Shaanxi BLOOM Tech Co., Ltd. is one of the most experienced manufacturers and suppliers of methyl 5-tert-butyl-2-hydroxybenzoate cas 52888-72-9 in China. Welcome to wholesale bulk high quality methyl 5-tert-butyl-2-hydroxybenzoate cas 52888-72-9 for sale here from our factory. Good service and reasonable price are available.
Methyl 5-tert-butyl-2-hydroxybenzoate, also known as tert butyl gallate, is an organic compound. It is a colorless or light yellow transparent liquid with a special odor. Molecular formula C12H16O3, CAS 52888-72-9. Easy to dissolve in organic solvents such as ethanol and ether, slightly soluble in water. It has a certain acidity and can react with alkali to form salts. Stable at room temperature, but prone to oxidation and discoloration in the presence of light and oxygen. During storage, it is necessary to avoid direct sunlight and maintain dry, dark, and ventilated conditions. It is an organic compound with extensive application value, playing an important role in multiple fields such as food, medicine, cosmetics, industrial oil products, and feed. It can be used as an industrial additive in the manufacturing process of industrial products such as plastics, rubber, and ink, playing a role as a promoter, stabilizer, plasticizer, etc., improving the performance and stability of products.
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Chemical Formula |
C12H16O3 |
|
Exact Mass |
208 |
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Molecular Weight |
208 |
|
m/z |
208 (100.0%), 209 (13.0%) |
|
Elemental Analysis |
C, 69.21; H, 7.74; O, 23.05 |
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Morphological |
powder |
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Color |
powder |
|
Melting point |
90-100 ° C |
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Boiling point |
360 ° C |
|
Density |
1.082 ± 0.06 g / cm3 (predicted) |
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|
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density 1.1±0.1 g/cm3, boiling point 252.1±20.0 °C at 760 mmHg, Molecular formula C11H14O2, molecular weight one hundred and seventy-eight point two two eight, flash point 104.0±14.4 °C, Precise quality one hundred and seventy-eight point zero nine nine three eight zero, PSA thirty-seven point three zero zero zero zero, LogP three point three zero, Vapor pressure 0.0±0.5 mmHg at 25°C, Refractive index one point five five four, Storage conditions, Sealed in a cool and dry place for storage, stability, Stable under normal temperature and pressure, molecular structure, Molar refractive index: 53.27, Molar volume (m3 / mol): 166.2, Isotonic specific volume (90.2k): 415.3, Surface tension (dyne/cm): 39.0, Dielectric constant (F / M): not available, Even distance (d): not available, Polarizability.
Methyl 5-tert-butyl-2-hydroxybenzoate is a benzoate compound with specific substituents, with a molecular formula of C ₁₂ H ₁₆ O3 and a molecular weight of 208.25. This compound has hydroxyl (- OH) and tert butyl (- C (CH ∝) ∝) substituents at positions 2 and 5 of the benzene ring, respectively, and is bound to methanol through ester bonds (- COOCH ∝).
1. Antioxidant effects in the food industry
As a phenolic antioxidant, the hydroxyl and tert butyl substituents in its structure endow it with excellent antioxidant properties. Its main mechanism of action is to interrupt the chain reaction of free radicals by providing hydrogen atoms, thereby delaying the oxidative rancidity of oils, oily foods, and foods rich in unsaturated fatty acids.
Application Scenario:
Oil preservation: Adding less than 0.02% (based on fat content) of this compound to vegetable and animal oils can significantly extend their shelf life. For example, adding 0.01% of 5-tert-butyl-2-hydroxybenzoic acid methyl ester to lard did not cause rancidity or discoloration after being stored at room temperature and in sunlight for 19 months.
Fried foods: In fried foods such as potato chips and instant noodles, this compound is used in combination with BHA (2,6-di-tert-butyl-4-methylphenol) and BHT (2,6-di-tert-butyl-4-hydroxytoluene) to synergistically inhibit oxidation reactions and maintain the crispy taste of the food.
Preservation of meat products: In cured meat products, the maximum usage amount is 0.2 grams/kilogram, which can prevent the production of halal flavor caused by fat oxidation and inhibit microbial growth.
Compound efficiency enhancement:
This compound is often used in combination with citric acid (0.001% -0.01%), which further enhances its antioxidant effect by chelating metal ions such as iron and copper. For example, when the ratio of BHT: BHA: citric acid in vegetable oil is 2:2:1, the antioxidant effect is better than using it alone.
2. Antioxidant protection in cosmetics and personal care products
In the cosmetics field, it is widely used in lotion, cream, lipstick and other oil-bearing formulations as an oil phase antioxidant. Its oil solubility characteristics enable it to effectively dissolve in mineral oil, silicone oil, vegetable oil and other substrates, preventing the oxidation of unsaturated fatty acids in the formula from causing rancidity, odor and color changes.
Mechanism of action:
By capturing peroxide free radicals (ROO ·) to generate stable phenoxide free radicals (ArO ·), the chain reaction of free radicals is interrupted.
When used in combination with vitamin E (tocopherol), it can synergistically protect cell membrane lipids from oxidative damage and enhance skin barrier function.
Application case:
Adding 0.1% -0.5% of this compound to sunscreen can prevent UV induced lipid oxidation and prolong product stability.
The combination of 0.05% 5-tert-butyl-2-hydroxybenzoate methyl ester and 0.1% BHT in lipstick can significantly inhibit the oxidative rancidity of wax and oil in lipstick, and maintain the texture and color of the product.
1. Drug molecule construction
As a key intermediate, it has significant value in drug synthesis. The hydroxyl and ester groups in its structure can serve as reaction sites, which can be converted into various functional groups through oxidation, reduction, hydrolysis, and other reactions, thereby constructing biologically active drug molecules.
Synthesis example:
Anti inflammatory drug synthesis: Through hydrolysis reaction, ester groups are converted into carboxyl groups to generate 5-tert-butyl-2-hydroxybenzoic acid, which can be used as a precursor for nonsteroidal anti-inflammatory drugs (NSAIDs) to further synthesize ibuprofen analogues.
Antioxidant derivatives: Nitro groups are introduced onto the benzene ring through nitration reaction to generate tert butyl 2-hydroxy-5-nitrobenzoate (CAS number: 155388-63-9). This compound has stronger antioxidant activity and can be used to develop novel free radical scavengers.
2. Stabilizers in pharmaceutical formulations
In pharmaceutical formulations, it can serve as a stabilizer to prevent the oxidative degradation of active ingredients in drugs. For example, adding 0.01% -0.05% of this compound to pharmaceutical excipients containing unsaturated fatty acids (such as soybean oil and medium chain triglycerides) can significantly prolong the drug's shelf life.
1. Antioxidant modification of polymer materials
5-tert-butyl-2-hydroxybenzoic acid methyl ester can serve as an antioxidant in polymer materials such as plastics and rubber, preventing degradation caused by thermal oxidation and photooxidation during processing and use.
Application Scenario:
Polyethylene (PE) film: Adding 0.1% -0.3% of this compound to food packaging film can prevent yellowing and mechanical property degradation of the film during high-temperature sterilization.
Rubber products: Compound 0.5% -1% 5-tert-butyl-2-hydroxybenzoate methyl ester and amine antioxidants (such as IPPD) in rubber products such as tires and sealing strips can synergistically inhibit crack formation caused by ozone and thermal oxidation.
2. Stabilizers for paints and inks
In coatings and inks, this compound can serve as a stabilizer to prevent discoloration and clumping of pigments and resins caused by oxidation during storage and use. For example, adding 0.2% -0.5% of 5-tert-butyl-2-hydroxybenzoic acid methyl ester to alkyd resin coatings can significantly extend the shelf life of the coatings.
1. Preservatives in the paper industry
In the paper industry, it can be used as a preservative to prevent mold and strength loss of pulp and paper caused by microbial growth during storage. Its mechanism of action extends the lifespan of paper by disrupting microbial cell membranes, inhibiting enzyme activity.
Application case:
Adding 0.05% -0.1% of this compound to cultural paper can effectively inhibit mold growth, prevent paper from turning yellow and brittle.
Compound 0.1% -0.2% of 5-tert-butyl-2-hydroxybenzoate methyl ester and carbendazim in packaging paper can synergistically enhance the anti-corrosion effect and meet food packaging hygiene standards.
2. Additives for lubricating oil
In lubricating oil, this compound can serve as an antioxidant additive to prevent viscosity reduction and sediment formation caused by oxidation under high temperature and high shear conditions. For example, adding 0.05% -0.1% of 5-tert-butyl-2-hydroxybenzoic acid methyl ester to hydraulic oil can significantly extend the oil change cycle.
We are the supplier of Methyl 5-Tert-Butyl-2-Hydroxybenzoate.
Remark: BLOOM TECH(Since 2008), ACHIEVE CHEM-TECH is our subsidiary of us.
Detailed steps for the synthesis of methyl 5-tert butyl-2-hydroxybenzoate by esterification method:
The chemical equation for the synthesis of methyl 5-tert butyl-2-hydroxybenzoate by esterification method:
C6H7NO+C4H10O → C11H17NO4S+H2O (condition: H2O4S)
C11H17NO4S+C2H4O2 → C12H16O3+C2H4O2 (conditions: neutralization reaction)
1. Prepare the required raw materials and reagents: o-aminophenol, tert butanol, ether, concentrated sulfuric acid, and glacial acetic acid. Ensure that all raw materials and reagents are fresh and of high quality to ensure the success of the experiment and the purity of the product.
2. In an appropriate reaction vessel, mix o-aminophenol and tert butanol together and stir evenly.
3. Slowly add an appropriate amount of concentrated sulfuric acid to the mixture while stirring to ensure thorough and even mixing.
4. Heat the reaction mixture to reflux temperature (usually boiling state) and maintain this temperature for a certain period of time to ensure complete esterification reaction.
5. After the reaction is complete, cool the reaction mixture to room temperature.
6. Add an appropriate amount of acetic acid to the cooled reaction mixture and stir evenly. The addition of acetic acid can neutralize excess acid during the reaction process, producing methyl 5-tert butyl-2-hydroxybenzoate.
7. Separate the generated methyl 5-tert butyl-2-hydroxybenzoate from the reaction mixture by filtration or centrifugation.
8. Purify the separated methyl 5-tert butyl-2-hydroxybenzoate, such as by crystallization or column chromatography, to obtain a high-purity product.
9. Finally, quality inspection is conducted on the purified methyl 5-tert butyl-2-hydroxybenzoate to ensure that it meets the expected specifications and quality requirements.
In addition, when adding acetic acid for neutralization reaction, attention should be paid to controlling the conditions of the neutralization reaction. If an excessive amount of acetic acid is added, it will cause the generated methyl 5-tert butyl-2-hydroxybenzoate to undergo hydrolysis reaction, thereby reducing the purity and yield of the product. Therefore, it is necessary to strictly control the amount of acetic acid added to ensure the generation of high-purity methyl 5-tert-butyl-2-hydroxybenzoate.
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