91991-98-9

Basic information

• Product Name: 1-Propanone, 1-(2-hydroxy-3-nitrophenyl)-
• Synonyms: 3-Nitro-2-hydroxypropiophenon
• CAS NO: 91991-98-9
• Molecular Formula: C9H9NO4
• Molecular Weight: 195.17200
• Mol File: 91991-98-9.mol
• Article Data: 1

Chemical Properties

• Melting Point: 95–97°C
• Boiling Point: 242.2±20.0 °C(Predicted)
• Density: 1.321±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 1-Propanone, 1-(2-hydroxy-3-nitrophenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Propanone, 1-(2-hydroxy-3-nitrophenyl)-(91991-98-9)
• EPA Substance Registry System: 1-Propanone, 1-(2-hydroxy-3-nitrophenyl)-(91991-98-9)

Safety Data

• Hazardous Substances Data: 91991-98-9(Hazardous Substances Data)

Usage

Preparation

Obtained by degradation of 3-methyl-8-nitro-chromone (m.p. 148–150°) with boiling 5% potassium hydroxide for 2 h (84%) Also obtained by reaction of fuming nitric acid (d = 1.52) with o-hydroxy-propiophenone in concentrated sulfuric acid at 0° for 2 h (38%).

Upstream product

• 610-99-1 1-(2-Hydroxy-phenyl)-propan-1-on 

Downstream Products

• 56822-94-7 8-amino-3-methyl-2-phenyl-chromen-4-one 
• 102028-40-0 8-acetylamino-3-methyl-2-phenyl-chromen-4-one 
• 132318-84-4 3-methyl-8-nitro-2-phenyl-chromen-4-one 

Relevant articles and documents

Structure-Activity Relationships of Nitro-Substituted Aroylhydrazone Iron Chelators with Antioxidant and Antiproliferative Activities

Aroylhydrazone iron chelators such as salicylaldehyde isonicotinoyl hydrazone (SIH) protect various cells against oxidative injury and display antineoplastic activities. Previous studies have shown that a nitro-substituted hydrazone, namely, NHAPI, displayed markedly improved plasma stability, selective antitumor activity, and moderate antioxidant properties. In this study, we prepared four series of novel NHAPI derivatives and explored their iron chelation activities, anti- or pro-oxidant effects, protection against model oxidative injury in the H9c2 cell line derived from rat embryonic cardiac myoblasts, cytotoxicities to the corresponding noncancerous H9c2 cells, and antiproliferative activities against the MCF-7 human breast adenocarcinoma and HL-60 human promyelocytic leukemia cell lines. Nitro substitution had both negative and positive effects on the examined properties, and we identified new structure-activity relationships. Naphthyl and biphenyl derivatives showed selective antiproliferative action, particularly in the breast adenocarcinoma MCF-7 cell line, where they exceeded the selectivity of the parent compound NHAPI. Of particular interest is a compound prepared from 2-hydroxy-5-methyl-3-nitroacetophenone and biphenyl-4-carbohydrazide, which protected cardiomyoblasts against oxidative injury at 1.8 ± 1.2 μM with 24-fold higher selectivity than SIH. These compounds will serve as leads for further structural optimization and mechanistic studies.