tert-Butylhydroquinone
[CAS# 1948-33-0]

Identification

• Classification: Organic raw materials >> Alcohols, phenols, phenolic compounds and derivatives >> Phenol and its halogenated, sulfonated, nitrated or nitrosated derivatives
• Name: tert-Butylhydroquinone
• Synonyms: Butylhydroquinone; TBHQ; 2-tert-Butylhydroquinone; 2-(1,1-Dimethylethyl)-1,4-benzenediol
• Molecular Formula: C₁₀H₁₄O₂
• Molecular Weight: 166.22
• CAS Registry Number: 1948-33-0
• EC Number: 217-752-2
• SMILES: CC(C)(C)C1=C(C=CC(=C1)O)O

Properties

• Density: 295
• Melting point: 125-130 ºC
• Boiling point: 273 ºC
• Flash point: 171 ºC

Safety Data

• Hazard Symbols: GHS07;GHS09 Warning
• Hazard Statements: H302+H312-H302-H312-H315-H317-H319-H335-H400-H410
• Precautionary Statements: P261-P264-P264+P265-P270-P271-P272-P273-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P317-P319-P321-P330-P332+P317-P333+P317-P337+P317-P362+P364-P391-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2	H319
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Skin sensitization	Skin Sens.	1	H317
Acute toxicity	Acute Tox.	4	H312
Skin irritation	Skin Irrit.	2	H315
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Specific target organ toxicity - single exposure	STOT SE	3	H335
Germ cell mutagenicity	Muta.	2	H341
Skin sensitization	Skin Sens.	1B	H317
Specific target organ toxicity - single exposure	STOT SE	2	H371
Eye irritation	Eye Irrit.	2A	H319

Discovory and Applicatios

tert-Butylhydroquinone (TBHQ) was synthesized in the early 20th century as a derivative of hydroquinone, a compound well-known for its antioxidant properties. Its discovery was driven by the need to develop more effective preservatives for fats and oils. Researchers found that the tert-butyl group attached to hydroquinone significantly enhanced its stability and antioxidant capabilities, leading to its commercial use as a food additive and preservative.

TBHQ is widely used in the food industry to extend the shelf life of processed foods. It effectively prevents the oxidation of fats and oils, which can lead to rancidity and off-flavors. Commonly found in products like snack foods, margarine, and frozen meats, TBHQ helps maintain freshness and quality.

In the cosmetics industry, TBHQ is used as an antioxidant to stabilize formulations containing oils and fats. It prevents the degradation of these ingredients, thereby maintaining the efficacy and shelf life of products such as lotions, creams, and lipsticks.

TBHQ is utilized in pharmaceuticals to enhance the stability of certain drug formulations. By preventing oxidative degradation, it ensures the longevity and effectiveness of medications.

Beyond food and cosmetics, TBHQ is used in industrial applications as an antioxidant in the stabilization of various oils and lubricants. Its ability to prevent oxidation makes it valuable in the production of biodiesel, where it helps maintain fuel quality during storage.

In the polymer industry, TBHQ is employed as a stabilizer to prevent the oxidative degradation of polymers during processing and storage. This helps in maintaining the physical and mechanical properties of plastics.

Emerging research suggests that TBHQ might have potential health benefits due to its antioxidant properties. Studies are exploring its role in reducing oxidative stress and inflammation, which are underlying factors in many chronic diseases.

References

2023. Analysis of the Effect of TBHQ and BHT Additives on Oxidation of Castor Oil. The 6th Mechanical Engineering, Science and Technology (MEST 2022) International Conference.
DOI: 10.2991/978-94-6463-134-0_27

2010. Sodium 2-propenyl thiosulfate derived from garlic induces phase II detoxification enzymes in rat hepatoma H4IIE cells. Nutrition research (New York, N.Y.), 30(6).
DOI: 10.1016/j.nutres.2010.06.007

2009. Skin fibroblast model to study an impaired glutathione synthesis: Consequences of a genetic polymorphism on the proteome. Brain Research Bulletin, 79(1).
DOI: 10.1016/j.brainresbull.2008.10.015