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| ln Vitro |
Sudan I, having the chemical formula 1-phenylazo-2-naphthol, is a monoazo dye. Sudan I is a possible mutagen and carcinogen that can develop cancers in the liver or bladder in mammals. In comparison to the AHH-1 cell line, Sudan I enhanced mutagenesis and clastogenesis in the MCL-5 cell line and produced genotoxic effects in HepG2 cells. Furthermore, Sudan I demonstrated mutagenicity against Salmonella Typhimurium using S9 activation, a post-mitochondrial component produced from rat liver, yielding favorable results [1].
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| ADME/Pharmacokinetics |
Metabolism / Metabolites
This dye undergoes reductive cleavage after oral administration to rabbits, but can also be metabolized via benzene ring hydroxylation. In rabbits and rats, it generates 2,6-dihydroxy-1-phenylazonaphthalene, 2-hydroxy-1-(p-hydroxyphenylazo)naphthalene, and 1-phenylhydrazine-2-naphthol. /Table/ ... Oral administration to rabbits, 1.2%... unchanged, 1.5% 1-p-hydroxyphenylazo-2-naphthol, 44% free and bound p-aminophenol, 24% p-aminophenyl glucuronide, 0.5% o-aminophenol, 1.1% aniline; acetaminophenyl glucuronide, 1-p-hydroxyphenylazo-2-naphthol glucuronide and 1-amino-2-naphthol... ...4',6-dihydroxy-1-phenylazo-2-naphthol and 4'- and 6-hydroxy-1-phenylazo-2-naphthol glucuronides are present in... rabbit bile and urine. The urine also contains 1-amino-2-naphthol hydrogen sulfate, 1-amino-2-naphthol glucuronide, and N-glucuronide of 1-phenylhydrazyl-2-naphthol and 4'-hydroxy-1-phenylhydrazyl-2-naphthol… For more complete data on the metabolism/metabolites of CI Solvent Yellow 14 (6 metabolites in total), please visit the HSDB record page. Known human metabolites of Sudan I include aniline and 1-amino-2-naphthol. |
| References | |
| Additional Infomation |
According to data from the National Toxicology Program (NTP), CI Solvent Yellow 14 is potentially carcinogenic. CI Solvent Yellow 14 appears as dark reddish-yellow flakes or orange powder with a slight odor. (NTP, 1992) Sudan I is a monoazo compound used as a dye, functioning similarly to 2-naphthol. Mechanism of Action: Sudan I, after activation by pre-incubation with rat liver microsomal enzymes, can covalently bind to calf thymus DNA. The benzenediazo ion generated by Sudan I activation via microsomal enzymes is its main active metabolite, which can bind to DNA. Enzymatic hydrolysis of modified 14(C)-labeled DNA, followed by separation of deoxyribonucleotides using a Sephadex G-10 column, showed that deoxyguanosine is the main target for Sudan I activation.
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| Molecular Formula |
C16H12N2O
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|---|---|
| Molecular Weight |
248.2793
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| Exact Mass |
248.094
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| CAS # |
842-07-9
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| Related CAS # |
Sudan I-d5;752211-63-5
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| PubChem CID |
13297
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| Appearance |
Red to reddish brown solid powder
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| Density |
1.2±0.1 g/cm3
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| Boiling Point |
443.7±28.0 °C at 760 mmHg
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| Melting Point |
131-133 °C
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| Flash Point |
290.2±13.3 °C
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| Vapour Pressure |
0.0±1.1 mmHg at 25°C
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| Index of Refraction |
1.634
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| LogP |
4.24
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
19
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| Complexity |
312
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
MRQIXHXHHPWVIL-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C16H12N2O/c19-15-11-10-12-6-4-5-9-14(12)16(15)18-17-13-7-2-1-3-8-13/h1-11,19H
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| Chemical Name |
1-phenyldiazenylnaphthalen-2-ol
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~10 mg/mL (~40.28 mM)
H2O : ~0.67 mg/mL (~2.70 mM) |
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.0277 mL | 20.1386 mL | 40.2771 mL | |
| 5 mM | 0.8055 mL | 4.0277 mL | 8.0554 mL | |
| 10 mM | 0.4028 mL | 2.0139 mL | 4.0277 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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