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
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
| 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 |
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 | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL3746 |
23.5 µM [IC50] | ||
Target ID: P09875 Gene ID: 286954.0 Gene Symbol: Ugt2b1 Target Organism: Rattus norvegicus (Rat) |
|||
Target ID: CHEMBL2077 |
13.7 µM [Ki] | ||
Target ID: CHEMBL2093866 |
4.9 µM [EC50] | ||
Target ID: CHEMBL1871 |
1.1 µM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Sulfation of environmental estrogen-like chemicals by human cytosolic sulfotransferases. | 2000 Jan 7 |
|
| Female infertility--effect of perinatal xenoestrogen exposure on reproductive functions in animals and humans. | 2001 |
|
| Direct detection of polyaromatic hydrocarbons, estrogenic compounds and pesticides in water using desorption chemical ionisation membrane inlet mass spectrometry. | 2001 |
|
| The determination of alkylphenols in aqueous samples from the Forth Estuary by SPE-HPLC-fluorescence. | 2001 Dec |
|
| Comparative assessment of endocrine modulators with oestrogenic activity: I. Definition of a hygiene-based margin of safety (HBMOS) for xeno-oestrogens against the background of European developments. | 2001 Jan |
|
| Endocrine disrupting compounds: effect of octylphenol on reproduction over three generations. | 2001 Jan 1 |
|
| Comparison of an array of in vitro assays for the assessment of the estrogenic potential of natural and synthetic estrogens, phytoestrogens and xenoestrogens. | 2001 Sep 14 |
|
| Developmental increases in rat hepatic microsomal UDP-glucuronosyltransferase activities toward xenoestrogens and decreases during pregnancy. | 2002 Feb |
|
| Occurrence and distribution of nonionic surfactants, their degradation products, and linear alkylbenzene sulfonates in coastal waters and sediments in Spain. | 2002 Jan |
|
| 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 Jul |
|
| Lack of modifying effects of 4-n-octylphenol on 3,2'-dimethyl-4-aminobiphenyl-induced prostate carcinogenesis in rats. | 2002 Mar |
|
| Comparative evaluation of alkylphenolic compounds on estrogenic activity in vitro and in vivo. | 2002 Mar |
|
| Induction of different types of uterine adenocarcinomas in Donryu rats due to neonatal exposure to high-dose p-t-octylphenol for different periods. | 2002 Oct |
|
| Development of a fish reporter gene system for the assessment of estrogenic compounds and sewage treatment plant effluents. | 2002 Sep |
|
| The fate of estrogenic compounds in the aquatic environment: sorption onto organic colloids. | 2003 |
|
| 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 Feb |
|
| Estrogenic effects of food wrap packaging xenoestrogens and flavonoids in female Wistar rats: a comparative study. | 2003 Jul-Aug |
|
| Sonolysis of alkylphenols in aqueous solution with Fe(II) and Fe(III). | 2003 Mar |
|
| Effects of endocrine disrupting compounds on the pathology and oestrogen receptor alpha and beta distribution in the uterus and cervix of ewe lambs. | 2003 Nov |
|
| Study of 202 natural, synthetic, and environmental chemicals for binding to the androgen receptor. | 2003 Oct |
|
| Transformation of 4-tert-octylphenol by UV irradiation and by an H2O2/UV process in aqueous solution. | 2003 Sep |
|
| Behavior of alkylphenol polyethoxylate metabolites during soil aquifer treatment. | 2003 Sep |
|
| Estrogenic effects in flounder Platichthys flesus orally exposed to 4-tert-octylphenol. | 2003 Sep 10 |
|
| 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 Feb |
Sample Use Guides
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 01:23:18 GMT 2023
by
admin
on
Sat Dec 16 01:23:18 GMT 2023
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| Record UNII |
7DF2B8LH3P
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| Record Status |
Validated (UNII)
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| Record Version |
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C080417
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217-302-5
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DTXSID9022312
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7DF2B8LH3P
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7DF2B8LH3P
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1806-26-4
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15730
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