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Merck

H6524

N-Hexanoyl-D-sphingosine

≥98% (TLC), synthetic

Synonym(s):

C6 ceramide, Caproyl ceramide, N-Caproyl-D-sphingosine

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About This Item

Empirical Formula (Hill Notation):
C24H47NO3
CAS Number:
124753-97-5
Molecular Weight:
397.63
NACRES:
NA.77
PubChem Substance ID:
24895750
UNSPSC Code:
12352211
MDL number:
MFCD00870174

Product Name

N-Hexanoyl-D-sphingosine, ≥98% (TLC), synthetic

Quality Level

200

InChI

1S/C24H47NO3/c1-3-5-7-8-9-10-11-12-13-14-15-16-18-19-23(27)22(21-26)25-24(28)20-17-6-4-2/h18-19,22-23,26-27H,3-17,20-21H2,1-2H3,(H,25,28)/b19-18+/t22-,23+/m0/s1

SMILES string

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

InChI key

NPRJSFWNFTXXQC-QFWQFVLDSA-N

biological source

synthetic

assay

≥98% (TLC)

lipid type

sphingolipids

storage temp.

−20°C

Biochem/physiol Actions

Cell-permeable analog of ceramide; stimulates protein phosphatase 2A; activates MAP kinase; induces apoptosis in human leukemia HL-60 cells

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000432231
0000432231
0000324763
0000324763
SLBG9063V

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Gemma Villorbina et al.
Bioorganic & medicinal chemistry, 15(1), 50-62 (2006-11-04)
Solid-phase synthesis of a small combinatorial library of dihydroceramide analogues as mixtures of erythro and threo diastereomers is described. Some dihydroceramide analogues cause growth arrest and apoptosis in a dose-dependent manner in human alveolar epithelial cells. This activity is likely
K Pahan et al.
Journal of neurochemistry, 73(2), 513-520 (1999-07-31)
The present study reports the effect of ceramide generated by hydrolysis of membrane sphingomyelin with bacterial sphingomyelinase (SMase) and of cell-permeable ceramide analogues on the expression of manganese superoxide dismutase (MnSOD). Incubation of the rat primary astrocytes with SMase led
C J Lo et al.
Shock (Augusta, Ga.), 11(6), 411-415 (1999-08-24)
Metabolism of macrophage (MO) membrane phospholipids produces key mediators of inflammation and major second messengers that modulate inflammatory responses during sepsis. Sphingomyelin is a major class of phospholipid that releases ceramide and sphingosine. This study was designed to investigate the
Daisuke Yamaguchi et al.
Scientific reports, 9(1), 7742-7742 (2019-05-28)
Phenotypic screening in drug discovery has been revived with the expectation of providing promising lead compounds and drug targets and improving the success rate of drug approval. However, target identification remains a major bottleneck in phenotype-based drug discovery. We identified
Susanne Vetterkind et al.
Scientific reports, 7(1), 9302-9302 (2017-08-26)
Ceramide, a bioactive lipid and signaling molecule associated with cardiovascular disease, is known to activate extracellular signal regulated kinases 1 and 2 (ERK1/2). Here, we determined that the effect of ceramide on ERK1/2 is mediated by ceramide signaling on an
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