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3-Amino-4-hydroxybenzoic acid Sale

(Synonyms: 3-氨基-4-羟基苯甲酸) 目录号 : GC38293

3-Amino-4-hydroxybenzoic acid is a monohydroxybenzoic acid.

3-Amino-4-hydroxybenzoic acid Chemical Structure

Cas No.:1571-72-8

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产品描述

3-Amino-4-hydroxybenzoic acid is a monohydroxybenzoic acid.

Chemical Properties

Cas No. 1571-72-8 SDF
别名 3-氨基-4-羟基苯甲酸
Canonical SMILES NC1=C(O)C=CC(=C1)C(O)=O
分子式 C7H7NO3 分子量 153.14
溶解度 Soluble in DMSO 储存条件 Store at -20°C
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1 mM 6.53 mL 32.6499 mL 65.2997 mL
5 mM 1.306 mL 6.53 mL 13.0599 mL
10 mM 0.653 mL 3.265 mL 6.53 mL
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Research Update

3-Amino-4-hydroxybenzoic acid production from glucose and/or xylose via recombinant Streptomyces lividans

J Gen Appl Microbiol 2022 Sep 15;68(2):109-116.PMID:35831135DOI:10.2323/jgam.2022.06.001.

The aromatic compound 3-Amino-4-hydroxybenzoic acid (3,4-AHBA) can be employed as a raw material for high-performance industrial plastics. The aim of this study is to produce 3,4-AHBA via a recombinant Streptomyces lividans strain containing griI and griH genes derived from Streptomyces griseus using culture medium with glucose and/or xylose, which are the main components in lignocellulosic biomass. Production of 3,4-AHBA by the recombinant S. lividans strain was successful, and the productivity was affected by the kind of sugar used as an additional carbon source. Metabolic profiles revealed that L aspartate-4-semialdehyde (ASA), a precursor of 3,4-AHBA, and coenzyme NADPH were supplied in greater amounts in xylose medium than in glucose medium. Moreover, cultivation in TSB medium with a mixed sugar (glucose/xylose) was found to be effective for 3,4-AHBA production, and optimal conditions for efficient production were designed by changing the ratio of glucose to xylose. The best productivity of 2.70 g/L was achieved using a sugar mixture of 25 g/L glucose and 25 g/L xylose, which was 1.5 times higher than the result using 50 g/L glucose alone. These results suggest that Streptomyces is a suitable candidate platform for 3,4-AHBA production from lignocellulosic biomass-derived sugars under appropriate culture conditions.

Enhanced production of γ-amino acid 3-Amino-4-hydroxybenzoic acid by recombinant Corynebacterium glutamicum under oxygen limitation

Microb Cell Fact 2021 Dec 23;20(1):228.PMID:34949178DOI:10.1186/s12934-021-01714-z.

Background: Bio-based aromatic compounds are of great interest to the industry, as commercial production of aromatic compounds depends exclusively on the unsustainable use of fossil resources or extraction from plant resources. γ-amino acid 3-Amino-4-hydroxybenzoic acid (3,4-AHBA) serves as a precursor for thermostable bioplastics. Results: Under aerobic conditions, a recombinant Corynebacterium glutamicum strain KT01 expressing griH and griI genes derived from Streptomyces griseus produced 3,4-AHBA with large amounts of amino acids as by-products. The specific productivity of 3,4-AHBA increased with decreasing levels of dissolved oxygen (DO) and was eightfold higher under oxygen limitation (DO = 0 ppm) than under aerobic conditions (DO ≥ 2.6 ppm). Metabolic profiles during 3,4-AHBA production were compared at three different DO levels (0, 2.6, and 5.3 ppm) using the DO-stat method. Results of the metabolome analysis revealed metabolic shifts in both the central metabolic pathway and amino acid metabolism at a DO of < 33% saturated oxygen. Based on this metabolome analysis, metabolic pathways were rationally designed for oxygen limitation. An ldh deletion mutant, with the loss of lactate dehydrogenase, exhibited 3.7-fold higher specific productivity of 3,4-AHBA at DO = 0 ppm as compared to the parent strain KT01 and produced 5.6 g/L 3,4-AHBA in a glucose fed-batch culture. Conclusions: Our results revealed changes in the metabolic state in response to DO concentration and provided insights into oxygen supply during fermentation and the rational design of metabolic pathways for improved production of related amino acids and their derivatives.

3-Amino-4-hydroxybenzoic acid production from sweet sorghum juice by recombinant Corynebacterium glutamicum

Bioresour Technol 2015 Dec;198:410-7.PMID:26409852DOI:10.1016/j.biortech.2015.09.024.

The production of the bioplastic precursor 3-Amino-4-hydroxybenzoic acid (3,4-AHBA) from sweet sorghum juice, which contains amino acids and the fermentable sugars sucrose, glucose and fructose, was assessed to address the limitations of producing bio-based chemicals from renewable feedstocks. Recombinant Corynebacterium glutamicum strain KT01 expressing griH and griI derived from Streptomyces griseus produced 3,4-AHBA from the sweet sorghum juice of cultivar SIL-05 at a final concentration (1.0 g l(-1)) that was 5-fold higher than that from pure sucrose. Fractionation of sweet sorghum juice by nanofiltration (NF) membrane separation (molecular weight cut-off 150) revealed that the NF-concentrated fraction, which contained the highest concentrations of amino acids, increased 3,4-AHBA production, whereas the NF-filtrated fraction inhibited 3,4-AHBA biosynthesis. Amino acid supplementation experiments revealed that leucine specifically enhanced 3,4-AHBA production by strain KT01. Taken together, these results suggest that sweet sorghum juice is a potentially suitable feedstock for 3,4-AHBA production by recombinant C. glutamicum.

Preparation, optimization and pharmacological evaluation of 99mTc- 4-hydroxy-3-(2-hydroxy-3-methoxybenzylideneamino) benzoic acid complex: as a novel potential radiopharmaceutical agent with hepatobiliary excretion

Mol Biol Rep 2018 Dec;45(6):2717-2723.PMID:30328001DOI:10.1007/s11033-018-4402-6.

Schiff base ligands are biologically active compounds in having antimicrobial, antiviral and antitumor activities etc. In this study, we have synthesized a Schiff base ligand namely 4-hydroxy-3-(2-hydroxy-3-methoxybenzylideneamino) benzoic acid, by reacting 3-Amino-4-hydroxybenzoic acid and 2-hydroxy-3-methoxy benzaldehyde in the presence of acetic acid and refluxing it. The resulting base ligand was characterized on HPLC and used for radiolabelling with technetium-99m. The ligand 4-hydroxy-3-(2-hydroxy-3-methoxybenzylideneamino) benzoic acid was labelled with 99mTc at pH 7, while reacting 230 µg of ligand with 15 mCi of 99mTcO-4 for 10 min at room temperature. The resulting 99mTc-ligand complex was characterized by paper chromatography, TLC, HPLC and electrophoresis technique. The stability of the complex was determined at room temperature and in human serum. The biodistribution of the complex was studied in mice and scintigraphy was performed in rabbit. The 99mTc-ligand complex showed high radiolabelling yield (up to 99 ± 1%) and high stability at room temperature and in human serum. The newly prepared complex exhibited no net charge. Our newly developed 99mTc-ligand complex demonstrated high accumulation in liver and spleen of mice as well as in rabbit. Based on these findings, we have suggested that this novel radioligand i.e., 99mTc- 4-hydroxy-3-(2-hydroxy-3-methoxybenzylideneamino) benzoic acid complex could be used for liver and spleen imaging.

Multifunctional Lanthanide-Based Metal-Organic Frameworks Derived from 3-Amino-4-hydroxybenzoate: Single-Molecule Magnet Behavior, Luminescent Properties for Thermometry, and CO2 Adsorptive Capacity

Inorg Chem 2022 Aug 22;61(33):12977-12990.PMID:35939069DOI:10.1021/acs.inorgchem.2c00544.

Herein, we describe and study a new family of isostructural multifunctional metal-organic frameworks (MOFs) with the formula {[Ln5L6(OH)3(DMF)3]·5H2O}n (where (H2L) is 3-Amino-4-hydroxybenzoic acid ligand) for magnetism and photoluminescence. Interestingly, three of the materials (Dy-, Er-, and Yb-based MOFs) present single-molecule magnet (SMM) behavior derived from the magnetic anisotropy of the lanthanide ions as a consequence of the adequate electronic distribution of the coordination environment. Additionally, photoluminescence properties of the ligand in combination with Eu and Tb counterparts were studied, including the heterometallic Eu-Tb mixed MOF that shows potential as ratiometric luminescent thermometers. Finally, the porous nature of the framework allowed showing the CO2 sorption capacity.