4-tert-Octylphenol

Chemical Properties

white powder

Uses

4-tert-Octylphenol (4t-OP) is used in manufacturing processes as an intermediate in the generation of surfactants, synthetic rubber additives, or resins. 4t-OP is also used to manufacture alkylphenol ethoxylates. It is found mainly in detergents, cleaning products, and emulsifiers and less frequently in paints, personal care products, pesticides, paper, pulp, and textiles.

Definition

ChEBI: 4-tert-Octylphenol is an alkylbenzene.

General Description

4-tert-Octylphenol is a potential environmental pollutant and it exhibits toxic and estrogenic effects on mammalian cells. It binds to estrogen receptors and exerts estrogenic actions in vitro. The transformation of the 4-tert-octylphenol upon irradiation at 253.7nm and by hydroxyl radicals generated by the photolysis (λ_exc = 253.7nm) of hydrogen peroxide in aqueous solution has been studied.

Health effects

4-tert-octylphenol (OP) is an endocrine-disrupting chemical that causes harmful effects to human health.a common environmental pollutant showing weak estrogenic effects. 4-tert-Octylphenol has been shown to cause harm to the male reproductive system of vertebrates.
High doses of several alkylphenols, including 4- tert-octylphenol, have altered estrogenic effects, including sex hormone levels, estrus cycles, reproductive outcomes, neonatal sexual development, as well as impaired production of steroid hormone and testicular atrophy.

Environmental Fate

Studies have shown that 4t-OP will adsorb to sediments.

Purification Methods

Crystallise the phenol from n-hexane and/or distil it in a vacuum. [Beilstein 6 III 2051, 6 IV 3484.]

Toxicity evaluation

4t-OP has been shown to be an estrogen receptor (ER) agonist. Estrogenic effects of 4t-OP have been demonstrated in human cells, with 4t-OP displacing the natural estrogen 17b estradiol from its receptor, and 4t-OP inducing cell proliferation in estrogen-dependent cell proliferation assays. In vivo confirmation of 4t-OP’s estrogenicity has been confirmed with the uterotrophic assay.