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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

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)

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’.

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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)
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
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
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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