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2,5-Dioxopyrrolidin-1-yl docosanoate

  • CAS No. 58047-86-2

  • Cat. No. CS-0158378
  • Purity≥95%
  • MDL No.MFCD30830339

*For research and further manufacturing use only, not for direct human use.

2,5-Dioxopyrrolidin-1-yl docosanoate|CS-0158378

Structure of 58047-86-2

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General Information

  • CAS No. 58047-86-2
  • Cat. No. CS-0158378
  • Purity ≥95%
  • MDL No. MFCD30830339
  • Storage -20°C, sealed storage, away from moisture
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₂₆H₄₇NO₄
  • Molecular Weight 437.66
  • Synonym(s) n-docosanoic acid N-hydroxysuccinimide ester(WS202146)
  • SMILES C(CCCCCCCCCCCCCCCCCCCCC)(=O)ON1C(=O)CCC1=O

Description

This 2,5-dioxopyrrolidin-1-yl docosanoate ester delivers a long-chain fatty acid moiety with enhanced reactivity and stability. The pyrrolidinone leaving group facilitates efficient coupling in synthetic workflows, while the C22 alkyl chain imparts hydrophobic character suitable for lipid-based conjugations and membrane-targeted applications.

Application

2,5-Dioxopyrrolidin-1-yl docosanoate serves as a stable, bench-friendly acylating agent derived from lauric acid. It facilitates efficient esterification and amide coupling reactions with alcohols and amines under mild conditions, offering excellent functional group tolerance and clean reaction profiles. The pyrrolidinone leaving group enhances reactivity while enabling straightforward purification by simple workup, making it ideal for building complex molecular architectures in synthetic organic chemistry workflows.

Synthesis

  • Route1

    References

    • Anzai; Lee; Osa Bulletin of the Chemical Society of Japan, 1989 , vol. 62, # 9 p. 3018 - 3020

Safety Information

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GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P405-P501

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Computational Chemistry Data

  • TPSA   63.68
  • LogP   7.4155
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   21

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