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

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

MedKoo CAT#: 564717

CAS#: 88-58-4

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

Chemical Structure

dtBHQ

CAS# 88-58-4

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 564717
Name: dtBHQ
CAS#: 88-58-4
Chemical Formula: C14H22O2
Exact Mass: 222.16
Molecular Weight: 222.328
Elemental Analysis: C, 75.63; H, 9.97; O, 14.39

Price and Availability

Size	Price	Availability	Quantity
25g	USD 350	2 weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

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:

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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/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	Ethanol	40.0	179.91

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:	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.
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.

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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.

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