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C24:1 3'-sulfo Galactosylceramide (d18:1/24:1(15Z))

CAS No.
151057-28-2
Chemical Name:
C24:1 3'-sulfo Galactosylceramide (d18:1/24:1(15Z))
Synonyms
C24:1 3’N-Tetracosenoyl-(cis-15)-sulfatide;-sulfo Galactosylceramide (d18:1/24:1(15Z));C24:1 3'-sulfo Galactosylceramide (d18:1/24:1(15Z));N-[(1S)-2R-hydroxy-1-[[(3-O-sulfo-β-D-galactopyranosyl)oxy]methyl]-3E-heptadecen-1-yl]-15Z-tetracosenamide;15-Tetracosenamide, N-[(1S,2R,3E)-2-hydroxy-1-[[(3-O-sulfo-β-D-galactopyranosyl)oxy]methyl]-3-heptadecen-1-yl]-, (15Z)-
CBNumber:
CB64666091
Molecular Formula:
C48H91NO11S
Molecular Weight:
890.3
MDL Number:
MOL File:
151057-28-2.mol
Last updated:2023-05-21 10:59:17

C24:1 3'-sulfo Galactosylceramide (d18:1/24:1(15Z)) Properties

storage temp. Store at -20°C
solubility Chloroform:Methanol (5:1): soluble
form A solid

C24:1 3'-sulfo Galactosylceramide (d18:1/24:1(15Z)) price More Price(1)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Cayman Chemical 24865 C24:1 3'-sulfo Galactosylceramide (d18:1/24:1(15Z)) ≥98% 151057-28-2 1mg $486 2024-03-01 Buy
Product number Packaging Price Buy
24865 1mg $486 Buy

C24:1 3'-sulfo Galactosylceramide (d18:1/24:1(15Z)) Chemical Properties,Uses,Production

Description

C24:1 3’-sulfo Galactosylceramide is a member of the sulfatide class of glycolipids. It is the predominate sulfatide species in mature myelin, and it accumulates at a higher rate than C24 3’-sulfo galactosylceramide in rat cerebellum from seven to 32 days of age when active myelination occurs.1 It interacts with C-type lectins and immunoglobulin-like receptors with the highest affinity for LMIR5.2 It induces production of MCP-1 in basophils but not mast cells and increases the activation of NFAT in a reporter assay via LMIR5. C24:1 3’-sulfo Galactosylceramide is an immunodominant species in myelin, is bound by CD1d in vitro, and increases proliferation in isolated mouse splenocytes.3 It reduces symptoms and increases survival in a mouse model of chronic relapsing-remitting experimental autoimmune encephalomyelitis (EAE) when used at a dose of 20 μg.4 It also decreases the number of inflammatory lesions and infiltrating mononuclear cells in the lumbar spinal cord of EAE mice. As this product is derived from a natural source, there may be variations in the sphingoid backbone.

Definition

ChEBI: 1-(3-O-sulfo-beta-D-galactosyl)-N-[(15Z)-tetracos-15-enoyl]sphingosine is an N-acyl-beta-D-galactosylsphingosine having a sulfo group at the 3-position on the galactose ring and (15Z)-tetracos-15-enoyl as the N-acyl group. It has a role as an epitope. It is a galactosylceramide sulfate and a N-acyl-beta-D-galactosylsphingosine. It is a conjugate acid of a 1-(3-O-sulfo-beta-D-galactosyl)-N-[(15Z)-tetracos-15-enoyl]sphingosine(1-).

References

1. Marbois, B.N., Faull, K.F., Fluharty, A.L., et al. Analysis of sulfatide from rat cerebellum and multiple sclerosis white matter by negative ion electrospray mass spectrometry Biochim. Biophys. Acta 1484(1),59-70(2000).
2. Phongsisay, V., Iizasa, E., Hara, H., et al. 3-O-sulfo-β-D-galactose moiety of endogenous sulfoglycolipids is a potential ligand for immunoglobulin-like receptor LMIR5 Mol. Immunol. 63(2),595-599(2015).
3. Zajonc, D.M., Maricic, I., Wu, D., et al. Structural basis for CD1d presentation of a sulfatide derived from myelin and its implications for autoimmunity J. Exp. Med. 202(11),1517-1526(2005).
4. Maricic, I., Halder, R., Bischof, F., et al. Dendritic cells and anergic type I NKT cells play a crucial role in sulfatide-mediated immune regulation in experimental autoimmune encephalomyelitis J. Immunol. 193(3),1035-1046(2014).

C24:1 3'-sulfo Galactosylceramide (d18:1/24:1(15Z)) Preparation Products And Raw materials

Raw materials

Preparation Products

C24:1 3'-sulfo Galactosylceramide (d18:1/24:1(15Z)) Suppliers

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C24:1 3'-sulfo Galactosylceramide (d18:1/24:1(15Z)) C24:1 3&rsquo -sulfo Galactosylceramide (d18:1/24:1(15Z)) 15-Tetracosenamide, N-[(1S,2R,3E)-2-hydroxy-1-[[(3-O-sulfo-β-D-galactopyranosyl)oxy]methyl]-3-heptadecen-1-yl]-, (15Z)- N-Tetracosenoyl-(cis-15)-sulfatide N-[(1S)-2R-hydroxy-1-[[(3-O-sulfo-β-D-galactopyranosyl)oxy]methyl]-3E-heptadecen-1-yl]-15Z-tetracosenamide 151057-28-2 C48H91NO11S