4-TERT-OCTYLPHENOL

Details

Stereochemistry	ACHIRAL
Molecular Formula	C14H22O
Molecular Weight	206.3239
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)(C)CC(C)(C)C1=CC=C(O)C=C1

InChI

InChIKey=ISAVYTVYFVQUDY-UHFFFAOYSA-N

InChI=1S/C14H22O/c1-13(2,3)10-14(4,5)11-6-8-12(15)9-7-11/h6-9,15H,10H2,1-5H3

HIDE SMILES / InChI

Molecular Formula	C14H22O
Molecular Weight	206.3239
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.ncbi.nlm.nih.gov/pubmed/15781295
Curator's Comment: Description was created based on several sources, including https://de.wikipedia.org/wiki/4-tert-Octylphenol

4-tert-octylphenol (OP) is a compound of the class of endocrine disruptors. In 2011 it was added to the list of Substances of Very High Concern (SVHCs) based on the results of an evaluation of the effects of 4-tert-octylphenol (OP) on the growth, survival, and steroid hormone and cAMP production by isolated 14-day-old rats (Sprague-Dawley) ovarian follicles. During a 5-day culture with isolated ovarian follicles, OP decreased estradiol and testosterone secretion in a dose-dependent manner, decreased forskolin-induced cAMP levels, and showed no effect on aromatase activity.

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
Infantile 4-tert-octylphenol exposure transiently inhibits rat ovarian steroidogenesis and steroidogenic acute regulatory protein (StAR) expression.	2005-08-22	16054900
An extensive new literature concerning low-dose effects of bisphenol A shows the need for a new risk assessment.	2005-08	16079060
Isolation and identification of Sphingomonas sp. that yields tert-octylphenol monoethoxylate under aerobic conditions.	2005-07	16041123
Stir bar sorptive extraction with in situ derivatization and thermal desorption-gas chromatography--mass spectrometry for measurement of phenolic xenoestrogens in human urine samples.	2005-06-05	15866492
Effects of selected xenoestrogens on liver peroxisomes, vitellogenin levels and spermatogenic cell proliferation in male zebrafish.	2005-06	16002344
Anti-estrogen prevents xenoestrogen-induced testicular pathology of eelpout (Zoarces viviparus).	2005-04-30	15820099
In vitro effects of diethylstilbestrol, genistein, 4-tert-butylphenol, and 4-tert-octylphenol on steroidogenic activity of isolated immature rat ovarian follicles.	2005-04-01	15781295
Bisphenol a accelerates terminal differentiation of 3T3-L1 cells into adipocytes through the phosphatidylinositol 3-kinase pathway.	2005-04	15659569
An assessment of endocrine disrupting activity changes during wastewater treatment through the use of bioassays and chemical measurements.	2005-03-16	15765931
Neonatally administered tert-octylphenol affects onset of puberty and reproductive development in female rats.	2005-03	15888928
Prepubertal exposure to 4-tert-octylphenol induces apoptosis of testicular germ cells in adult rat.	2005-01-27	15669608
Novel progestogenic activity of environmental endocrine disruptors in the upregulation of calbindin-D9k in an immature mouse model.	2005-01	15509668
Deviation from additivity with estrogenic mixtures containing 4-nonylphenol and 4-tert-octylphenol detected in the E-SCREEN assay.	2004-12-01	15597891
[Estimation of daily intake of phenols in hospital meal samples].	2004-12	15794093
Upregulation of estrogen receptor alpha and vitellogenin in eelpout (Zoarces viviparus) by waterborne exposure to 4-tert-octylphenol and 17beta-estradiol.	2004-10-07	15878695
Binding of xenoestrogens to the sex steroid-binding protein in plasma from Arctic charr (Salvelinus alpinus L.).	2004-10	15556074
Indoor air pollution by alkylphenols in Tokyo.	2004-10	15330792
Determination of 4-tert-octylphenol, 4-nonylphenol and bisphenol A in surface waters from the Haihe River in Tianjin by gas chromatography-mass spectrometry with selected ion monitoring.	2004-09	15276724
Comparative study of analytical methods involving gas chromatography-mass spectrometry after derivatization and gas chromatography-tandem mass spectrometry for the determination of selected endocrine disrupting compounds in wastewaters.	2004-08-20	15481468
Trace analysis of phenolic xenoestrogens in water samples by stir bar sorptive extraction with in situ derivatization and thermal desorption-gas chromatography-mass spectrometry.	2004-07-02	15281250
Transfer of maternally injected endocrine disruptors through breast milk during lactation induces neonatal Calbindin-D9k in the rat model.	2004-07	15219628
Effects of prolonged exposure to 4-tert-octylphenol on toxicity and indices of oestrogenic exposure in the sand goby (Pomatoschistus minutus, Pallas).	2004-07	15046944
Microwave-assisted extraction followed by gas chromatography-mass spectrometry for the determination of endocrine disrupting chemicals in river sediments.	2004-06-04	15233517
Exposure to 4-tert-octylphenol, an environmentally persistent alkylphenol, enhances interleukin-4 production in T cells via NF-AT activation.	2004-05-15	15126071
Sertoli cell junctional proteins as early targets for different classes of reproductive toxicants.	2004-05	15082077
Lack of modifying effects of 4-ter t-octylphenol and benzyl butyl phthalate on 3,2-dimethyl-4-aminobiphenyl-induced prostate carcinogenesis in rats.	2004-04	15072586
Comparative responses of three rat strains (DA/Han, Sprague-Dawley and Wistar) to treatment with environmental estrogens.	2004-04	14689164
Retrospective monitoring of alkylphenols and alkylphenol monoethoxylates in aquatic biota from 1985 to 2001: results from the German Environmental Specimen Bank.	2004-03-15	15074671
Ionic liquid-based liquid-phase microextraction, a new sample enrichment procedure for liquid chromatography.	2004-02-13	14763740
Comparative responses of molluscs and fish to environmental estrogens and an estrogenic effluent.	2004-02-10	15046010
p-Nonylphenol, 4-tert-octylphenol and bisphenol A increase the expression of progesterone receptor mRNA in the frontal cortex of adult ovariectomized rats.	2004-02	14763995
Stir bar sorptive extraction and thermal desorption-gas chromatography-mass spectrometry for the measurement of 4-nonylphenol and 4-tert-octylphenol in human biological samples.	2004-01-05	14659443
Simultaneous determination of endocrine disrupting phenolic compounds and steroids in water by solid-phase extraction-gas chromatography-mass spectrometry.	2004-01-02	14753785
Development of vitellogenin assay for endocrine disrupters using medaka (Oryzias latipes).	2004	15746892
Simultaneous determination of 4-tert-octylphenol, 4-nonylphenol and bisphenol A in Guanting Reservoir using gas chromatography-mass spectrometry with selected ion monitoring.	2004	15559821
Maternal-fetal transfer of endocrine disruptors in the induction of Calbindin-D9k mRNA and protein during pregnancy in rat model.	2003-12-30	14654251
Simultaneous measurement of urinary bisphenol A and alkylphenols by automated solid-phase extractive derivatization gas chromatography/mass spectrometry.	2003-12-15	14670041
Comparative responses of molluscs and fish to environmental estrogens and an estrogenic effluent.	2003-10-29	12946619
Male reproductive effects of octylphenol and estradiol in Fischer and Wistar rats.	2003-10-14	14555199
Effects of 4-tert-octylphenol, 4-tert-butylphenol, and diethylstilbestrol on prenatal testosterone surge in the rat.	2003-10-14	14555198
Separation and on-line concentration of bisphenol A and alkylphenols by micellar electrokinetic chromatography with anionic surfactant.	2003-10-03	14558616
Determination of the estrogenic and antiestrogenic effects of environmental contaminants in chicken embryo hepatocyte cultures by quantitative-polymerase chain reaction.	2003-10	14551996
Comparison of vitellogenin responses in zebrafish and rainbow trout following exposure to environmental estrogens.	2003-10	12927559
Altered sexual characteristics in guppies (Poecilia reticulata) exposed to 17beta-estradiol and 4-tert-octylphenol during sexual development.	2003-10	12927554
Stimulated embryo production as a parameter of estrogenic exposure via sediments in the freshwater mudsnail Potamopyrgus antipodarum.	2003-09-10	12878414
Estrogenic effects in flounder Platichthys flesus orally exposed to 4-tert-octylphenol.	2003-09-10	12878410
Transformation of 4-tert-octylphenol by UV irradiation and by an H2O2/UV process in aqueous solution.	2003-09	14560813
Determination of 4-octylphenol and 4-nonylphenol congeners in composite foods.	2003-09	13129780
Effects of 4-tert-octylphenol given in drinking water for 4 months on the male reproductive system of Fischer 344 rats.	2003-07-14	15013063
Multiwalled carbon nanotubes as a solid-phase extraction adsorbent for the determination of bisphenol A, 4-n-nonylphenol, and 4-tert-octylphenol.	2003-05-15	12919000

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Primary Leydig cells obtained from bank vole testes and the established tumor Leydig cell line (MA-10) were treated with two concentrations of 4-tert-octylphenol (OP_ (10(-4) M, 10(-8) M) alone or concomitantly with anti-estrogen ICI 182,780 (1 μM).

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:40:27 GMT 2025` Edited by `admin` on `Mon Mar 31 19:40:27 GMT 2025`
Record UNII	IOY9FVU3J3
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

4-(1,1,3,3-TETRAMETHYLBUTYL)PHENOL

Preferred Name

English

4-TERT-OCTYLPHENOL

Systematic Name

English

4-(2,4,4-TRIMETHYLPENTAN-2-YL)PHENOL

Systematic Name

English

PHENOL, 4- (1,1,3,3-TETRAMETHYLBUTYL)-

Systematic Name

English

4-(1,1,3,3-TETRAMETHYLBUTYL)PHENOL [HSDB]

Common Name

English

OCTYLPHENOL, 4-TERT-

Systematic Name

English

NSC-5427

Code

English

NSC-7248

Code

English

4-(2,4,4-TRIMETHYL-2-PENTANYL)PHENOL

Systematic Name

English

PHENOL, P- (1,1,3,3-TETRAMETHYLBUTYL)-

Common Name

English

P-(1,1,3,3-TETRAMETHYLBUTYL)PHENOL

Common Name

English

4-T-OCTYLPHENOL

Systematic Name

English

Code System Code Type Description

FDA UNII

IOY9FVU3J3