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394815

Sigma-Aldrich

N-Maleoyl-β-alanine

greener alternative

97%

Synonym(s):
3-Maleimidopropionic acid, N-(2-Carboxyethyl)maleimide
Empirical Formula (Hill Notation):
C7H7NO4
CAS Number:
Molecular Weight:
169.13
Beilstein:
1528952
MDL number:
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.

mp

103-106 °C (lit.)

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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This Item
476129137529138428
N-Maleoyl-β-alanine 97%

Sigma-Aldrich

394815

N-Maleoyl-β-alanine

N,N-Diethylacetamide 97%

Sigma-Aldrich

137529

N,N-Diethylacetamide

form

powder

form

-

form

liquid

form

liquid

mp

103-106 °C (lit.)

mp

-

mp

-

mp

-

storage temp.

2-8°C

storage temp.

-

storage temp.

-

storage temp.

-

Quality Level

200

Quality Level

100

Quality Level

100

Quality Level

100

greener alternative product score

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

greener alternative product score

-

greener alternative product score

-

greener alternative product score

-

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

Signal Word

Warning

Hazard Statements

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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)
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
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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