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Merck

43659

Glucosylsphingosine

≥98.0% (TLC)

Synonym(s):

(2S,3R,4E)-2-Amino-3-hydroxy-4-octadecen-1-yl β-D-glucopyranoside, 1-β-D-Glucosylsphingosine, Glucosyl-C18-sphingosine

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About This Item

Empirical Formula (Hill Notation):
C24H47NO7
CAS Number:
52050-17-6
Molecular Weight:
461.63
MDL number:
MFCD07374303
UNSPSC Code:
12352211
PubChem Substance ID:
329756364
NACRES:
NA.85
Beilstein/REAXYS Number:
4333674

Product Name

Glucosylsphingosine, ≥98.0% (TLC)

SMILES string

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

InChI key

HHJTWTPUPVQKNA-JLRUQHRASA-N

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

assay

≥98.0% (TLC)

form

powder

lipid type

sphingolipids

storage temp.

−20°C

Quality Level

100

Related Categories

Biochem/physiol Actions

Glucosylsphingosine is a cytotoxic compound. Accumulation of glucosylsphingosine in brain and other tissues occurs in patients with Gaucher disease, which is an inherited deficiency of lysosomal glucocerebrosidase, which converts glucosylsphingosine to glucose and sphingosine.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
BCCN1134
BCCM1226
BCCJ9970
BCCG2390
BCCD1062

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Lulu Kang et al.
Journal of human genetics, 62(8), 763-768 (2017-03-31)
Gaucher disease (GD) is an inherited metabolic disorder that involves accumulation of glycolipid glucocerebroside in monocyte-macrophage cells, which can result in multiple organ damage. Enzyme replacement and substrate reduction therapies have improved the potential for early diagnosis and treatment. Determining
E Beutler
Blood reviews, 2(1), 59-70 (1988-03-01)
Gaucher disease is a glycolipid storage disorder characterized by accumulation of glucocerebroside in the liver, spleen, and bones, and caused by a deficiency of glucocerebrosidase. Glucocerebrosidase cDNA has been cloned and sequenced, and much has been learned about the synthesis
A Kaloterakis et al.
Journal of internal medicine, 246(6), 587-590 (2000-01-05)
Chronic Gaucher disease [GD] in association with systemic AL amyloidosis is extremely rare. We describe a 46-year-old Greek male with chronic GD confirmed by low glucocerebroside activity in fibroblasts and N370S/L444P mutations at the cerebrosidase gene, who also had systemic
Shiny Nair et al.
Molecular genetics and metabolism, 129(4), 286-291 (2020-02-12)
In Gaucher disease type 1 (GD1), genetic deficiency of lysosomal glucocerebrosidase results in the accumulation of glucosylceramide and glucosylsphingosine (GlcSph), that underlie chronic lipid-mediated metabolic inflammation. An important age-related phenotype is high risk of monoclonal gammopathy (MG), including multiple myeloma.
N G Conradi et al.
Acta neuropathologica, 75(4), 385-390 (1988-01-01)
Splenectomy in children with the Norrbottnian type of Gaucher disease is followed by increased blood levels of glucosylceramide and impaired neurological and mental status. High blood levels are associated with an increased accumulation of glucosylceramide in perivascular Gaucher cells in
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