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58199

Sigma-Aldrich

N-Lauroyl-D-sphingosine

≥98.0% (TLC)

Synonym(s):

Cer(d18:1/12:0), (2S,3R,4E)-2-(Lauroylamino)-4-octadecene-1,3-diol, N-Dodecanoyl-D-sphingosine, N-Lauroyl-D-erythro-sphingosine, N-[(1S,2R,3E)-2-Hydroxy-1-(hydroxymethyl)-3-heptadecen-1-yl]dodecanamide, C12 Ceramide (d18:1/12:0), C12-Ceramide

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About This Item

Empirical Formula (Hill Notation):
C30H59NO3
CAS Number:
74713-60-3
Molecular Weight:
481.79
Beilstein:
1717021
MDL number:
MFCD02259133
UNSPSC Code:
12352211
PubChem Substance ID:
329758407

Assay

≥98.0% (TLC)

composition

carbon content, 74.79%
hydrogen content, 12.34%
nitrogen content, 2.91%

lipid type

sphingolipids

storage temp.

−20°C

SMILES string

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

InChI

1S/C30H59NO3/c1-3-5-7-9-11-13-14-15-16-18-19-21-23-25-29(33)28(27-32)31-30(34)26-24-22-20-17-12-10-8-6-4-2/h23,25,28-29,32-33H,3-22,24,26-27H2,1-2H3,(H,31,34)/b25-23+/t28-,29+/m0/s1

InChI key

HXFPPRPLRSPNIB-VARSQMIESA-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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T Momoi et al.
The Biochemical journal, 205(2), 419-425 (1982-08-01)
The specific activity of acid ceramidase (N-acylsphingosine deacylase, EC 3.5.1.23) was measured at pH4.5 in normal fibroblasts and in fibroblasts from patients with Farber disease and obligate heterozygotes. Greater activity was found when the synthetically made ceramide substrates contained shorter-chain
Sandra Buratta et al.
PloS one, 12(11), e0188840-e0188840 (2017-11-29)
Cells release extracellular vesicles (EVs) in their environment and cellular lipids play an important role in their formation, secretion and uptake. Besides, there is also evidence that EV transferred lipids impact on recipient's cell signaling. Cellular senescence is characterized by
Jin Park et al.
Biochemical pharmacology, 71(8), 1229-1239 (2006-02-02)
Allergic diseases are hypersensitivity disorders that are associated with the generation of specific immunoglobulin E (IgE) in response to environmental allergens. Interleukin (IL)-4, which is primarily produced by the CD4(+) T cells, is an important stimulus for the switching of
G van Echten-Deckert et al.
Journal of lipid research, 38(12), 2569-2579 (1998-02-11)
De novo synthesis and turnover of endogenous ceramide in cultured skin fibroblasts from patients affected with Farber lipogranulomatosis were studied by biosynthetical labeling of cellular sphingolipids with [14C]serine. The cellular uptake of [14C]serine and incorporation into de novo synthesized ceramide
Eunice W M Chin et al.
Neuromolecular medicine, 18(3), 364-377 (2016-07-06)
Rett syndrome (RTT) is a postnatal neurodevelopmental disorder that primarily affects girls. Mutations in the methyl-CpG-binding protein 2 (MECP2) gene account for approximately 95 % of all RTT cases. To model RTT in vitro, we generated induced pluripotent stem cells (iPSCs)
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