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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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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.
Peter J Jervis et al.
The Journal of organic chemistry, 76(1), 320-323 (2010-12-16)
A concise route to the 6-azido-6-deoxy-α-galactosyl-phytosphingosine derivative 9 is reported. Orthogonal protection of the two amino groups allows elaboration of 9 into a range of 6-N-derivatized α-galactosyl ceramides by late-stage introduction of the acyl chain of the ceramide and the
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
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
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
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