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
MDL number:
UNSPSC Code:
12352211
PubChem Substance ID:
NACRES:
NA.77
Recommended Products
biological source
synthetic
Quality Level
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 Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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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
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
Jin Yao et al.
International journal of molecular sciences, 14(5), 10355-10368 (2013-05-21)
Ultraviolet (UV) radiation and reactive oxygen species (ROS) impair the physiological functions of retinal pigment epithelium (RPE) cells by inducing cell apoptosis, which is the main cause of age-related macular degeneration (AMD). The mechanism by which UV/ROS induces RPE cell
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
Nahuel Zamponi et al.
Traffic (Copenhagen, Denmark), 18(9), 604-621 (2017-07-12)
Our understanding of protein and lipid trafficking in eukaryotic cells has been challenged by the finding of different forms of compartmentalization and cargo processing in protozoan parasites. Here, we show that, in the absence of a Golgi compartment in Giardia
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