Butylated hydroxytoluene

Phytoplankton, including the green algae Botryococcus braunii, as well as three different cyanobacteria (Cylindrospermopsis raciborskii, Microcystis aeruginosa and Oscillatoria sp.) are capable of producing BHT as a natural product.^[8] The fruit lychee also produces BHT in its pericarp.^[9]

Several fungi (for example Aspergillus conicus) living in olives produce BHT. Volatile organic compounds such as BHT and odor chemicals are produced by resident fungi when olives are being stored awaiting pressing.^[10]

It has been detected in higher plants and herbivorous insects, but it is not clear whether the BHT is produced by the plant, the insect, or some other organism living in association.^[11]

The species behaves as a synthetic analog of vitamin E, primarily acting as a terminating agent that suppresses autoxidation, a process whereby unsaturated (usually) organic compounds are attacked by atmospheric oxygen. BHT stops this autocatalytic reaction by converting peroxy radicals to hydroperoxides. It effects this function by donating a hydrogen atom:

RO₂• + ArOH → ROOH + ArO•

RO₂• + ArO• → nonradical products

where R is alkyl or aryl, and where ArOH is BHT or related phenolic antioxidants. Each BHT consumes two peroxy radicals.^[13][14] The electron-donating alkyl groups on the ortho and para positions of BHT increase the electron density of the phenolic hydroxyl moiety through the inductive effect and the hyperconjugation effect,^[15] reduce the bond dissociation energy of the phenolic hydroxyl group, and enhance its reactivity to lipid free radicals. Meanwhile, the phenoxy radical generated by BHT is stabilized due to the delocalization of unpaired electrons around the aromatic ring^[15][16] and the steric hindrance effect of ortho tert-butyl groups.^[17][18] Isobutene is one of the possible degradation products formed by BHT oxidation with computational studies suggesting that there are two possible mechanism that can lead to isobutene formation with the OH addition pathways at the C2 site of BHT more likely to result in isobutene formation than pathways of H abstracts from the t-butyl group.^[19]

BHT is listed by the NIH Hazardous Substances Data Bank under several categories in catalogues and databases, such as food additive, household product ingredient, industrial additive, personal care product/cosmetic ingredient, pesticide ingredient, plastic/rubber ingredient and medical/veterinary/research.^[20]

Like many closely related phenol antioxidants, BHT has low acute toxicity^[5] (e.g., the desmethyl analog of BHT, 2,6-di-tert-butylphenol, has an LD₅₀ of >9 g/kg^[12]). The US Food and Drug Administration classifies BHT as generally recognized as safe (GRAS) food preservative when used in an approved manner.^[36][37] In 1979, the National Cancer Institute determined that BHT was noncarcinogenic in a mouse model.^[22]

The World Health Organization discussed a possible link between BHT and cancer risk in a 1986 report concluding there is limited evidence for carcinogenicity from animal studies.^[38] Primary research studies in the 1970s–1990s reported both potential for increased risk and potential for decreased risk in the area of oncology.^[39] A review report published in 2002 noted that BHT has shown anticarcinogenic effects, no effect, or tumor promoting effects depending on animal species and target organ considered.^[39] Because of this uncertainty, the Center for Science in the Public Interest puts BHT in its "caution" column and recommends avoiding it.^[40]