Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

H6524

Sigma-Aldrich

N-Hexanoyl-D-sphingosine

≥98% (TLC), synthetic

Synonym(s):

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Customers Also Viewed

Slide 1 of 1

1 of 1

GW4869 ≥90% (NMR)

Sigma-Aldrich

D1692

GW4869

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
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
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
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
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service