52050-17-6

Basic information

• Product Name: GLUCOPSYCHOSINE
• Synonyms: sphingosylbeta-glucoside;2-(2-amino-3-hydroxy-octadec-4-enoxy)-6-(hydroxymethyl)oxane-3,4,5-triol;1-β-D-Glucosylsphingosine;(2S,3R,4E)-2-AMino-3-hydroxy-4-octadecenyl β-D-Glucopyranoside;2-AMino-3-hydroxy-4-octadecenyl β-D-Glucopyranoside;Glucosyl-C18-sphingosine;D-glucosyl-1-1'-D-erythro-sphingosine;1--D-Glucosylsphingosine (d18:1)
• CAS NO: 52050-17-6
• Molecular Formula: C₂₄H₄₇NO₇
• Molecular Weight: 461.635
• Product Categories: Amino Acids & Derivatives;Protein Kinase Inhibitors and Activators
• Mol File: 52050-17-6.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 664.3°Cat760mmHg
• Flash Point: 355.6°C
• Appearance: /
• Density: 1.14g/cm³
• Vapor Pressure: 1.77E-20mmHg at 25°C
• Refractive Index: 1.535
• Storage Temp.: −20°C
• Solubility: DMSO (Slightly), Methanol (Slightly, Heated, Sonicated)
• Stability: Hygroscopic
• BRN: 4333674
• CAS DataBase Reference: GLUCOPSYCHOSINE(CAS DataBase Reference)
• NIST Chemistry Reference: GLUCOPSYCHOSINE(52050-17-6)
• EPA Substance Registry System: GLUCOPSYCHOSINE(52050-17-6)

Safety Data

• Hazard Codes: B
• WGK Germany: 3
• Hazardous Substances Data: 52050-17-6(Hazardous Substances Data)

Usage

Description

GLUCOPSYCHOSINE, also known as Glucosyl Sphingosine, is a lyso derivative of glucosylceramide (GlcCer). It is a sphingolipid compound with light brown residue properties, which has been identified in various biological contexts and has potential applications in the medical field.

Uses

Used in Medical Research:
GLUCOPSYCHOSINE is used as a biomarker for the identification of lipids that rapidly and reversibly alter transepithelial electrical resistance (TER) or tight junction (TJ) permeability in epithelial tissue. This application aids in understanding the underlying mechanisms of various diseases and conditions affecting epithelial tissues.
Used in Gaucher Disease Diagnostics:
GLUCOPSYCHOSINE is used as an internal standard for the quantification of glucosyl sphingosine in Gaucher patients. This application is crucial for the accurate diagnosis and monitoring of Gaucher disease, a genetic disorder characterized by the accumulation of glucosylceramide in various tissues.
Used in Liquid Chromatography Electrospray Ionization Tandem Mass Spectrometric (LC/ESI-MS/MS):
GLUCOPSYCHOSINE is used as an internal standard in LC/ESI-MS/MS for the quantification of lysoglucosylceramide in plasma. This application is essential for the diagnosis and management of Gaucher disease, as it helps in measuring the levels of lysoglucosylceramide, a biomarker for the disease.
Used in Preeclampsia Research:
GLUCOPSYCHOSINE is used as a sphingosine derivative and a sphingolipid compound found in the umbilical cord artery of women with preeclampsia. This application helps in understanding the role of GLUCOPSYCHOSINE in the development of preeclampsia and its potential as a therapeutic target.
Used in Liquid Chromatography with Tandem Mass Spectrometry (LC-MS/MS):
GLUCOPSYCHOSINE is used in LC-MS/MS for the quantification of lysoglucosylceramide in plasma for Gaucher disease. This application is vital for the accurate measurement of lysoglucosylceramide levels, which can help in the diagnosis and treatment of Gaucher disease.

Biochem/physiol Actions

Glucosyl?sphingosine is a potential biomarker for Gaucher′s?disease.?It modulates?Ca2+?release?in the brain?microsomes.

InChI:InChI=1/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-/m1/s1

Upstream product

• 2021-84-3 α-galactosyl fluoride 
• 123-78-4 (2S,3R,4E)-2-amino-4-octadecene-1,3-diol 
• 118605-55-3 (2,3,4,6-tetra-O-pivaloyl-α-D-galactopyranoside)-1-trichloroacetimidate 
• 118711-45-8 (2S,3R,4E)-2-azido-1-(galactopyranosyloxy)octadec-4-en-3-ol 
• 916159-70-1 (2S,3R)-(E)-2-azido-1-(tert-butyldiphenylsilyloxy)octadec-4-en-3-ol 
• 103348-50-1 (2S,3R,4E)-2-azido-3-benzoyloxy-4-octadecen-1-ol 
• 131105-38-9 (2S,3R,4E)-3-O-benzoyl-1-O-(tetra-O-acetyl-β-D-glucopyranosyl)-N-trifluoroacetyl-4-sphingenine 
• 172340-52-2 Benzoic acid (E)-(R)-1-[(S)-1-azido-2-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-ethyl]-hexadec-2-enyl ester 
• 108283-60-9 (2S,3R,4E)-β-D-glucopyranosyl-(1'<->1)-2-azido-4-octadecene-1,3-diol 
• 3947-62-4 2,3,4,5-tetra-O-acetyl-D-glucopyranose 
• 112-71-0 1-Bromotetradecane 
• 103348-49-8 2-azido-sphingosine 
• 108283-57-4 (2S,3R,4E)-2-azido-1-(triphenylmethyl)-4-octadecene-1,3-diol 
• 25791-20-2 (n-tetradecyl)triphenylphosphonium bromide 

Downstream Products

• 74365-77-8 glucosylceramide 
• 36271-49-5 (2S,3R,4E)-1-(β-D-galactopyranosyloxy)-2-(octadecanoylamino)-3-hydroxyoctadec-4-ene 
• 17283-91-9 (2S,3R,4E)-1-(β-D-galactopyranosyloxy)-2-(15(Z)-tetracosenoylamino)-3-hydroxyoctadec-4-ene 
• 34324-89-5 (2S,3R,4E)-1-(β-D-galactopyranosyloxy)-2-(hexadecanoylamino)-3-hydroxyoctadec-4-ene 
• 35823-61-1 N-Acetylpsychosine 
• 41613-16-5 C₃₂H₆₁NO₈ 
• 73039-25-5 erythro-N-oleoyl-1-O-β-D-galactosyl-D-sphingosine 
• 173067-83-9 4,6-O-p-methoxybenzylidene-β-D-galactopyranosyl-(1<*>1)-(2S,3R,4E)-2-dichloroacetamido-4-octadecen-1,3-diol 
• 173067-85-1 2,3-di-O-benzoyl-β-D-galactopyranosyl-(1<*>1)-(2S,3R,4E)-3-O-benzoyl-2-dichloroacetamido-4-octadecen-1,3-diol 
• 173067-86-2 2,3,6-tri-O-benzoyl-β-D-galactopyranosyl-(1<*>1)-(2S,3R,4E)-3-O-benzoyl-2-dichloroacetamido-4-octadecen-1,3-diol 
• 173067-84-0 2,3-di-O-benzoyl-4,6-O-p-methoxybenzylidene-β-D-galactopyranosyl-(1<*>1)-(2S,3R,4E)-3-O-benzoyl-2-dichloroacetamido-4-octadecen-1,3-diol 
• 173067-87-3 2,3,6-tri-O-benzoyl-4-O-trifluoromethylsulfonyl-β-D-galactopyranosyl-(1<*>1)-(2S,3R,4E)-3-O-benzoyl-2-dichloroacetamido-4-octadecen-1,3-diol 
• 173067-88-4 S-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1<*>4)-2,3,6-tri-O-benzoyl-4-thio-β-D-glucopyranosyl-(1<*>1)-(2S,3R,4E)-3-O-benzoyl-2-dichloroacetamido-4-octadecen-1,3-diol 
• 88035-98-7 2-Hydroxy-N-[(E)-2-hydroxy-1-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl)-heptadec-3-enyl]-malonamic acid tetradecyl ester 

Relevant articles and documents

3-O-SULFO-GALACTOSYLCERAMIDE ANALOGS AS ACTIVATORS OF TYPE II NKT CELLS AND USES THEREOF

Disclosed is a compound of the formula (I) or (II): wherein a f are as described herein. The compounds are useful in the activation of Type II NKT cells and in treating cancer.

Synthesis and biological evaluation of antifungal activities of novel 1,2-trans glycosphingolipids

The synthesis and in-vitro biological evaluation of antifungal activities of a series of 1,2-trans glycosphingolipids (GSL) against Candida albicans, Candida parapsilosis, and Candida tropicalis were described. The preliminary study indicated that the sor

Synthesis of Sphingosine Relatives, IX. Synthesis of (2S,3R,4E)-1-O-(β-D-Glucopyranosyl)-N--4-sphingenine. The Structure Proposed for the Esterified Cerebroside in the Epidermis of Guinea Pigs

(2S,3R,4E)-1-O-(β-D-Glucopyranosyl)-N--4-sphingenine (1) was synthesized from D-glucose (A), (2S,3R,4E)-4-sphingenine (sphingosine, B), 24-hydroxytetracosanoic acid (C) and linoleic acid (D).The 1H-NMR spectrum of the synthetic 1 was different from that of the esterified cerebroside which was isolated as a tissue-characteristic compound in the epidermis of foodpad and dorsal skin of guinea pigs.