4-N-OCTYLPHENOL

Possibly Marketed Outside US

First approved in 2017

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

CCCCCCCCC1=CC=C(O)C=C1

InChI

InChIKey=NTDQQZYCCIDJRK-UHFFFAOYSA-N

InChI=1S/C14H22O/c1-2-3-4-5-6-7-8-13-9-11-14(15)12-10-13/h9-12,15H,2-8H2,1H3

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: https://www.ncbi.nlm.nih.gov/pubmed/18174953 | https://www.ncbi.nlm.nih.gov/pubmed/12117780 | https://www.ncbi.nlm.nih.gov/pubmed/23435201 | https://www.ncbi.nlm.nih.gov/pubmed/20668312

4-n-octylphenol is alkylphenol widely used as a surfactant. 4-n-octylphenol exposure was associated with idiopathic male infertility. Fetal exposure to the very weak estrogenicity of 4-n-octylphenol could enhance the induction of mammary carcinomas but not affect the induction of benign proliferative lesions. It is an endocrine-disrupting chemical. 4-n-octylphenol is an agonist and antagonist of estrogen receptor and androgen receptor, respectively. 4-n-octylphenol at high doses caused reduction in mammary tumor development in female human c-Ha-ras proto-oncogene transgenic rats and possibly non-transgenic rats.

Approval Year

Targets

Primary Target	Pharmacology	Potency
11-beta-hydroxysteroid dehydrogenase 2 3 Target ID: CHEMBL3746 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16184081	Inhibitor 8504	23.5 µM [IC50]
UDP-glucuronosyltransferase 2B1 1 Target ID: P09875 Gene ID: 286954.0 Gene Symbol: Ugt2b1 Target Organism: Rattus norvegicus (Rat) Sources: https://www.ncbi.nlm.nih.gov/pubmed/18625249	Substrate 661
Alcohol sulfotransferase 2 Target ID: CHEMBL2077 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18174950	Inhibitor 8504	13.7 µM [Ki]
Estrogen receptor 72 Target ID: CHEMBL2093866 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18174953	Agonist 2752	4.9 µM [EC50]
Androgen Receptor 169 Target ID: CHEMBL1871 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18174953	Antagonist 2849	1.1 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cancer 609 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12117780	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Development of direct ELISA for the determination of 4-nonylphenol and octylphenol.	2004-02-15	14961734
Bioluminescence inhibition assays for toxicity screening of wood extractives and biocides in paper mill process waters.	2004-02	14982380
Integrated procedure for determination of endocrine-disrupting activity in surface waters and sediments by use of the biological technique recombinant yeast assay and chemical analysis by LC-ESI-MS.	2004-02	14658021
Identification of estrogen-responsive genes by complementary deoxyribonucleic acid microarray and characterization of a novel early estrogen-induced gene: EEIG1.	2004-02	14605097
Differential effects of the endocrine-disrupting compounds bisphenol-A and octylphenol on gonadotropin secretion, in prepubertal ewe lambs.	2004-01	14732453
Simultaneous measurement of urinary bisphenol A and alkylphenols by automated solid-phase extractive derivatization gas chromatography/mass spectrometry.	2003-12-15	14670041
Simultaneous determination of degradation products of nonylphenol polyethoxylates and their halogenated derivatives by solid-phase extraction and gas chromatography-tandem mass spectrometry after trimethylsilylation.	2003-12-12	14661741
Induction of vitellogenin synthesis in an Atlantic salmon (Salmo salar) hepatocyte culture: a sensitive in vitro bioassay for the oestrogenic and anti-oestrogenic activity of chemicals.	2003-11-07	14602523
Effects of endocrine disrupting compounds on the pathology and oestrogen receptor alpha and beta distribution in the uterus and cervix of ewe lambs.	2003-11	14652134
Male reproductive effects of octylphenol and estradiol in Fischer and Wistar rats.	2003-10-14	14555199
Potential of microemulsion electrokinetic chromatography for the separation of priority endocrine disrupting compounds.	2003-10-03	14558619
Study of 202 natural, synthetic, and environmental chemicals for binding to the androgen receptor.	2003-10	14565775
Lethal and sublethal effects of atrazine, carbaryl, endosulfan, and octylphenol on the streamside salamander (Ambystoma barbouri).	2003-10	14552003
Sulfonation of environmental estrogens by zebrafish cytosolic sulfotransferases.	2003-09-12	12943655
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
Behavior of alkylphenol polyethoxylate metabolites during soil aquifer treatment.	2003-09	12867334
Determination of alkylphenol and alkylphenolethoxylates in biota by liquid chromatography with detection by tandem mass spectrometry and fluorescence spectroscopy.	2003-08-22	14503813
Estrogenic effects of food wrap packaging xenoestrogens and flavonoids in female Wistar rats: a comparative study.	2003-07-10	12849853
Exposure to 4-tert-octylphenol accelerates sexual differentiation and disrupts expression of steroidogenic factor 1 in developing bullfrogs.	2003-04	12676615
Environmental estrogens alter early development in Xenopus laevis.	2003-04	12676604
Identification of endocrine-disrupting effects in aquatic vertebrates and invertebrates: report from the European IDEA project.	2003-03	12651186
Estrogenic effects of phenolic compounds on glucose-6-phosphate dehydrogenase in MCF-7 cells and uterine glutathione peroxidase in rats.	2003-03	12547330
Sonolysis of alkylphenols in aqueous solution with Fe(II) and Fe(III).	2003-03	12531707
Estrogenic effect of dietary 4-tert-octylphenol in rainbow trout (Oncorhynchus mykiss).	2003-02-26	12595169
Effect of neonatal treatment of rats with potent or weak (environmental) oestrogens, or with a GnRH antagonist, on Leydig cell development and function through puberty into adulthood.	2003-02	12534935
The effects of anti-androgenic and estrogenic disrupting contaminants on breeding gland (nuptial pad) morphology, plasma testosterone levels, and plasma vitellogenin levels in male Xenopus laevis (African clawed frog).	2003-02	12520397
Oocyte number in newborn mice after prenatal octylphenol exposure.	2003-01-01	12507659
Effects of octylphenol and 17beta-estradiol on the gonads of guppies (Poecilia reticulata) exposed as adults via the water or as embryos via the mother.	2003-01	12524017
Biodegradation of octylphenol polyethoxylates by denitrification.	2003	14640214
Mass spectrometric behaviour of carboxylated polyethylene glycols and carboxylated octylphenol ethoxylates.	2003	12939494
The fate of estrogenic compounds in the aquatic environment: sorption onto organic colloids.	2003	12830944
Stimulation of alkaline phosphatase activity in Ishikawa cells induced by various phytoestrogens and synthetic estrogens.	2002-12	12650720
An avian bioassay for environmental estrogens: the growth response of zebra finch (Taeniopygia guttata) chick oviduct to oral estrogens.	2002-12	12463562
Improvement of a sensitive enzyme-linked immunosorbent assay for screening estrogen receptor binding activity.	2002-12	12463546
Effect of maternal exposure to the environmental estrogen, octylphenol, during fetal and/or postnatal life on onset of puberty, endocrine status, and ovarian follicular dynamics in ewe lambs.	2002-12	12444047
Effects of waterborne exposure of octylphenol and oestrogen on pregnant viviparous eelpout (Zoarces viviparus) and her embryos in ovario.	2002-12	12432009
Determination of endocrine-disrupting compounds in environmental samples using gas and liquid chromatography with mass spectrometry.	2002-10-18	12458934
Induction of different types of uterine adenocarcinomas in Donryu rats due to neonatal exposure to high-dose p-t-octylphenol for different periods.	2002-10	12376485
Isolation of bacterial strains that produce the endocrine disruptor, octylphenol diethoxylates, in paddy fields.	2002-09	12400675
Development of a fish reporter gene system for the assessment of estrogenic compounds and sewage treatment plant effluents.	2002-09	12206426
Analysis of trace organic contaminants in sediment, pore water, and water samples from Onsan Bay, Korea: instrumental analysis and in vitro gene expression assay.	2002-09	12206418
Effects of perinatal octylphenol on ultrasound vocalization, behavior and reproductive physiology in rats.	2002-08	12127004
High glucuronidation activity of environmental estrogens in the carp (Cyprinus carpino) intestine.	2002-07-12	12084386
Environmental fate of alkylphenols and alkylphenol ethoxylates--a review.	2002-07	12222618
Is exposure to endocrine disrupting compounds during fetal/post-natal development affecting the reproductive potential of farm animals?	2002-07	12142238
Inhibitory effects of 17beta-estradiol and 4-n-octylphenol on 7,12-dimethylbenz[a]anthracene-induced mammary tumor development in human c-Ha-ras proto-oncogene transgenic rats.	2002-07	12117780
Pressurized liquid extraction followed by liquid chromatography-mass spectrometry for the determination of alkylphenolic compounds in river sediment.	2002-06-14	12141540
Exposure to octylphenol increases basal testosterone formation by cultured adult rat Leydig cells.	2002-06	12137809

Patents

Sample Use Guides

In Vivo Use Guide

1000 or 100 p.p.m. for 12 weeks

Route of Administration: Oral

In Vitro Use Guide

Treatment of TE 671 cells with 0.005–0.5 uM 4-n-octylphenol showed significant dosedependent decreases in SUOX (p < 0.02) and PAPSS1 (p < 0.001) steady-state mRNA levels. CDO1 mRNA expression also showed a dose-dependent decreasing trend.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 20:49:17 GMT 2025` Edited by `admin` on `Mon Mar 31 20:49:17 GMT 2025`
Record UNII	7DF2B8LH3P
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

4-OCTYLPHENOL

Preferred Name

English

4-N-OCTYLPHENOL

Common Name

English

4-OCTYLPHENOL [HSDB]

Common Name

English

PARA-OCTYLPHENOL

Systematic Name

English

PHENOL, 4-OCTYL-

Systematic Name

English

4-OCTYLBENZOLOL

Common Name

English

Code System Code Type Description

MESH

C080417