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394815

Sigma-Aldrich

N-Maleoyl-β-alanine

greener alternative

97%

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C7H7NO4
Numéro CAS:
7423-55-4
Poids moléculaire :
169.13
Numéro Beilstein :
1528952
Numéro MDL:
MFCD00043030
Code UNSPSC :
12352100
ID de substance PubChem :
24864618
Nomenclature NACRES :
NA.22

Niveau de qualité

200

Pureté

97%

Forme

powder

Score du produit alternatif plus écologique

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

Caractéristiques du produit alternatif plus écologique

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

Pf

103-106 °C (lit.)

Autre catégorie plus écologique

, Re-engineered

Température de stockage

2-8°C

Chaîne SMILES 

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)

Clé InChI

IUTPJBLLJJNPAJ-UHFFFAOYSA-N

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Description générale

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.

Conditionnement

Bottomless glass bottle. Contents are inside inserted fused cone.

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H315,H319,H335

Classification des risques

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

Organes cibles

Respiratory system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

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Certificats d'analyse (COA)

Lot/Batch Number
BGBC0754V
BGBB7332V
BGBB7705V
BCBG8685V
BCBC4852V

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Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

Consulter la Bibliothèque de documents

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)
Lauren L Cline et al.
Bioconjugate chemistry, 22(11), 2210-2216 (2011-10-12)
A series of diwalled and tetrawalled molecular umbrellas have been synthesized using cholic acid, spermidine, and lysine as starting materials. Coupling of these molecular umbrellas to an octaarginine peptide afforded agents that were capable of promoting the transport of small
Néstor López Mora et al.
Chemical communications (Cambridge, England), 50(16), 1953-1955 (2014-01-11)
We present a novel chemically cross-linked dextran-poly(ethylene glycol) hydrogel substrate for the preparation of dense vesicle suspensions under physiological ionic strength conditions. These vesicles can be easily diluted for individual study. Modulating the degree of cross-linking within the hydrogel network
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