1571-72-8

Basic information

• Product Name: 3-Amino-4-hydroxybenzoic acid
• Synonyms: 3-amino-4-hydroxybenzenecarboxylic acid;3-Amino-4-hydroxybenzoic acid,98%;2-Amino-4-carboxyphenol, 5-Carboxy-2-hydroxyaniline;3-AMino-4-hydroxybenzoic acid, 98% 25GR;3-AMino-4-hydroxybenzoic acid, 98% 5GR;TIMTEC-BB SBB006740;BENZOIC ACID, 3-AMINO-4-HYDROXY-;3-AMINO-4-HYDROXYBENZOIC ACID
• CAS NO: 1571-72-8
• Molecular Formula: C7H7NO3
• Molecular Weight: 153.14
• EINECS: 216-390-2
• Product Categories: Mass Spectrometry;Matrix Materials (MALDI-TOF-MS);Analytical Chemistry;Carboxylic Acids;Phenyls & Phenyl-Het;Aromatic Amino Acids;Peptide Synthesis;Unnatural Amino Acid Derivatives;Alcohols and Derivatives;Amino Acids and Derivatives;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Carboxylic Acids;Phenyls & Phenyl-Het;API intermediates
• Mol File: 1571-72-8.mol
• Article Data: 8

Chemical Properties

• Melting Point: 208 °C (dec.)(lit.)
• Boiling Point: 276.03°C (rough estimate)
• Flash Point: 189 °C
• Appearance: Beige-gray to brown/Crystalline Powder
• Density: 1.3585 (rough estimate)
• Vapor Pressure: 9.63E-07mmHg at 25°C
• Refractive Index: 1.5500 (estimate)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: Soluble in solvents.
• PKA: 9.06±0.18(Predicted)
• Sensitive: Light Sensitive
• BRN: 972238
• CAS DataBase Reference: 3-Amino-4-hydroxybenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Amino-4-hydroxybenzoic acid(1571-72-8)
• EPA Substance Registry System: 3-Amino-4-hydroxybenzoic acid(1571-72-8)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• HazardClass: IRRITANT, AIR SENSITIVE, LIGHT S
• Hazardous Substances Data: 1571-72-8(Hazardous Substances Data)

Usage

Description

3-Amino-4-hydroxybenzoic acid, also known as para-aminosalicylic acid (PAS), is a monohydroxybenzoic acid derivative that carries an additional amino substituent at the 3rd position. It is a beige-grey to brown crystalline powder and is known for its chemical properties and various applications across different industries.

Uses

Used in Pharmaceutical Industry:
3-Amino-4-hydroxybenzoic acid is used as an intermediate in the synthesis of various pharmaceutical compounds. For instance, it is used to produce 4-acetoxy-3-acetylamino-benzoic acid with acetic acid anhydride at a temperature of 0 20°C. This reaction requires reagents such as aqueous hydrochloric acid (aq. HCl) and sodium acetate (NaOAc). The synthesized compounds can be further utilized in the development of drugs for treating various medical conditions.
Used in Chemical Synthesis:
3-Amino-4-hydroxybenzoic acid serves as a key building block in the chemical synthesis of various organic compounds. Its unique structure allows it to be a versatile starting material for the creation of a wide range of molecules with potential applications in different industries, such as agriculture, materials science, and environmental science.
Used in Research and Development:
Due to its unique chemical properties, 3-Amino-4-hydroxybenzoic acid is also used in research and development for studying various chemical reactions and exploring new synthetic pathways. It can be employed as a model compound to understand the reactivity and behavior of similar molecules, contributing to the advancement of chemical knowledge and the development of new technologies.

Synthesis Reference(s)

The Journal of Organic Chemistry, 54, p. 3740, 1989 DOI: 10.1021/jo00276a044

InChI:InChI=1/C7H7NO3/c8-5-3-4(7(10)11)1-2-6(5)9/h1-3,9H,8H2,(H,10,11)/p-1

Upstream product

• 861550-32-5 4-hydroxy-3-phenylazo-benzoic acid 
• 616-82-0 3-nitro-4-hydroxybenzoic acid 
• 91004-38-5 3-acetamido-4-hydroxybenzoic acid 
• 536-25-4 methyl 3-amino-4-hydroxybenzoate 
• 13052-92-1 ethyl 3-amino-4-hydroxybenzoate 
• 23685-91-8 3-amino-4-hydroxy-benzoic acid butyl ester 
• 140648-39-1 4-Hydroxy-3-(4-sulfamoyl-phenylazo)-benzoic acid 
• 99-42-3 methyl (4-hydroxy-3-nitro)benzoate 
• 19013-10-6 ethyl 4-hydroxy-3-nitrobenzoate 
• 99-96-7 4-hydroxy-benzoic acid 
• 94-26-8 4-hydroxybenzoic acid, butyl ester 
• 96-99-1 4-chloro-3-nitrobenzoate 

Downstream Products

• 90322-32-0 2-methyl-1,3-benzoxazole-5-carboxylic acid 
• 21095-64-7 2-phenylbenzo[d]oxazole-5-carboxylic acid 
• 861782-65-2 4-hydroxy-3-(toluene-4-sulfonylamino)-benzoic acid 
• 23685-91-8 3-amino-4-hydroxy-benzoic acid butyl ester 
• 536-25-4 methyl 3-amino-4-hydroxybenzoate 
• 15112-41-1 1,3-benzoxazol-5-carboxylic acid 
• 13052-92-1 ethyl 3-amino-4-hydroxybenzoate 
• 37470-46-5 4-hydroxy-3-iodobenzoic acid 
• 95-55-6 2-amino-phenol 
• 7341-98-2 2-thioxo-2,3-dihydrobenzo[d]oxazole-5-carboxylic acid 
• 107618-48-4 2-Hydroxy-2-phenyl-2H-1,4-benzoxazin-carbonsaeure-⁽⁶⁾ 
• 120623-43-0 4-hydroxy-3-(2,4,6-trimethyldeca-2,4-dienylcarbonylamino)benzoic acid 
• 17903-99-0 4-Acetoxy-3-(acetylamino)benzoic acid 

Relevant articles and documents

Novel SIRT1 activator MHY2233 improves glucose tolerance and reduces hepatic lipid accumulation in db/db mice

The NAD+-dependent deacetylase SIRT1, which is associated with the improvement of metabolic syndromes, such as type 2 diabetes, is a well-known longevity-related gene. Several in vitro and in vivo studies have shown the known protective effects of SIRT1 activators, such as resveratrol and SRT1720, on diabetes- or obesity-induced fatty liver and insulin resistance. Here, we newly synthesized 18 benzoxazole hydrochloride derivatives based on the structure of resveratrol and SRT1720. We performed an in vitro SIRT1 activity assay to identify the strongest SIRT1 activator. The assay confirmed MHY2233 to be the strongest SIRT1 activator (1.5-fold more potent than resveratrol), and docking simulation showed that the binding affinity of MHY2233 was higher than that of resveratrol and SRT1720. To investigate its beneficial effects, db/db mice were orally administered MHY2233 for 1 month, and various metabolic parameters were assessed in the serum and liver tissues. MHY2233 markedly ameliorated insulin signaling without affecting body weight in db/db mice. In particular, the mRNA expression of lipogenic genes, such as acetyl CoA carboxylase, fatty acid synthase, and sterol regulatory element-binding protein, which increased in db/db mice, decreased following oral treatment with MHY2233. In conclusion, the novel SIRT1 activator MHY2233 reduced lipid accumulation and improved insulin resistance. This finding may contribute toward therapeutic approaches for fatty liver disease and glucose tolerance.

Novel SIRT 1 activator and medical use thereof

The present invention relates to an SIRT 1 activator and a medical purpose thereof. According to the present invention, the novel SIRT 1 activator based on a benzo[d]oxazole frame, a hydrate thereof, a crystal form thereof, and salt thereof are manufactured. According to the present invention, it is confirmed that the SIRT 1 activator has improvement effects on obesity, insulin resistance, and dyslipidemia, improvement effect on fatty liver, prevention effects on cell aging and oxidation stress, and collagen composition and wrinkle improvement effect. Therefore, the novel SIRT 1 activator having the same effect can be usefully used as a pharmaceutical composition for preventing or treating a metabolic and liver diseases, a cosmetic composition for preventing or treating wrinkles, and a health food composition for preventing cell aging, wherein the metabolic disease includes obesity, diabetes, and dyslipidemia and the liver disease includes an alcoholic or nonalcoholic fatty liver and fatty hepatitis.COPYRIGHT KIPO 2018

Amino-benzoic acids and derivatives, and methods of use

The present invention relates to compounds, compositions and methods for inhibiting nonenzymatic cross-linking (protein aging). Accordingly, a composition is disclosed which comprises an agent capable of inhibiting the formation of advanced glycosylation endproducts of target proteins by reacting with a carbonyl moiety of the early glycosylation product of such target proteins formed by their initial glycosylation. The method comprises contacting the target protein with the composition. Both industrial and therapeutic applications for the invention are envisioned, as food spoilage and animal protein aging can be treated.