Trimethylhydroquinone
[CAS# 700-13-0]

Identification

• Classification: Chemical reagent >> Organic reagent >> Fatty ketone (including enol)
• Name: Trimethylhydroquinone
• Synonyms: 2,3,5-Trimethylhydroquinone
• Molecular Formula: C₉H₁₂O₂
• Molecular Weight: 152.19
• CAS Registry Number: 700-13-0
• EC Number: 211-838-3
• SMILES: CC1=CC(=C(C(=C1O)C)C)O

Properties

• Melting point: 169-174 °C
• Boiling point: 295 °C (759.8513 mmHg)
• Flash point: 191 °C
• Water solubility: 2 g/L (20 °C)

Safety Data

• Hazard Symbols: GHS05;GHS07;GHS09 Danger
• Risk Statements: H332-H335-H315-H318-H317-H400-H410
• Safety Statements: P261-P264-P264+P265-P271-P272-P273-P280-P302+P352-P304+P340-P305+P354+P338-P317-P319-P321-P332+P317-P333+P317-P362+P364-P391-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H332
Serious eye damage	Eye Dam.	1	H318
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Skin sensitization	Skin Sens.	1	H317
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Acute toxicity	Acute Tox.	3	H311

• Transport Information: UN 3077

Discovery and Applications

Trimethylhydroquinone is an organic compound that belongs to the hydroquinone family, which is characterized by the presence of two hydroxyl groups attached to a benzene ring. Specifically, trimethylhydroquinone has three methyl groups substituting hydrogen atoms on the benzene ring, enhancing its chemical properties and utility in various applications. The compound is primarily recognized for its antioxidant properties and has gained significant interest in the fields of cosmetics, pharmaceuticals, and food preservation.

The discovery of trimethylhydroquinone can be traced back to the early studies of hydroquinone derivatives in the late 19th and early 20th centuries. Researchers were exploring the synthesis of modified hydroquinones to improve their stability and effectiveness as antioxidants. The introduction of methyl groups not only enhances the solubility of the compound but also increases its electron-donating ability, which is crucial for its antioxidant function. This modification allows trimethylhydroquinone to scavenge free radicals effectively, making it a valuable additive in various formulations.

One of the primary applications of trimethylhydroquinone is in the cosmetic industry. Its antioxidant properties help protect skin cells from oxidative stress caused by environmental factors such as UV radiation and pollution. As a result, trimethylhydroquinone is often included in skincare products, such as creams and lotions, where it contributes to skin protection and anti-aging benefits. Its ability to stabilize formulations and extend shelf life makes it an important ingredient in cosmetic formulations, ensuring product efficacy and safety.

In addition to its cosmetic applications, trimethylhydroquinone is also utilized in the pharmaceutical industry. Its antioxidant activity is beneficial in the formulation of various therapeutic products. By preventing the oxidation of active pharmaceutical ingredients, trimethylhydroquinone enhances the stability and efficacy of these compounds. This property is particularly important for drugs sensitive to oxidative degradation, ensuring that patients receive effective treatments throughout the product's shelf life.

Furthermore, trimethylhydroquinone has found applications in the food industry as a preservative. Its ability to inhibit oxidation helps extend the shelf life of food products by preventing the rancidity of fats and oils. This function is crucial in maintaining the quality and safety of food items, particularly in processed foods where prolonged storage is common. By incorporating trimethylhydroquinone into food formulations, manufacturers can provide consumers with products that are not only safe but also retain their flavor and nutritional value over time.

Research continues to explore the potential of trimethylhydroquinone in new areas, including its role in environmental protection. Studies have indicated that this compound may have applications in reducing oxidative stress in various biological systems, suggesting potential uses in agriculture and environmental remediation. Its effectiveness as an antioxidant may help protect crops from oxidative damage, promoting healthier growth and yield.

Despite its numerous benefits, the handling of trimethylhydroquinone requires careful consideration. While it is generally regarded as safe for use in cosmetics and food products at appropriate concentrations, excessive exposure may pose health risks. Manufacturers must adhere to regulatory guidelines to ensure consumer safety, and proper safety measures should be implemented during production and handling.

In conclusion, trimethylhydroquinone is a versatile compound with significant applications in the cosmetic, pharmaceutical, and food industries. Its antioxidant properties make it a valuable ingredient for protecting products from oxidative degradation, enhancing their stability and efficacy. Ongoing research aims to uncover new applications for trimethylhydroquinone, further solidifying its role in various sectors and highlighting its importance in modern chemistry.

References

2023. Can vitamin E ester derivatives be excellent alternatives of vitamin E: state of art. Bioprocess and Biosystems Engineering, 46(8).
DOI: 10.1007/s00449-023-02918-w

2021. Biocatalyst for the environmentally friendly synthesis of vitamin E intermediate. Clean Technologies and Environmental Policy, 23(5).
DOI: 10.1007/s10098-021-02093-0

2017. Oxidation of 2,3,6-trimethylphenol to 2,3,5-trimethyl-1,4-benzoquinone over binary xerogels TiO2—SiO2 in the three-phase system. Russian Chemical Bulletin, 66(4).
DOI: 10.1007/s11172-017-1791-y