536-14-1

Basic information

• Product Name: N-palmitoyl-D-erythro-sphingomyelin
• CAS NO: 536-14-1
• Molecular Weight: 703.04
• Mol File: 536-14-1.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: N-palmitoyl-D-erythro-sphingomyelin(CAS DataBase Reference)
• NIST Chemistry Reference: N-palmitoyl-D-erythro-sphingomyelin(536-14-1)
• EPA Substance Registry System: N-palmitoyl-D-erythro-sphingomyelin(536-14-1)

Safety Data

• Hazardous Substances Data: 536-14-1(Hazardous Substances Data)

Upstream product

• 75-50-3 trimethylamine 
• 127028-37-9 (2S,3R,4E)-2-hexadecanoylamino-1-phosphorylcholine-3-(tert-butyldimethylsilyloxy)-octadecene 
• 875112-70-2 2-bromoethyl (2S)-N-(1-oxohexadecyl)amino-(3R)-hydroxy-(4E)-octadecenyl methyl phosphate 
• 905266-75-3 1-(tert-butyldimethylsilyloxy)-(2S)-(N-tert-butyloxycarbonyl)amino-3-oxo-4-pentene 
• 3163-37-9 (E)-hexadec-2-enal 
• 26993-32-8 (E)-hexadec-2-en-1-ol 
• 135251-95-5 (2E)-ethyl 2-hexadecenoate 
• 124-25-4 myristylaldehyde 
• 123-78-4 (2S,3R,4E)-2-amino-4-octadecene-1,3-diol 
• 4201-55-2 (2S,3R,4E)-3-benzoyl-2-(hexadecanamido)-4-octadecene-1,3-diol 
• 100680-49-7 (2S,3R,4E)-3-benzoyl-1-(triphenylmethyl)-2-(hexadecanamido)-4-octadecene-1,3-diol 
• 94198-71-7 (2S,3R,4E)-1-(triphenylmethyl)-2-(hexadecanamido)-4-octadecene-1,3-diol 
• 4201-58-5 (2S,3R,4E)-2-(hexadecanoylamido)-4-octadecene-1,3-diol 
• 57-10-3 1-hexadecylcarboxylic acid 

Relevant articles and documents

An efficient route to N palmitoyl D crythro sphingomyelin and its 13C-labeled derivatives

We describe here a practical and efficient route to a homogeneous N palmitoyl D crythro sphingomyelin and its 13C-labeled derivatives. (2S, 3R,4E)-2-Azido-3-(tert-butyldimethylsilyloxy)-4-octadecene-l-ol1 was converted to the sphingosine equivalent 2 by treatment with triphenylphosphine and water. Amine 2 was then coupled with palmitic acid, affording the ceramide derivative 3a. In the following two reactions the phosphorylcholine functional group was generated by using 2-chloro-2-oxo-1,3,2-dioxaphospholane and trimethylamine, respectively. The final deprotection of the secondary hydroxyl group in 5a produced the desired N palmitoyl D crythro sphingomyelin 6a. The overall yield of this five-step synthesis is 43%. The melting point, 213-215°C, the specific rotation, [α]20D - +6.8 (c= 1-3, CH2Cl2MeOH 1:1) and 1H-and 13C-NMR data indicate that the synthetic sphingomyelin is enantiomerically pure. The 13C-labeled derivatives 6b, 6c and 6d were synthesized by employing the same scheme.

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.

Versatile synthetic method for sphingolipids and functionalized sphingosine derivatives via olefin cross metathesis

A highly efficient and versatile method for the synthesis of various sphingolipids, such as sphingomyelin, ceramide, sphingosine, sphingosine 1-phosphate, and functionalized sphingosine derivatives, was established by two types of combinations of the olefin cross metathesis reaction. One reaction was between the same olefin part and appropriate amino alcohols, which were prepared starting from N-Boc-L-serine, and the other was between appropriate olefins and the same amino alcohol.