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Merck

394815

Sigma-Aldrich

N-Maleoyl-β-alanine

greener alternative

97%

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C7H7NO4
Número de CAS:
Peso molecular:
169.13
Beilstein/REAXYS Number:
1528952
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

97%

form

powder

greener alternative product score

old score: 18
new score: 7
Find out more about DOZN™ Scoring

greener alternative product characteristics

Less Hazardous Chemical Syntheses
Safer Solvents and Auxiliaries
Inherently Safer Chemistry for Accident Prevention
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

mp

103-106 °C (lit.)

functional group

carboxylic acid
imide
maleimide

greener alternative category

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

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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.
We are committed to bringing you Greener Alternative Products, which adhere to one of the four categories of Greener Alternatives . This product belongs to category of Re-engineered products, showing key improvements in Green Chemistry Principles “Less Hazardous Chemical Syntheses”, "Safer Solvents and Auxiliaries" and “Inherently Safer Chemistry for Accident Prevention”. Click here to view its DOZN scorecard.

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

Bottomless glass bottle. Contents are inside inserted fused cone.

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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Visite la Librería de documentos

Christopher P Leamon et al.
The Journal of pharmacology and experimental therapeutics, 336(2), 336-343 (2010-10-28)
During a phase I trial of EC145 (a folate-targeted vinca alkaloid conjugate), constipation was identified as the dose-limiting toxicity, probably from a nonfolate receptor-related liver clearance process capable of releasing unconjugated vinca alkaloid from EC145 and shuttling it to the
A new strategy for the preparation of maleimide-functionalised gold surfaces.
Electrochemistry Communications 12.10 (2010): 1403-1406.
Zhang X, et al
Electrochemical Communications, 12(10), 1403-1406 (2010)
Swarna S Ramaswamy et al.
The Journal of biological chemistry, 288(50), 35896-35903 (2013-11-08)
Acid-sensing ion channels are cation channels activated by external protons and play roles in nociception, synaptic transmission, and the physiopathology of ischemic stroke. Using luminescence resonance energy transfer (LRET), we show that upon proton binding, there is a conformational change
Protecting keratin fiber with water soluble N-substituted maleimides in high temperature processes.
Cai JY, et al.
Fibers and Polymers, 15(11), 2247-2252 (2014)
Organotin (IV) derivatives of N-maleoylamino acids: their synthesis and structural elucidation.
Bhatti MH, et al
Turkish Journal of Chemistry, 29(5), 463-476 (2005)

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