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67576

Sigma-Aldrich

(2S,3S,4R)-1-O-(α-D-Galactosyl)-N-hexacosanoyl-2-amino-1,3,4-octadecanetriol

≥95% (TLC)

Synonym(s):

α-GalCer, α-Galactosylceramide, KRN7000

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About This Item

Empirical Formula (Hill Notation):
C50H99NO9
CAS Number:
158021-47-7
Molecular Weight:
858.32
MDL number:
MFCD00939559
UNSPSC Code:
12352211
PubChem Substance ID:
329760622
NACRES:
NA.85

Quality Level

100

Assay

≥95% (TLC)

form

powder

functional group

amide

lipid type

sphingolipids

storage temp.

−20°C

SMILES string

CCCCCCCCCCCCCCCCCCCCCCCCCC(=O)N[C@@H](CO[C@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O)[C@H](O)[C@H](O)CCCCCCCCCCCCCC

InChI

1S/C50H99NO9/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-25-26-27-29-31-33-35-37-39-45(54)51-42(41-59-50-49(58)48(57)47(56)44(40-52)60-50)46(55)43(53)38-36-34-32-30-28-16-14-12-10-8-6-4-2/h42-44,46-50,52-53,55-58H,3-41H2,1-2H3,(H,51,54)/t42-,43+,44+,46-,47-,48-,49+,50-/m0/s1

InChI key

VQFKFAKEUMHBLV-BYSUZVQFSA-N

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class Code

11 - 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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Esther Dawen Yu et al.
The Journal of biological chemistry, 287(2), 1269-1278 (2011-11-24)
Natural killer T (NKT) cells express a semi-invariant Vα14 T cell receptor (TCR) and recognize structurally diverse antigens presented by the antigen-presenting molecule CD1d that range from phosphoglycerolipids to α- and β-anomeric glycosphingolipids, as well as microbial α-glycosyl diacylglycerolipids. Recently
Sourav Paul et al.
Journal for immunotherapy of cancer, 7(1), 208-208 (2019-08-08)
NKT cells play an important role in anti-tumor immunity. Alpha-galactosylceramide (α-GalCer), a synthetic glycolipid is presented to natural killer T (NKT) cells by most antigen-presenting cells through CD1d molecules leading to activation of NKT cells. However, the precise mechanisms of
Aline Banchet-Cadeddu et al.
Organic & biomolecular chemistry, 9(9), 3080-3104 (2011-03-12)
Associated with the CD1d protein, KRN 7000, a potent synthetic α-galactosylceramide, is known to activate the invariant NKT immune cells. This stimulation then leads to the production of different cytokines modulating a T(H)1/T(H)2 immune response balance involved in protection against
Richard J Betts et al.
European journal of immunology, 47(7), 1171-1180 (2017-04-26)
Allergic contact dermatitis is a primarily T-cell-mediated inflammatory skin disease induced by exposure to small molecular-weight haptens, which covalently bind to proteins. The abundance of cutaneous T cells that recognize CD1a antigen-presenting molecules raises the possibility that MHC-independent antigen presentation
Julie Hunault et al.
Journal of medicinal chemistry, 55(3), 1227-1241 (2012-01-17)
We propose here the synthesis and biological evaluation of 3,4-dideoxy-GalCer derivatives. The absence of the 3- and 4-hydroxyls on the sphingoid base is combined with the introduction of mono or difluoro substituent at C3 (analogues 8 and 9, respectively) to
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