860463P
Avanti
N-C16-desoxymethylsphinganine
Avanti Polar Lipids 860463P, powder
Synonym(s):
N-palmitoyl-1-desoxymethylsphinganine (m17:0/16:0)
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About This Item
Empirical Formula (Hill Notation):
C33H67NO2
CAS Number:
Molecular Weight:
509.89
UNSPSC Code:
12352211
NACRES:
NA.25
form
powder
packaging
pkg of 1 × 1 mg (860463P-1mg)
pkg of 1 × 5 mg (860463P-5mg)
manufacturer/tradename
Avanti Polar Lipids 860463P
lipid type
sphingolipids
bioactive lipids
shipped in
dry ice
storage temp.
−20°C
SMILES string
[H][C@](CCCCCCCCCCCCCCC)(O)CNC(CCCCCCCCCCCCCCC)=O
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 Code
11 - Combustible Solids
WGK
WGK 3
Certificates of Analysis (COA)
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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-
Sarah T Pruett et al.
Journal of lipid research, 49(8), 1621-1639 (2008-05-24)
"Sphingosin" was first described by J. L. W. Thudichum in 1884 and structurally characterized as 2S,3R,4E-2-aminooctadec-4-ene-1,3-diol in 1947 by Herb Carter, who also proposed the designation of "lipides derived from sphingosine as sphingolipides." This category of amino alcohols is now
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