6918-49-6

Basic information

• Product Name: (2S,3R,E)-2-Amino-4-icosene-1,3-diol
• Synonyms: (2S,3R,E)-2-Amino-4-icosene-1,3-diol;C20-Sphingosine;Eicosasphingenine;Gangliosphingosine;D-erythro-Sphingosine C-20;D-erythro-sphingosine (C20 base);(2S,3R,4E)-2-Amino-4-eicosene-1,3-diol;(2S,3R,4E)-4-Icosasphingenine
• CAS NO: 6918-49-6
• Molecular Formula: C₂₀H₄₁NO₂
• Molecular Weight: 327.6
• Mol File: 6918-49-6.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• Storage Temp.: ?20°C
• BRN: 3547228
• CAS DataBase Reference: (2S,3R,E)-2-Amino-4-icosene-1,3-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3R,E)-2-Amino-4-icosene-1,3-diol(6918-49-6)
• EPA Substance Registry System: (2S,3R,E)-2-Amino-4-icosene-1,3-diol(6918-49-6)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 6918-49-6(Hazardous Substances Data)

Usage

Description

Sphingosines are long-chain base precursors of cellular sphingolipids used directly in the synthesis of ceramide, which in combination with sialic acid forms ganglioside. Sphingosine can exist in four stereoisomers, however only sphingosine occurs naturally. Compared to other sphingolipids throughout the body, which are predominantly composed of C-18 sphingosine, only central nervous system (CNS) gangliosides contain significant amounts of sphingosine. The concentration of sphingosine within mammalian brain gangliosides apparently increases with developmental maturation. Furthermore, the ratio of C-18 to C-20 sphingosine in the brain is thought to be related to some nervous system degeneration processes.

Uses

Different sources of media describe the Uses of 6918-49-6 differently. You can refer to the following data:
1. 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.
2. D-erythro-Sphingosine-C20 is an antagonist in cell-signaling functions however it displays an opposite modulation of cathepsin D.

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.

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.

Upstream product

• 115822-53-2 O,N-isopropylidene-N-(tert-butoxycarbonyl)-C₂₀-D-erythro-sphingosine 
• 103411-92-3 (2S,3R,4E)-2-Azido-4-icosadecen-1,3-diol 
• 132910-83-9 tert-Butyl (4S,1'R)-2,2-dimethyl-4-(1'-hydroxy-2'-octadecynyl)-3-oxazolidinecarboxylate 
• 128751-67-7 <2(S),3(R),4E>-2-amino-2-N,3-O-carbonyl-4-eicosene-1,3-diol 
• 103411-89-8 (2R,3R,4E)-1,3-O-Benzyliden-4-icosadecen-1,2,3-triol 
• 103411-91-2 (2S,3R,4E)-2-Azido-1,3-O-benzyliden-4-icosadecen-1,3-diol 
• 103411-90-1 hexadecanyltriphenylphosphonium iodide 
• 67-56-1 methanol 

Downstream Products

• 132910-87-3 (2S,3R,4E)-N-Trichloroacetyl-3-O-(tert-butyldiphenylsilyl)-4-icosasphingosine 
• 132910-86-2 (2S,3R,4E)-N-Trichloroacetyl-1-O-trityl-4-icosasphingenine 
• 132910-98-6 (2S,3R,4E)-1-O-(β-D-Glucopyranosyl)-3-O-(tert-butyldiphenylsilyl)-4-icosasphingenine 
• 142921-04-8 N-[(E)-(1S,2R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-trityloxymethyl-nonadec-3-enyl]-2,2,2-trichloro-acetamide 
• 132910-97-5 (2S,3R,4E)-N-Trichloroacetyl-1-O-(tetra-O-acetyl-β-D-glucopyranosyl)-3-O-(tert-butyldiphenylsilyl)-4-icosasphingenine 

Relevant articles and documents

New cytotoxic cerebrosides from the red sea cucumber Holothuria spinifera supported by in-silico studies

Bioactivity-guided fractionation of a methanolic extract of the Red Sea cucumber Holothuria spinifera and LC-HRESIMS-assisted dereplication resulted in the isolation of four compounds, three new cerebrosides, spiniferosides A (1), B (2), and C (3), and cholesterol sulfate (4). The chemical structures of the isolated compounds were established on the basis of their 1D NMR and HRMS spectral data. Metabolic profiling of the H. spinifera extract indicated the presence of diverse secondary metabolites, mostly hydroxy fatty acids, diterpenes, triterpenes, and cerebrosides. The isolated compounds were tested for their in vitro cytotoxicities against the breast adenocarcinoma MCF-7 cell line. Compounds 1, 2, 3, and 4 displayed promising cytotoxic activities against MCF-7 cells, with IC50 values of 13.83, 8.13, 8.27, and 35.56 μM, respectively, compared to that of the standard drug doxorubicin (IC50 8.64 μM). Additionally, docking studies were performed for compounds 1, 2, 3, and 4 to elucidate their binding interactions with the active site of the SET protein, an inhibitor of protein phosphatase 2A (PP2A), which could explain their cytotoxic activity. This study highlights the important role of these metabolites in the defense mechanism of the sea cucumber against fouling organisms and the potential uses of these active molecules in the design of new anticancer agents.

Process for the preparation of sphingosine derivatives

The invention relates to a new process for the preparation of the sphingosine derivatives described in European Patent Application No. 146,810, of the formula: STR1 It comprises protecting D-galactose in the 4,6-position and oxidizing it to the corresponding D-threose protected in the 2,4-position, condensing an aliphatic chain (R3) onto the latter by a Wittig reaction, converting the free hydroxyl group into a azido group and splitting off the protective group, protecting the resulting 2-azido-1,3-dihydroxy compound selectively in the 1-position and blocking it in the 3-position, liberating the 1-hydroxy group again, glycosidating the resulting compound or the abovementioned 2-azido-1,3-dihydroxy compound with the 0-trifluoro- or 0-trichloro-acetimade or the 1-halogen derivative of a 2,3,4,6-0-tetraacyl-D-glucose, splitting off the acyl groups of these and the protective group in the 3-position, converting the azido group into an amino group and acylating the amino compound with a fatty acid R1 --OH. The process gives the compounds of the therapeutically more active D series in a high yield in relatively few stages without resolving diastereomers.

An efficient, stereoselective synthesis of 4-E- and 4-Z-D-erythro-sphingenine and related compounds from 2-amino-2-deoxy-D-glucose.

Efficient, stereoselective synthesis of 4-E- and 4-Z-D-erythro-sphingenines having C16, C18, and C20 carbon-chains was achieved in 13 steps, starting from allyl 2-benzyloxycarbonylamino-2-deoxy-alpha-D-glucopyranoside. 2-Amino-1,6-di-O-tert- butyldiphenylsilyl-2-N,3-O-carbonyl-2-deoxy-D -allitol was used as the key intermediate.