3-Amino-4-hydroxybenzoic acid
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| Category | Others |
| Catalog number | BBF-04662 |
| CAS | 1571-72-8 |
| Molecular Weight | 153.1 |
| Molecular Formula | C7H7NO3 |
| Purity | 98.0% |
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Description
3-Amino-4-hydroxybenzoic acid (CAS# 1571-72-8) is a useful research chemical.
Specification
| Synonyms | Benzoic acid, 3-amino-4-hydroxy-; 3,4-AHBA |
| IUPAC Name | 3-amino-4-hydroxybenzoic acid |
| Canonical SMILES | C1=CC(=C(C=C1C(=O)O)N)O |
| InChI | InChI=1S/C7H7NO3/c8-5-3-4(7(10)11)1-2-6(5)9/h1-3,9H,8H2,(H,10,11) |
| InChI Key | MRBKRZAPGUCWOS-UHFFFAOYSA-N |
Properties
| Appearance | Crystalline powder |
| Boiling Point | 388.8 ℃ at 760 mmHg |
| Melting Point | 208 ℃ (dec.)(lit.) |
| Density | 1.491 g/cm3 |
| LogP | 1.25380 |
Reference Reading
1. 3-Amino-4-hydroxybenzoic acid production from glucose and/or xylose via recombinant Streptomyces lividans
Satoko Niimi-Nakamura, Hideo Kawaguchi, Kouji Uematsu, Hiroshi Teramura, Sachiko Nakamura-Tsuruta, Norimasa Kashiwagi, Yoshinori Sugai, Yohei Katsuyama, Yasuo Ohnishi, Chiaki Ogino, Akihiko Kondo J Gen Appl Microbiol. 2022 Sep 15;68(2):109-116. doi: 10.2323/jgam.2022.06.001. Epub 2022 Jul 12.
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.
2. Enhanced production of γ-amino acid 3-amino-4-hydroxybenzoic acid by recombinant Corynebacterium glutamicum under oxygen limitation
Hideo Kawaguchi, Tomohisa Hasunuma, Yasuo Ohnishi, Takashi Sazuka, Akihiko Kondo, Chiaki Ogino Microb Cell Fact. 2021 Dec 23;20(1):228. doi: 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. Multifunctional Lanthanide-Based Metal-Organic Frameworks Derived from 3-Amino-4-hydroxybenzoate: Single-Molecule Magnet Behavior, Luminescent Properties for Thermometry, and CO2 Adsorptive Capacity
Estitxu Echenique-Errandonea, Ricardo F Mendes, Flávio Figueira, Duane Choquesillo-Lazarte, Garikoitz Beobide, Javier Cepeda, Duarte Ananias, Antonio Rodríguez-Diéguez, Filipe A Almeida Paz, José M Seco Inorg Chem. 2022 Aug 22;61(33):12977-12990. doi: 10.1021/acs.inorgchem.2c00544. Epub 2022 Aug 8.
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.
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Bio Calculators
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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
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Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
