394815
N-Maleoyl-β-alanine
97%
Synonym(s):
3-Maleimidopropionic acid, N-(2-Carboxyethyl)maleimide
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All Photos(6)
About This Item
Empirical Formula (Hill Notation):
C7H7NO4
CAS Number:
Molecular Weight:
169.13
Beilstein:
1528952
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
Assay
97%
form
powder
greener alternative product score
old score: 18
new score: 7
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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.
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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.
- 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.
Signal Word
Warning
Hazard Statements
Precautionary 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
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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
Néstor López Mora et al.
Chemical communications (Cambridge, England), 50(16), 1953-1955 (2014-01-11)
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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
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