GLUCOPSYCHOSINE CAS#: 52050-17-6; ChemWhat Code: 852968

IdentificationPhysical DataSpectra
Route of Synthesis (ROS)Safety and HazardsOther Data

Identification

Product NameGLUCOPSYCHOSINE
IUPAC Name(2R,3R,4S,5S,6R)-2-[(E,2S,3R)-2-amino-3-hydroxyoctadec-4-enoxy]-6-(hydroxymethyl)oxane-3,4,5-triol 
Molecular StructureGLUCOPSYCHOSINE-CAS-52050-17-6
CAS Registry Number 52050-17-6
Beilstein Registry Number4333674
Synonymsglucosylsphingosine
52050-17-6
Glucopsychosine
D-Glucosylsphingosine
lyso-GlcCer
Lyso GlcCer
Glucosyl-C18-sphingosine
Glucosyl sphingosine
beta-D-glucosylsphingosine
1-glucosyl-sphing-4-enine
Glucosphingosine
(2S,3R,4E)-1-O-beta-(D-glucopyranosyl)-4-sphingenine
Lyso-Gb1
(2S,3R,4E)-2-amino-1-(beta-D-glucopyranosyloxy)-4-octadecen-3-ol
(2S,3R,4E)-2-amino-1-(beta-D-glucopyranosyloxy)octadec-4-en-3-ol
(2S,3R,4E)-2-amino-3-hydroxyoctadec-4-en-1-yl beta-D-glucopyranoside
(2S,3R,4E)-beta-D-glucopyranosyl-(1′<->1)-2-amino-4-octadecene-1,3-diol
SCHEMBL9746342
CHEBI:71981
DTXSID101315465
GLXC-19134
HY-N7745
D-glucosyl-?1-1′-D-erythro-sphingosine
(2R,3R,4S,5S,6R)-2-[(E,2S,3R)-2-amino-3-hydroxyoctadec-4-enoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
DA-73775
MS-28477
CS-0136821
D-Glucosyl-beta1-1′-D-erythoro-Sphingosine
NS00074121
C03108
(2s,3r,4e)-2-amino-1-(beta-d-glucopyranosyloxy)-3-hydroxy-4-octadecene
beta-D-Glucopyranoside, (2S,3R,4E)-2-amino-3-hydroxy-4-octadecen-1-yl
beta-D-Glucopyranoside,(2S,3R,4E)-2-amino-3-hydroxy-4-octadecen-1-yl
Molecular FormulaC24H47NO7 
Molecular Weight461.6
InChIInChI=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 KeyHHJTWTPUPVQKNA-JIAPQYILSA-N
Isomeric SMILESCCCCCCCCCCCCC/C=C/[C@H]([C@H](CO[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)N)O

Physical Data

AppearanceWhite Powder

Spectra

Description (NMR Spectroscopy)Nucleus (NMR Spectroscopy)Solvents (NMR Spectroscopy)
1HCDCl3, tetradeuteriomethanol
Chemical shifts1HCDCl3, tetradeuteriomethanol

Route of Synthesis (ROS)

Route of Synthesis (ROS) of GLUCOPSYCHOSINE CAS 52050-17-6
Route of Synthesis (ROS) of GLUCOPSYCHOSINE CAS 52050-17-6
ConditionsYield
With pyridine; hydrogen sulfide In water for 48h;88%
With pyridine In methanol; chloroform; water

Experimental Procedure
2.r (r)
(r) 2S,3R-2-Amino-3-hydroxy-1-(β-D-glucopyranosyloxy)-4- trans-octadecene (18) 1.65 g (3.4 mmol) of compound (17) are dissolved in 50 ml of a mixture of pyridine/water (1:1). The solution is saturated with hydrogen sulphide. The mixture is stirred at room temperature for 24 hours. It is concentrated to dryness and chromatographed over silica gel, first with chloroform/methanol (9:1) and then with chloroform/methanol/water (5:4:1). Yield: 1.47 g (94%) RF =0.64 in chloroform/methanol/water (5:4:1). 1 H-NMR (250 MHz, DMSO-d6 in ppm) of compound (18): 4.10 (d, 1H, H-1, J=7.6 Hz).		1.47 g (94%)

Safety and Hazards

GHS Hazard StatementsNot Classified

Other Data

HS Code
StorageStore at -20°, Sealed and keep dry.
Shelf Life2 years
Market Price
Druglikeness
Lipinski rules component
Molecular Weight461.64
logP4.91
HBA8
HBD6
Matching Lipinski Rules3
Veber rules component
Polar Surface Area (PSA)145.63
Rotatable Bond (RotB)18
Matching Veber Rules0
Use Pattern
GLUCOPSYCHOSINE CAS#: 52050-17-6 is a metabolite of sphingolipids and has significant applications in biomedical and clinical research. Glucosylsphingosine is an important biomarker for Gaucher disease, a lysosomal storage disorder caused by a deficiency of the enzyme glucocerebrosidase.

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Ulcho Biochemical Limitedhttp://www.ulcho.com/
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