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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 of 4-N-OCTYLPHENOL

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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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 TargetPharmacologyConditionPotency
23.5 µM [IC50]
13.7 µM [Ki]
4.9 µM [EC50]
1.1 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

PubMed

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
Record UNII
7DF2B8LH3P
Record Status Validated (UNII)
Record Version