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P9256

Sigma-Aldrich

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:
2238-90-6
Molecular Weight:
461.63
MDL number:
MFCD00057505
UNSPSC Code:
12352211
PubChem Substance ID:
24899021
NACRES:
NA.77

Quality Level

200

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Lysosphingolipids and sphingolipidoses: Psychosine in Krabbe's disease
Spassieva S and Bieberich E
Journal of Neuroscience Research, 94(11), 974-981 (2016)
Ludovico Cantuti Castelvetri et al.
Acta neuropathologica, 122(1), 35-48 (2011-03-05)
Loss-of-function of the lysosomal enzyme galactosyl-ceramidase causes the accumulation of the lipid raft-associated sphingolipid psychosine, the disruption of postnatal myelination, neurodegeneration and early death in most cases of infantile Krabbe disease. This work presents a first study towards understanding the
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)
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
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
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