1-β-D-Glucosylsphingosine

Name: 1-β-D-Glucosylsphingosine
CAS#: 52050-17-6
Chemical Formula: C24H47NO7
Exact Mass: 461.3353
Molecular Weight: 461.64
Elemental Analysis: C, 62.44; H, 10.26; N, 3.03; O, 24.26

Description: 1-β-D-Glucosylsphingosine is a glucosylsphingosine, which are deacetylated lysolipid derivatives of glucocerebrosides. They are formed when sphingosines undergo glucosidation by UDP-glucose. Glucosylsphingosines completely reduce neurite outgrowth and induce death of LA-N-2 cells when used at concentrations of 10 and 50 μM, respectively. They also decrease the activity of glucocerebrosidase in LA-N-2 cells in a concentration-dependent manner. Glucosylsphingosine levels are elevated in patients with Gaucher's disease, both in the spleen and brain, thus, glucosylsphingosine has been used as a key biomarker of the disease. This product contains 1-β-D-glucosylsphingosine (d18:1) isolated from bovine buttermilk.

IUPAC/Chemical Name: (2R,3R,4S,5S,6R)-2-(((2S,3R,E)-2-amino-3-hydroxyoctadec-4-en-1-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

InChi Key: HHJTWTPUPVQKNA-JIAPQYILSA-N

InChi Code: 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

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

Appearance: Solid powder