3-Tert-butyl-4-hydroxyanisole BHA

During the course of screening antioxidants from plants, Baek et al. isolated a neolignan from the bark of M. officinalis [37]. A biphenyl compound, 5, 5 -di-2-propenyl-2-hydroxy-3, 2, 3 -trimethoxy-l-l -biphenyl (15), was found to have antioxidant activity similar to commercial synthetic antioxidants 2, 6-di-ter/-butyl-4-methylphenol (BHT) or 3-tert-butyl-4-hydroxyanisole (BHA). Antioxidants are compounds that inactivate free radicals in the body. Free radicals can cause cancer since it can promote the growth of cells by initiating spontaneous mitosis. Furthermore, phenolic antioxidants in wine, especially resveratrol (16), have demonstrated the ability to inhibit human low density lipid (LDL) oxidation in vitro [38]. Frankel mentions other studies suggesting... 

BHA 2-tert-butyl-4-hydroxyanisole 3-tert-butyl-4-hydroxyanisole... 

SYNS ANTRANCINE 12 BHA (FCC) D BUTYL-HYDROXYANISOLE tert-BUTYLHYDROXYANISOLE ten-BUTYI 4-HYDROXYANISOLE 2(3)-tert-BUTYL-4-HYDROXYANISOLE BUTYLOHYDROKSYANIZOL (POLISH) EMBANOX FEMA No. 2183 ... 

Butylated hydioxyanisole (BHA) (Figure 9.21) is a mixture of two isomeric organic compounds, 2-tert-butyl-4-hydroxyanisole and 3-tert-butyl-4-hydroxyanisole. The conjugated aromatic ring of BHA is able to act as a free radical scavenger, and thus further free radical reactions are prevented. 

The widely used antioxidant and food preservative called BHA (butylated hydroxyanisole) is actually a mixture of 2-iert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol. BHA is synthesized from p-methoxyphenol and 2-methylpropene. (a) Suggest how this is done, (b) Another widely used antioxidant is BHT (butylated hydroxy-toluene). BHT is actually 2,6-di-iert-butyl-4-methylphenol, and the raw materials used in its production are p-cresol and 2-methylpropene. What reaction is used here ... 

Dimethylethyl)-4-methoxyphenol Anisole, butylated hydroxy- Antioxyne B Antrancine 12 BHA BOA (antioxidant) Butyl hydroxyanisole Butylated hydroxyanisole Butylhydroxyanisole 2-terc.Butyl-4-methoxyifenol 2(3)-t-Butyl-4-hydroxyanisole 3-t-Butyl-4-hydroxyanisole t-Butyl hydroxyanisole tert-Butyl-4-hydroxyanisole Butylohydroksyanizol CCRIS 102 EEC No, E320 EINECS 246-563-8 Embanox FEMA No. 2183 HSDB 3913 Nepantiox 1-F Nipantiox 1-F Phenol, 1,1-dimethylethyl)-4-methoxy- Phenol, tert-butyl-4-methoxy- Protex Sustane 1-F Tenox BHA. Mixture of isomers of t-butyl-substituted 4-methoxyphenols antioxidant and preservative for foods mp = 48-55 bp 33 = 264-270 insoluble in H2O, soluble in organic solvents LDm (rat orl) = 2200 mg/kg. Eastman Cham. Co. Mpa Penta Mfg. UOP. 

FIGURE 5.3.2.2 BHA [mixture of (a) 2-tert-butyl-4-hydroxyanisole and (b) 3-teri-butyl-4-hydroxyanisole]. 

Butylated Hydroxyanisole. 2- and 3-/ i -Butyl-4-methoxyphenol (butylated hydroxyanisole (BHA)) is prepared from 4-methoxyphenol and tert-huty alcohol over siUca or alumina at 150°C or from hydroquinone and tert-huty alcohol or isobutene, using an acid catalyst and then methylating. It is widely used in all types of foods such as butter, lard, and other fats, meats, cereals, baked goods, candies, and beer as an antioxidant (see Antioxidants Eood additives). Its antioxidant properties are not lost during cooking so that flour, fats, and other BHA-stabiLized ingredients may be used to produce stabilized products. 

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