Stearic acid N-hydroxysuccinimide ester - ≥98% , CAS No.14464-32-5

CAS: 14464-32-5 Cat. No.: S486709 Molecular Weight: 381.55 PubChem CID: 3552761

GRADE & PURITY ≥98%

Synonyms

A1-11950 | J-007984 | Octadecanoic acid, 2,5-dioxo-1-pyrrolidinyl ester | DTXSID90393574 | 2,5-DIOXOPYRROLIDIN-1-YL OCTADECANOATE | MFCD00050403 | (2,5-dioxopyrrolidin-1-yl) Octadecanoate | Stearic acid-N-hydroxysuccinimide ester | N-(Stearoyloxy)succinim

Storage

Store at 2-8°C,Argon charged

Shipped In

Wet ice

Overview

Stearic acidN-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. 

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

Specifications

Synonyms

A1-11950 | J-007984 | Octadecanoic acid, 2, 5-dioxo-1-pyrrolidinyl ester | DTXSID90393574 | 2, 5-DIOXOPYRROLIDIN-1-YL OCTADECANOATE | MFCD00050403 | (2, 5-dioxopyrrolidin-1-yl) Octadecanoate | Stearic acid-N-hydroxysuccinimide ester | N-(Stearoyloxy)succinim

Specifications & Purity

≥98%

Storage

Store at 2-8°C, Argon charged

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥98%

Names and Identifiers

• Canonical Smiles: CCCCCCCCCCCCCCCCCC(=O)ON1C(=O)CCC1=O
• IUPAC Name: (2,5-dioxopyrrolidin-1-yl) octadecanoate
• InChIKey: ZERWDZDNDJBYKA-UHFFFAOYSA-N
• 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
• Isomeric SMILES: CCCCCCCCCCCCCCCCCC(=O)ON1C(=O)CCC1=O
• PubChem CID: 3552761
• Molecular Weight: 381.55

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Pyrrolidines
      • Subclass Pyrrolidones

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Pyrrolidines
• Subclass: Pyrrolidones
• Intermediate Tree Nodes: Not available
• Direct Parent: Pyrrolidine-2-ones
• Alternative Parents: Dicarboximides Lactams Monocarboxylic acids and derivatives Azacyclic compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic heteromonocyclic compounds
• Substituents: 2-pyrrolidone - Dicarboximide - Lactam - Azacycle - Monocarboxylic acid or derivatives - Carboxylic acid derivative - Organic nitrogen compound - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Carbonyl group - Aliphatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as pyrrolidine-2-ones. These are pyrrolidines which bear a C=O group at position 2 of the pyrrolidine ring.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Sensitivity: Moisture sensitive
• Melt Point(°C): 71-76 °C
• Molecular Weight: 381.500 g/mol
• XLogP3: 7.600
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 18
• Exact Mass: 381.288 Da
• Monoisotopic Mass: 381.288 Da
• Topological Polar Surface Area: 63.700 Ų
• Heavy Atom Count: 27
• Formal Charge: 0
• Complexity: 420.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Weiwei Tang, Andrew Gordon, Hui-ying Wang, Ping Li, Jun Chen, Bin Li.  (2021)  Development of MALDI MS peptide array for thrombin inhibitor screening.  TALANTA,      [PMID:33676683] [10.1016/j.talanta.2021.122129]