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42137

Sigma-Aldrich

Lactosylsphingosine

≥98.0% (TLC)

Synonym(s):

(2S,3R,4E)-2-Amino-3-hydroxy-4-octadecen-1-yl 4-O-β-D-galactopyranosyl-β-D-glucopyranoside

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About This Item

Empirical Formula (Hill Notation):
C30H57NO12
CAS Number:
109785-20-8
Molecular Weight:
623.77
Beilstein:
5680460
UNSPSC Code:
12352211
PubChem Substance ID:
329756195
NACRES:
NA.85

Assay

≥98.0% (TLC)

form

powder

lipid type

sphingolipids

storage temp.

−20°C

SMILES string

OC1[C@@H](O)[C@H](OC[C@@H](N)[C@@H](O)/C=C/CCCCCCCCCCCCC)OC(CO)[C@H]1O[C@H]2[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O2

InChI

1S/C30H57NO12/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-20(34)19(31)18-40-29-27(39)25(37)28(22(17-33)42-29)43-30-26(38)24(36)23(35)21(16-32)41-30/h14-15,19-30,32-39H,2-13,16-18,31H2,1H3/b15-14+/t19-,20+,21?,22?,23+,24-,25-,26?,27-,28?,29-,30+/m1/s1

InChI key

MQKSCOKUMZMISB-VOCCQAPRSA-N

Biochem/physiol Actions

Lactosylsphingosine is relevant for cancer, as lactosyl-reative antibodies occur in sera of cancer patients.

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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Kevin Mills et al.
Rapid communications in mass spectrometry : RCM, 19(12), 1739-1748 (2005-05-24)
Novel internal standards have been synthesised for the quantitative determination by tandem mass spectrometry (MS/MS) of the sphingolipids that accumulate in lysosomal storage diseases. The [d4]C16- and [d47]C24-isoforms of galactosylceramide (CMH), lactosylceramide (CDH), globotriaosylceramide (CTH), cerebroside sulphate, sphingomyelin and G(M1)-
Margarita L Malakhova et al.
The Journal of biological chemistry, 280(28), 26312-26320 (2005-05-20)
Mammalian glycolipid transfer proteins (GLTPs) facilitate the selective transfer of glycolipids between lipid vesicles in vitro. Recent structural determinations of the apo- and glycolipid-liganded forms of human GLTP have provided the first insights into the molecular architecture of the protein
Takehiro Nagatsuka et al.
ACS applied materials & interfaces, 5(10), 4173-4180 (2013-05-15)
We have detected biological toxins using localized surface plasmon resonance (LSPR) and synthetic glycosyl ceramides (β-lactoside, globosyl trisaccharide (Gb3), or GM1 pentasaccharide) attached to gold (Au) nanoparticles. The particle diameters ranged from 5-100 nm. The detection sensitivity for three toxins
Sumita Mishra et al.
Glycobiology, 24(6), 518-531 (2014-03-25)
Hypertrophy is central to several heart diseases; however, not much is known about the role of glycosphingolipids (GSLs) in this phenotype. Since GSLs have been accorded several physiological functions, we sought to determine whether these compounds affect cardiac hypertrophy. By
Xavier Buton et al.
Biochemistry, 41(43), 13106-13115 (2002-10-23)
The transbilayer movement of glycosphingolipids has been characterized in Golgi, ER, plasma, and model membranes using spin-labeled and fluorescent analogues of the monohexosylsphingolipids glucosylceramide and galactosylceramide and of the dihexosylsphingolipid lactosylceramide. In large unilamellar lipid vesicles, monohexosylsphingolipids underwent a slow
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