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About This Item
Empirical Formula (Hill Notation):
C20H41NO2
CAS Number:
Molecular Weight:
327.55
MDL number:
UNSPSC Code:
12352211
NACRES:
NA.25
Product Name
Sphingosine (d20:1), Avanti Research™ - A Croda Brand 860660P, powder
Assay
>99% (TLC)
form
powder
packaging
pkg of 1 × 5 mg (860660P-5mg)
manufacturer/tradename
Avanti Research™ - A Croda Brand 860660P
lipid type
sphingolipids
shipped in
dry ice
storage temp.
−20°C
SMILES string
OC[C@@](N)([H])[C@]([H])(O)/C=C/CCCCCCCCCCCCCCC
InChI
1S/C20H41NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)19(21)18-22/h16-17,19-20,22-23H,2-15,18,21H2,1H3/b17-16+/t19-,20+/m0/s1
InChI key
HTJSZHKGNMXZJN-YIVRLKKSSA-N
General description
Sphingosine (d20:1), also known as icosasphingosine, is a synthetic sphingosine with 20 carbon long chain bases (LCB). It is directly produced by the sphingolipid de novo synthesis pathway and not by hydrolysis of complex sphingolipids. In higher animals, it is one of the most abundant sphingoid bases of gangliosides.
Application
Sphingosine (d20:1) has been used as a reference substance in liquid chromatography/tandem mass spectrometry analysis to quantitatively analyze sphingolipids with C20- long chain bases in human central nervous tissue.
Biochem/physiol Actions
Sphingosine (d20:1) or C20-sphingosine acts as an intermediate in the synthesis of ceramides, which are vital components of mammalian epidermis. It may be involved in regulation of epidermal differentiation. C20 long chain bases-containing sphingolipids might exhibit detrimental effect on protein homeostasis and neural functions.
Packaging
5 mL Amber Glass Screw Cap Vial (860660P-5mg)
Legal Information
Avanti Research is a trademark of Avanti Polar Lipids, LLC
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
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De novo sphingolipid biosynthesis: a necessary, but dangerous, pathway.
Alfred H Merrill
The Journal of biological chemistry, 277(29), 25843-25846 (2002-05-16)
Lihong Zhao et al.
Proceedings of the National Academy of Sciences of the United States of America, 112(42), 12962-12967 (2015-10-07)
Sphingolipids typically have an 18-carbon (C18) sphingoid long chain base (LCB) backbone. Although sphingolipids with LCBs of other chain lengths have been identified, the functional significance of these low-abundance sphingolipids is unknown. The LCB chain length is determined by serine
P W Wertz et al.
Biochimica et biophysica acta, 1002(2), 213-217 (1989-04-03)
Sphingosines and phytosphingosines serve as intermediates in the synthesis of ceramides and glucosylceramides, which are prominent components of mammalian epidermis. In the present study, we have investigated the possibility that free sphingoid bases also may be present in epidermal tissue.
Thomas Kolter
ISRN biochemistry, 2012, 506160-506160 (2012-01-01)
Gangliosides are sialic acid-containing glycosphingolipids. They occur especially on the cellular surfaces of neuronal cells, where they form a complex pattern, but are also found in many other cell types. The paper provides a general overview on their structures, occurrence
Rajkumar Vutukuri et al.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 34(3), 3932-3942 (2020-01-17)
Sphingosine 1-phosphate (S1P) signaling influences numerous cell biological mechanisms such as differentiation, proliferation, survival, migration, and angiogenesis. Intriguingly, our current knowledge is based solely on the role of S1P with an 18-carbon long-chain base length, S1P d18:1. Depending on the
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