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Sigma-Aldrich

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:
14464-32-5
Molecular Weight:
381.55
MDL number:
MFCD00050403
UNSPSC Code:
12162002
PubChem Substance ID:
329767307
NACRES:
NA.23

form

solid

mp

71-76 °C

storage temp.

2-8°C

SMILES string

CCCCCCCCCCCCCCCCCC(=O)ON1C(=O)CCC1=O

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

InChI key

ZERWDZDNDJBYKA-UHFFFAOYSA-N

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.

Application

Used in the synthesis of ceramides and in the hydrophobication of amines.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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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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