P-TERT-PENTYLPHENOL

Details

Stereochemistry	ACHIRAL
Molecular Formula	C11H16O
Molecular Weight	164.2441
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCC(C)(C)C1=CC=C(O)C=C1

InChI

InChIKey=NRZWYNLTFLDQQX-UHFFFAOYSA-N

InChI=1S/C11H16O/c1-4-11(2,3)9-5-7-10(12)8-6-9/h5-8,12H,4H2,1-3H3

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19233257 | https://www.gov.uk/government/uploads/system/uploads/attachment_data/file/290845/scho0208bnqr-e-e.pdf

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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Estrogen receptor alpha 127 Target ID: CHEMBL206 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19233257 \| https://www.ncbi.nlm.nih.gov/pubmed/12765246 \| https://www.ncbi.nlm.nih.gov/pubmed/12504345	Agonist 2678

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bronchial spasm 78 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14353164	Primary		Not Provided 504	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Determination of phenolic disinfectant agents in commercial formulations by liquid chromatography.	2001 May-Jun	11417646
[Study on para-derivative of phenol as enhancers of chemiluminescence].	2002 Dec	12914157
Utility of a juvenile fathead minnow screening assay for detecting (anti-)estrogenic substances.	2002 Feb	11833800
Comparison of the reporter gene assay for ER-alpha antagonists with the immature rat uterotrophic assay of 10 chemicals.	2003 Apr 30	12765246
Fish full life-cycle testing for the weak estrogen 4-tert-pentylphenol on medaka (Oryzias latipes).	2003 Jul	12836973
Study of 202 natural, synthetic, and environmental chemicals for binding to the androgen receptor.	2003 Oct	14565775
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.	2006 Nov	16497524
Removal of p-alkylphenols from aqueous solutions by combined use of mushroom tyrosinase and chitosan beads.	2006 Oct	17031033
Towards high-throughput identification of endocrine disrupting compounds with mass spectrometry.	2009 Jun	19233257
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	20629411

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

For the agonist assay, 4-tert-Pentylphenol diluted in DMSO was added to the wells to final concentrations of 10 uM, 1 uM, 100 nM, 10 nM, 1 nM, 100 pM, and 10 pM, in quadruplicate. A stable transfected cell line, hERa/HeLa, was used.

Name

Type

Language

P-TERT-PENTYLPHENOL

Common Name

English

P-TERT-AMYLPHENOL

Common Name

English

PENTAPHEN

Systematic Name

English

4-(1,1-DIMETHYLPROPYL)PHENOL [HSDB]

Common Name

English

2-METHYL-2-P-HYDROXYPHENYLBUTANE

Common Name

English

NSC-403672

Code

English

AMYLPHENOL [MART.]

Common Name

English

P-TERT-PENTYLPHENOL [MI]

Common Name

English

4-TERT-AMYLPHENOL

Systematic Name

English

AMYLPHENOL

Systematic Name

English

AMYLPHENOL, P-TERT-

Common Name

English

TERTIARY AMYL PHENOL

Common Name

English

4-(2-METHYLBUTAN-2-YL)PHENOL

Systematic Name

English

4-(1,1-DIMETHYLPROPYL)PHENOL

Systematic Name

English

Classification Tree Code System Code

EPA PESTICIDE CODE

64101