860469P
Avanti
3-deoxy sphingosine
Avanti Research™ - A Croda Brand 860469P, powder
Synonym(s):
(R,E)-2-aminooctadec-4-en-1-ol
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About This Item
Empirical Formula (Hill Notation):
C18H37NO
CAS Number:
Molecular Weight:
283.49
UNSPSC Code:
12352211
NACRES:
NA.25
Recommended Products
form
powder
packaging
pkg of 1 × 1 mg (860469P-1mg)
manufacturer/tradename
Avanti Research™ - A Croda Brand 860469P
lipid type
sphingolipids
shipped in
dry ice
storage temp.
−20°C
SMILES string
CCCCCCCCCCCCC/C=C/C[C@@H](N)CO
General description
3-deoxy-sphingosine is a structural analog of the long chain sphingoid base, sphingosine. It has four diastereoisomer, namely (R,E)-,(R,Z)-,(S,E)-,(S,Z)-produced from D- and L-serine.
Application
3-deoxy sphingosine has been used in the synthesis of ceramide analogs.
Packaging
5 mL Amber Glass Screw Cap Vial (860469P-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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Synthesis of sphingosine analogues: stereoselective synthesis of 3-deoxysphingosine and cis-isomers.
T Kawate et al.
Chemical & pharmaceutical bulletin, 45(12), 2116-2118 (1998-01-20)
Lukasz Japtok et al.
Allergo journal international, 23(2), 54-59 (2014-01-01)
Sphingolipids are essential molecules of the mammalian epidermis. Keratinocytes generate and secrete huge amounts of ceramide-precursors to the extracellular domain of the stratum corneum, where they are further metabolized to specific ceramide species. The arrangement of ceramides to well-organized lipid
Andrej Kováčik et al.
Scientific reports, 10(1), 3832-3832 (2020-03-04)
Ceramides (Cer) are essential components of the skin permeability barrier. To probe the role of Cer polar head groups involved in the interfacial hydrogen bonding, the N-lignoceroyl sphingosine polar head was modified by removing the hydroxyls in C-1 (1-deoxy-Cer) or
William J Valentine et al.
Methods in molecular biology (Clifton, N.J.), 874, 77-87 (2012-04-25)
Intracellular Ca(2+) mobilization is a useful readout to screen for agonists or antagonists of G-protein -coupled receptors (GPCRs). Here, we describe methods to conduct high-throughput screening of stably or transiently transfected HTC4 cells expressing the individual S1P1-5 receptor subtypes. The
Anna Mouts et al.
Langmuir : the ACS journal of surfaces and colloids (2018-12-07)
Ceramides are important intermediates in sphingolipid biosynthesis (and degradation) and are normally present in only small amounts in unstressed cells. However, following receptor-mediated activation of neutral sphingomyelinase, sphingomyelin can acutely give rise to substantial amounts of ceramides, which dramatically alter
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