Nonylphenol (NP) is a subset of the alkylphenols. NP is a precursor of nonylphenol ethoxylates, which are widely used as industrial surfactants and in a variety of pesticides and consumer products. NP can bind to estrogen receptors and elicit estrogenic action in vivo and in vitro.

Structure

NP features both polar and hydrophobic subunits, the phenol and the hydrocarbon tail. Technically, nonylphenol contains approximately 20 isomers and predominantly para-substituted nonylphenol.

Properties

A pale yellow viscous liquid, molecular formula C15H24O, Mr. 220.34, density 0.95g/mL (20°C), melting point - 8°C. Poorly soluble in water but soluble in alcohol. 

Production 

Nonylphenol is produced by the acid-catalyzed alkylation of phenol with a mixture of nonenes. 

Application 

Nonylphenol is subjected to ethoxylation to give nonylphenol ethoxylates, which are widely used as industrial surfactants and as lubricant additives, polymer stabilizers, antioxidants, and agricultural chemicals.

Biological activity

NP has estrogenic activity by binding to estrogen receptors (ERs) in both in vitro and in vivo assay systems. In 1991, Soto et al. reported that polystyrene tubes used in routine laboratory procedures released a substance with estrogenic properties; they identified the substance as a nonylphenol. They showed that NP induced cell proliferation and progesterone receptor gene expression in MCF-7 cells, and activated cell proliferation in the ovariectomized rat endometrium.