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MedKoo Cat#: 461693 | Name: Disperse Red 1

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Disperse Red 1 is an azo dye that contributes to the toxicity and pollution of wastewater.

Chemical Structure

Disperse Red 1
Disperse Red 1
CAS#2872-52-8

Theoretical Analysis

MedKoo Cat#: 461693

Name: Disperse Red 1

CAS#: 2872-52-8

Chemical Formula: C16H18N4O3

Exact Mass: 314.1379

Molecular Weight: 314.34

Elemental Analysis: C, 61.14; H, 5.77; N, 17.82; O, 15.27

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Synonym
Disperse Red 1; Celliton Red B; Celliton Scarlet B; Diacelliton Scarlet B; Fenacet Scarlet B; Neosetile Scarlet B; WO 4; WO-4; WO4;
IUPAC/Chemical Name
(E)-2-(ethyl(4-((4-nitrophenyl)diazenyl)phenyl)amino)ethan-1-ol
InChi Key
FOQABOMYTOFLPZ-ISLYRVAYSA-N
InChi Code
InChI=1S/C16H18N4O3/c1-2-19(11-12-21)15-7-3-13(4-8-15)17-18-14-5-9-16(10-6-14)20(22)23/h3-10,21H,2,11-12H2,1H3/b18-17+
SMILES Code
O=[N+](C1=CC=C(/N=N/C2=CC=C(N(CCO)CC)C=C2)C=C1)[O-]
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Disperse Red 1, an azobenzene derivative, is an azo textile dye extensively used for dyeing polyester fabrics in textile industry.
In vitro activity:
This study investigated photoalignment for various nematics at the interface with the photosensitive polymer layer polymethyl methacrilate functionalised with azo dye Disperse Red 1. It was found that the efficiency of photoalignment exhibits marked differences depending on the structure of the rigid core of the liquid crystal molecules. Reference: Polymers (Basel). 2021 Dec 31;14(1):159. https://pubmed.ncbi.nlm.nih.gov/35012181/
In vivo activity:
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 mouse 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 (disperse red 1), indicating the harmful activity of this dye on reproductive health. Reference: Reprod Toxicol. 2015 Jun;53:75-81. https://pubmed.ncbi.nlm.nih.gov/25883024/
Solvent mg/mL mM
Solubility
DMSO 83.3 265.09
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 314.34 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Jánossy I, Tóth-Katona T. Photo-Orientation of Liquid Crystals on Azo Dye-Containing Polymers. Polymers (Basel). 2021 Dec 31;14(1):159. doi: 10.3390/polym14010159. PMID: 35012181; PMCID: PMC8747469. 2. da Silva Leite L, de Souza Maselli B, de Aragão Umbuzeiro G, Pupo Nogueira RF. Monitoring ecotoxicity of disperse red 1 dye during photo-Fenton degradation. Chemosphere. 2016 Apr;148:511-7. doi: 10.1016/j.chemosphere.2016.01.053. Epub 2016 Feb 4. PMID: 26841294. 3. Fernandes FH, Bustos-Obregon E, Salvadori DM. Disperse Red 1 (textile dye) induces cytotoxic and genotoxic effects in mouse germ cells. Reprod Toxicol. 2015 Jun;53:75-81. doi: 10.1016/j.reprotox.2015.04.002. Epub 2015 Apr 13. PMID: 25883024. 4. Fernandes FH, Botasso-Nasciutti MO, Svio ALV, Souza LDCM, Fernandes-Cal JR, Cardoso FF, Fontes MRM, Albuquerque AF, Munari CC, Kummrow F, Umbuzeiro GA, Salvadori DMF. In Vivo genotoxicity of a commercial C.I. Disperse Red 1 dye. Environ Mol Mutagen. 2018 Dec;59(9):822-828. doi: 10.1002/em.22226. Epub 2018 Aug 27. PMID: 30152043.
In vitro protocol:
1. Jánossy I, Tóth-Katona T. Photo-Orientation of Liquid Crystals on Azo Dye-Containing Polymers. Polymers (Basel). 2021 Dec 31;14(1):159. doi: 10.3390/polym14010159. PMID: 35012181; PMCID: PMC8747469. 2. da Silva Leite L, de Souza Maselli B, de Aragão Umbuzeiro G, Pupo Nogueira RF. Monitoring ecotoxicity of disperse red 1 dye during photo-Fenton degradation. Chemosphere. 2016 Apr;148:511-7. doi: 10.1016/j.chemosphere.2016.01.053. Epub 2016 Feb 4. PMID: 26841294.
In vivo protocol:
1. Fernandes FH, Bustos-Obregon E, Salvadori DM. Disperse Red 1 (textile dye) induces cytotoxic and genotoxic effects in mouse germ cells. Reprod Toxicol. 2015 Jun;53:75-81. doi: 10.1016/j.reprotox.2015.04.002. Epub 2015 Apr 13. PMID: 25883024. 2. Fernandes FH, Botasso-Nasciutti MO, Svio ALV, Souza LDCM, Fernandes-Cal JR, Cardoso FF, Fontes MRM, Albuquerque AF, Munari CC, Kummrow F, Umbuzeiro GA, Salvadori DMF. In Vivo genotoxicity of a commercial C.I. Disperse Red 1 dye. Environ Mol Mutagen. 2018 Dec;59(9):822-828. doi: 10.1002/em.22226. Epub 2018 Aug 27. PMID: 30152043.
1: Fernandes FH, Bustos-Obregon E, Salvadori DM. Disperse Red 1 (textile dye) induces cytotoxic and genotoxic effects in mouse germ cells. Reprod Toxicol. 2015 Jun;53:75-81. doi: 10.1016/j.reprotox.2015.04.002. Epub 2015 Apr 13. PubMed PMID: 25883024. 2: da Silva Leite L, de Souza Maselli B, de Aragão Umbuzeiro G, Pupo Nogueira RF. Monitoring ecotoxicity of disperse red 1 dye during photo-Fenton degradation. Chemosphere. 2016 Apr;148:511-7. doi: 10.1016/j.chemosphere.2016.01.053. Epub 2016 Feb 4. PubMed PMID: 26841294. 3: Smithson CS, Wu Y, Wigglesworth T, Zhu S. A more than six orders of magnitude UV-responsive organic field-effect transistor utilizing a benzothiophene semiconductor and Disperse Red 1 for enhanced charge separation. Adv Mater. 2015 Jan 14;27(2):228-33. doi: 10.1002/adma.201404193. Epub 2014 Nov 3. PubMed PMID: 25367245. 4: Vacchi FI, Von der Ohe PC, Albuquerque AF, Vendemiatti JAS, Azevedo CCJ, Honório JG, Silva BFD, Zanoni MVB, Henry TB, Nogueira AJ, Umbuzeiro GA. Occurrence and risk assessment of an azo dye - The case of Disperse Red 1. Chemosphere. 2016 Aug;156:95-100. doi: 10.1016/j.chemosphere.2016.04.121. Epub 2016 May 9. PubMed PMID: 27174821. 5: Ferraz ER, Umbuzeiro GA, de-Almeida G, Caloto-Oliveira A, Chequer FM, Zanoni MV, Dorta DJ, Oliveira DP. 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. doi: 10.1002/tox.20576. Epub 2010 Apr 12. PubMed PMID: 20549607. 6: Ferraz ER, Li Z, Boubriak O, de Oliveira DP. Hepatotoxicity assessment of the azo dyes disperse orange 1 (DO1), disperse red 1 (DR1) and disperse red 13 (DR13) in HEPG2 cells. J Toxicol Environ Health A. 2012;75(16-17):991-9. doi: 10.1080/15287394.2012.696513. PubMed PMID: 22852849. 7: Chequer FM, Angeli JP, Ferraz ER, Tsuboy MS, Marcarini JC, Mantovani MS, de Oliveira DP. The azo dyes Disperse Red 1 and Disperse Orange 1 increase the micronuclei frequencies in human lymphocytes and in HepG2 cells. Mutat Res. 2009 May 31;676(1-2):83-6. doi: 10.1016/j.mrgentox.2009.04.004. Epub 2009 Apr 14. Erratum in: Mutat Res. 2010 Sep 30;702(1):129. PubMed PMID: 19442572. 8: Li H, Wang J, Wang C, Zeng P, Pan Y, Yang Y. Enhanced diffraction properties of photoinduced gratings in nematic liquid crystals doped with Disperse Red 1. Proc Jpn Acad Ser B Phys Biol Sci. 2016;92(8):330-335. PubMed PMID: 27725471; PubMed Central PMCID: PMC5243948. 9: Oliveira GA, Ferraz ER, Chequer FM, Grando MD, Angeli JP, Tsuboy MS, Marcarini JC, Mantovani MS, Osugi ME, Lizier TM, Zanoni MV, Oliveira DP. Chlorination treatment of aqueous samples reduces, but does not eliminate, the mutagenic effect of the azo dyes Disperse Red 1, Disperse Red 13 and Disperse Orange 1. Mutat Res. 2010 Dec 21;703(2):200-8. doi: 10.1016/j.mrgentox.2010.09.001. Epub 2010 Sep 20. PubMed PMID: 20851777. 10: Chequer FM, Lizier TM, de Felício R, Zanoni MV, Debonsi HM, Lopes NP, Marcos R, de Oliveira DP. Analyses of the genotoxic and mutagenic potential of the products formed after the biotransformation of the azo dye Disperse Red 1. Toxicol In Vitro. 2011 Dec;25(8):2054-63. doi: 10.1016/j.tiv.2011.05.033. Epub 2011 Aug 30. PubMed PMID: 21907275. 11: Cinar M, Coruh A, Karabacak M. FT-IR, UV-vis, 1H and 13C NMR spectra and the equilibrium structure of organic dye molecule disperse red 1 acrylate: a combined experimental and theoretical analysis. Spectrochim Acta A Mol Biomol Spectrosc. 2011 Dec;83(1):561-9. doi: 10.1016/j.saa.2011.09.003. Epub 2011 Sep 9. PubMed PMID: 21958518. 12: Yu TH, Dafre AL, de Aragão Umbuzeiro G, Franciscon E. CYP-dependent induction of glutathione S-transferase in Daphnia similis exposed to a disperse azo dye. Ecotoxicology. 2015 Jan;24(1):232-7. doi: 10.1007/s10646-014-1348-x. Epub 2014 Sep 14. PubMed PMID: 25218178. 13: Bianchini R, Rolla M, Isaad J, Catelani G, Guazzelli L, Corsi M, Bonanni M. Efficient double glycoconjugation to naturalize high molecular weight disperse dyes. Carbohydr Res. 2012 Jul 15;356:104-9. doi: 10.1016/j.carres.2011.10.036. Epub 2011 Oct 29. PubMed PMID: 22137592. 14: Vacchi FI, Albuquerque AF, Vendemiatti JA, Morales DA, Ormond AB, Freeman HS, Zocolo GJ, Zanoni MV, Umbuzeiro G. Chlorine disinfection of dye wastewater: implications for a commercial azo dye mixture. Sci Total Environ. 2013 Jan 1;442:302-9. doi: 10.1016/j.scitotenv.2012.10.019. Epub 2012 Nov 22. PubMed PMID: 23178834. 15: Isaksson M, Ale I, Andersen KE, Diepgen T, Goh CL, Goossens R A, Jerajani H, Maibach HI, Sasseville D, Bruze M. Patch testing to a textile dye mix by the international contact dermatitis research group. Dermatitis. 2015 Jul-Aug;26(4):170-6. doi: 10.1097/DER.0000000000000125. PubMed PMID: 26172486. 16: Sonnenburg A, Ahuja V, Schreiner M, Platzek T, Stahlmann R. Assessment of the sensitizing potential of textile disperse dyes and some of their metabolites by the loose-fit coculture-based sensitization assay (LCSA). Arch Toxicol. 2012 May;86(5):733-40. doi: 10.1007/s00204-012-0811-9. Epub 2012 Feb 18. PubMed PMID: 22349058. 17: Poprawa-Smoluch M, Baggerman J, Zhang H, Maas HP, De Cola L, Brouwer AM. Photoisomerization of disperse red 1 studied with transient absorption spectroscopy and quantum chemical calculations. J Phys Chem A. 2006 Nov 2;110(43):11926-37. PubMed PMID: 17064180. 18: Fujii S, Morita T, Kimura S. Second-harmonic generation from Langmuir-Blodgett film of cyclic peptide carrying two disperse red 1 on fused quartz surface. J Pept Sci. 2008 Dec;14(12):1295-302. doi: 10.1002/psc.1074. PubMed PMID: 18951418. 19: Ribeiro AR, Umbuzeiro GA. Effects of a textile azo dye on mortality, regeneration, and reproductive performance of the planarian, Girardia tigrina. Environ Sci Eur. 2014;26(1):22. Epub 2014 Aug 21. PubMed PMID: 27752419; PubMed Central PMCID: PMC5044942. 20: Isaksson M, Ryberg K, Goossens A, Bruze M. Recommendation to include a textile dye mix in the European baseline series. Contact Dermatitis. 2015 Jul;73(1):15-20. doi: 10.1111/cod.12400. Epub 2015 Apr 27. PubMed PMID: 25925831.

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