Information about Tert-Butylhydroquinone

Tert-Butylhydroquinone (TBHQ, tertiary butylhydroquinone) is an aromatic organic compound which is a type of phenol. It is a derivative of hydroquinone, substituted with tert-butyl group.

Tert-Butylhydroquinone,584-84-9

1.Action

Tert-butylhydroquinone (Tert-Butylhydroquinone), the major metabolite of butylated hydroxyanisole, induces an antioxidant response through the redox-sensitive transcription factor, nuclear factor-E2-related factor-2 (Nrf2). However, the mechanism by which Tert-Butylhydroquinone induces Nrf2 activity is not entirely understood. Here, we show that Tert-Butylhydroquinone preferentially alters the redox status in the mitochondrial compartment in HeLa cells. HeLa cells treated with Tert-Butylhydroquinone showed a preferential oxidation of mitochondrial thioredoxin-2 (Trx2), while cellular glutathione and cytosolic thioredoxin-1 were not affected. Preferential mitochondrial oxidation by Tert-Butylhydroquinone was supported by detection of reactive oxygen species (ROS) specific to this compartment. To determine the role of Trx2 in regulating downstream effects of Tert-Butylhydroquinone, HeLa cells were transiently transfected with an empty, Trx2, or C93S (Cys93Ser) Trx2 dominant-negative mutant expression vector. Overexpression of Trx2 decreased basal mitochondrial ROS production, whereas expression of C93S Trx2 enhanced it. In addition, under untreated conditions, expression of C93S Trx2 led to an increase in the basal activities of Nrf2. With Tert-Butylhydroquinone treatments, Trx2 overexpression suppressed Nrf2 accumulation and activity, whereas expression of C93S Trx2 had no effect on the degree of inducibility or Nrf2 accumulation but did increase the overall activity of Nrf2. Quantitative polymerase chain reaction analysis of Nrf2-regulated gene expression corroborate Trx2 control of Tert-Butylhydroquinone-mediated Nrf2 activation. These data show a compartment-specific effect where Tert-Butylhydroquinone-induced Nrf2 signaling is mediated by Trx2 and suggest that antioxidant status in various compartments would provide different levels of control of redox signaling.

2.Application

Tert-Butylhydroquinone is a highly effective antioxidant.

In foods, it is used as a preservative for unsaturated vegetable oils and many edible animal fats.It does not cause discoloration even in the presence of iron, and does not change flavor or odor of the material to which it is added.It can be combined with other preservatives such as butylated hydroxyanisole (BHA).

As a food additive, its E number is E319. It is added to a wide range of foods, with the highest limit (1 gram/kg) permitted for frozen fish and fish products. Its primary advantage is enhancing storage life.

It is used industrially as a stabilizer to inhibit autopolymerization of organic peroxides. 

It is also used as a corrosion inhibitor in biodiesel.

In perfumery, it is used as a fixative to lower the evaporation rate and improve stability. 

It is also added to varnishes, lacquers, resins, and oil field additives.

3.Side effect

Consuming high doses (between 1 and 4 grams) of Tert-Butylhydroquinone can cause nausea, delirium, collapse, tinnitus (ringing in the ears), and vomiting.There are also suggestions that it may lead to hyperactivity in children as well as asthma, rhinitis and dermatitis. It may also further aggravate ADHD symptoms and cause restlessness.Long term, high doses of Tert-Butylhydroquinone in laboratory animals have shown a tendency for them to develop cancerous precursors in their stomachs, as well as cause DNA damage to them. It is also suggested that it may be responsible for affecting estrogen levels in women.