2,5-Di-tert-butylhydroquinone
Basic information
- CAS
1322-72-1- Standard SMILES
CC(C)(C)c1cc(O)c(C(C)(C)C)cc1O- InChIKey
JZODKRWQWUWGCD-UHFFFAOYSA-N- Molecular formula
- C14H22O2
- Average molar mass
- 222.32 g/mol
- Monoisotopic mass
- 222.16197994
Overview
2,5-di-tert-butylbenzene-1,4-diol is a member of the class of hydroquinones that is benzene-1,4-diol substituted by tert-butyl groups at position 2 and 5.
Names & identifiers
- Preferred name
- 2,5-Di-tert-butylhydroquinone
- IUPAC
- 2,5-ditert-butylbenzene-1,4-diol
- English name
- 2,5-Di-tert-butylhydroquinone
- Molecular formula
- C14H22O2
- Molecular weight
- 222.32
Names & synonyms
2,5-Di-tert-butylhydroquinone88-58-42,5-Di-tert-butylbenzene-1,4-diolDTBHQDibugDybugDi-t-butylhydroquinoneSantovar O2,5-Di-tert-butylquinolNonflex AlbaNaugard 451Antage DBH
Show more names
BHQDBHQBlack Hole QuencherProbesANTIOXIDANT DTBHQDibutylhydroquinone2,5-ditertiary butyl hydroquinone2-carbamoyl-2-propylpentanoic acid
Nocrac NS 71,4-Benzenediol, 2,5-bis(1,1-dimethylethyl)-2,5-Di-tert-butyl-1,4-benzenediol2,5-Di-tert-butyl-1,4-hydroquinonedi-tert-butylhydroquinone1,4-Dihydroxy-2,5-di-tert-butylbenzene2,5-Di-tert-butyl-1,4-benzohydroquinoneDTXSID8041248
Database identifiers
- CAS
1322-72-1、88-58-4- PubChem CID
- 2374
- DTXSID
DTXSID8041248- ChEMBL
CHEMBL480626- ChEBI
CHEBI:41094
Properties
Computed structural properties
- XLogP
- 4.6
- Topological polar surface area
- 40.5 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 2
- Heavy atoms
- 16
- Formal charge
- 0
- Complexity
- 208
Experimental & physicochemical properties
Chemical ClassesOther Classes -> Phenols
DrugsPharmaceuticals -> Listed in ZINC15
Cosmetics
Cosmetic ingredients (Di-t-Butylhydroquinone) -> CIR (Cosmetic Ingredient Review)
Antioxidant
Food Contact SubstancesFCS -> FDA Inventory of Food Contact Substances Listed in 21 CFR
Physical Description
CBI
Off-white crystalline powder; [Alfa Aesar MSDS]
Collision Cross Section155.1 Ų [M]+ [CCS Type: DT; Buffer gas: N2; Ionization: APCI+; Dataset: TOXCAST; Source Identifier: DTXSID8041248]
Physicochemical properties
- Melting point
- 216 · 216-218 °C(lit.)
- Boiling point
- 321 °C · 321°C
- Density
- 1 · 1,07 g/cm3
- refractive index
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 0.7% (2 of 279) of reports.
Danger
H301 (46.6%): Toxic if swallowed [Danger Acute toxicity, oral]
P260, P261, P264, P264+P265, P270, P271, P272, P273, P280, P301+P316, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 279 reports by companies from 19 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: 1,4-Benzenediol, 2,5-bis(1,1-dimethylethyl)-
1,4-Benzenediol, 2,5-bis(1,1-dimethylethyl)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,4-Benzenediol, 2,5-bis(1,1-dimethylethyl)- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
REACH registered substance: 2,5-di-tert-butylhydroquinone (EC: 201-841-8)
2,5-Di-tert-butylhydroquinone: Does not have an individual approval but may be used under an appropriate group standard
Hazards Summary
Causes lung and liver changes in 2-day intermittent oral studies of mice; Causes changes in clotting factors in 3-week constant oral studies rats; [RTECS] A skin and strong eye irritant; Harmful by ingestion; [Alfa Aesar MSDS] See t-Butylhydroquinone. See 2,5-Di-t-pentylhydroquinone.
Hazard Classes and CategoriesAcute Tox. 3 (46.6%)
Safety & protection
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues.
Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.
Uses & manufacturing
Uses
CIR ingredient: Di-t-Butylhydroquinone
Ca2+-ATPase antagonist. [ChemIDplus]
U.S. Production2023: 75,000 - <500,000 lb
Consumer UsesNot Known or Reasonably Ascertainable
Industry UsesNot Known or Reasonably Ascertainable
Use ClassificationCosmetics -> Antioxidant
General Manufacturing Information
All Other Basic Organic Chemical Manufacturing
1,4-Benzenediol, 2,5-bis(1,1-dimethylethyl)-: ACTIVE
Applications
Description2,5-Di-tert-butylhydroquinone, also known as 2,5-TBHQ or DTBHQ, belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety. It is a phenol derivative containing 2 phenol groups and 2 alkyl groups, each consisting of three methyl groups.
Uses2,5-Di-tert-butylhydroquinone is the oxidation substrate used to measure the catalytic activity of the copper(II) enzyme-like catalysts.
Mobilizes Ca2+ specifically from the Ins(1,4,5)P3-sensitive Ca2+ stores by inhibiting microsomal and sarcoplasmic reticulum Ca2+-ATPase activity. Does not affect mitochondrial Ca2+ fluxes or plasma membrane Ca2+/Mg2+ ATPase activity. Useful for the study of endomembrane Ca2+ stores and plasma membrane Ca2+ permeability pathways.
Related reactions
22 records
Compound notes
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