144236-99-7

Basic information

• Product Name: N-palmitoyl-D-erythro-sphingomyelin-1'-13C
• CAS NO: 144236-99-7
• Molecular Weight: 704.029
• Mol File: 144236-99-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: N-palmitoyl-D-erythro-sphingomyelin-1'-13C(CAS DataBase Reference)
• NIST Chemistry Reference: N-palmitoyl-D-erythro-sphingomyelin-1'-13C(144236-99-7)
• EPA Substance Registry System: N-palmitoyl-D-erythro-sphingomyelin-1'-13C(144236-99-7)

Safety Data

• Hazardous Substances Data: 144236-99-7(Hazardous Substances Data)

Upstream product

• 150543-08-1 (2S,3R,4E)-2-(1'-13C-hexadecanoylamino)-1-phosphorylcholine-3-(tert-butyldimethylsilyloxy)-octadecene 
• 150543-07-0 (2S,3R,4E)-2-(1'-13C-hexadecanoylamino)-3-(tert-butyldimethylsilyloxy)-4-octadecene-1-ol 
• 137905-29-4 (2S,3R,4E)-2-amino-3-(tert-butyldimethylsilyloxy)-4-octadecene-1-ol 
• 114299-64-8 (2S,3S,4E)-2-azido-3-O-(tert-butyldimethylsilyl)-4-octadecen-1,3-diol 
• 57677-53-9 1-¹³C-palmitic 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.