6982-09-8

Basic information

• Product Name: (2S,3R,4E)-2-Amino-4-hexadecene-1,3-diol
• Synonyms: (2S,3R,4E)-2-Amino-4-hexadecene-1,3-diol;(2S,3R,E)-2-Amino-4-hexadecene-1,3-diol;16:Sphingosine;C16-Sphingosine;Hexadecasphing-4-enine;Hexadecasphingenine;(E,2S,3R)-2-aminohexadec-4-ene-1,3-diol
• CAS NO: 6982-09-8
• Molecular Formula: C16H33NO2
• Molecular Weight: 271.44
• Mol File: 6982-09-8.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (2S,3R,4E)-2-Amino-4-hexadecene-1,3-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3R,4E)-2-Amino-4-hexadecene-1,3-diol(6982-09-8)
• EPA Substance Registry System: (2S,3R,4E)-2-Amino-4-hexadecene-1,3-diol(6982-09-8)

Safety Data

• Hazardous Substances Data: 6982-09-8(Hazardous Substances Data)

Usage

Uses

C16-Sphingosine has shown cytotoxicity towards human colon cancer cells.

Upstream product

• 709026-56-2 (E)-(S)-1-(tert-Butyl-dimethyl-silanyloxy)-2-(trityl-amino)-hexadec-4-en-3-one 
• 67-56-1 methanol 
• 112-54-9 Dodecanal 
• 128745-52-8 <2(S),3(R),4E>-2-amino-2-N,3-O-carbonyl-4-hexadecene-1,3-diol 

Downstream Products

• 709026-60-8 sphingosine-1-phosphate 

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.

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.