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Details

Stereochemistry ACHIRAL
Molecular Formula C10H13O.Na
Molecular Weight 172.1994
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SODIUM 4-TERT-BUTYLPHENATE

SMILES

[Na+].CC(C)(C)C1=CC=C([O-])C=C1

InChI

InChIKey=QDJPHAPWEUQBKS-UHFFFAOYSA-M
InChI=1S/C10H14O.Na/c1-10(2,3)8-4-6-9(11)7-5-8;/h4-7,11H,1-3H3;/q;+1/p-1

HIDE SMILES / InChI
Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula C10H13O
Molecular Weight 149.2096
Charge -1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including: http://www.drugfuture.com/chemdata/p-tert-Butylphenol.html https://www.ncbi.nlm.nih.gov/pubmed/73913

p-tert-butylphenol is in public use since the 1930s. It is used as an intermediate in the manufacture of varnish and lacquer resin. It has apparently not been reported to occur in nature. There is an abundant literature dealing with the well-established sensitization and depigmentation (vitiligo) properties of p-tert-butylphenol.

Originator

Lewis, E.W.
2
Sources: DOI: 10.1039/CT9038300329
Curator's Comment: earlier patent: https://worldwide.espacenet.com/publicationDetails/originalDocument?CC=DE&NR=17311C&KC=C&FT=D&ND=3&DB=&locale=en_EP

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Substrate
661
 10.0 µM [IC50]
Substrate
661
Binding Agent
1064
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
Approved
8429
TRUE Test

Approved Use

p-tert-Butylphenol formaldehyde resin (purity ≥95%) is used to formulate patch #13
PubMed

PubMed

TitleDatePubMed
Altered gene expression in melanocytes exposed to 4-tertiary butyl phenol (4-TBP): upregulation of the A2b adenosine receptor 1.
1999 Nov
Comparative metabolism, covalent binding and toxicity of BHT congeners in rat liver slices.
2001 Nov 28
Effects of bisphenol A and its derivatives on the response of GABA(A) receptors expressed in Xenopus oocytes.
2001 Sep
Developmental aspects of human hepatic drug glucuronidation in young children and adults.
2002 Feb
Comparative evaluation of alkylphenolic compounds on estrogenic activity in vitro and in vivo.
2002 Mar
Band splitting in overloaded isocratic elution chromatography II. New competitive adsorption isotherms.
2003 Aug 1
Shoe contact dermatitis in Israel.
2003 Mar
Preparation of uniformly sized molecularly imprinted polymers for phenolic compounds and their application to the assay of bisphenol A in river water.
2003 May
Study of 202 natural, synthetic, and environmental chemicals for binding to the androgen receptor.
2003 Oct
Phthalates, alkylphenols, pesticides, polybrominated diphenyl ethers, and other endocrine-disrupting compounds in indoor air and dust.
2003 Oct 15
Effects of 4-tert-octylphenol, 4-tert-butylphenol, and diethylstilbestrol on prenatal testosterone surge in the rat.
2003 Sep-Oct
Azolium-linked cyclophanes: a comprehensive examination of conformations by 1H NMR spectroscopy and structural studies.
2004 Oct 29
4-Tertiary butyl phenol exposure sensitizes human melanocytes to dendritic cell-mediated killing: relevance to vitiligo.
2005 Apr
Estrogenic effects of environmental chemicals: an interspecies comparison.
2005 Jul
Water purification through bioconversion of phenol compounds by tyrosinase and chemical adsorption by chitosan beads.
2005 May-Jun
Allergic contact dermatitis due to orthopedic shoes and a prosthesis for an amputated foot.
2006 Aug
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.
2006 Nov
[Kinetics of endocrine disrupting chemical 4-tert-butylphenol during chlorination in aqua].
2007 Jul
Characterization of alkylphenol metabolites in fish bile by enzymatic treatment and HPLC-fluorescence analysis.
2008 Apr
A review of 241 subjects who were patch tested twice: could fragrance mix I cause active sensitization?
2008 Mar
Determination of dimethyl fumarate and other potential allergens in desiccant and antimould sachets.
2009 Aug
Increase in the levels of chaperone proteins by exposure to beta-estradiol, bisphenol A and 4-methoxyphenol in human cells transfected with estrogen receptor alpha cDNA.
2009 Jun
Comparison of relative binding affinities to fish and mammalian estrogen receptors: the regulatory implications.
2010 Feb 15
Patents

Patents

04098717
2
04535087
6
04892952
5
04959103
3
05155130
9
05382682
2
05478849
2
05482764
3
05663441
2
06392056
4
06573318
2
07019024
3
07153850
4
07259183
6
08030516
2
08741925
11
JP2000001048A
2
JP2000016956A
2
JP2000212269A
2
JP2005515246A
2
JP2006517999A
8
JP2009196918A
2
JP2009528925A
2
JPH01128939A
3
JPH02199122A
2
JPH02258865A
3
JPH04287044A
3
JPH06183159A
2
JPH08143494A
4
JPH10236997A
3
JPH1161073A
2
JPS52118438A
2
JPS5337627A
2
JPS58219246A
3
JPS59127794A
2
JPS59191719A
2
JPS60255880A
2
JPS62260147A
2
JPS63205317A
2

Sample Use Guides

In Vivo Use Guide
The product is formulated to contain 45 ug/cm2 of p-tert-butylphenol formaldehyde resin, which corresponds to 36 ug of p-tert-butylphenol formaldehyde resin per patch. Schedule patients to return approximately 48 hours after patch test application to have the panels removed.
Route of Administration: Topical
In Vitro Use Guide
BP at 107 M and 106 M significantly decreased estradiol levels in the culture medium of isolated rat ovarian follicles.
Substance Class Chemical
Created
by admin
on Sat Dec 16 08:59:50 GMT 2023
Edited
by admin
on Sat Dec 16 08:59:50 GMT 2023
Record UNII
335O2WP1H4
Record Status Validated (UNII)
Record Version
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Name Type Language
SODIUM 4-TERT-BUTYLPHENATE
Common Name English
SODIUM P-TERT-BUTYLPHENOLATE
Common Name English
PHENOL, 4-(1,1-DIMETHYLETHYL)-, SODIUM SALT
Systematic Name English
SODIUM P-TERT-BUTYLPHENOXIDE
Common Name English
SODIUM P-TERT-BUTYLPHENATE
Common Name English
SODIUM 4-TERT-BUTYLPHENOXIDE
Systematic Name English
4-TERT-BUTYLPHENOL SODIUM SALT
Common Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 64115
Created by admin on Sat Dec 16 08:59:50 GMT 2023 , Edited by admin on Sat Dec 16 08:59:50 GMT 2023
Code System Code Type Description
CAS
5787-50-8
Created by admin on Sat Dec 16 08:59:50 GMT 2023 , Edited by admin on Sat Dec 16 08:59:50 GMT 2023
PRIMARY
FDA UNII
335O2WP1H4
Created by admin on Sat Dec 16 08:59:50 GMT 2023 , Edited by admin on Sat Dec 16 08:59:50 GMT 2023
PRIMARY
EPA CompTox
DTXSID2042351
Created by admin on Sat Dec 16 08:59:50 GMT 2023 , Edited by admin on Sat Dec 16 08:59:50 GMT 2023
PRIMARY
ECHA (EC/EINECS)
227-318-4
Created by admin on Sat Dec 16 08:59:50 GMT 2023 , Edited by admin on Sat Dec 16 08:59:50 GMT 2023
PRIMARY
PUBCHEM
23668059
Created by admin on Sat Dec 16 08:59:50 GMT 2023 , Edited by admin on Sat Dec 16 08:59:50 GMT 2023
PRIMARY
NIH
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