150338-90-2

Basic information

• Product Name: (2R,3S,4E)-2-(acetylamino)-4-octadecen-1,3-diol
• CAS NO: 150338-90-2
• Molecular Weight: 341.535
• Mol File: 150338-90-2.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (2R,3S,4E)-2-(acetylamino)-4-octadecen-1,3-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S,4E)-2-(acetylamino)-4-octadecen-1,3-diol(150338-90-2)
• EPA Substance Registry System: (2R,3S,4E)-2-(acetylamino)-4-octadecen-1,3-diol(150338-90-2)

Safety Data

• Hazardous Substances Data: 150338-90-2(Hazardous Substances Data)

Usage

General Description

(2R,3S,4E)-2-(acetylamino)-4-octadecen-1,3-diol, also known as palmitoleoyl ethanolamide, is a chemical compound with a long chain fatty acid and an amide group. It is a type of N-acyl ethanolamine, which are bioactive lipids involved in various physiological processes. This particular compound is an endogenous lipid found in the brain and other tissues, and is believed to play a role in regulating pain and inflammation. It has also been studied for its potential therapeutic effects in conditions such as Parkinson's disease and cancer. Additionally, it has been implicated in the modulation of appetite and energy metabolism, making it a potential target for obesity research.

Upstream product

• 94676-99-0 N-((1RS,2SR)-2-hydroxy-1-hydroxymethyl-heptadec-3-ynyl)-acetamide 
• 94676-99-0 N-((1RS,2RS)-2-hydroxy-1-hydroxymethyl-heptadec-3-ynyl)-acetamide 
• 143516-95-4 N-{(E)-(1R,2S)-2-Methoxymethoxy-1-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-heptadec-3-enyl}-acetamide 
• 143516-99-8 N-{(1R,2R)-3-Hydroxy-2-methoxymethoxy-1-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-propyl}-acetamide 
• 143516-94-3 N-{(1R,2R)-2-Methoxymethoxy-1-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-3-oxo-propyl}-acetamide 
• 201340-33-2 N-((E)-(1R,2S)-2-Hydroxy-1-hydroxymethyl-heptadec-3-enyl)-acetamide 
• 6036-75-5 (2R,3S,4E)-2-aminooctadec-4-ene-1,3-diol 
• 75-36-5 acetyl chloride 
• 128387-02-0 (2R,3S,4E)-2-acetylamino-1,3-diacetoxyoctadec-4-ene 
• 114697-01-7 (+/-)-N-(4t-pentadec-1-ynyl-2r-phenyl-[1,3]dioxan-5t-yl)-acetamide 
• 114697-01-7 (+/-)-N-(4c-pentadec-1-ynyl-2r-phenyl-[1,3]dioxan-5c-yl)-acetamide 
• 2482-37-3 (+/-)-erythro-1,3-diacetoxy-2-acetylamino-octadec-4c-ene 

Downstream Products

• 2482-37-3 (+/-)-erythro-1,3-diacetoxy-2-acetylamino-octadec-4c-ene 
• 2482-37-3 (+/-)-threo-1,3-diacetoxy-2-acetylamino-octadec-4c-ene 

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.

Syntheses of two pairs of enantiomeric C18-sphingosines and a palmitoyl analogue of gaucher spleen glucocerebroside

Sixteen kinds of chiral C4-epoxides [(-)-10a-d,(+)-10a-d,(-)-11a-d,(+)-11a-d], which are synthons in our synthetic strategy for complex lipids, have been prepared from (2Z)-2-butene-1,4-diol (6) by employing a Sharpless asymmetric epoxidation. By using the chiral C4-epoxides [(+)-10a,(-)-10a,(-)-11a,(+)-11a] as starting compounds, two pairs of enantiomeric (D-erythro, L-erythro, D-threo, and L-threo)-C18-sphingosines (1, 2, 3, 4) have been synthesized via a regioselective ring-opening of the epoxide ring with azide anion followed by reduction of the azide group to an amino group and a Wittig reaction. Furthermore, D-erythro-C18-sphingosine (1) has been converted to a palmitoyl analogue (5a) of Gaucher spleen glucocerebroside (5) through a reaction pathway including successive condensations with palmitic acid and D-glucose.

Diastereoselektive Synthese von D,L-Sphingosin

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