| Size | Price | |
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| Other Sizes |
| Targets |
Methyl Orange does not target specific biological receptors but rather functions as a chemical indicator based on protonation state. As an azo dye, it interacts with acidic and basic environments through protonation and deprotonation of its azo and sulfonate groups, resulting in a color change. In biological systems, the compound may interact with cellular components non-specifically, leading to cytotoxicity and DNA damage at high concentrations. The compound's mechanism of action is primarily chemical rather than pharmacological, making it useful for pH determination and staining applications.
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|---|---|
| ln Vitro |
In vitro, Methyl Orange is extensively used as a pH indicator in acid-base titrations and other analytical applications. Its color change properties are well-characterized, with the transition range of pH 3.1 to 4.4. At concentrations of 500 mg/L, Methyl Orange has been shown to exhibit cytotoxic effects and can induce DNA damage, making it relevant for studies in cytotoxicity and genotoxicity. The compound is also used as a biological stain for microscopy, particularly for detecting connective tissue in trichrome stains. It is used as a cytoplasmic stain and for pollen tube staining.
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| ln Vivo |
In vivo, Methyl Orange is not used as a therapeutic agent but rather as a research tool and diagnostic stain. Its use in living systems is limited due to its potential toxicity. The compound is primarily used ex vivo for staining biological specimens in histological and cytological applications. Its effects on living organisms have been studied primarily in the context of toxicology and environmental monitoring, where it serves as a model compound for studying azo dye metabolism and toxicity.
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| Enzyme Assay |
Cell-free biochemical assays for Methyl Orange involve its use as a pH indicator in spectrophotometric assays and titrations. The compound's absorbance properties are characterized by a maximum absorbance wavelength of 505 nm. Its color change properties are exploited in analytical chemistry for determining the endpoint of acid-base titrations. The compound's solubility in water is approximately 5 g/L, and it is slightly soluble in hot water but practically insoluble in ethanol. Its purity is typically >98.0% as determined by HPLC.
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| Cell Assay |
In cellular assays, Methyl Orange may be used as a stain for certain cellular structures and as a pH indicator in cell culture applications. At high concentrations (500 mg/L), the compound exhibits cytotoxicity and can cause DNA damage. Studies have investigated its effects on cell viability and genotoxicity in various cell lines. The compound's staining properties make it useful for histological applications, particularly for detecting connective tissue and cytoplasmic structures. Its use in live cell applications is limited due to its cytotoxic effects at higher concentrations.
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| Animal Protocol |
Animal studies for Methyl Orange are limited, as the compound is primarily used as a dye and indicator rather than a therapeutic agent. Toxicological studies have been conducted to assess its safety profile. The oral LD50 in rats is 60 mg/kg. The compound is considered toxic if ingested or inhaled. Studies have examined its effects on various organ systems and its potential as a mutagen. The compound's toxicity is attributed to its azo dye structure and its potential to be metabolized to aromatic amines, which are known carcinogens.
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| ADME/Pharmacokinetics |
Absorption, Distribution and Excretion
Biliary excretion kinetics analysis of intravenously injected [(3)H]methyl orange and its demethylated products (monomethyl and dimethyl) showed that successive removal of methyl groups significantly accelerated the bile excretion rate of CMPD. A one-compartment pharmacokinetic model was illustrated using the bile excretion of methyl orange and its metabolites 4'-sulfo-4-methylaminoazobenzene and 4'-sulfo-4-aminoazobenzene via intravenous injection in rats as an example, in which the drug underwent two consecutive metabolic processes. Metabolism/Metabolites 4'-methylaminoazobenzene-4-sulfonic acid was generated in rats and mice. /From Table/ Methyl orange was converted to N,N-dimethyl-p-phenylenediamine by intestinal anaerobic bacteria. Sulfanilic acid is another metabolite. Pharmacokinetic data for Methyl Orange are not typically reported, as it is not a therapeutic agent. The compound has a molecular weight of 327.33 g/mol and a molecular formula of C14H14N3NaO3S. It is soluble in water (approximately 5 g/L) and slightly soluble in hot water. The CAS number is 547-58-0. The compound should be stored in a cool, dry place away from light. Standard handling procedures for dyes and chemical indicators apply. |
| Toxicity/Toxicokinetics |
Methyl Orange is considered moderately toxic with an oral LD50 of 60 mg/kg in rats. It is a skin and eye irritant. The compound is toxic if ingested or inhaled, and overexposure may result in serious illness or death. At concentrations of 500 mg/L, it exhibits cytotoxicity and can cause DNA damage. The compound should be handled with appropriate personal protective equipment, including gloves and safety glasses. It should be stored away from strong oxidizing agents and strong bases. Disposal should follow local regulations for hazardous waste.
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| References | |
| Additional Infomation |
Sodium 4-dimethylaminoazobenzene-4-sulfonate is an orange powder. (NTP, 1992)
Methyl Orange is a pH indicator dye widely used in analytical chemistry and biological staining. It exhibits a distinct color change from red at pH 3.1 to orange-yellow at pH 4.4. The compound is used as an acid-base indicator, as a decolorizing indicator for strong reducing and oxidizing agents, as a cytoplasmic stain, and as a histological contrast stain. It is also used in textile dyeing and as a staining agent for pollen tubes. The compound is available at >98.0% purity. The CAS number is 547-58-0. |
| Molecular Formula |
C14H14N3NAO3S
|
|---|---|
| Molecular Weight |
327.33
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| Exact Mass |
327.065
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| CAS # |
547-58-0
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| Related CAS # |
502-02-3 (Parent)
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| PubChem CID |
23673835
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| Appearance |
Orange to red solid powder
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| Density |
0.987 g/mL at 25 °C
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| Boiling Point |
100ºC
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| Melting Point |
300 °C
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| Flash Point |
37 °C
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| LogP |
4.152
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
6
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| Rotatable Bond Count |
4
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| Heavy Atom Count |
22
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| Complexity |
448
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| Defined Atom Stereocenter Count |
0
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| SMILES |
S(C1C([H])=C([H])C(=C([H])C=1[H])/N=N/C1C([H])=C([H])C(=C([H])C=1[H])N(C([H])([H])[H])C([H])([H])[H])(=O)(=O)[O-].[Na+]
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| InChi Key |
STZCRXQWRGQSJD-UHFFFAOYSA-M
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| InChi Code |
InChI=1S/C14H15N3O3S.Na/c1-17(2)13-7-3-11(4-8-13)15-16-12-5-9-14(10-6-12)21(18,19)20;/h3-10H,1-2H3,(H,18,19,20);/q;+1/p-1
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| Chemical Name |
sodium;4-[[4-(dimethylamino)phenyl]diazenyl]benzenesulfonate
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| Synonyms |
Methyl Orange NSC9416 NSC-9416NSC 9416
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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 |
| 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 : ~62.5 mg/mL (~190.94 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (6.35 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.08 mg/mL (6.35 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.0550 mL | 15.2751 mL | 30.5502 mL | |
| 5 mM | 0.6110 mL | 3.0550 mL | 6.1100 mL | |
| 10 mM | 0.3055 mL | 1.5275 mL | 3.0550 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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