| Identification | More | [Name]
3-Maleimidopropionic acid | [CAS]
7423-55-4 | [Synonyms]
3-(2,5-DIOXO-2,5-DIHYDRO-1H-PYRROL-1-YL)PROPANOIC ACID
3-(2,5-DIOXO-2,5-DIHYDRO-PYRROL-1-YL)-PROPIONIC ACID
3-MALEIMIDOPROPIONIC ACID
AKOS BC-0729
BETA-MALEIMIDOPROPIONIC ACID
BMPA
MALEOYL-BETA-ALA-OH
MPA
MPA-OH
N-(2-CARBOXYETHYL)MALEIMIDE
N-BETA-MALEIMIDOPROPIONIC ACID
N-MALEOYL-BETA-ALANINE
RARECHEM AL CD 0912
B-MALEIMIDOPROPIONIC ACID
3-Maleinimidopropionicacid
3-Maleimidopropionic
n-maleoyl-β-alanine
3-MALEIMIDOPROPIONOIC ACID DIHYDRATE
3-(2,5-Dioxo-2,5-dihydro-pyrrol-1-yl)-prop
3-Maleimidopropionic acid, N-(2-Carboxyethyl)maleimide | [EINECS(EC#)]
616-069-0 | [Molecular Formula]
C7H7NO4 | [MDL Number]
MFCD00043030 | [Molecular Weight]
169.13 | [MOL File]
7423-55-4.mol |
| Chemical Properties | Back Directory | [Appearance]
White to Pale Yellow Solid | [Melting point ]
103-106 °C (lit.) | [Boiling point ]
382.5±25.0 °C(Predicted) | [density ]
1.473±0.06 g/cm3(Predicted) | [storage temp. ]
-15°C | [solubility ]
DMSO (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
4.18±0.10(Predicted) | [color ]
White | [Water Solubility ]
Soluble in methanol, dimethyl formamide, alcohol and dimethyl sulfoxide. Slightly soluble in water. | [Sensitive ]
Moisture Sensitive | [Usage]
A sulfhydryl reactive heterobifunctional crosslinking reagent. | [Detection Methods]
HPLC,NMR | [BRN ]
1528952 | [InChI]
InChI=1S/C7H7NO4/c9-5-1-2-6(10)8(5)4-3-7(11)12/h1-2H,3-4H2,(H,11,12) | [InChIKey]
IUTPJBLLJJNPAJ-UHFFFAOYSA-N | [SMILES]
N1(CCC(O)=O)C(=O)C=CC1=O | [CAS DataBase Reference]
7423-55-4(CAS DataBase Reference) | [Storage Precautions]
Moisture sensitive;Store under nitrogen |
| Hazard Information | Back Directory | [Description]
3-Maleimidopropionic acid contains a maleimide group and a terminal carboxylic acid. The terminal carboxylic acid can react with primary amine groups in the presence of activators (e.g. EDC, or HATU) to form a stable amide bond. The maleimide group will react with a thiol group to form a covalent bond, enabling the connection of biomolecule with a thiol. | [Chemical Properties]
White to Pale Yellow Solid | [Uses]
A sulfhydryl reactive heterobifunctional crosslinking reagent. | [Application]
3-Maleimidopropionic acid (3MP) is a molecule that can be used for the treatment of cancer. 3MP has been shown to inhibit the growth of tumor cells and induce apoptosis. It also inhibits the production of reactive oxygen species, which are produced by cancer cells as a result of chemotherapy. 3MP has potent inhibitory activity against bacterial organisms such as methicillin-resistant Staphylococcus aureus (MRSA) and Clostridium perfringens and antiviral properties against HIV infection. This molecule can also be used in conjunction with monoclonal antibodies or other immunotherapy techniques to improve their efficacy. | [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. | [Synthesis]
An acetic acid solution of maleic anhydride (5.00 g in 50 mL) was added dropwise to an acetic acid solution of β-alanine (4.54 g in 50 mL). The mixture was stirred at room temperature. After 3 h, AcOH (70 mL ) was added and the temperature was raised to 115 °C under stirred overnight. After 1 hour, an orange oil was obtained. The solvent excess was removed under reduced pressure and the product was washed with toluene (3 × 30 mL). The product was then purified by flash chromatography using a silica column (DCM/ethylacetate 9:1) to obtain the white solid 3-Maleimidopropionic acid.
 | [References]
[1] International Journal of Molecular Sciences, 2017, vol. 18, # 9,
[2] Journal of Medicinal Chemistry, 2013, vol. 56, # 24, p. 9955 - 9968
[3] Journal of Controlled Release, 2015, vol. 220, p. 660 - 670
[4] Chemistry - A European Journal, 2015, vol. 21, # 38, p. 13186 - 13190
[5] Journal of the American Chemical Society, 2013, vol. 135, # 11, p. 4333 - 4363 |
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