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
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 |
|---|---|---|
| Effect of phthalate esters and alkylphenols on steroidogenesis in human adrenocortical H295R cells. | 2001 Jul |
|
| Phenylphenols, biphenols, bisphenol-A and 4-tert-octylphenol exhibit alpha and beta estrogen activities and antiandrogen activity in reporter cell lines. | 2002 Jul 31 |
|
| Induction of an estrogen-responsive reporter gene in rainbow trout hepatoma cells (RTH 149) at 11 or 18 degrees C. | 2003 Apr |
|
| Comparison of the reporter gene assay for ER-alpha antagonists with the immature rat uterotrophic assay of 10 chemicals. | 2003 Apr 30 |
|
| Immature rat uterotrophic assay of 18 chemicals and Hershberger assay of 30 chemicals. | 2003 Feb 1 |
|
| Fish full life-cycle testing for the weak estrogen 4-tert-pentylphenol on medaka (Oryzias latipes). | 2003 Jul |
|
| Study of 202 natural, synthetic, and environmental chemicals for binding to the androgen receptor. | 2003 Oct |
|
| [Estimation of daily intake of phenols in hospital meal samples]. | 2004 Dec |
|
| Structural identification of extractables from rubber closures used for pre-filled semisolid drug applicator by chromatography, mass spectrometry, and organic synthesis. | 2004 Mar 10 |
|
| Effects of 4-tert-pentylphenol on the gene expression of P450 11beta-hydroxylase in the gonad of medaka (Oryzias latipes). | 2005 Jan 26 |
|
| Impurities in a lyophilized formulation of BMS-204352: identification and role of sanitizing agents. | 2006 |
|
| 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 May 10 |
|
| Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods. | 2006 Nov |
|
| Removal of p-alkylphenols from aqueous solutions by combined use of mushroom tyrosinase and chitosan beads. | 2006 Oct |
|
| 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 May |
|
| Comparison of relative binding affinities to fish and mammalian estrogen receptors: the regulatory implications. | 2010 Feb 15 |
|
| Single-laboratory validation of a method for the determination of phenols and phenates in disinfectant formulations by liquid chromatography with UV detection. | 2010 May-Jun |
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
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EPA PESTICIDE CODE |
64112
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250-595-8
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DTXSID7035725
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SUBSTANCE RECORD
