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| | 2,5-Di-tert-butylhydroquinone Basic information |
| | 2,5-Di-tert-butylhydroquinone Chemical Properties |
| Melting point | 216-218 °C(lit.) | | Boiling point | 321°C | | density | 1,07 g/cm3 | | refractive index | 1.4576 (estimate) | | Fp | 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. | | Cosmetics Ingredients Functions | ANTIOXIDANT | | Cosmetic Ingredient Review (CIR) | 2,5-Di-tert-butylhydroquinone (88-58-4) | | InChI | 1S/C14H22O2/c1-13(2,3)9-7-12(16)10(8-11(9)15)14(4,5)6/h7-8,15-16H,1-6H3 | | InChIKey | JZODKRWQWUWGCD-UHFFFAOYSA-N | | SMILES | CC(C)(C)c1cc(O)c(cc1O)C(C)(C)C | | LogP | 274 at 30℃ | | 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) |
| Hazard Codes | Xi,Xn | | Risk Statements | 36/37/38-22 | | Safety Statements | 26-24/25 | | WGK Germany | 3 | | RTECS | MX5160000 | | Autoignition Temperature | 790 °F | | Hazard Note | Irritant | | TSCA | TSCA listed | | HS Code | 29072900 | | Storage Class | 6.1D - Non-combustible acute toxic Cat.3
toxic hazardous materials or hazardous materials causing chronic effects | | Hazard Classifications | Acute Tox. 3 Oral
Aquatic Acute 1
Aquatic Chronic 1
Skin Sens. 1
STOT SE 3 |
| | 2,5-Di-tert-butylhydroquinone Usage And Synthesis |
| 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. |
| | 2,5-Di-tert-butylhydroquinone Preparation Products And Raw materials |
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