2673-72-5

Basic information

• Product Name: D-SPHINGOSINE HCL
• Synonyms: TRANS-D-ERYTHRO-2-AMINO-4-OCTADECENE-1,3-DIOL HCL;D-SPHINGOSINE HCL;D-erythro-Sphingosine hydrochloride, 97%;D-Sphingosine hydrochloride;D-Sphingosine/HCl: trans-D-erythro-2-Amino-4-octadecene-1,3-diol/HCl
• CAS NO: 2673-72-5
• Molecular Formula: C₁₈H₃₇NO₂*ClH
• Molecular Weight: 335.95
• Mol File: 2673-72-5.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: D-SPHINGOSINE HCL(CAS DataBase Reference)
• NIST Chemistry Reference: D-SPHINGOSINE HCL(2673-72-5)
• EPA Substance Registry System: D-SPHINGOSINE HCL(2673-72-5)

Safety Data

• Hazardous Substances Data: 2673-72-5(Hazardous Substances Data)

Usage

Uses

Inhibitor of protein kinase C and calmodulin-dependent enzymes, but may stimulate mast cells by activation of protein kinase C

Upstream product

• 115464-03-4 tert-butyl (4S)-4-[(1R,2E)-1-hydroxy-2-hexadecenyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate 
• 116467-63-1 N-tert-butyloxycarbonylsphingosine 
• 20717-86-6 triisopropoxytitanium(IV) chloride 
• 3163-37-9 (E)-hexadec-2-enal 
• 124-25-4 myristylaldehyde 
• 26993-32-8 (E)-hexadec-2-en-1-ol 
• 113890-30-5 2-((E)-((1S,2S,5S)-2-hydroxy-2,6,6-trimethylbicyclo[3.1.1]heptan-3-ylidene)amino) acetate 
• 112-72-1 1-Tetradecanol 

Downstream Products

• 103348-49-8 2-azido-sphingosine 
• 16170-10-8 N-myristoylceramide 
• 4201-58-5 (2S,3R,4E)-2-(hexadecanoylamido)-4-octadecene-1,3-diol 
• 54336-64-0 (2S,3R,4E)-2-(N-stearoylamino)-4-octadecene-1,3-diol 
• 111122-57-7 Cer(d18:1/10:0) 
• 74713-60-3 N-lauroylceramide 
• 74713-59-0 N-octanoylsphingosine 
• 3102-57-6 N-acetyl-D-erythro-sphingosine 
• 2482-37-3 (2S,3R,4E)-2-acetamido-1,3-diacetoxyoctadec-4-ene 
• 1294447-01-0 N-((2S,3R,4E)-1,3-dihydroxyoctadec-4-en-2-yl)-2-phenylacetamide 
• 109785-20-8 O-(β-D-galactopyranosyl)-(1→4)-(β-D-glucopyranosyl)-(1→1)-(2S, 3R, 4E)-2-aminooctadec-4-ene-1,3-diol 
• 1239518-22-9 (2S,3R,4E)-2-((E)-benzylideneamino)octadec-4-ene-1,3-diol 

Relevant articles and documents

Chiral combinatorial preparation and biological evaluation of unique ceramides for inhibition of sphingomyelin synthase

Enantiomers or diastereomers of chiral bioactive compounds often exhibit different biological and toxicological properties. Here, we report the efficient synthesis of four stereoisomers of sphingosine and derivatization of unique chiral ceramides through a combinatorial chemistry by solid-phase activated resin ester. In addition, to test the effectivity of stereochemistry of ceramide, we demonstrated a cell-based assay of sphingomyelin synthase inhibition in the presence ofchiral unique ceramides, which suggested that libraries of this sort will be a rich source of biologically active synthetic molecules.

Studies on the inhibition of sphingosine-1-phosphate lyase by stabilized reaction intermediates and stereodefined azido phosphates

Two kinds of inhibitors of the PLP-dependent enzyme sphingosine-1-phosphate lyase have been designed and tested on the bacterial (StS1PL) and the human (hS1PL) enzymes. Amino phosphates 1, 12, and 32, mimicking the intermediate aldimines of the catalytic process, were weak inhibitors on both enzyme sources. On the other hand, a series of stereodefined azido phosphates, resulting from the replacement of the amino group of the natural substrates with an azido group, afforded competitive inhibitors in the low micromolar range on both enzyme sources. This similar behavior represents an experimental evidence of the reported structural similarities for both enzymes at their active site level. Interestingly, the anti-isomers of the non-natural enantiomeric series where the most potent inhibitors on hS1PL.

METHODS FOR THE SYNTHESIS OF SPHINGOMYELINS AND DIHYDROSPHINGOMYELINS

The present invention includes methods for the synthesis of sphingomyelins and dihydrosphingomyelins. The present invention also includes methods for the synthesis of sphingosines and dihydrosphingosines. The present invention further includes methods for the synthesis of ceramides and dihydroceramides.