4-TERT-BUTYLCATECHOL

Details

Stereochemistry	ACHIRAL
Molecular Formula	C10H14O2
Molecular Weight	166.217
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=XESZUVZBAMCAEJ-UHFFFAOYSA-N

InChI=1S/C10H14O2/c1-10(2,3)7-4-5-8(11)9(12)6-7/h4-6,11-12H,1-3H3

HIDE SMILES / InChI

Molecular Formula	C10H14O2
Molecular Weight	166.217
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.chemicalland21.com/specialtychem/perchem/TBC.htm | https://www.ncbi.nlm.nih.gov/pubmed/6775084

4-tert-Butylcatechol is usually added as a stabilizer and an inhibitor of polymerization to butadiene, styrene and other reactive monomer streams. It is 25 times higher than hydroquinone at 60 deg C for polymerization inhibitory effect. It is used as a polymerization inhibitor in processing Styrene, Butadiene, and Vinyl Acetate monomers, Polyester resins. Also used as a stabilizer in the manufacture of polyurethane foam. Because of the sterically hindered group, tert-butylphenolic compounds have an antioxidizing action and also act as UV stabilisers. It also can be used as antioxidants for synthetic rubber, polymers and oil derivatives, it can be used as purification agent for aminoformate catalysts. TBC is available in a form of a solid crystal and 85% solution in methanol or water. 4-tert-Butylcatechol inhibits the activity of tyrosinase at concentrations higher than 1×10(−3)M.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Tyrosinase 41 Target ID: CHEMBL1973 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6775084	Inhibitor 8297
glutathione transferase activity 6 Target ID: GO:0004364 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6140289	Activator 1430
Gamma-glutamyltranspeptidase 1 2 Target ID: Q60928 Gene ID: 14598.0 Gene Symbol: Ggt1 Target Organism: Mus musculus (Mouse) Sources: https://www.ncbi.nlm.nih.gov/pubmed/6140289	Activator 1430

Conditions

Condition	Modality	Targets	Highest Phase	Product
Neurodegenerative diseases 14 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18499097	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Tyrosinase action on monophenols: evidence for direct enzymatic release of o-diphenol.	2001 Aug 13	11513969
Chromium(VI) reduction by catechol(amine)s results in DNA cleavage in vitro: relevance to chromium genotoxicity.	2001 May	11368547
Contact allergy to the monomers in p-tert-butylphenol-formaldehyde resin.	2002 Sep	12492546
Comparative study of the uterotrophic potency of 14 chemicals in a uterotrophic assay and their receptor-binding affinity.	2004 Jan 15	14643963
Enzymatic and spectroscopic studies on the activation or inhibition effects by substituted phenolic compounds in the oxidation of aryldiamines and catechols catalyzed by Rhus vernicifera laccase.	2006 Dec	16959319
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.	2006 Nov	16497524
Indirect oxidation of the antitumor agent procarbazine by tyrosinase--possible application in designing anti-melanoma prodrugs.	2008 Jun 1	18457951
Screen-printed immunosensor modified with carbon nanotubes in a continuous-flow system for the Botrytis cinerea determination in apple tissues.	2009 Aug 15	19576430
Chemical leukoderma: what's new on etiopathological and clinical aspects?	2010 Jul-Sep	21063518
Discovery of a new tyrosinase-like enzyme family lacking a C-terminally processed domain: production and characterization of an Aspergillus oryzae catechol oxidase.	2010 Mar	19798497
Molecular modeling of peroxidase and polyphenol oxidase: substrate specificity and active site comparison.	2010 Sep 14	20957092

Patents

Sample Use Guides

In Vivo Use Guide

Mice: Topical application of 1 M TBC(4-tert-Butylcatechol)-DMSO-acetone solution on the ear skin elevated GST activity about 27%, and activities of GGT and GR to 35% and 19%, respectively, within 1 week.

Route of Administration: Topical

In Vitro Use Guide

4-tert-Butylcatechol at 2 ug/ml inhibited the LPS-induced expression of iNOS and TNF-α in LPS-stimulated BV-2 microglia cells. 4-tert-Butylcatechol at 2 ug/ml inhibited rat neuroblastoma B35 cell death induced by activated BV-2 microglia cells by 47%

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:32:25 GMT 2023` Edited by `admin` on `Fri Dec 15 18:32:25 GMT 2023`
Record UNII	9A069144KR
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

4-TERT-BUTYLCATECHOL

Systematic Name

English

NSC-5310

Code

English

BUTYL CATECHOL, P-TERT-

Common Name

English

P-TERT-BUTYLCATECHOL

Common Name

English

P-TERT-BUTYL CATECHOL

Common Name

English

Code System Code Type Description

CAS

98-29-3