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Merck

43799

N-Palmitoyl-D-sphingosine

≥98.0% (TLC)

Synonym(s):

Cer(d18:1/16:0), (2S,3R,4E)-2-(Palmitoylamino)-4-octadecene-1,3-diol, N-Hexadecanoyl-D-sphingosine, N-Palmitoyl-D-erythro-sphingosine, N-[(1S,2R,3E)-2-Hydroxy-1-(hydroxymethyl)-3-heptadecen-1-yl]hexadecanamide, C16 Ceramide (d18:1/16:0), C16-Ceramide

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About This Item

Empirical Formula (Hill Notation):
C34H67NO3
CAS Number:
24696-26-2
Molecular Weight:
537.90
NACRES:
NA.85
PubChem Substance ID:
329756403
UNSPSC Code:
12352211
MDL number:
MFCD00871748

Key Documents

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Product Name

N-Palmitoyl-D-sphingosine, ≥98.0% (TLC)

InChI key

YDNKGFDKKRUKPY-TURZORIXSA-N

SMILES string

OC[C@]([H])(NC(CCCCCCCCCCCCCCC)=O)[C@]([H])(O)/C=C/CCCCCCCCCCCCC

InChI

1S/C34H67NO3/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-33(37)32(31-36)35-34(38)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h27,29,32-33,36-37H,3-26,28,30-31H2,1-2H3,(H,35,38)/b29-27+/t32-,33+/m0/s1

assay

≥98.0% (TLC)

form

powder or solid

composition

carbon content, 75.92%
hydrogen content, 12.55%
nitrogen content, 2.60%

functional group

amide

lipid type

sphingolipids

shipped in

wet ice

storage temp.

−20°C

Quality Level

100

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
BCCB5820
BCBT2507
BCBR4644V
BCBQ2399V
BCBH6549V

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Gloria I Perez et al.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 19(7), 860-862 (2005-02-25)
An age-dependent acceleration of apoptosis occurs in female germ cells (oocytes), and this requires communication between the oocyte and its surrounding somatic (cumulus) cells. Here we show in aged mice that ceramide is translocated from cumulus cells into the adjacent
S White-Gilbertson et al.
Oncogene, 28(8), 1132-1141 (2009-01-13)
We have previously shown that the death receptor ligand TRAIL (tumor necrosis factor-related apoptosis-inducing ligand) induces an increase of intracellular C(16)-ceramide in sensitive SW480 but not in resistant SW620 cells. Resistance in SW620 cells was overcome by exogenous ceramide, leading
Claudia Almeida et al.
PloS one, 13(8), e0201373-e0201373 (2018-08-11)
Biological membranes contain a large variety of lipids species compartmentalized in different domains heterogeneous in size, composition and dynamics. Cholesterol induces membrane ordered domains thanks to its affinity for saturated lipids. Membrane domains had been studied with fluorescent probes either
Daniel Dindo et al.
Molecular cancer therapeutics, 5(6), 1520-1529 (2006-07-05)
Ceramides are sphingolipid second messengers that are involved in the mediation of cell death. There is accumulating evidence that mitochondria play a central role in ceramide-derived toxicity. We designed a novel cationic long-chain ceramide [omega-pyridinium bromide D-erythro-C16-ceramide (LCL-30)] targeting negatively
Jérôme Becam et al.
Scientific reports, 7(1), 17627-17627 (2017-12-17)
Certain fatty acids and sphingoid bases found at mucosal surfaces are known to have antibacterial activity and are thought to play a more direct role in innate immunity against bacterial infections. Herein, we analysed the antibacterial activity of sphingolipids, including
View All Related Papers

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