860461P
Avanti
N-C12-desoxymethylsphinganine
N-lauroyl-1-desoxymethylsphinganine (m17:0/12:0), powder
Synonym(s):
N-dodecanoyl-1-desoxymethylsphinganine (m17:0/12:0); N-C12-1-desoxyMeDHCer; 110959
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All Photos(2)
About This Item
Empirical Formula (Hill Notation):
C29H59NO2
CAS Number:
Molecular Weight:
453.78
UNSPSC Code:
12352211
NACRES:
NA.25
Assay
>99% (TLC)
form
powder
packaging
pkg of 1 × 1 mg (860461P-1mg)
manufacturer/tradename
Avanti Research™ - A Croda Brand 860461P
lipid type
sphingolipids
bioactive lipids
shipped in
dry ice
storage temp.
−20°C
General description
Commonly referred to as 1-desoxymethyldihydroceramide (1-desoxyMeDHCer), this product is the N-acylated form of 1-desoxymethylsphinganine, a potent inhibitor of sphingolipid metabolism. The biological activity of 1-desoxyMeDHCer is not clearly understood at this time.
N-C12-desoxymethylsphinganine commonly referred to as 1-deoxydihydroceramide (1-deoxyDHCer), is the N-acylated form of 1-deoxysphinganine, a potent inhibitor of sphingolipid metabolism.
Biochem/physiol Actions
Ceramide synthases (CerS) catalyzes the acylation of sphingoid bases using fatty acyl-CoA and its inhibition results in decrease of desoxymethylsphinganine (N-acylsphinganines (dihydroceramides)) levels and accumulation of sphinganine (Sa). Dihydroceramides (DHCer) are intermediates of ceramide biosynthesis.
Packaging
5 mL Amber Glass Screw Cap Vial (860461P-1mg)
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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Ceramide synthase inhibition by fumonisin B1 causes accumulation of 1-deoxysphinganine a novel category of bioactive 1-deoxysphingoid bases and 1-deoxydihydroceramides biosynthesized by mammalian cell lines and animals
Zitomer NC, et al.
The Journal of Biological Chemistry, 284(8), 4786-4795 (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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