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H6524

Sigma-Aldrich

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
MDL number:
MFCD00870174
UNSPSC Code:
12352211
PubChem Substance ID:
24895750
NACRES:
NA.77

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 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

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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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
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
Joffrey De Larichaudy et al.
Skeletal muscle, 2(1), 2-2 (2012-01-20)
Muscle atrophy associated with various pathophysiological conditions represents a major health problem, because of its contribution to the deterioration of patient status and its effect on mortality. Although the involvement of pro-inflammatory cytokines in this process is well recognized, the
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