Skip to Content
MilliporeSigma
All Photos(1)

Documents

C7980

Sigma-Aldrich

Dihydroceramide C2

≥97% (TLC), solid

Synonym(s):

D-erythro-N-Acetylsphinganine

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

About This Item

Empirical Formula (Hill Notation):
C20H41NO3
Molecular Weight:
343.54
MDL number:
MFCD00236495
UNSPSC Code:
12352211
PubChem Substance ID:
24892995
NACRES:
NA.77

Quality Level

200

assay

≥97% (TLC)

form

solid

color

white

solubility

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

storage temp.

−20°C

SMILES string

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

InChI key

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

Biochem/physiol Actions

Dihydroceramide C2 is a precursor of ceramide.

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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

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
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
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
Elisa Ferrari et al.
Molecular cell, 67(2), 266-281 (2017-06-27)
Mec1
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