4-Amino-3-hydroxybenzoic acid
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| Category | Others |
| Catalog number | BBF-04663 |
| CAS | 2374-03-0 |
| Molecular Weight | 153.1 |
| Molecular Formula | C7H7NO3 |
| Purity | 98.0% |
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Description
4-Amino-3-hydroxybenzoic acid (CAS# 2374-03-0) is disubsituted benzoic acid used in the preparation of various pharmaceutical compounds such as sphingosine kinase inhibitors.
Specification
| Synonyms | benzoic acid, 4-amino-3-hydroxy-; 3-hydroxy-4-aminobenzoic acid |
| IUPAC Name | 4-amino-3-hydroxybenzoic acid |
| Canonical SMILES | C1=CC(=C(C=C1C(=O)O)O)N |
| InChI | InChI=1S/C7H7NO3/c8-5-2-1-4(7(10)11)3-6(5)9/h1-3,9H,8H2,(H,10,11) |
| InChI Key | NFPYJDZQOKCYIE-UHFFFAOYSA-N |
Properties
| Appearance | Yellowish brown solid |
| Boiling Point | 385.7 ℃ at 760 mmHg |
| Melting Point | 211-215 ℃ (lit.) |
| Density | 1.028 g/cm3 |
| LogP | 1.25380 |
Reference Reading
1. Designing of modified ion-imprinted chitosan particles for selective removal of mercury (II) ions
Amira K Hajri, Bassem Jamoussi, Aishah E Albalawi, Ohud H N Alhawiti, Amal A Alsharif Carbohydr Polym. 2022 Jun 15;286:119207. doi: 10.1016/j.carbpol.2022.119207. Epub 2022 Feb 8.
Ion-imprinting methodology was utilized in the fabrication of mercury ion-imprinted sorbent derived from modified chitosan derivatives. The Schiff base ligand was first derived from 4-amino-3-hydroxybenzoic acid and 2-pyridinecarboxaldehyde (HPB) and then incorporated with chitosan via amide bonds. The obtained modified chitosan polymeric ligand (PBCS) was combined with Hg(II) ions to produce the corresponding polymeric complex and the imprinting was then achieved upon the glutaraldehyde cross-linking and eliminating the incorporated Hg(II) ions to finally have the Hg(II) ion-imprinted sorbent material (Hg-PBCS). The materials have been investigated using various techniques such as NMR and FTIR and the obtained sorbent was examined to evaluate its selective affinity to capture the target Hg(II) ions. The developed Hg-PBCS sorbent exhibited a higher tendency toward the targeted Hg(II) ions compared to the control non-imprinted sorbent particle (NI-PBCS) with a maximum capacity of 315 mg/g. Also, the sorbent displayed relatively rapid adsorption kinetics that best correlated with the pseudo-second-order model.
2. Unveiling self-sensitized photodegradation pathways by DFT calculations: A case of sunscreen p-aminobenzoic acid
Siyu Zhang, Jingwen Chen, Qing Zhao, Qing Xie, Xiaoxuan Wei Chemosphere. 2016 Nov;163:227-233. doi: 10.1016/j.chemosphere.2016.08.028. Epub 2016 Aug 16.
Self-sensitized photodegradation has been observed for diverse aquatic organic pollutants. However, photodegradation pathways have not been clarified in previous experimental studies. Here, we attempted to probe self-sensitized photodegradation pathways of organic pollutants employing both photolytic experiments and density functional theory calculations. By performing photolytic experiments, we found that singlet state oxygen ((1)O2) play an essential role in photodegradation of a sunscreen p-aminobenzoic acid (PABA). PABA can photogenerate (1)O2 and react fast with (1)O2. We hypothesized that PABA underwent (1)O2 induced self-sensitized photodegradation. By calculating transition states, intermediates and reaction barriers, we found that (1)O2 can oxidize PABA through electrophilic attacks on the benzene ring to abstract one H atom of the amino group following a 1,3-addition mechanism or to induce decarboxylation. Either pathway produces a hydroperoxide. O-O bond cleavage of the hydroperoxides occurring at ground states or the lowest triplet excited states can produce phenoxyl radical precursors of 4-amino-3-hydroxybenzoic acid and 4-aminophenol, which are photodegradation products detected in experiments. Thus, a viable (1)O2 self-sensitized photodegradation mechanism was unveiled for PABA.
3. CO2 Improved Synthesis of Benzimidazole with the Catalysis of a New Calcium 4-Amino-3-hydroxybenzoate
Ruo-Xuan Gao, Yuan-Yuan Gao, Ning Zhu, Li-Min Han Acta Chim Slov. 2021 Mar;68(1):205-211.
In this paper, we explored the synthesis of benzimidazole by the reaction of DMF and o-phenylenediamine. In the process of catalyst screening, we found that 4-amino-3-hydroxybenzoic acid, benzoic acid, and benzene-1,3,5-tricarboxylic acid could catalyze the reaction. Moreover, the calcium 4-amino-3-hydroxybenzoate and CO2 could more effectively catalyze the reaction, the synergistic effect of CO2 and 4-amino-3-hydroxybenzoic acid calcium salt can increase the yield of benzimidazole from 28% to 94%.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
