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What is Butylated hydroxytoluene(BHT)?

Feb 20，2020

Butylated hydroxytoluene(BHT) is white or light yellow crystal. BHT has a melting point of 71°C, a boiling point of 265°C, a relative density of 1.048 (20/4°C), and a refractive index of 1.4859 (75°C). Solubility of BHT at normal temperature: methanol 25, ethanol 25-26, isopropanol 30, mineral oil 30, acetone 40, petroleum ether 50, benzene 40, lard (40-50°C ) 40-50, corn oil and soybean oil 40-50. BHT is insoluble in water, 10NaOH solution, glycerol, and propylene glycol. BHT is odorless, odorless with good thermal stability.BHT, also known as dibutylhydroxytoluene, is a lipophilic organic compound, chemically a derivative of phenol, that is useful for its antioxidant properties.

Fig 1. Chemical structure formula of BHT

BHT is obtained after isobutanol is vaporized and dehydrated in the presence of a catalyst to produce isobutene, which is obtained by alkylation with cresol.

BHT is a phenolic antioxidant. BHT can inhibit lipid peroxidation and cause lung injury in mice and promote tumor growth, which may be due to the metabolites of BHT, 6-tert-butyl-2-[2′-(2′-hydroxymethyl)-propyl]-4-Methylphenol. BHT metabolites have also been reported to cause DNA strand breaks in cultured cells and DNA breaks between nucleosomes (a typical feature of apoptosis). A single intraperitoneal injection of BHT (60mg/kg body weight) into rats caused a significant increase in nuclear DNA methyltransferase activity in the liver, kidney, heart, spleen, brain, and lung. Incubation of alveolar macrophages with BHT can significantly reduce TNF-α levels, which may explain the mechanism by which this antioxidant relieves inflammation. Pre-incubation of aspirin-treated platelets with BHT inhibits secretion, aggregation, and protein phosphorylation caused by protein kinase C activators. BHT also inhibits liver cancer formation induced by aflatoxin B1[1-3].

Because BHT prevent rancidity, antioxidants are of great interest to the food industry. For example, BHT, butylated hydroxyanisole (BHA), and EDTA are frequently used to preserve various foods, such as cheese or fried products. BHT is a powerful inhibitor of lipid peroxidation, yet large doses of BHT can induce oxidative DNA damage and cancer development in the rat forestomach.BHT is also known as butylated hydroxy toluene. It is an anti-oxidant that also has preservative and masking capabilities.BHT is an antioxidant that functions similarly to butylated hydroxyanisole (BHA) but is less stable at high temperatures. BHT is also termed 2,6-di-tert-butyl-para-cresol.

References

[1]Arimura G I , K?Pke S , Kunert M , et al. Effects of Feeding Spodoptera littoralis on Lima Bean Leaves: IV. Diurnal and Nocturnal Damage Differentially Initiate Plant Volatile Emission[J]. Plant Physiology, 2008, 146(3):965-973.

[2]Martinez-Bujidos M , Rull A , Gonzalez-Cura B , et al. Clusterin/apolipoprotein J binds to aggregated LDL in human plasma and plays a protective role against LDL aggregation[J]. The FASEB Journal, 2015, 29(5):1688-1700.

[3]Sieber-Ruckstuhl N S , Burla B , Spoerel S , et al. Changes in the Canine Plasma Lipidome after Short- and Long-Term Excess Glucocorticoid Exposure[J]. Scientific Reports, 2019, 9(1).

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