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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

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)

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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
Michael D Nissen et al.
Cancer immunology research, 6(1), 98-109 (2017-11-18)
β-Adrenergic receptor (βAR) signaling regulates many physiological processes, including immune system responses. There is growing evidence also for βAR-induced modulation of cancer growth and metastasis. In the Eμ-myc mouse model of B-cell lymphoma, we investigated the effects of chronically elevated
Famke L Schneiders et al.
Clinical immunology (Orlando, Fla.), 140(2), 130-141 (2010-12-21)
For over a century, research has sought ways to boost the immune system in order to eradicate tumors and viruses that exist after escaping immunosurveillance. For the treatment of cancer and hepatitis immunotherapeutic strategies have overall had limited clinical success.
Joshua Richter et al.
Blood, 121(3), 423-430 (2012-10-27)
Natural killer T (iNKT) cells can help mediate immune surveillance against tumors in mice. Prior studies targeting human iNKT cells were limited to therapy of advanced cancer and led to only modest activation of innate immunity. Clinical myeloma is preceded
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