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
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. |
Computed Descriptors for 2,5-Di-tert-butylhydroquinone
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