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43659

Sigma-Aldrich

Glucosylsphingosine

≥98.0% (TLC)

Sinónimos:

(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

Fórmula empírica (notación de Hill):
C24H47NO7
Número de CAS:
52050-17-6
Peso molecular:
461.63
Beilstein/REAXYS Number:
4333674
UNSPSC Code:
12352211
PubChem Substance ID:
329756364
NACRES:
NA.85

Quality Level

100

assay

≥98.0% (TLC)

form

powder

lipid type

sphingolipids

storage temp.

−20°C

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

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-JLRUQHRASA-N

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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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
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
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
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
Chengfang Tang et al.
Clinical biochemistry, 87, 79-84 (2020-11-15)
Gaucher disease (GD) is caused by a deficiency of β-glucosidase (GCase), leading to accumulation of glucosylceramide (GlcC) and glucosylsphingosine (Lyso-Gb1). Lyso-Gb1 is a reliable biomarker for GD. This study aims to develop a simple, effective and accurate method for the
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