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.
There is a paucity of data on food levels of 4t-OP, with
one study reporting 19 ng g-1 wet weight 4t-OP in baby food
and similar concentrations reported in seafood. Urinary 4t-OP
reflects recent exposure; the 95th percentile (confidence
interval) urine concentration of 4t-OP in the US population as
reported by the US Centers for Disease Control in the National
Health and Nutrition Examination Survey is 2.2 (1.6–3.2)
mg l-1.
Uses
A common environmental pollutant showing weak estrogenic effects. 4-tert-Octylphenol has been shown to cause harm to the male reproductive system of vertebrates.
Uses
Surfactants, Tackifier Resins, Ink Resins, Polycarbonate Chain Terminator, Ultraviolet Stabilizers
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 (λexc = 253.7nm) of hydrogen peroxide in aqueous solution has been studied.
Health effects
4-tert-octylphenol can affect the reproductive system of animals and affect how babies develop. It can also affect how hormones are produced in animals.
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.
