142731-63-3Relevant articles and documents
Synthesis of tertiary 14C-labelled nonylphenol isomers
Vinken, Ralph,Schmidt, Burkhard,Schaeffer, Andreas
, p. 1253 - 1263 (2002)
The ring-14C-labelled p-nonylphenol (NP) isomers 4(3′,5′-dimethyl-3′-heptyl)-phenol (p353NP), 4(3′,6′-dimethyl-3′-heptyl)-phenol (p363NP) and 4(2′,6′-dimethyl-2′-heptyl)-phenol (p262NP) were synthesized for application in metabolism and sorption studies. Friedel-Crafts alkylation of 14C-labelled phenol and the corresponding tertiary nonylalcohol with BF3 as catalyst was used. After clean-up of p262NP and p363NP by preparative thin-layer chromatography radiochemical yields amounted to 62.8 and 64.6%, specific radioactivities were 332 and 88.2 MBq/mmol, and radiochemical purities 97.6 and 99.0%. For both isomers, a large-scale synthesis with non-labelled phenol was additionally developed, which led to pure products (96 and 99%, respectively) without further purification steps. In the case of p353NP, which was formed as a diastereomeric mixture, the crude synthetic product had a radiochemical purity of 96.9% (radiochemical yield: 76.0%; specific activity: 298MBq/mmol); thus, purification was not necessary. All products were characterized by means of gas chromatography-mass spectroscopy, 1H- and 13C-NMR, as well as IR. Copyright
Estrogen equivalent concentration of 13 branched para-nonylphenols in three technical mixtures by isomer-specific determination using their synthetic standards in SIM mode with GC-MS and two new diasteromeric isomers
Katase, Takao,Okuda, Keiji,Kim, Yun-Seok,Eun, Heesoo,Takada, Hideshige,Uchiyama, Taketo,Saito, Hiroaki,Makino, Mitsuko,Fujimoto, Yasuo
, p. 1961 - 1972 (2008/09/20)
Thirteen isomers of branched para-nonylphenols (para-NP) in three technical mixtures were isomer-specifically determined using their synthesized standards by SIM of structurally specific ions, m/z 135, 149 or 163 with GC-MS. Of the 13 isomers, four isomers, 4-(2,4-dimethylheptan-4-yl)phenol, 4-(4-methyloctan-4-yl)phenol, 4-(3-ethyl-2-methylhexan-2-yl)phenol (3E22NP) and 4-(2,3-dimethylheptan-2-yl)phenol synthesized for their determinations were first used as standard substances. The 13 isomers in the technical mixtures individually occurred at mass percent portion of more than 2%. The total mass percent portions in the mixtures from Tokyo Chemical Industry (TCI), Aldrich, and Fluka covered with 89 ± 2%, 75 ± 4% and 77 ± 2%, respectively. The abundance of 4-(3,6-dimethylheptan-3-yl)phenol in the three mixtures was the largest with 11.1 ± 2% to 9.9 ± 0.3%, while that of 4-(2-methyloctan-2-yl)phenol was the smallest with 2.9 ± 0.3% to 3.0 ± 0.2%. Additionally, structures of four new isomers of more than 1% portion present in a technical mixture were elucidated as two pairs of diastereomeric isomers: two types of 4-(3,4-dimethylheptan-4-yl)phenol (344NP) and those of 4-(3,4-dimethylheptan-3-yl)phenol (343NP). By estrogenic assay of 13 isomers with yeast estrogen screen system, the activity of 3E22NP was the highest, while that of 4-(3-methyloctan-3-yl)phenol was the least. Their relative activities to that of 3E22NP were individually calculated. Estrogenic equivalent concentrations of the three technical mixtures were predictively evaluated. The ratio of the EEC to the conventional concentration, total mass percent portions of the 13 isomers in technical mixtures were 0.208 for TCI, 0.206 for Aldrich and 0.205 for Fluka. The predicted estrogenic activity of measured concentration of para-NP in technical mixtures was approximately 5-fold greater than the measured estrogen agonist activity.
Regioselective synthesis of a branched isomer of nonylphenol, 4-(3′,6′-dimethyl-3′-heptyl)phenol, and determination of its important environmental properties
Lalah, Joseph O.,Schramm, Karl-W.,Lenoir, Dieter,Henkelmann, Bernhard,Hertkorn, Norbert,Matuschek, Georg,Kettrup, Antonius,Guenther, Klaus
, p. 4790 - 4795 (2007/10/03)
A method for the synthesis of a pure nonylphenol isomer, 4-(3′,6′-dimethyl-3′-heptyl)phenol, by Friedel-Crafts reaction between anisole and 3-bromo-3,6-dimethylheptane that gives a 47.3% overall yield is reported. The reactions were followed by GC-MS, and
