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Merck

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

Product Name

Psychosine from bovine brain, lyophilized powder, ≥98% (TLC)

InChI key

HHJTWTPUPVQKNA-PIIMIWFASA-N

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

assay

≥98% (TLC)

form

lyophilized powder

storage temp.

−20°C

Quality Level

200

Related Categories

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

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000141105
0000224896
0000224896
0000141105
0000180975

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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
Conserved roles of C. elegans and human MANFs in sulfatide binding and cytoprotection
Bai M, et al.
Nature Communications, 9(1), 897-897 (2018)
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
Hiroshi Yamamoto et al.
Archives of biochemistry and biophysics, 506(1), 83-91 (2010-11-18)
Sphingolipids act as signaling mediators that regulate a diverse range of cellular events. Although numerous sphingolipid functions have been studied, little is known about the effect of sphingolipids on monocyte differentiation into macrophages. Here, we report that two lysosphingolipids, sphingosylphosphorylcholine
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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