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3-Aminosalicylic Acid Sale

(Synonyms: 3-氨基水杨酸) 目录号 : GC49849

A salicylic acid derivative

3-Aminosalicylic Acid Chemical Structure

Cas No.:570-23-0

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产品描述

3-Aminosalicylic acid is a salicylic acid derivative and potential impurity in commercial preparations of 5-aminosalicylic acid.1,2 It protects against apoptosis, as well as reverses reductions in mitochondrial complex I, also known as NADH dehydrogenase, activity and increases in reactive oxygen species (ROS) production induced by manganese in SK-N-MC cells when used at a concentration of 1 µM.1

1.Yoon, H., Lee, G.-H., Kim, D.-S., et al.The effects of 3, 4 or 5 amino salicylic acids on manganese-induced neuronal death: ER stress and mitochondrial complexesToxicol. In Vitro25(7)1259-1268(2011) 2.Gotti, R., Pomponio, R., Bertucci, C., et al.Determination of 5-aminosalicylic acid related impurities by micellar electrokinetic chromatography with an ion-pair reagentJ. Chromatogr. A916(1-2)175-183(2001)

Chemical Properties

Cas No. 570-23-0 SDF Download SDF
别名 3-氨基水杨酸
Canonical SMILES O=C(C1=CC=CC(N)=C1O)O
分子式 C7H7NO3 分子量 153.1
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1 mM 6.5317 mL 32.6584 mL 65.3168 mL
5 mM 1.3063 mL 6.5317 mL 13.0634 mL
10 mM 0.6532 mL 3.2658 mL 6.5317 mL
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Research Update

Cotton swabs decorated with Ag@BPQD for the fluorescence determination of 3-aminosalicylic and 5-aminosalicylic acid

Mikrochim Acta 2023 Feb 7;190(3):82.PMID:36746802DOI:10.1007/s00604-023-05665-7.

Novel and portable cotton swab-based fluorometry was constructed for the first time for 3-Aminosalicylic Acid (3-ASA) and 5-aminosalicylic acid (5-ASA) detection. It was carried out by fluorescence enhancement on silver (Ag)-doped black phosphorus quantum dots (Ag@BPQD). Ag@BPQD were prepared from AgNO3 and bulk black phosphorus in N, N-dimethylformamide (DMF) solution by solvothermal decomposition after mechanical exfoliation. Ag@BPQD show blue fluorescence with a quantum yield (QY) of 2.43%. In the presence of Ag@BPQD, 3-ASA exhibited bright blue fluorescence (λex = 328 nm, λem = 448 nm). The fluorescence of 5-ASA was also enhanced significantly and exhibited bright green emission (λex = 328 nm, λem = 484 nm). The linear range of 3-ASA is 0-90 μM with a detection limit (LOD) of 0.10 μM, relative standard deviation (RSD) ≤ 2.04%, and a recovery range of 98.0-104.3%. The linear range of 5-ASA is 0-120 μM with a LOD of 0.12 μM, RSD ≤ 1.34%, and a recovery range of 98.0-101.3%. When 3-ASA and 5-ASA were mixed in different ratios, the fluorescence showed different colors. The possible mechanism of the interaction between 3-ASA (or 5-ASA) and Ag@BPQD may be ascribed to the generation of excited-state intramolecular proton transfer. To realize convenient detection of 3-ASA and 5-ASA, a Ag@BPQD portable sensing method using cotton swabs were built. The proposed approach provides the detection of 3-ASA and 5-ASA in environmental and biological samples with high efficiency, accuracy and portability.

Determination of 5-aminosalicylic acid related impurities by micellar electrokinetic chromatography with an ion-pair reagent

J Chromatogr A 2001 May 4;916(1-2):175-83.PMID:11382289DOI:10.1016/s0021-9673(00)01097-9.

A micellar electrokinetic chromatographic (MEKC) method was developed for the quantification of mesalazine or 5-aminosalicylic acid (5-ASA) and its major impurities 3-Aminosalicylic Acid, salicylic acid, sulfanilic acid and 4-aminophenol. The optimisation of the experimental conditions was carried out considering some important requirements: resolution, reproducibility, detection limits of 0.1% (m/m) or less, short total analysis time. Preliminary investigations employing sodium dodecyl sulfate (SDS) as surfactant did not lead to the necessary resolution of the studied compounds; the addition of tetrabutylammonium bromide (TBAB) to the SDS micellar system resulted in the complete separation of all the compounds. The effects on the separation by several parameters such as TBAB concentration, SDS concentration, background electrolyte pH and concentration, were evaluated. Using a fused-silica capillary (8.5 cm effective length) complete analysis was obtained in a very short time. Under the optimised final conditions [120 mM 3-(cyclohexylamino)-2-hydroxy-1-propanesulfonic acid buffer, pH 10.20, 65 mM SDS in the presence of 55 mM TBAB and 5% methanol] the method was validated for specificity, precision, linearity, limits of detection and quantitation, and robustness: the 5-ASA related impurities can be quantified at least at the 0.1% (m/m) level.

Phenolic metabolism in the hornwort Anthoceros agrestis: 4-coumarate CoA ligase and 4-hydroxybenzoate CoA ligase

Plant Cell Rep 2020 Sep;39(9):1129-1141.PMID:32405654DOI:10.1007/s00299-020-02552-w.

4-Coumarate coenzyme A ligase and 4-hydroxybenzoate coenzyme A ligase from the hornwort Anthoceros agrestis expressed in E. coli were characterized on biochemical and molecular levels and showed interesting substrate specificities. Acyl-activating enzymes are associated with the biosynthesis or degradation of various metabolic products such as lipids, amino acids, sugars, and natural compounds. In this work, cDNA sequences encoding 4-coumarate coenzyme A ligase (4CL) and 4-hydroxybenzoate coenzyme A ligase (4HBCL) were amplified from the hornwort Anthoceros agrestis. The coding sequences were expressed in E. coli and purified by Ni-chelate chromatography. The CoA ligases exhibited different substrate specificities. 4CL catalyzed the activation of 4-coumaric acid, 3-coumaric acid, 2-coumaric acid, caffeic acid, isoferulic acid, ferulic acid, and cinnamic acid but lacked activities towards sinapic acid and benzoic acids. In contrast, 4HBCL preferred 4-hydroxybenzoic acid and benzoic acid, but also accepted other benzoic acid derivatives except salicylic acid and 3-Aminosalicylic Acid. Furthermore, 4HBCL also activated isoferulic acid, cinnamic acid, 2-coumaric acid, 3-coumaric acid, 4-coumaric acid and caffeic acid, but lacked affinity for ferulic acid and sinapic acid. These substrate specificities could be related to the phenolic compounds identified in Anthoceros agrestis.

On the antioxidant properties of therapeutic drugs: quenching of singlet molecular oxygen by aminosalicylic acids

Redox Rep 2002;7(4):229-33.PMID:12396669DOI:10.1179/135100002125000613.

The ability of the widely employed therapeutic drugs 4-aminosalicylic acid and 5-aminosalicylic acid to act as singlet molecular oxygen (O(2)((1)delta(g))) scavengers was investigated at pH 7 and pH 12. The isomer 3-Aminosalicylic Acid was also included in the study for comparative purposes. All three compounds quench photochemically generated O(2)((1)delta(g)) with rate constants in the range of 10(7)-10(8) x M(-1)s(-1), depending on the experimental conditions. No chemical reaction (oxidation of the aminosalicylic acids) was detected at the neutral pH, whereas at pH 12 both chemical and physical interactions with O(2)((1)delta(g)) operated. The physical process implies the de-activation of the oxidant species without destruction of the aminosalicylic acid. The quotients between the overall and reactive rate constants for O(2)((1)delta(g)) quenching at pH 12 (k(r)/k(t) ratios), which account for the actual effectiveness of photodegradation, were relatively low (0.22, 0.04, and 0.06 for 3-, 4- and 5-aminosalicylic acids, respectively). This indicates that the drugs, particularly the 4- and 5-amino derivatives, de-activate the excited oxygen species, at both pH values studied, mainly in a physical fashion, preventing its photodegradation and providing an antioxidative protection for possible photo-oxidizable biological targets in the surroundings.

CO2 Preactivation in Photoinduced Reduction via Surface Functionalization of TiO2 Nanoparticles

J Phys Chem Lett 2013 Feb 7;4(3):475-9.PMID:26281743DOI:10.1021/jz3020327.

Salicylate and salicylic acid derivatives act as electron donors via charge-transfer complexes when adsorbed on semiconducting surfaces. When photoexcited, charge is injected into the conduction band directly from their highest occupied molecular orbital (HOMO) without needing mediation by the lowest unoccupied molecular orbital (LUMO). In this study, we successfully induce the chemical participation of carbon dioxide in a charge transfer state using 3-Aminosalicylic Acid (3ASA). We determine the geometry of CO2 using a combination of ultraviolet-visible spectroscopy (UV-vis), surface enhanced Raman scattering (SERS), (13)C NMR, and electron paramagnetic resonance (EPR). We find CO2 binds on Ti sites in a carbonate form and discern via EPR a surface Ti-centered radical in the vicinity of CO2, suggesting successful charge transfer from the sensitizer to the neighboring site of CO2. This study opens the possibility of analyzing the structural and electronic properties of the anchoring sites for CO2 on semiconducting surfaces and proposes a set of tools and experiments to do so.