dtBHQ | CAS# 88-58-4 | Oxidizable Phenol

MedKoo Cat#: 564717 | Name: dtBHQ

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

dtBHQ is a non-arylating oxidizable phenol as the source of reactive oxygen species (ROS).

Chemical Structure

dtBHQ

CAS#88-58-4

Theoretical Analysis

MedKoo Cat#: 564717

Name: dtBHQ

CAS#: 88-58-4

Chemical Formula: C14H22O2

Exact Mass: 222.1620

Molecular Weight: 222.33

Elemental Analysis: C, 75.63; H, 9.97; O, 14.39

Price and Availability

Size	Price	Availability	Quantity
5g	USD 250.00	2 weeks
25g	USD 450.00	2 weeks

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Synonym

2,5-Di-tert-butylhydroquinone; dt-BHQ; dt BHQ; dtBHQ

IUPAC/Chemical Name

2,5-Di-tert-butylhydroquinone

InChi Key

JZODKRWQWUWGCD-UHFFFAOYSA-N

InChi Code

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

SMILES Code

OC1=CC(C(C)(C)C)=C(O)C=C1C(C)(C)C

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

2,5-Di-tert-butylhydroquinone (DTBHQ), the indirect food additive, regulates the activity of 5-lipoxygenase as well as the activity of COX-2 (IC50=1.8 and 14.1 μM for 5-LO and COX-2, respectively) .

In vitro activity:

Similarly no activity against COX-1 and -2 was observed for its metabolite TBQ at a concetration of 50 µM. In contrast, DTBHQ inhibited COX-2 with an IC50 of 14.1 µM. Reference: Food and Agricultural Immunology. 2014 Jun 16;504-511. https://pubmed.ncbi.nlm.nih.gov/10672316/

In vivo activity:

Synaptic vesicle membranes in the DTBHQ group were weakly labeled at 1 week, but strongly at 6 weeks. The results strongly suggest that DTBHQ targets the motor endplates in the rat lumbrical muscles, causing depletion of neurocalcin in the synaptic vesicles followed by their loss. Reference: Acta Neuropathol. 2000 Feb;99(2):109-16. https://pubmed.ncbi.nlm.nih.gov/10672316/

	Solvent	mg/mL	mM
Solubility
	Ethanol	40.0	179.91

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 222.33 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Kutil Z, Kvasnicova M, Temml V, Schuster D, Vanek T, Fernandez E, Malik J, Landa P. The influence of the quinone antioxidants tert-butylhydroquinone and 2,5-di-tert-butylhydroquinone on the arachidonic acid metabolism in vitro. Food and Agricultural Immunology. 2014 Jun 16;504-511. doi: 10.1080/09540105.2014.988126. 2. Bauman BM, Jeong C, Savage M, Briker AL, Janigian NG, Nguyen LL, Kemmerer ZA, Eggler AL. Dr. Jekyll and Mr. Hyde: Oxidizable phenol-generated reactive oxygen species enhance sulforaphane's antioxidant response element activation, even as they suppress Nrf2 protein accumulation. Free Radic Biol Med. 2018 Aug 20;124:532-540. doi: 10.1016/j.freeradbiomed.2018.06.039. Epub 2018 Jun 30. PMID: 29969714. 3. Imazawa T, Mitsumori K, Kitajima S, Onodera H, Tamura T, Takahashi M, Hirose M. Time course of ultrastructural changes and immunoelectron microscopic localization of neurocalcin in motor endplates of the lumbrical muscles of rats given a single administration of 2,5-di(tert-butyl)-1,4-hydroquinone. Acta Neuropathol. 2000 Feb;99(2):109-16. doi: 10.1007/pl00007413. PMID: 10672316. 4. Mitsumori K, Imazawa T, Onodera H, Takahashi M, Kitajima S, Inoue T, Kurokawa Y. Ultrastructural changes in motor endplates of the lumbrical muscles of rats induced by a microsomal Ca2+ ATPase inhibitor, 2,5-di(tert-butyl)-1,4-hydroquinone. Arch Toxicol. 1998;72(2):115-8. doi: 10.1007/s002040050477. PMID: 9456084.

In vitro protocol:

In vivo protocol:

1. Imazawa T, Mitsumori K, Kitajima S, Onodera H, Tamura T, Takahashi M, Hirose M. Time course of ultrastructural changes and immunoelectron microscopic localization of neurocalcin in motor endplates of the lumbrical muscles of rats given a single administration of 2,5-di(tert-butyl)-1,4-hydroquinone. Acta Neuropathol. 2000 Feb;99(2):109-16. doi: 10.1007/pl00007413. PMID: 10672316. 2. Mitsumori K, Imazawa T, Onodera H, Takahashi M, Kitajima S, Inoue T, Kurokawa Y. Ultrastructural changes in motor endplates of the lumbrical muscles of rats induced by a microsomal Ca2+ ATPase inhibitor, 2,5-di(tert-butyl)-1,4-hydroquinone. Arch Toxicol. 1998;72(2):115-8. doi: 10.1007/s002040050477. PMID: 9456084.

1: Bauman BM, Jeong C, Savage M, Briker AL, Janigian NG, Nguyen LL, Kemmerer ZA, Eggler AL. Dr. Jekyll and Mr. Hyde: Oxidizable phenol-generated reactive oxygen species enhance sulforaphane's antioxidant response element activation, even as they suppress Nrf2 protein accumulation. Free Radic Biol Med. 2018 Aug 20;124:532-540. doi: 10.1016/j.freeradbiomed.2018.06.039. Epub 2018 Jun 30. PubMed PMID: 29969714.