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C7980

Sigma-Aldrich

Dihydroceramide C2

≥97% (TLC), solid

Synonyme(s) :

D-erythro-N-Acetylsphinganine

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About This Item

Formule empirique (notation de Hill):
C20H41NO3
Poids moléculaire :
343.54
Numéro MDL:
MFCD00236495
Code UNSPSC :
12352211
ID de substance PubChem :
24892995
Nomenclature NACRES :
NA.77

Niveau de qualité

200

Pureté

≥97% (TLC)

Forme

solid

Couleur

white

Solubilité

DMSO: 5 mg/mL (Dissolve in hot DMSO, then cool to RT.)
ethanol: 5 mg/mL

Température de stockage

−20°C

Chaîne SMILES 

OC[C@]([H])(NC(C)=O)[C@]([H])(O)CCCCCCCCCCCCCCC

InChI

1S/C20H41NO3/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-20(24)19(17-22)21-18(2)23/h19-20,22,24H,3-17H2,1-2H3,(H,21,23)/t19-,20+/m0/s1

Clé InChI

CRJGESKKUOMBCT-VQTJNVASSA-N

Application

Dihydroceramide C2 has been used as a:
  • negative control to study its effects on dopaminergic neuroblastoma cells
  • negative control to study its effects on acrosomal exocytosis in boar spermatozoa
  • ceramide precursor to study its effects on mitochondrial cell death in yeast

Actions biochimiques/physiologiques

Dihydroceramide C2 is a precursor of ceramide.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

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Consulter la Bibliothèque de documents

T Shimada et al.
Life sciences, 68(5), 539-546 (2001-02-24)
Forced overexpression of cyclooxygenase-2 (COX-2) in intestinal cells has been shown to be associated with resistance to apoptosis. However, the role of physiologically-induced COX-2 in the regulation of apoptosis remains unclear. In the present study, we examined whether hepatocyte growth
Tetsuma Murase et al.
The Journal of reproduction and development, 50(6), 667-674 (2005-01-14)
Mammalian spermatozoa must undergo acrosomal exocytosis prior to penetration of the oocyte at fertilization. The mechanisms underlying acrosomal exocytosis have not yet been fully elucidated. This study explored the possible involvement of ceramide in exocytosis of the boar sperm acrosome.
L R Vann et al.
The Journal of biological chemistry, 275(18), 13275-13281 (2000-05-02)
Synthesis of 6(R)-5,6,7,8-tetrahydrobiopterin (BH(4)), a required cofactor for inducible nitric-oxide synthase (iNOS) activity, is usually coordinately regulated with iNOS expression. In C6 glioma cells, tumor necrosis factor-alpha (TNF-alpha) concomitantly potentiated the stimulation of nitric oxide (NO) and BH(4) production induced
Didac Carmona-Gutierrez et al.
Cell cycle (Georgetown, Tex.), 10(22), 3973-3978 (2011-11-11)
The activation of ceramide-generating enzymes, the blockade of ceramide degradation, or the addition of ceramide analogues can trigger apoptosis or necrosis in human cancer cells. Moreover, endogenous ceramide plays a decisive role in the killing of neoplastic cells by conventional
Pratyusha Mandal et al.
Immunity, 49(1), 42-55 (2018-07-19)
The execution of shock following high dose E. coli lipopolysaccharide (LPS) or bacterial sepsis in mice required pro-apoptotic caspase-8 in addition to pro-pyroptotic caspase-11 and gasdermin D. Hematopoietic cells produced MyD88- and TRIF-dependent inflammatory cytokines sufficient to initiate shock without any
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