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

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
Biological production of optically active muconolactones by Rhodococcus rhodochrous.	2001 Aug	11549019
Patch test sensitization caused by para-tertiary-butylcatechol. Results of a prospective study with a dilution series.	2001 Oct	11683828
Low-molecular-weight contact allergens in p-tert-butylphenol-formaldehyde resin.	2002 Dec	12478534
Sensitizing capacity of some trimers in p-tert-butylphenol-formaldehyde resin.	2002 Jul	12225412
Occupational dermatoses among fibreglass-reinforced plastics factory workers.	2002 Jun	12190622
Mechanistic implications of variable stoichiometries of oxygen consumption during tyrosinase catalyzed oxidation of monophenols and o-diphenols.	2002 May 20	12009413
Solvent deuterium isotope effect on the oxidation of o-diphenols by tyrosinase.	2003 Aug 21	12922176
Polymeric enzyme mimics: catalytic activity of ribose-containing polymers for a phosphate substrate.	2003 Jul 7	12945697
[Inhibition of peroxidase oxidation of aromatic amines by substituted phenols].	2003 Jul-Aug	14520958
Partial purification of latent persimmon fruit polyphenol oxidase.	2003 Mar 26	12643673
Polyphenol oxidase from Dominga table grape.	2005 Jul 27	16029000
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.	2006 Nov	16497524
Binding of catechols to mononuclear titanium(IV) and to 1- and 5-nm TiO2 nanoparticles.	2008 May 5	18366179
Production of o-diphenols by immobilized mushroom tyrosinase.	2009 Jan 15	19047003

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%

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