619-14-7

Basic information

• Product Name: 3-Hydroxy-4-nitrobenzoic acid
• Synonyms: 3-HYDROXY-4-NITROBENZOIC ACID;3-HYDROXYL-4-NITROBENZOIC ACID;4-NITRO-3-HYDROXYBENZOIC ACID;RARECHEM AL BE 0673;Benzoic acid, 3-hydroxy-4-nitro-;3-Hydroxyl-4-nitrobenzoic;3-HYDROXY-4-NITROBENZOIC ACID 99%;3-Hydroxy-4-nitrobenzoic acid,98%
• CAS NO: 619-14-7
• Molecular Formula: C7H5NO5
• Molecular Weight: 183.12
• EINECS: 210-580-9
• Product Categories: Benzene derivatives;FINE Chemical & INTERMEDIATES;blocks;Carboxes;NitroCompounds;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Carboxylic Acids;Phenyls & Phenyl-Het;Carboxylic Acids;Phenyls & Phenyl-Het;C7;Carbonyl Compounds
• Mol File: 619-14-7.mol

Chemical Properties

• Melting Point: 229-231 °C(lit.)
• Boiling Point: 316.77°C (rough estimate)
• Flash Point: 175.4 °C
• Appearance: Yellow to brown/Powder
• Density: 1.6074 (rough estimate)
• Vapor Pressure: 1.74E-06mmHg at 25°C
• Refractive Index: 1.6280 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: 1.08g/l (calculated)
• PKA: 3.30±0.10(Predicted)
• Water Solubility: insoluble
• BRN: 2107564
• CAS DataBase Reference: 3-Hydroxy-4-nitrobenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Hydroxy-4-nitrobenzoic acid(619-14-7)
• EPA Substance Registry System: 3-Hydroxy-4-nitrobenzoic acid(619-14-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 619-14-7(Hazardous Substances Data)

Usage

Uses

Used in Agriculture:
3-Hydroxy-4-nitrobenzoic acid is used as a growth inhibitor for [application type] in [application reason] to prevent chloroplast development in linseed and oat seedlings. This can be beneficial in controlling the growth of these plants and understanding the underlying mechanisms of chloroplast development.
Used in Pharmaceutical Industry:
3-Hydroxy-4-nitrobenzoic acid is used as a potential therapeutic agent for [application type] in [application reason] to treat cancer. Its inhibitory effects on Ras proteins, which are often mutated in various types of cancer, make it a promising compound for developing new cancer treatments. Further research and development are needed to fully understand its potential and optimize its use in cancer therapy.

InChI:InChI=1/C7H5NO5/c9-6-3-4(7(10)11)1-2-5(6)8(12)13/h1-3,9H,(H,10,11)/p-2

Upstream product

• 700-38-9 2-nitro-5-methylphenol 
• 704-13-2 5-formyl-2-nitrophenol 
• 6968-22-5 3-amino-4-nitrobenzoic acid 
• 99-06-9 3-Carboxyphenol 
• 55894-52-5 4-nitro-3-(octanoyloxy)-benzoic acid 
• 115162-21-5 3-(butyryloxy)-4-nitrobenzoic acid 
• 102607-50-1 3-(hexanoyloxy)-4-nitrobenzoic acid 
• 115162-22-6 3-(heptanoyloxy)-4-nitrobenzoic acid 
• 115162-23-7 4-nitro-3-(nonanoyloxy)benzoic acid 
• 55894-53-6 3-(decanoyloxy)-4-nitrobenzoic acid 
• 115162-24-8 4-nitro-3-(undecanoyloxy)benzoic acid 
• 85724-92-1 3-(dodecanoyloxy)-4-nitrobenzoic acid 
• 7697-37-2 nitric acid 
• 98-95-3 nitrobenzene 

Downstream Products

• 713-52-0 methyl 3-hydroxy-4-nitrobenzoate 
• 717-01-1 ethyl 3-hydroxy-4-nitro-benzoate 
• 5081-36-7 3-methoxy-4-nitrobenzoic acid 
• 10098-40-5 4-acetamido-3-hydroxybenzoic acid 
• 2374-03-0 4-aminosalicylic acid 
• 875846-16-5 3-propyloxy-4-nitrobenzoic acid 
• 85724-92-1 3-(dodecanoyloxy)-4-nitrobenzoic acid 
• 115162-23-7 4-nitro-3-(nonanoyloxy)benzoic acid 
• 55894-52-5 4-nitro-3-(octanoyloxy)-benzoic acid 
• 115162-20-4 4-nitro-3-<<4'-nitro-3'-(octanoyloxy)benzoyl>oxy>-benzoic acid 
• 115162-24-8 4-nitro-3-(undecanoyloxy)benzoic acid 
• 61161-83-9 5-(hydroxymethyl)-2-nitrophenol 
• 51257-24-0 3-Acetoxy-4-Nitrobenzoic Acid 
• 102607-50-1 3-(hexanoyloxy)-4-nitrobenzoic acid 

Relevant articles and documents

As neuroprotective agents of pharmaceutical compounds

The invention discloses a medicinal compound as a neuroprotective agent. The medicinal compound is a neuronal nitric oxide synthase-postsynaptic density protein 95 (nNOS-PSD95) decoupling agent. The medicinal compound is a benzene ring derivative shown in the general formula (I) or its pharmaceutically acceptable salt. The invention further discloses a preparation method of the medicinal compound and a use of the medicinal compound in prevention and treatment on neuronal damage influence-caused diseases.

3-Hydroxyl-4-nitrobenzoic acid and preparation method thereof

The invention aims to provide 3-hydroxyl-4-nitrobenzoic acid and a preparation method thereof. The preparation method includes: subjecting low-price and easily obtainable m-cresol as a raw material to nitration and then oxidation; with H2O2 serving as an oxidant, oxidizing a methyl group into a carboxyl group so as to obtain 3-hydroxyl-4-nitrobenzoic acid. The method has the advantages of low material cost, operation simplicity, low byproduct output, high yield and mild reaction environmental conditions and is suitable for large-scale industrial production.

Evaluation of snake venom phospholipase A2: Hydrolysis of non-natural esters

Phospholipase A2 from the rattlesnake Crotalus durissus terrificus was employed for the first time to test its enantioseletivity on the hydrolysis of different non-natural esters. It was observed that the structure of this small enzyme is restrictive in the choice of its lipase action with non-natural substrates. Two forms of the enzyme were used; free and as its cross-linked enzyme aggregate (CLEA). With all substrates, the free enzyme showed activity similar to the CLEA preparation. The advantage of the CLEA phospholipase is the possibility to reuse it in several consecutive reactions without a decrease of activity and selectivity with good but higher yields and ee than with the free enzyme.

Regio- and chemoselective enzymatic N-oxygenation in vivo, in vitro, and in flow

(Chemical Equation Presented) Action by the para: Evaluation of the nitro-group-forming N-oxygenase AurF in vivo, in vitro, and immobilized as a fusion protein with simply H2O2 as oxidant (peroxide shunt) reveals para-regioselective oxygenation of aromatic amines (see scheme). This effect includes the selective oxygenation of diamino compounds.

Nitrophenol derivatives oxidized by cerium(IV) ammonium nitrate (CAN) and their cytotoxicity

Oxidation of a series of phenols with cerium(IV) ammonium nitrate (CAN) in acetonitrile undermild conditions yields the mixture of corresponding nitrophenols. In the cases of methylphenols and hydroxy-carboxylic acids, the steric effect may reduce the nitration reaction. Compounds 3 a and 4b showed selective activities to Hep 3B and Hep G2 cancer cell lines, respectively. Compound 2c showed selective activities to Hep G2 and MDA-MB-231 cancer cell lines. Further more, com pound 10b showed selective activities to Hep G2, Hep 3B, MCF-7 and MDA-MB-231 cancer cell lines.

Lipoamino acids and lipopeptides as amphiphilic compounds

Lipoamino acids and lipopeptides are amphiphilic compounds or cationic surfactants which are able to form micellar vesicles and are capable of splitting off long-chained esteratic compounds. For example the reaction of H-Lys-(H-Lys)NHC18H37·3 HCl with 4-nitro-3-(octanoyloxy)-benzoic acid results in a non-enzymatic hydrolysis of the ester compound.

A New Class of Phospholipase A2 Substrates: Kinetics of the Phospholipase A2 Catalyzed Hydrolysis of 3-(Acyloxy)-4-nitrobenzoic Acids

3-(Acyloxy)-4-nitrobenzoic acids were synthesized with acyl groups ranging from butyryl to dodecanoyl.All these compounds yielded monomeric solutions in water with 1.6percent (v/v) acetonitrile in the neutral pH range, and they were hydrolyzed by catalytic amounts of phospholipases A2 from a variety of sources as shown by the spectral change at 425 nm due to the appearance of nitrophenolate ion.Most of the kinetic studies were performed using Agkistrodon piscivorus piscivorus phospholipase A2, but similar results were obtained with porcine pancreatic and Crotalus atrox phospholipase A2.The catalytic reaction requires the presence of Ca2+, but unlike the hydrolysis of lecithins, the hydrolysis of these substrates also occurs in the presence of Ba2+ and Sr2+, while Mg2+ and Zn2+ are not catalytically competent.Increasing the acyl chain length increases the enzymatic rate mainly by enhancing the hydrophobic interaction in the E-Ca2+-S complex.Among structural isomers of the octanoyl compound, 3-nitro-4-(octanoyloxy)benzoic acid shows the highest specificity toward the enzyme, suggesting that it is in this compound that the distance between the negatively charged carboxylate and the reactive ester approximates best that found in the lecithin-enzyme complex.All kinetic characteristics of the enzymatic hydrolysis indicate that the reaction occurs by the same mechanism as that of the hydrolysis of lecithins.The highest catalytic efficiency observed with this series of substrates occurs with 3-dodecanoyl-4-nitrobenzoic acid, and the second-order rate constant of this reaction (kcat/Km = 9.1 x 1E+4 M-1 s-1) is only 1 order of magnitude lower than that of the hydrolysis of egg phosphatidylcholine in unilamellar vesicles.The reactivity of all isomers, especially that of the p-carboxy ester, shows that Ca2+ does not act as a catalyst in the phospholipase A2 catalyzed hydrolysis but rather serves to bind and orient the substrate at the active site of the enzyme.The octanoyl compounds, 1 and 2, are ideally suited for a rapid and sensitive spectrophotometric assay of phospholipases A2, and the conditions for the assay are described.

THE SUBSTRATE SPECIFICITY OF PHOSPHOLIPASE A2 : THE REACTION OF THE ENZYME WITH 3-OCTANOYLOXY-4-NITROBENZOIC ACID

3-Octanoyloxy-4-nitrobenzoic acid is hydrolyzed by the phospholipase A2(D-49) from the venom of Agkistrodon piscivorus.The hydrolytic reaction is truly catalytic, requiring the presence of calcium ion (Kd=3.3 +/- 0.7mM).At pH=7.0 the value of the enzymatic rate constant is (Kcat/Km)max=175 +/- 14 M-1 sec-1, comparable to that of the enzymatic hydrolysis of 3-sn-dibutyryl lecithin.