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Metilox is an organic phenolic ester containing a hindered hydroxyl group and two tert-butyl groups on an aromatic ring.
This molecular structure gives the compound antioxidant characteristics, allowing Metilox to act as a stabilizing component in formulations where protection against oxidation is required.
The compound is a solid material and has been reported as white to almost white powder or crystals.
Its reported melting point is approximately 60–67 °C.
CAS No.6386-38-5
Chemical Name:Methyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate
CBNumber:CB3475740
Molecular Formula:C18H28O3
Molecular Weight:292.41
MDL Number:MFCD00210461
MOL File:6386-38-5.mol
Synonyms : Metilox, 3,5-Methyl Ester, 3-(3,5-DI-TERT-BUTYL-4-HYDROXY-PHENYL)-PROPIONIC ACID METHYL ESTER, ralox35, Methyl 3-(3, Methyl 3-(3,5-di-ter, Propofol Impurity 35, Propofol Related Compound 3, 3,5-di-tert-butyl-4-hydroxyphenyl, METHYL DI-t-BUTYL HYDROXYHYDROCINNAMATE.
Description
Metilox is a hindered phenolic antioxidant.
Metilox features a substituted phenol ring that stops oxidative degradation in polymers, plastics, and industrial chemical products.
Properties
Melting point: 60-67°C
Boiling point: 125-130 °C (Press: 0.1 Torr)
Density: 1.006±0.06 g/cm3 (Predicted)
refractive index: 1.5034
storage temp.: Inert atmosphere, Room Temperature
solubility: soluble in Methanol
form: powder to crystal
pka: 12.17±0.40 (Predicted)
color: White to Almost white
Water Solubility: 2.2mg/L at 20℃
Cosmetics Ingredients Functions: PERFUMING: ANTIOXIDANT
InChI: InChI=1S/C18H28O3/c1-17(2,3)13-10-12(8-9-15(19)21-7)11-14(16(13)20)18(4,5)6/h10-11,20H,8-9H2,1-7H3
InChIKey: PXMJCECEFTYEKE-UHFFFAOYSA-N
LogP: 4.866 (est)
Antioxidant Properties
Metilox is particularly notable for its antioxidant activity. The hindered phenolic hydroxyl group can participate in radical-scavenging reactions, helping to interrupt oxidation processes. A crystallographic study specifically describes methyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate as an antioxidant.
Uses
Methyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate is an antioxidant that is used in polyethylene.
Uses of Metilox
Metilox, also known as methyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate, is primarily associated with antioxidant and stabilization applications.
1. Antioxidant
Metilox is used as a hindered phenolic antioxidant to inhibit oxidation and free-radical reactions.
2. Polymer Stabilization
Metilox can be used in polymer and plastic formulations to help protect materials from oxidative degradation caused by heat, oxygen, and processing conditions.
3. Rubber Stabilization
Metilox may be used as an antioxidant or stabilizing agent in rubber-related formulations to improve resistance to oxidative aging.
4. Cosmetic Applications
Metilox is listed with cosmetic ingredient functions including antioxidant and perfuming.
Metilox can help protect formulations from oxidation.
5. Chemical Research
Metilox is used as a reference compound and analytical standard in chemical and pharmaceutical research.
6. Oxidation-Inhibition Studies
Because of its hindered phenolic structure, Metilox is useful in laboratory studies investigating free-radical reactions, oxidation mechanisms, and antioxidant performance.
7. Formulation Stabilizer
Metilox can serve as a stabilizing component in formulations where protection against oxidative deterioration is required.
Applications
Metilox is associated with antioxidant applications and is listed with the cosmetic ingredient functions “perfuming” and “antioxidant.”
Metilox can be used as a reference or analytical compound in chemical and pharmaceutical research. Commercial analytical standards are also available under the name Metilox.
Because of its phenolic antioxidant structure, the compound is of interest in research involving oxidation inhibition, stabilization and degradation processes.
Definition
ChEBI: Benzenepropanoic acid, 3,5-bis(1,1-dimethylethyl)-4-hydroxy-, methyl ester is an alkylbenzene.
Synthesis
(1) 2,6-di-tert-butylphenol (20.6 g), zinc carbonate (mass ratio 1.5) and tributyltin acetate (0.072 g) were added to a three-necked flask fitted with a mechanical stirrer, a nitrogen introduction tube and a dropping funnel under nitrogen atmosphere.
The mixture was melted under nitrogen protection and heating conditions to form a reaction system.
(2) When the temperature of the reaction system rose to 70°C, methyl acrylate (8.24 g) was slowly added through a dropping funnel.
After the dropwise addition was completed, the reaction was continued with stirring for 0.5 hours.
The reaction temperature was then raised to 90 °C and maintained for 1 hour.
After completion of the reaction, it was cooled to 80 °C and the reaction solution was adjusted to neutral with dilute hydrochloric acid to induce crystallization of the product.
After filtration, methyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate was obtained in 99% yield and 99.5% purity without recrystallization.
Storage
Commercial analytical material is reported to be stored at approximately +4 °C.
Other property data indicate storage under an inert atmosphere at room temperature.
Specific storage conditions should therefore follow the supplier's safety data sheet and product specification.
Safety and Handling
GHS/Hazard: May cause irritation to skin, eyes, and respiratory system.
Precautions: Use protective gloves, safety goggles, and work in a fume hood.
