723-62-6Relevant articles and documents
Fluorometric analysis of chlorite via oxidation of 9-anthracenecarboxaldehyde
Lee, Kang Min,Choi, Myung Gil,Yoo, Jae Hoon,Ahn, Sangdoo,Chang, Suk-Kyu
, (2021)
We investigated a simple fluorescence signaling method for the convenient analysis of a practical oxidant—chlorite—via the oxidation of 9-anthracenecarboxaldehyde to the corresponding carboxylic acid. 9-Anthracenecarboxaldehyde exhibited a marked ratiometric fluorescence signaling toward chlorite through manipulating its aggregation-induced emission property. The probe showed high chlorite-selectivity over other oxychlorine species as well as common metal ions, anions, and oxidants. Interference from a closely related oxidant, hypochlorite, was efficiently removed using DMSO as a scavenger. The proposed probe also exhibited a prominent ratiometric response through changes in UV–vis absorption behavior. Among the tested aromatic aldehydes (naphthaldehydes, anthracenecarboxaldehyde, and pyrenecarboxaldehyde), anthracene-based carboxaldehyde exhibited the most pronounced signaling contrast and the fastest signaling speed. The detection limit of chlorite determination was found to be 1.1 × 10–7 M. Exploitation of the probe for the convenient analysis of chlorite in tap water via a recovery test was conducted.
4-Biphenylaldehyde and 9-anthraldehyde: Two fluorescent substrates for determining P450 enzyme activities in rat and human
Marini,Grasso,Longo,Puccini,Riccardi,Gervasi, P. Giovanni
, p. 1 - 11 (2003)
1. 4-Biphenylaldehyde (4-BA) and 9-anthraldehyde (9-AA) were examined as substrates for cytochrome P450 (CYPs) enzymes in rat and human. Both aldehydes were oxidized by CYPs to fluorescent carboxylic acids, which can be assayed with a high sensitivity by an easy fluorimetric method. 2. With liver microsomes from control and induced rats, the oxidation of both 9-AA and 4-BA followed simple Michaelis-Menten kinetics. Only microsomes from rats pretreated with phenobarbital (a strong inducer of P4502B1/2) could increase (about threefold) the oxidation rates (Vmax) of both aldehydes above the control values, which were 6.7 ± 1.1 and 3.3 ± 0.6 nmolmin-1 mg-1 protein for 4-BA and 9-AA, respectively. On the other hand, the Km's, which were similar for both aldehydes (about 25 μM), did not change significantly with any inducer. The use of purified rat CYP1A1, 2E1, 2B1 and 2C11 in a reconstituted system showed that only 2B1 and 2C11 could oxidize both substrates with a high turnover. 3. In human liver microsomes, the oxidation rates of these aldehydes (1.6 ± 0.2 and 0.42 ± 0.1 nmolmin-1 mg-1 protein for 4-BA and 9-AA, respectively) were lower than those of rat but with similar Km's (20-26 μM). 4. The oxidation of these aldehydes was also determined with cDNA-expressed CYP1A1, 1A2, 2A6, 2B6, 2C9, 2D6, 2E1 and 3A4 and with a characterized bank of 14 human liver microsomes. In a reconstituted system, only CYP2B6, 2A6, 3A4 and with a lower turnover 2C9 oxidized both substrates. 5. Among the CYP marker activities of the 14 human samples, good correlations were only observed between CYP3A-dependent 6β-testosterone hydroxylase and the oxidation of 4-BA (r = 0.74) or 9-AA (r = 0.80) and between the oxidation of 4-BA versus 9-AA (r = 0.74). Weak correlations were also found between the 2B6-linked S-mephenytoin Ndemethylase and the oxidation of 4-BA (r = 0.58) or 9-AA (r = 0.65). 6. Inhibition experiments revealed that the oxidation of these aldehydes was inhibited by ketoconazole, 8-methoxypsoralene and sulphophenazole, selective inhibitors for P4503A6, 2A6 and 2C9, respectively. 7. In summary, based on the use of cDNA-expressed CYPs, correlation analysis and chemical inhibition, the metabolism in human liver microsomes of these aldehydes appears primarily catalysed by CYP3A, although CYP2A6, 2B6 and 2C9 may play a role. 9-AA and particularly 4-BA, owing to the high rate of its metabolism, may be two novel useful fluorescent probe substrates for assaying CYP activities in various species.
Synthesis method of 9-anthracenecarboxylic acid
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Paragraph 0031; 0032; 0036-0041, (2022/01/07)
The present invention relates to the field of synthesis technology of dye intermediates and electronic fluorescent materials, providing a new synthesis method of 9-anthracenecarboxylic acid, comprising the following steps: 9- anthracenecarboxaldehyde as raw material, reacting under the action of oxidants and auxiliaries and pH buffers, after the completion of the reaction, the solvent is evaporated, the pH = 1-5, the organic matter is extracted, and then the organic phase is evaporated, which can be prepared to give 9-anthracenecarboxylic acid. The present invention solves the prior art synthesis of 9- anthracenecarboxy acid by-products more, low yield and other issues, synthesis of 9- anthracene formaldehyde as raw material, under the action of oxidants and auxiliaries and pH buffers for reaction, the prepared yellow solid for nuclear magnetic hydrogen spectrometry identification and liquid chromatography detection, the results show that the prepared product structure is 9-anthracic acid, purity up to 99% or more, thus illustrating that the synthesis method of the present invention is less by-product, easy to purify, mild reaction conditions, simple operation, stable product quality, Suitable for industrial production.
Method for copper-catalyzed carboxylation reaction of arylboronic acid and carbon dioxide
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Paragraph 0095; 0096, (2019/12/29)
The invention discloses a method for a copper-catalyzed carboxylation reaction of arylboronic acid and carbon dioxide. According to the method, carbon dioxide is used as a C1 source, copper catalysisis adopted, alkoxide serves as alkali, and a reaction is carried out in an organic solvent; the method is simple in process and easy to implement, and shows wide functional group compatibility; the method allows various arylboronic acids such as monosubstituted or polysubstituted phenylboronic acid, polycyclic aromatic hydrocarbon boronic acid and benzoheterocyclic boronic acid to be converted into corresponding arylcarboxylic acids with considerable yield under mild conditions; and the produced carboxylic acids have important application value, and can be used for deriving a great number of other common chemical substances, such as acyl halide, acid anhydride, ester and amide.
