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18448

Sigma-Aldrich

N-Stearoyl-D-sphingosine

≥98.0% (TLC)

Synonym(s):

Cer(d18:1/18:0), (2S,3R,4E)-2-(Stearoylamino)-4-octadecene-1,3-diol, N-Octadecanoyl-D-sphingosine, N-Stearoyl-D-erythro-sphingosine, N-[(1S,2R,3E)-2-Hydroxy-1-(hydroxymethyl)-3-heptadecen-1-yl]octadecanamide, C18 Ceramide (d18:1/18:0), C18-Ceramide

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About This Item

Empirical Formula (Hill Notation):
C36H71NO3
CAS Number:
2304-81-6
Molecular Weight:
565.95
Beilstein:
1717539
MDL number:
MFCD02259139
UNSPSC Code:
12352211
PubChem Substance ID:
329751672
NACRES:
NA.85

Assay

≥98.0% (TLC)

form

powder or crystals

composition

carbon content, 76.40%
hydrogen content, 12.64%
nitrogen content, 2.47%

functional group

amide

lipid type

sphingolipids

shipped in

wet ice

storage temp.

−20°C

SMILES string

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

InChI

1S/C36H71NO3/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-36(40)37-34(33-38)35(39)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h29,31,34-35,38-39H,3-28,30,32-33H2,1-2H3,(H,37,40)/b31-29+/t34-,35+/m0/s1

InChI key

VODZWWMEJITOND-NXCSZAMKSA-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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Li-Pin Kao et al.
Journal of lipid research, 60(9), 1590-1602 (2019-08-01)
The combination of daunorubicin (dnr) and cytarabine (Ara-C) is a cornerstone of treatment for acute myelogenous leukemia (AML); resistance to these drugs is a major cause of treatment failure. Ceramide, a sphingolipid (SL), plays a critical role in cancer cell
M Mirzaian et al.
Clinica chimica acta; international journal of clinical chemistry, 466, 178-184 (2017-01-17)
Free sphingoid bases (lysosphingolipids) of primary storage sphingolipids are increased in tissues and plasma of several sphingolipidoses. As shown earlier by us, sphingoid bases can be accurately quantified using UPLC-ESI-MS/MS, particularly in combination with identical
Birgit Plochberger et al.
Langmuir : the ACS journal of surfaces and colloids, 26(22), 17322-17329 (2010-10-15)
We investigated the mobility and phase-partitioning of the fluorescent oxidized phospholipid analogue 1-palmitoyl-2-glutaroyl-sn-glycero-3-phospho-N-Alexa647-ethanolamine (PGPE-Alexa647) in supported lipid bilayers. Compared to the conventional phospholipid dihexadecanoylphosphoethanolamine (DHPE)-Bodipy we found consistently higher diffusion constants. The effect became dramatic when immobile obstacles were inserted
Emile Zakiev et al.
Journal of clinical lipidology, 13(3), 468-480 (2019-04-21)
Familial apolipoprotein A-I (apoA-I) deficiency (FAID) involving low levels of both apoA-I and high-density lipoprotein (HDL) cholesterol is associated with accelerated atherosclerosis. The objective of this study was to define distinctive patterns in the lipidome of HDL subpopulations in FAID
Erik B Watkins et al.
Biophysical journal, 114(5), 1103-1115 (2018-03-15)
The influence of carbohydrate structure on the ordering of glycosphingolipids (GSLs) and surrounding phospholipids was investigated in monolayers at the air-water interface. Binary mixtures composed of GSLs, chosen to span a range of carbohydrate complexity, and zwitterionic dipalmitoylphosphatidylcholine phospholipid, were
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