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394815 Sigma-Aldrich

N-Maleoyl-β-alanine

Green Alternative

97%

Synonym: 3-Maleimidopropionic acid, N-(2-Carboxyethyl)maleimide

  • CAS Number 7423-55-4

  • Empirical Formula (Hill Notation) C7H7NO4

  • Molecular Weight 169.13

  •  Beilstein/REAXYS Number 1528952

  •  MDL number MFCD00043030

  •  PubChem Substance ID 24864618

  •  NACRES NA.22

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Properties

Related Categories Building Blocks, Carbonyl Compounds, Chemical Synthesis, Cyclic Imides, Greener Alternative Products,
Quality Level   200
assay   97%
greener alternative product score   old score: 17
new score: 6
Find out more about DOZN™ Scoring.
greener alternative product characteristics   Atom Economy
Design for Energy Efficiency
Use of Renewable Feedstocks
Learn more about the Principles of Green Chemistry.
mp   103-106 °C (lit.)
greener alternative category   Re-engineered
storage temp.   2-8°C
SMILES string   OC(=O)CCN1C(=O)C=CC1=O
InChI   1S/C7H7NO4/c9-5-1-2-6(10)8(5)4-3-7(11)12/h1-2H,3-4H2,(H,11,12)
InChI key   IUTPJBLLJJNPAJ-UHFFFAOYSA-N

Description

General description

N-Maleoyl-β-alanine (3-maleimidopropanoic acid) is an aliphatic N-substituted maleimide. It is one of the component of the stabilizing solution for EC145 (a folate-targeted vinca alkaloid conjugate) used in rodent pharmacokinetic studies.

Application

N-Maleoyl-β-alanine (3-maleimidopropanoic acid, N-(2-carboxyethyl)maleimide)) is the suitable reagent used in the following studies:
• To decrease the biotin binding affinity of Avd(S16C) (avidin with a single point mutation S16C).
• As a side chain reactive agent to modify tryptic peptides that result in mass shifts indicating the presence of cysteine residues.
• To preblock Xenopus laevis oocytes for exposed cysteines used as an expression system in the study of conformational changes in cASIC1a Receptors.
It may be used in the following studies:
• As a protective agent for keratin fiber in high temperature process.
• As a non-cleavable maleimido moiety during the synthesis of tetrawalled molecular umbrella-octaarginine conjugates.
• Synthesis of organotin carboxylates of N-Maleoyl-β-alanine.
• To functionalize the gold surfaces to interact with cysteine-modified peptide.
• Preparation of cross-linked dextran–poly(ethylene glycol) hydrogel substrate.

Packaging

1 g in glass bottle

250 mg in glass bottle

Bottomless glass bottle. Contents are inside inserted fused cone.

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Target organs 
Respiratory system
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

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Protocols & Articles
Peer-Reviewed Papers
15

References

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