2,5-Di-tert-butylhydroquinone

Synonym(s):2,5-Di-( t-butyl)-1,4-hydroquinone, t-BuBHQ;2,5-Di-(t-butyl)-1,4-hydroquinone, t-BuBHQ;2,5-Di-tert-butylhydroquinone;BHQ - CAS 88-58-4 - Calbiochem

CAS NO.：88-58-4
Empirical Formula: C14H22O2
Molecular Weight: 222.32
MDL number: MFCD00008825
EINECS: 201-841-8
SAFETY DATA SHEET (SDS)
Update Date: 2024-06-25 10:53:43

2,5-Di-tert-butylhydroquinone Structural

What is 2,5-Di-tert-butylhydroquinone?

Description

2,5-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.

Chemical properties

cream or pale brown solid

The Uses of 2,5-Di-tert-butylhydroquinone

2,5-Di-tert-butylhydroquinone is the oxidation substrate used to measure the catalytic activity of the copper(II) enzyme-like catalysts.

What are the applications of Application

2,5-Di-tert-butylhydroquinone (DBHQ) is an inducer of Ca2+

Definition

ChEBI: A member of the class of hydroquinones that is benzene-1,4-diol substituted by tert-butyl groups at position 2 and 5.

General Description

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.

Biological Activity

A selective inhibitor of endoplasmic reticulum Ca 2+ -ATPase.

Biochem/physiol Actions

2,5-Di-tert-butylhydroquinone specifically inhibits the sarcoplasmic reticulum (SR) Ca2+ uptake in the rat ventricle.

Purification Methods

Crystallise the hydroquinone from *C6H6 or AcOH. [Beilstein 6 III 4741.]

References

[1]. hasséssian h, vaca l, kunze dl. blockade of the inward rectifier potassium current by the ca(2+)-atpase inhibitor 2',5'-di(tert-butyl)-1,4-benzohydroquinone (bhq). br j pharmacol, 1994, 112(4): 1118-1122.
[2]. fusi f, gorelli b, valoti m, et al. effects of 2,5-di-t-butyl-1,4-benzohydroquinone (bhq) on rat aorta smooth muscle. eur j pharmacol, 1998, 346(2-3): 237-243.
[3]. fusi f, saponara s, gagov h, et al. 2,5-di-t-butyl-1,4-benzohydroquinone (bhq) inhibits vascular l-type ca(2+) channel via superoxide anion generation. br j pharmacol, 2001, 133(7): 988-996.
[4]. jan cr, ho cm, wu sn, et al. mechanism of rise and decay of 2,5-di-tert-butylhydroquinone-induced ca2+ signals in madin darby canine kidney cells. eur j pharmacol, 1999, 365(1): 111-117.

Properties of 2,5-Di-tert-butylhydroquinone

Melting point:	216-218 °C(lit.)
Boiling point:	321°C
Density	1,07 g/cm³
refractive index	1.4576 (estimate)
Flash point:	216 °C
storage temp.	Store below +30°C.
solubility	almost transparency in Methanol
pka	11.89±0.23(Predicted)
form	Crystalline Powder
color	Light beige to pink-beige
Water Solubility	3.8mg/L at 20℃
BRN	2049542
Stability:	Stable. Incompatible with oxidizing agents.
CAS DataBase Reference	88-58-4(CAS DataBase Reference)
NIST Chemistry Reference	1,4-Benzenediol, 2,5-bis(1,1-dimethylethyl)-(88-58-4)
EPA Substance Registry System	1,4-Benzenediol, 2,5-bis(1,1-dimethylethyl)- (88-58-4)

Safety information for 2,5-Di-tert-butylhydroquinone

Signal word	Danger
Pictogram(s)	Skull and Crossbones Acute Toxicity GHS06 Environment GHS09
GHS Hazard Statements	H301:Acute toxicity,oral H317:Sensitisation, Skin H335:Specific target organ toxicity, single exposure;Respiratory tract irritation H410:Hazardous to the aquatic environment, long-term hazard
Precautionary Statement Codes	P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P273:Avoid release to the environment. P280:Wear protective gloves/protective clothing/eye protection/face protection. P301+P310:IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. P302+P352:IF ON SKIN: wash with plenty of soap and water.