88-58-4 Usage
Description
2,5-Di-tert-butylhydroquinone is a member of the class of hydroquinones, which is a benzene-1,4-diol substituted by tert-butyl groups at positions 2 and 5. It is a cream or pale brown solid and is known for its ability to mobilize Ca2+ specifically from the Ins(1,4,5)P3-sensitive Ca2+ stores by inhibiting microsomal and sarcoplasmic reticulum Ca2+-ATPase activity. 2,5-Di-tert-butylhydroquinone does not affect mitochondrial Ca2+ fluxes or plasma membrane Ca2+/Mg2+ ATPase activity, making it a useful tool for studying endomembrane Ca2+ stores and plasma membrane Ca2+ permeability pathways.
Uses
Used in Enzyme Catalysis Research:
2,5-Di-tert-butylhydroquinone is used as an oxidation substrate for measuring the catalytic activity of copper(II) enzyme-like catalysts. This application is crucial for understanding the efficiency and effectiveness of these catalysts in various chemical reactions.
Used in Cellular Calcium Signaling Studies:
In the field of cellular biology, 2,5-Di-tert-butylhydroquinone is used as a research tool to study endomembrane Ca2+ stores and plasma membrane Ca2+ permeability pathways. Its ability to specifically mobilize Ca2+ from Ins(1,4,5)P3-sensitive stores without affecting mitochondrial Ca2+ fluxes or plasma membrane Ca2+/Mg2+ ATPase activity makes it a valuable compound for investigating the complex mechanisms of cellular calcium signaling.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 88-58-4 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 8 respectively; the second part has 2 digits, 5 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 88-58:
(4*8)+(3*8)+(2*5)+(1*8)=74
74 % 10 = 4
So 88-58-4 is a valid CAS Registry Number.
InChI:InChI=1/C14H22O2/c1-13(2,3)9-7-12(16)10(8-11(9)15)14(4,5)6/h7-8,15-16H,1-6H3
88-58-4Relevant articles and documents
Preparation method of 2, 5-di-tert-butyl-p-dimethoxybenzene
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Paragraph 0033-0035; 0038-0040; 0043-0045; 0048-0050; 0053, (2021/06/02)
The invention discloses a preparation method of 2, 5-di-tert-butyl-p-dimethoxybenzene, which comprises the following steps: (1) reacting tert-butyl alcohol with hydroquinone in a first solvent under the action of a first catalyst, cooling and crystallizing after the reaction is finished, filtering, washing and drying to obtain 2,5-di-tert-butyl hydroquinone; and (2) reacting the 2, 5-di-tert-butyl hydroquinone obtained in the step (1) with methyl iodide in a second solvent under the action of a second catalyst, cooling to room temperature after the reaction is finished, adding brine and an organic solvent into the reaction liquid for extraction, washing the obtained organic layer, and performing vacuum drying to obtain the 2, 5-di-tert-butyl-p-dimethoxybenzene product. The method has the advantages of simple process, mild reaction conditions, environmental protection, low cost and high yield.
1-Methyl-1,4-cyclohexadiene as a Traceless Reducing Agent for the Synthesis of Catechols and Hydroquinones
Baschieri, Andrea,Amorati, Riccardo,Valgimigli, Luca,Sambri, Letizia
, p. 13655 - 13664 (2019/10/28)
Pro-aromatic and volatile 1-methyl-1,4-cyclohexadiene (MeCHD) was used for the first time as a valid H-atom source in an innovative method to reduce ortho or para quinones to obtain the corresponding catechols and hydroquinones in good to excellent yields. Notably, the excess of MeCHD and the toluene formed as the oxidation product can be easily removed by evaporation. In some cases, trifluoroacetic acid as a catalyst was added to obtain the desired products. The reaction proceeds in air and under mild conditions, without metal catalysts and sulfur derivatives, resulting in an excellent and competitive method to reduce quinones. The mechanism is attributed to a radical reaction triggered by a hydrogen atom transfer from MeCHD to quinones, or, in the presence of trifluoroacetic acid, to a hydride transfer process.
Diels-Alder trapping of in situ generated dienes from 3,4-dihydro-2H-pyran with p-quinone catalysed by p-toluenesulfonic acid
Mohan Raj, Radhakrishnan,Balasubramanian, Kalpattu K.,Easwaramoorthy, Deivanayagam
, p. 1115 - 1121 (2017/02/10)
This comprehensive study portrays that p-toluenesulfonic acid is a more efficient catalyst for the reaction between p-quinones and 3,4-dihydro-2H-pyran, than the Lewis acids. The products were accomplished by the Diels-Alder cycloaddition reaction and their mechanistic pathways have been formulated. The impact of C2 and C2,5 substituents of the p-quinones on the cycloaddition reaction has been explored. Remarkably, it is the first report to explore this kind of in situ generated diene for the Diels-Alder cycloaddition reaction.