| Identification | More | [Name]
2,5-Di-tert-butylhydroquinone | [CAS]
88-58-4 | [Synonyms]
1,4-DIHYDROXY-2,5-DI-TERT-BUTYLBENZENE
2,5-BIS(2-METHYL-2-PROPYL)-1,4-BENZENEDIOL
2,5-DI-(T-BUTYL)-1,4-BENZOHYDROQUINONE
2,5-DI-(T-BUTYL)-1,4-HYDROQUINONE
2,5-DI-T-BUTYLHYDROQUINONE
2,5-DI(TERT-BUTYL)-1,4-BENZENEDIOL
2,5-DI-TERT-BUTYL-1,4-HYDROQUINONE
2,5-DI-TERT-BUTYLHYDROQUINONE
2,5-DI-TERT-BUTYL HYDROXYQUINONE
2,5-ditertiary butyl hydroquinone
BHQ
BUTYLHYDROQUINONE-TERT
DBHQ
Dibutylhydroquinone
DI-T-BUTYLHYDROQUINONE
DI-TERT-BUTYL HYDROQUINONE(2,5-)
TBUBHQ
T-BUTYLATED HYDROQUINONE
1,4-Benzenediol,2,5-bis(1,1-dimethylethyl)-
2,5-bis(1,1-dimethylethyl)-4-benzenediol | [EINECS(EC#)]
201-841-8 | [Molecular Formula]
C14H22O2 | [MDL Number]
MFCD00008825 | [Molecular Weight]
222.32 | [MOL File]
88-58-4.mol |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
3
| [RTECS ]
MX5160000
| [Autoignition Temperature]
790 °F | [Hazard Note ]
Irritant | [TSCA ]
Yes | [HS Code ]
29072900 |
| Hazard Information | Back Directory | [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 | [Uses]
2,5-Di-tert-butylhydroquinone is the oxidation substrate used to measure the catalytic activity of the copper(II) enzyme-like catalysts. | [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. | [Synthesis]
General procedure for the synthesis of 2,5-di-tert-butylhydroquinone from 2,5-di-tert-butyl-1,4-benzoquinone: To a Teflon tubular glass ampoule with stopper was added about 4.8 mL volume of 0.166 mmol 2,5-di-tert-butyl-1,4-benzoquinone, a stirring bar, and 0.25 mL of a toluene solution containing 0.5 mg iPrPCPIrH4. Subsequently, the solution was subjected to two freeze-pump-thaw degassing cycles and sealed under a 1 atm hydrogen atmosphere. The sealed vessel was placed in an aluminum heating block, heated at the indicated temperature and stirred for the specified time. Upon completion of the reaction, volatiles were removed by depressurization until only a few μL of toluene remained, and the ampoule was quickly sealed. Finally, 0.5 mL of THF-d8 was added and the solution was transferred to an NMR tube for NMR analysis. | [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. |
|
|