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MedKoo Cat#: 462628 | Name: C.I. Solvent Yellow 3
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Description:

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

C.I. Solvent Yellow 3 has been evaluated as a possible human carcinogen. In rodents, it is carcinogenic mainly in the liver, and also in lung following long term administration.

Chemical Structure

C.I. Solvent Yellow 3
C.I. Solvent Yellow 3
CAS#97-56-3

Theoretical Analysis

MedKoo Cat#: 462628

Name: C.I. Solvent Yellow 3

CAS#: 97-56-3

Chemical Formula: C14H15N3

Exact Mass: 225.1266

Molecular Weight: 225.30

Elemental Analysis: C, 74.64; H, 6.71; N, 18.65

Price and Availability

Size Price Availability Quantity
25g USD 350.00 2 Weeks
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Related CAS #
No Data
Synonym
o-Aminoazotoluene; NSC1797; NSC 1797; NSC-1797; C.I. Solvent Yellow 3; 2-Aminoazotoluene; Fast Garnet GBC Base; C.I. 11160; CI 11160; C.I. 11160B; NSC-26821; NSC26821; NSC 26821
IUPAC/Chemical Name
(E)-2-methyl-4-(o-tolyldiazenyl)aniline
InChi Key
PFRYFZZSECNQOL-WUKNDPDISA-N
InChi Code
InChI=1S/C14H15N3/c1-10-5-3-4-6-14(10)17-16-12-7-8-13(15)11(2)9-12/h3-9H,15H2,1-2H3/b17-16+
SMILES Code
Cc1c(/N=N/c2cc(C)c(N)cc2)cccc1
Appearance
Solid powder
Purity
>97% (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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 225.30 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
1: o-Aminoazotoluene. Rep Carcinog. 2004;11:III12-3. PMID: 21105242. 2: National Toxicology Program. o-Aminoazotoluene. Rep Carcinog. 2011;12:37-8. PMID: 21829248. 3: National Toxicology Program. o-Aminoazotoluene. Rep Carcinog. 2002;10:12-3. Update in: Rep Carcinog. 2004;11:III12-3. PMID: 15317117. 4: Ovchinnikova LP, Bogdanova LA, Kaledin VI. Mutagenic activation reduces carcinogenic activity of ortho-aminoazotoluene for mouse liver. Bull Exp Biol Med. 2013 Mar;154(5):664-8. doi: 10.1007/s10517-013-2025-4. PMID: 23658894. 5: Mikhailova ON, Vasyunina EA, Ovchinnikova LP, Gulyaeva LF, Timofeeva OA, Filipenko ML, Kaledin VI. o-Aminoazotoluene does induce the enzymes of its own mutagenic activation in mouse liver. Toxicology. 2005 Jul 1;211(1-2):132-8. doi: 10.1016/j.tox.2005.03.006. Epub 2005 Apr 18. PMID: 15863256. 6: Morozkova TS, Bogdanova LA, Semenov DE, Zhukova NA, Popova NA. PT/Y Mice Are Sensitive to the Inhibitory Effect of o-Aminoazotoluene on Glucocorticoid Induction of Tyrosine Aminotransferase and Its Hepatocarcinogenic Effect. Bull Exp Biol Med. 2015 Apr;158(6):789-93. doi: 10.1007/s10517-015-2863-3. Epub 2015 Apr 21. PMID: 25894779. 7: Kohara A, Suzuki T, Honma M, Hirano N, Ohsawa K, Ohwada T, Hayashi M. Mutation spectrum of o-aminoazotoluene in the cII gene of lambda/lacZ transgenic mice (MutaMouse). Mutat Res. 2001 Apr 5;491(1-2):211-20. doi: 10.1016/s1383-5718(01)00143-7. PMID: 11287313. 8: Timofeeva OA, Eremeev AV, Goloshchapov A, Kalashnikova E, Ilnitskaya S, Setkov NA, Kobzev V, Buzard GS, Filipenko ML, Kaledin VI, Merkulova TI. Effects of o-aminoazotoluene on liver regeneration and p53 activation in mice susceptible and resistant to hepatocarcinogenesis. Toxicology. 2008 Dec 5;254(1-2):91-6. doi: 10.1016/j.tox.2008.09.013. Epub 2008 Sep 21. PMID: 18852010. 9: FUKUOKA F, NAKAHARA W. Difference in tissue affinity between o-aminoazotoluene and its non-carcinogenic isomer, p-aminoazotoluene. Gan. 1953 Mar;44(1):13-6. PMID: 13107892. 10: Ohsawa K, Hirano N, Sugiura M, Nakagawa S, Kimura M. Genotoxicity of o-aminoazotoluene (AAT) determined by the Ames test, the in vitro chromosomal aberration test, and the transgenic mouse gene mutation assay. Mutat Res. 2000 Nov 20;471(1-2):113-26. doi: 10.1016/s1383-5718(00)00120-0. PMID: 11080667. 11: Degawa M, Kanazawa C, Hashimoto Y. In vitro metabolism of o-aminoazotoluene and mutagenesis of Salmonella by the metabolites. Carcinogenesis. 1982;3(10):1113-7. doi: 10.1093/carcin/3.10.1113. PMID: 6756667. 12: Baginskaya NV, Il'nitskaya SI, Nikitenko EV, Kaledin VI. Promoting effect of o-aminoazotoluene on hepatocarcinogenesis is accompanied by the increase in inflammatory and proliferative processes in liver tissue and decrease in the concentration of free thyroxin in the blood. Bull Exp Biol Med. 2007 Dec;144(6):821-4. doi: 10.1007/s10517-007-0440-0. PMID: 18856210. 13: Kovalev IE, Polevaia OIu, Danilova NP, Robakidze TN, Shumova SL. Poluchenie antitel k o-aminoazotoluolu s pomoshch'iu sintezirovannykh khimicheskim i fermentativnym metodami kon''iugirovannykh antigenov [Preparation of antibodies against o-aminoazotoluene using chemically and enzymatically synthesized conjugated antigens]. Eksp Onkol. 1984;6(1):38-42. Russian. PMID: 6209089. 14: Merkulova TI, Kaledin VI, Kropachev KIu, Kobzev VF, Vasil'ev GV. Vliianie o-aminoazotoluola na gliukokortikoidnuiu induktsiiu tirozinaminotransferazy u chuvstvitel'nykh k ego gepatokantserogennomu deĭstviiu mysheĭ realizuetsia cherez faktor transkriptsii HNF3gamma [The effect of o-aminoazotoluene on glucocorticoid induction of tyrosine aminotransferase in mice sensitive to its hepatocarcinogenic activity is mediated by transcription factor HNF3gamma]. Dokl Akad Nauk. 1998 Aug;361(5):700-3. Russian. PMID: 9785020. 15: Kaledin VI, Il'nitskaia SI, Popova NA, Baginskaia NV, Bagdanova LA, Perepechaeva ML, Grishanova AIu. [Inhibitory effect of ortho-aminoazotoluene on diethylnirtosamine hepatocarcinogenesis in suckling mice. Phenomenon and possible mechanism]. Biofizika. 2014 Jul-Aug;59(4):776-84. Russian. PMID: 25707246. 16: Zacharova LY, Gulyaeva LF, Lyakhovich VV, Mikhailova ON, Timofeeva OA, Filipenko ML, Kaledin VI. Cytochrome P4501A1 and 1A2 gene expression in the liver of 3-methylcholanthrene- and o-aminoazotoluene-treated mice: a comparison between PAH-responsive and PAH-nonresponsive strains. Toxicol Sci. 2003 May;73(1):108-13. doi: 10.1093/toxsci/kfg053. Epub 2003 Apr 15. PMID: 12700417. 17: Lawson TA. The binding of o-aminoazotoluene to deoxyribonucleic acid, ribonucleic acid and protein in the C57 mouse. Biochem J. 1968 Oct;109(5):917-20. doi: 10.1042/bj1090917. PMID: 5696871; PMCID: PMC1187044. 18: Smetanina MA, Pakharukova MY, Kurinna SM, Dong B, Hernandez JP, Moore DD, Merkulova TI. Ortho-aminoazotoluene activates mouse constitutive androstane receptor (mCAR) and increases expression of mCAR target genes. Toxicol Appl Pharmacol. 2011 Aug 15;255(1):76-85. doi: 10.1016/j.taap.2011.05.019. Epub 2011 Jun 6. PMID: 21672546; PMCID: PMC3148291. 19: Kaledin VI, Il'nitskaya SI, Popova NA, Bogdanova LA. Suppression of sulfoconjugation reduces the protective effect of ortho-aminoazotoluene on hepatocarcinogenesis induced by diethylnitrosamine in mice. Bull Exp Biol Med. 2014 Jul;157(3):368-70. doi: 10.1007/s10517-014-2568-z. Epub 2014 Jul 29. PMID: 25065317. 20: Kaledin VI, Il'nitskaia SI. [Metabolism inhibition stimulates, metabolism activation inhibits cancerogenic activity of ortho-aminoazotoluene in mouse liver]. Vopr Onkol. 2011;57(2):216-20. Russian. PMID: 21809668.