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:
Molecular Weight:
397.63
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352211
MDL number:
Assay:
≥98% (TLC)
Quality level:
Quality Level
biological source
synthetic
assay
≥98% (TLC)
lipid type
sphingolipids
storage temp.
−20°C
SMILES string
OC[C@]([H])(NC(CCCCC)=O)[C@]([H])(O)/C=C/CCCCCCCCCCCCC
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
InChI key
NPRJSFWNFTXXQC-QFWQFVLDSA-N
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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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
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
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