92944-71-3

Basic information

• Product Name: BENZOPHENONE-4-MALEIMIDE
• Synonyms: 4-(N-MALEIMIDO)BENZOPHENONE;4-(MALEIMIDO)BENZOPHENONE;AKOS MSC-0079;1-(4-BENZOYLPHENYL)-1H-PYRROLE-2,5-DIONE;BENZOPHENONE-4-MALEIMIDE;4-(Maleinimido)benzophenone;1-(4-Benzoylphenyl)-;Benzophenone-4-MaleiMide [4-(N-MaleiMido)benzophenone]
• CAS NO: 92944-71-3
• Molecular Formula: C₁₇H₁₁NO₃
• Molecular Weight: 277.27
• Product Categories: Maleimide Derivatives;Cross Linking Reagents;MTS & Sulfhydryl Active Reagents;Linking Reagents;Aromatics;Heterocycles;Heterobifunctional Cross-Linking Reagents;Protein Modification;Protein Structural Analysis;Building Blocks;Carbonyl Compounds;Chemical Synthesis;Crosslinking;Cyclic Imides;Organic Building Blocks;Proteomics
• Mol File: 92944-71-3.mol
• Article Data: 4

Chemical Properties

• Melting Point: 155-157°C
• Boiling Point: 472.9°Cat760mmHg
• Flash Point: 223.7°C
• Appearance: /
• Density: 1.33g/cm³
• Vapor Pressure: 4.12E-09mmHg at 25°C
• Refractive Index: 1.651
• Storage Temp.: 2-8°C
• Solubility: chloroform: 50 mg/mL
• PKA: -3.80±0.20(Predicted)
• CAS DataBase Reference: BENZOPHENONE-4-MALEIMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: BENZOPHENONE-4-MALEIMIDE(92944-71-3)
• EPA Substance Registry System: BENZOPHENONE-4-MALEIMIDE(92944-71-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 92944-71-3(Hazardous Substances Data)

Usage

Chemical Properties

Light Beige Solid

Uses

Different sources of media describe the Uses of 92944-71-3 differently. You can refer to the following data:
1. 4-(N-Maleimido)benzophenone can be used as a sulfhydryl reactive heterobifunctional photocrosslinking reagent. It generates photoactivatable conjugates from thiols
2. Maleimide-containing benzophenone as photoinitiator
3. A heterobifunctional cross-linking reagent containing a sulfhydryl-specific group and a photo-active group. Typically, coupled initially by thioether to molecule containing free sulfhydryl buffered at pH 6.8 (6.5-7.0). Second bonding occurs during UV irradiation (250 nm) via diradical excited state. Benzophenones demonstrate greater specificity for C-H insertion and are more stable in water than analogous reagents. In general they are more efficient in attachment because they may be repeatedly irradiated; however, a more intense irradiation may be required. The benzophenone is not sensitive to

InChI:InChI=1/C17H11NO3/c19-15-10-11-16(20)18(15)14-8-6-13(7-9-14)17(21)12-4-2-1-3-5-12/h1-11H

Upstream product

• 304456-51-7 C₁₇H₁₃NO₄ 
• 108-31-6 maleic anhydride 
• 1137-41-3 (4-aminophenyl)(phenyl)methanone 
• 304456-51-7 N-(4-benzoylphenyl)maleamic acid 

Downstream Products

• 1233082-70-6 C₃₂H₂₃NO₅ 
• 1233082-62-6 C₃₀H₂₁NO₅ 

Relevant articles and documents

Rational Design of Calpain Inhibitors Based on Calpastatin Peptidomimetics

Our previously reported structures of calpain bound to its endogenous inhibitor calpastatin have motivated the use of aziridine aldehyde-mediated peptide macrocyclization toward the design of cyclic peptides and peptidomimetics as calpain inhibitors. Inspired by nature's hint that a β-turn loop within calpastatin forms a broad interaction around calpain's active site cysteine, we have constructed and tested a library of 45 peptidic compounds based on this loop sequence. Four molecules have shown reproducibly low micromolar inhibition of calpain-2. Further systematic sequence changes led to the development of probes that displayed increased potency and specificity of inhibition against calpain over other cysteine proteases. Calculated Ki values were in the low micromolar range, rivaling other peptidomimetic calpain inhibitors and presenting an improved selectivity profile against other therapeutically relevant proteases. Competitive and mixed inhibition against calpain-2 was observed, and an allosteric inhibition site on the enzyme was identified for a noncompetitive inhibitor.

Compounds containing a michael-acceptor, especially maleimide or maleic acid derivatives, directly or indirectly linked to a chromophore and their use in long lasting sunscreen compositions

The present invention relates to compounds which are useful as sunscreens. The compounds persist on the skin for much longer than conventional sunscreens because they comprise a Michael acceptor linked directly or indirectly to a chromophore. The Michael acceptor is capable of undergoing a conjugate addition reaction with thiol groups present in cysteine residues of keratin and thus the compound is chemically bound to the skin and will not be removed by immersion in water.