocorticoid-induced thymocyte apoptosis in mice deficient for the T-cell death-associated gene 8 receptor
Radu CG, et al.
Molecular and cellular biology, 26(2), 668-677 (2006)
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, jlr-D089797 (2018)
Lipid and glycolipid isomer analyses using ultra-high resolution ion mobility spectrometry separations
Wojcik R, et al.
International Journal of Molecular Sciences, 18(1), 183-183 (2017)
Comprehensive profiling of glycosphingolipid glycans using a novel broad specificity endoglycoceramidase in a high-throughput workflow
Albrecht S, et al.
Analytical Chemistry, 88(9), 4795-4802 (2016)
Galactosylsphingosine (psychosine)-induced demyelination is attenuated by sphingosine 1-phosphate signalling
OSullivan C and Dev KK
Journal of Cell Science, 128(21), 3878-3887 (2015)
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