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Merck

H6524

Sigma-Aldrich

N-Hexanoyl-D-sphingosine

≥98% (TLC), synthetic

Synonym(e):

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

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About This Item

Empirische Formel (Hill-System):
C24H47NO3
CAS-Nummer:
Molekulargewicht:
397.63
MDL-Nummer:
UNSPSC-Code:
12352211
PubChem Substanz-ID:
NACRES:
NA.77

Biologische Quelle

synthetic

Qualitätsniveau

Assay

≥98% (TLC)

Lipid-Typ

sphingolipids

Lagertemp.

−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

InChIKey

NPRJSFWNFTXXQC-QFWQFVLDSA-N

Biochem./physiol. Wirkung

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

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Gloves, type N95 (US)


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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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