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About This Item
Empirical Formula (Hill Notation):
C33H67NO2
CAS Number:
Molecular Weight:
509.89
MDL number:
UNSPSC Code:
12352211
NACRES:
NA.25
Product Name
N-C16-desoxymethylsphinganine, Avanti Research™ - A Croda Brand 860463P, powder
assay
>99% (TLC)
form
powder
packaging
pkg of 1 × 1 mg (860463P-1mg), pkg of 1 × 5 mg (860463P-5mg)
manufacturer/tradename
Avanti Research™ - A Croda Brand 860463P
lipid type
sphingolipids
bioactive lipids
shipped in
dry ice
storage temp.
−20°C
SMILES string
[H][C@](CCCCCCCCCCCCCCC)(O)CNC(CCCCCCCCCCCCCCC)=O
InChI
1S/C33H67NO2/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-32(35)31-34-33(36)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h32,35H,3-31H2,1-2H3,(H,34,36)/t32-/m1/s1
InChI key
SCCABQBVDWFVHP-JGCGQSQUSA-N
General description
N-C16-desoxymethylsphinganine is the N-acylated form of 1-desoxymethylsphinganine, a potent inhibitor of sphingolipid metabolism. Ceramide synthases (CerS) catalyzes the acylation of sphingoid bases using fatty acyl-CoA and its inhibition results in decrease of N-acylsphinganines (dihydroceramides) levels and accumulation of sphinganine. Dihydroceramides (DHCer) are intermediates of ceramide biosynthesis.
Biochem/physiol Actions
Dihydroceramides are also used for dihydrosphingolipids synthesis. Treatment of MCF7 cancer cells with fenretinide alters sphingolipid metabolism.
Packaging
5 mL Amber Glass Screw Cap Vial (860463P-1mg)
5 mL Amber Glass Screw Cap Vial (860463P-5mg)
Legal Information
Avanti Research is a trademark of Avanti Polar Lipids, LLC
Storage Class
11 - Combustible Solids
wgk
WGK 3
Regulatory Information
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Sphingolipidomics: a valuable tool for understanding the roles of sphingolipids in biology and disease
Merrill AH, et al.
Journal of Lipid Research, 50, S97-S102 (2009)
Thematic Review Series: Sphingolipids. Biodiversity of sphingoid bases (?sphingosines?) and related amino alcohols
Pruett ST, et al.
Journal of Lipid Research, 49(8), 1621-1639 (2008)
Noemi Jiménez-Rojo et al.
Biophysical journal, 107(12), 2850-2859 (2014-12-18)
Ceramides and dihydroceramides are N-acyl derivatives of sphingosine and sphinganine, respectively, which are the major sphingoid-base backbones of mammals. Recent studies have found that mammals, like certain other organisms, also produce 1-deoxy-(dihydro)ceramides (1-deoxyDHCers) that contain sphingoid bases lacking the 1-hydroxyl-
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 860463P-1MG | 04061835317042 |
| 860463P-5MG | 04061835317059 |