Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C11H15O.Na |
| Molecular Weight | 186.226 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].CCC(C)(C)C1=CC=C([O-])C=C1
InChI
InChIKey=QZIINTXQNXZHLR-UHFFFAOYSA-M
InChI=1S/C11H16O.Na/c1-4-11(2,3)9-5-7-10(12)8-6-9;/h5-8,12H,4H2,1-3H3;/q;+1/p-1
| Molecular Formula | C11H15O |
| Molecular Weight | 163.2362 |
| Charge | -1 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | Na |
| Molecular Weight | 22.98976928 |
| Charge | 1 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
4-tert-Pentylphenol (4-tert-Amylphenol) is used to make phenolic resins (novolaks and resoles),
which are used in paints and varnishes and as printing ink resins. The
ethoxylated novolaks are used as oil field demulsifiers. Because of the high
cost of 4-tert-pentylphenol, which is related to the high cost of the starting
material, many of the resin applications have been reformulated using 4-tertbutylphenol. The substance is also used as a germicide in cleaning solutions, although it is
being replaced by quaternary ammonium salts. Kegley et al. (2007) confirm
that both the substance and its potassium and sodium salts are antimicrobial
or fungicidal active ingredients of several disinfectant products that are
currently registered with the US authorities. It appears that some of these
products are used in animal husbandry, including the control of highly
infectious diseases such as avian influenza (US EPA, 2007d). 4-tert-Amylphenol was used as an esterogen receptor (ER) ligand.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Single-laboratory validation of a method for the determination of phenols and phenates in disinfectant formulations by liquid chromatography with UV detection. | 2010-07-16 |
|
| Effects of a weak oestrogenic active chemical (4-tert-pentylphenol) on pair-breeding and F1 development in the fathead minnow (Pimephales promelas). | 2010-05-10 |
|
| Comparison of relative binding affinities to fish and mammalian estrogen receptors: the regulatory implications. | 2010-02-15 |
|
| Towards high-throughput identification of endocrine disrupting compounds with mass spectrometry. | 2009-06 |
|
| A simple and rapid matrix-assisted laser desorption/ionization time of flight mass spectrometry method to screen fish plasma samples for estrogen-responsive biomarkers. | 2008-05 |
|
| A proteomic (SELDI-TOF-MS) approach to estrogen agonist screening. | 2007-01 |
|
| Development of chronic tests for endocrine active chemicals. Part 2: an extended fish early-life stage test with an androgenic chemical in the fathead minnow (Pimephales promelas). | 2006-11-16 |
|
| Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods. | 2006-11 |
|
| Removal of p-alkylphenols from aqueous solutions by combined use of mushroom tyrosinase and chitosan beads. | 2006-10 |
|
| In vitro cytotoxicity assessment of the biocidal agents sodium o-phenylphenol, sodium o-benzyl-p-chlorophenol, and sodium p-tertiary amylphenol using established fish cell lines. | 2006-10 |
|
| Development of chronic tests for endocrine active chemicals. Part 1. An extended fish early-life stage test for oestrogenic active chemicals in the fathead minnow (Pimephales promelas). | 2006-05-10 |
|
| Impurities in a lyophilized formulation of BMS-204352: identification and role of sanitizing agents. | 2006 |
|
| Ecotoxicological evaluation of the biocidal agents sodium o-phenylphenol, sodium o-benzyl-p-chlorophenol, and sodium p-tertiary amylphenol. | 2005-02 |
|
| Effects of 4-tert-pentylphenol on the gene expression of P450 11beta-hydroxylase in the gonad of medaka (Oryzias latipes). | 2005-01-26 |
|
| [Estimation of daily intake of phenols in hospital meal samples]. | 2004-12 |
|
| Structural identification of extractables from rubber closures used for pre-filled semisolid drug applicator by chromatography, mass spectrometry, and organic synthesis. | 2004-03-10 |
|
| Study of 202 natural, synthetic, and environmental chemicals for binding to the androgen receptor. | 2003-10 |
|
| Fish full life-cycle testing for the weak estrogen 4-tert-pentylphenol on medaka (Oryzias latipes). | 2003-07 |
|
| Comparison of the reporter gene assay for ER-alpha antagonists with the immature rat uterotrophic assay of 10 chemicals. | 2003-04-30 |
|
| Induction of an estrogen-responsive reporter gene in rainbow trout hepatoma cells (RTH 149) at 11 or 18 degrees C. | 2003-04 |
|
| Immature rat uterotrophic assay of 18 chemicals and Hershberger assay of 30 chemicals. | 2003-02-01 |
|
| [Study on para-derivative of phenol as enhancers of chemiluminescence]. | 2002-12 |
|
| Phenylphenols, biphenols, bisphenol-A and 4-tert-octylphenol exhibit alpha and beta estrogen activities and antiandrogen activity in reporter cell lines. | 2002-07-31 |
|
| Utility of a juvenile fathead minnow screening assay for detecting (anti-)estrogenic substances. | 2002-02 |
|
| Effect of phthalate esters and alkylphenols on steroidogenesis in human adrenocortical H295R cells. | 2001-07 |
|
| Determination of phenolic disinfectant agents in commercial formulations by liquid chromatography. | 2001-06-22 |
Patents
Sample Use Guides
In Vivo Use Guide
Curator's Comment: 4-tert-pentylphenol was administered by oral
gavage to pregnant Sprague-Dawley rats (25 per dose) from gestation day 6 to 15. Doses
were 0, 50, 200 and 500 mg/kg/d and dams and litters were sacrificed and examined after
termination of the study on gestation day 20. There was evidence of significant maternal
toxicity at the top two doses; the incidence of hair loss, abnormal respiratory sounds and
mucoid/soft stools were increased and body weight gain and food consumption were
decreased by 10–50%. The NOAEL for repeat dose toxicity for this study was 50 mg/kg/d.
Acute oral toxicity tests have been conducted with 4-tert-pentylphenol in the rat. In the more recent study, conducted to OECD guidelines, five male and five female animals were given 4-tert-pentylphenol in corn oil by gavage at a limit
dose of 2,000 mg/kg.
Route of Administration:
Oral
| Substance Class |
Chemical
Created
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admin
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Mon Mar 31 22:06:52 GMT 2025
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Mon Mar 31 22:06:52 GMT 2025
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| Record UNII |
OLB88WK93S
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| Record Status |
Validated (UNII)
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| Record Version |
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EPA PESTICIDE CODE |
64112
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250-595-8
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23707506
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OLB88WK93S
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DTXSID7035725
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