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860469P

Avanti

3-deoxy sphingosine

Avanti Research™ - A Croda Brand 860469P, powder

Synonyma:

(R,E)-2-aminooctadec-4-en-1-ol

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About This Item

Empirický vzorec (Hillův zápis):
C18H37NO
Číslo CAS:
126624-36-0
Molekulová hmotnost:
283.49
MDL number:
MFCD28143633
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

InChI

1S/C18H37NO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-18(19)17-20/h14-15,18,20H,2-13,16-17,19H2,1H3/b15-14+/t18-/m1/s1

InChI key

LRKJGQMJFYRTHF-LGHUBQEGSA-N

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

11 - Combustible Solids

wgk_germany

WGK 3

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Lot/Batch Number

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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
Tania C B Santos et al.
Langmuir : the ACS journal of surfaces and colloids, 36(21), 6007-6016 (2020-05-06)
Compared to the canonical sphingoid backbone of sphingolipids (SLs), atypical long-chain bases (LCBs) lack C1-OH (1-deoxy-LCBs) or C1-CH2OH (1-deoxymethyl-LCBs). In addition, when unsaturated, they present a cis-double bond instead of the canonical  Δ4-5 trans-double bond. These atypical LCBs are directly
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