P9256
Psychosine from bovine brain
lyophilized powder, ≥98% (TLC)
Synonym(s):
1-β-D-Galactosylsphingosine
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About This Item
Empirical Formula (Hill Notation):
C24H47NO7
CAS Number:
Molecular Weight:
461.63
MDL number:
UNSPSC Code:
12352211
PubChem Substance ID:
NACRES:
NA.77
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Quality Level
Assay
≥98% (TLC)
form
lyophilized powder
storage temp.
−20°C
SMILES string
CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](N)CO[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[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-PIIMIWFASA-N
Application
Psychosine has been used as a lipid in lipid-protein overlay binding assay.
Biochem/physiol Actions
Psychosine is a neurotoxic lysosphingolipid and a glycolipid precursor for the synthesis of cerebrosides. It is synthesized from galactosylceramide, phrenosin. Elevated psychosine levels are implicated in Krabbe disease. It mediates demyelination and consequently oligodendrocytes degeneration. Psychosine is also correlated to neurological disease, Globoid cell leukodystrophy (GLD), where in galactosylceramidase (GALC) enzyme deficiency leads to its accumulation.
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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Wei-Lien Chuang et al.
Clinica chimica acta; international journal of clinical chemistry, 419, 73-76 (2013-02-20)
New York State has screened over 1.2 million newborns for Krabbe disease, and we identified 4 newborns with infantile Krabbe disease. In addition, 6 other newborns were identified with very low galactosylcerebrosidase (GALC) activity. Because these patients remain asymptomatic, we
Benjamin Smith et al.
ASN neuro, 3(4), doi:10-doi:10 (2011-09-21)
Infantile Krabbe disease results in the accumulation of lipid-raft-associated galactosylsphingosine (psychosine), demyelination, neurodegeneration and premature death. Recently, axonopathy has been depicted as a contributing factor in the progression of neurodegeneration in the Twitcher mouse, a bona fide mouse model of
Wenjin Li et al.
Journal of enzyme inhibition and medicinal chemistry, 35(1), 1503-1512 (2020-07-14)
Metachromatic leukodystrophy (MLD) is a rare genetic disease characterised by a dysfunction of the enzyme arylsulphatase A leading to the lysosomal accumulation of cerebroside sulphate (sulphatide) causing subsequent demyelination in patients. The enzyme galactosylceramide (cerebroside) sulphotransferase (CST) catalyses the transfer
Psychosine enhances the shedding of membrane microvesicles: Implications in demyelination in Krabbe?s disease
DAuria L, et al.
PLoS ONE, 12(5), e0178103-e0178103 (2017)
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