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43799

Sigma-Aldrich

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
MDL number:
MFCD00871748
UNSPSC Code:
12352211
PubChem Substance ID:
329756403
NACRES:
NA.85

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

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

InChI key

YDNKGFDKKRUKPY-TURZORIXSA-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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Sharon Epstein et al.
Journal of lipid research, 53(3), 412-420 (2012-01-03)
Sphingolipids are not only important components of membranes but also have functions in protein trafficking and intracellular signaling. The LCB1 gene encodes a subunit of the serine palmitoyltransferase, which is responsible for the first step of sphingolipid synthesis. Here, we
Sherry S W Leung et al.
Biophysical journal, 103(12), 2465-2474 (2012-12-25)
Ceramide produced from sphingomyelin in the plasma membrane is purported to affect signaling through changes in the membrane's physical properties. Thermal behavior of N-palmitoyl sphingomyelin (PSM) and N-palmitoyl ceramide (PCer) mixtures in excess water has been monitored by ²H NMR
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
Andrew K Rudd et al.
Proceedings of the National Academy of Sciences of the United States of America, 115(29), 7485-7490 (2018-07-04)
Mammalian cells synthesize thousands of distinct lipids, yet the function of many of these lipid species is unknown. Ceramides, a class of sphingolipid, are implicated in several cell-signaling pathways but poor cell permeability and lack of selectivity in endogenous synthesis
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
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