767352
Stearic acid N-hydroxysuccinimide ester
Synonym(s):
NHS protected stearate, NHS-octadecanoic acid, Octadecanoic acid N-hydroxysuccinimide ester
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About This Item
Empirical Formula (Hill Notation):
C22H39NO4
CAS Number:
Molecular Weight:
381.55
NACRES:
NA.23
PubChem Substance ID:
UNSPSC Code:
12162002
MDL number:
InChI
1S/C22H39NO4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-22(26)27-23-20(24)18-19-21(23)25/h2-19H2,1H3
SMILES string
CCCCCCCCCCCCCCCCCC(=O)ON1C(=O)CCC1=O
InChI key
ZERWDZDNDJBYKA-UHFFFAOYSA-N
form
solid
mp
71-76 °C
storage temp.
2-8°C
Quality Level
Related Categories
Application
Used in the synthesis of ceramides and in the hydrophobication of amines.
General description
Stearic acid N-hydroxysuccinimide ester is an N-Hydroxysuccinimide ester of fatty acid. They are used in the synthesis of N-acyl amino acids and fatty acyl CoA. They are also used in the direct N-acylation of sphingenine or sphinganine thus leading to the formation of ceramides.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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D E Ong et al.
Journal of lipid research, 13(6), 819-822 (1972-11-01)
Fatty acyl esters of N-hydroxysuccinimide have been used to directly N-acylate sphingenine or sphinganine, forming the corresponding ceramides. The reaction proceeds in excellent yield (84-96%) from small amounts of starting material (10-20 mg). The product ceramides are pure after one
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