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

(2S,3R,E)-2-Amino-4-icosene-1,3-diol is a chiral amino alcohol with a specific stereochemistry, featuring a 2S, 3R configuration and an E geometry of the double bond. It is a long-chain molecule with 20 carbon atoms, making it a component of various biologically active compounds and a potential candidate for pharmaceutical and chemical applications.

Uses

Used in Pharmaceutical Industry:
(2S,3R,E)-2-Amino-4-icosene-1,3-diol is used as a chiral building block for the synthesis of various pharmaceutical compounds, including drugs targeting the central nervous system and other therapeutic areas. Its unique stereochemistry allows for the creation of enantiomerically pure compounds with specific biological activities.
Used in Chemical Industry:
(2S,3R,E)-2-Amino-4-icosene-1,3-diol is used as a chiral ligand or catalyst in asymmetric synthesis, enabling the production of enantiomerically pure compounds with high selectivity. This is particularly important in the synthesis of active pharmaceutical ingredients (APIs) and other chiral molecules with specific biological properties.
Used in Research and Development:
(2S,3R,E)-2-Amino-4-icosene-1,3-diol is used as a reference compound in the development and optimization of analytical methods for the separation and detection of chiral compounds. Its unique stereochemistry makes it a valuable tool for studying the behavior of chiral molecules in various chemical and biological systems.
Used in Cosmetic Industry:
(2S,3R,E)-2-Amino-4-icosene-1,3-diol can be used as a chiral ingredient in cosmetic formulations, providing specific benefits based on its stereochemistry. Its long-chain structure may contribute to the development of novel cosmetic products with improved properties, such as enhanced skin penetration or targeted delivery of active ingredients.

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

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

Downstream Products

• 132910-97-5 (2S,3R,4E)-N-Trichloroacetyl-1-O-(tetra-O-acetyl-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 
• 132910-98-6 (2S,3R,4E)-1-O-(β-D-Glucopyranosyl)-3-O-(tert-butyldiphenylsilyl)-4-icosasphingenine 
• 132910-86-2 (2S,3R,4E)-N-Trichloroacetyl-1-O-trityl-4-icosasphingenine 
• 132910-87-3 (2S,3R,4E)-N-Trichloroacetyl-3-O-(tert-butyldiphenylsilyl)-4-icosasphingosine 

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.