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(Synonyms: 分散红 1) 目录号 : GC60141

DisperseRed1,一种偶氮苯衍生物,是一种偶氮纺织品染料,广泛用于纺织工业中的聚酯织物染色。

Disperse Red 1 Chemical Structure

Cas No.:2872-52-8

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250mg
¥450.00
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500mg
¥765.00
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产品描述

Disperse Red 1, an azobenzene derivative, is an azo textile dye extensively used for dyeing polyester fabrics in textile industry[1][2].

Exposure of human lymphocytes and a human hepatoma (HepG2) cell line to Disperse Red 1 in vitro at concentrations of 1.0 μg/mL and 2.0 μg/mL increases the frequency of micronuclei and also causes mutations in the Salmonella assay (13 revertants/μg)[2].

To assess the toxic effects of Disperse Red 1 (DR1), on reproduction, sexually mature male mice (Mus musculus, strain CF-1) are orally (gavage) treated with single doses of the compound (20-500 mg/kg). Disperse Red 1 treatment causes testicular toxicity, increases frequency of sperm with abnormal morphology and decreases fertility. An increased amount of DNA damage is also detected in testis cells 16.6 and 24.9 days after treatments with 100 and 500 mg/kg[2].

[1]. LaÍs da Silva Leite, et al. Monitoring Ecotoxicity of Disperse Red 1 Dye During photo-Fenton Degradation. Chemosphere. 2016 Apr;148:511-7. [2]. FÁbio Henrique Fernandes, et al. Disperse Red 1 (Textile Dye) Induces Cytotoxic and Genotoxic Effects in Mouse Germ Cells. Reprod Toxicol. 2015 Jun;53:75-81.

Chemical Properties

Cas No. 2872-52-8 SDF
别名 分散红 1
Canonical SMILES O=[N+](C1=CC=C(/N=N/C2=CC=C(N(CCO)CC)C=C2)C=C1)[O-]
分子式 C16H18N4O3 分子量 314.34
溶解度 DMSO: 16.67 mg/mL (53.03 mM) 储存条件 Store at -20°C
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储备液的保存方式和期限:-80°C 储存时,请在 6 个月内使用,-20°C 储存时,请在 1 个月内使用。
为了提高溶解度,请将管子加热至37℃,然后在超声波浴中震荡一段时间。
Shipping Condition 评估样品解决方案:配备蓝冰进行发货。所有其他可用尺寸:配备RT,或根据请求配备蓝冰。

溶解性数据

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1 mg 5 mg 10 mg
1 mM 3.1813 mL 15.9063 mL 31.8127 mL
5 mM 0.6363 mL 3.1813 mL 6.3625 mL
10 mM 0.3181 mL 1.5906 mL 3.1813 mL
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Research Update

Isomerization and reorientation of Disperse Red 1 in poly(ethyl methacrylate)

J Chem Phys 2021 Oct 28;155(16):164901.PMID:34717357DOI:10.1063/5.0063031.

Irradiation of azobenzene-containing polymer materials with light causes cis-trans isomerization and reorientation of azobenzene moieties and thereby changes in the optical properties of the materials. In this study, the film of poly(ethyl methacrylate) doped with the azobenzene derivative Disperse Red 1 (DR1) has been irradiated with the linearly polarized light of 546 nm. The time profiles of optical anisotropy and absorbance measured during irradiation have been analyzed using a kinetic model. Based on the analysis of the time profiles, we conclude that the light-induced reorientation of DR1 molecules occurs in confined environments where trans → cis isomerization is hindered, while in roomy environments, there is no reorientation. In the confined environment, reorientation occurs due to the environmental changes caused by the isomerization attempts of the DR1 molecule. The polymer environment affects thermal cis → trans and light-induced trans → cis isomerizations of the DR1 molecule differently, suggesting that the spatial requirements for these processes to proceed are different. The thermal isomerization does not result in the reorientation of DR1 molecules in roomy environments.

Decolorization of acid blue 29, Disperse Red 1 and congo red by different indigenous fungal strains

Chemosphere 2021 May;271:129532.PMID:33429264DOI:10.1016/j.chemosphere.2021.129532.

Azo dyes are toxic and recalcitrant environmental pollutants in wastewater and soil in many industrial sites in Asia and Arabic countries. The aim of this study was to find fungal species useful in wastewater treatment and soil remediation efforts. We assessed the ability of different indigenous Aspergillus strains (i.e. A. flavus, A. fumigatus, A. niger and A. terreus) to degrade the azo dyes Acid Blue 29 (AB29), Disperse Red 1 (DR1) and Congo Red (CR). The optimal conditions for dye decolorization by the above-mentioned strains appeared to be as follows: temperature range 30-35 °C, pH 7, glucose as the carbon source (10 g/L), ammonium sulphate as the nitrogen source (1.5 g/L) and 100 mg/L initial dye concentration. The Aspergillus strains decolorized all azo dyes more than 86%. The HPLC and GC-MS analyses confirmed that aniline (retention time 9.0 min), 3-nitroaniline (retention time 15.92 min), 4-nitroanline (retention time 17.81 min), N,N' diethyl-1,4-phenylendiamine (retention time 18.184 min), and benzidine (retention time 15.07 min) were formed as the intermediate metabolites of dye degradation. All Aspergillus strains decolorized 85% of the dyes in synthetic wastewater.

Disperse Red 1 (textile dye) induces cytotoxic and genotoxic effects in mouse germ cells

Reprod Toxicol 2015 Jun;53:75-81.PMID:25883024DOI:10.1016/j.reprotox.2015.04.002.

Disperse Red 1 (DR1), which is widely used in the textile industry, is an azo dye that contributes to the toxicity and pollution of wastewater. To assess the toxic effects of DR1 on reproduction, sexually mature male mice (Mus musculus, strain CF-1) were orally (gavage) treated with single doses of the compound at 20, 100 and 500 mg/kg body weight. Testicular features and sperm parameters were evaluated 8.3, 16.6 and 24.9 days after treatments. In addition to testicular toxicity caused by the dye, the data clearly showed an increased frequency of sperm with abnormal morphology and decreased fertility. An increased amount of DNA damage was also detected in testis cells 16.6 and 24.9 days after treatments with 100 and 500 mg/kg. This study demonstrated the toxic and genotoxic effects of DR1, indicating the harmful activity of this dye on reproductive health.

Differential toxicity of Disperse Red 1 and Disperse Red 13 in the Ames test, HepG2 cytotoxicity assay, and Daphnia acute toxicity test

Environ Toxicol 2011 Oct;26(5):489-97.PMID:20549607DOI:10.1002/tox.20576.

Azo dyes are of environmental concern due to their degradation products, widespread use, and low-removal rate during conventional treatment. Their toxic properties are related to the nature and position of the substituents with respect to the aromatic rings and amino nitrogen atom. The dyes Disperse Red 1 and Disperse Red 13 were tested for Salmonella mutagenicity, cell viability by annexin V, and propidium iodide in HepG2 and by aquatic toxicity assays using daphnids. Both dyes tested positive in the Salmonella assay, and the suggestion was made that these compounds induce mainly frame-shift mutations and that the enzymes nitroreductase and O-acetyltransferase play an important role in the observed effect. In addition, it was shown that the presence of the chlorine substituent in Disperse Red 13 decreased the mutagenicity about 14 times when compared with Disperse Red 1, which shows the same structure as Disperse Red 13, but without the chlorine substituent. The presence of this substituent did not cause cytotoxicity in HepG2 cells, but toxicity to the water flea Daphnia similis increased in the presence of the chlorine substituent. These data suggest that the insertion of a chlorine substituent could be an alternative in the design of dyes with low-mutagenic potency, although the ecotoxicity should be carefully evaluated.

Monitoring ecotoxicity of Disperse Red 1 dye during photo-Fenton degradation

Chemosphere 2016 Apr;148:511-7.PMID:26841294DOI:10.1016/j.chemosphere.2016.01.053.

The present work assessed the ecotoxicity of the commercially available form of the azo dye Disperse Red 1 (DR1) and the main degradation products generated during photo-Fenton degradation. The acute toxicity tests with the microcrustacean Daphnia similis showed that toxicity increased after 10 min of treatment, when 35% of the original concentration of the dye has been degraded but without decrease in total organic carbon concentration (TOC). The increase of toxicity was a consequence of generation of degradation products of higher toxicity than DR1, which achieved maximum concentration after 10 min reaction. The structures identified using LC/MS indicated that most of the intermediates were formed after addition of hydroxyl radical to benzenic ring but the cleavage of azo bond was also observed. The intermediates were further degraded and toxicity was then reduced to non toxic levels after 45 min experiment, when 98% of the initial concentration of DR1 was degraded and mineralization achieved 55%. The results of this study showed that the textile dye DR1 can be degraded by photo-Fenton process with removal of acute toxicity to D. similis even with incomplete mineralization.