Ethoxyquin | CAS#91-53-2 | HSP90 inhibitor | antioxidant

MedKoo Cat#: 540127 | Name: Ethoxyquin

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Description:

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

Ethoxyquin is an HSP90 inhibitor and antioxidant used as a pesticide and preservative in animal feed.

Chemical Structure

Ethoxyquin

CAS#91-53-2

Theoretical Analysis

MedKoo Cat#: 540127

Name: Ethoxyquin

CAS#: 91-53-2

Chemical Formula: C14H19NO

Exact Mass: 217.1467

Molecular Weight: 217.31

Elemental Analysis: C, 77.38; H, 8.81; N, 6.45; O, 7.36

Price and Availability

Size	Price	Availability	Quantity
1g	USD 250.00	2 Weeks
5g	USD 450.00	2 Weeks

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Related CAS #

91-53-2 74681-77-9 (dimer)

Synonym

Ethoxyquin; Ethoxyquine; Santoquin; NSC-6795; NSC6795; NSC 6795;

IUPAC/Chemical Name

6-ethoxy-2,2,4-trimethyl-1,2-dihydroquinoline

InChi Key

DECIPOUIJURFOJ-UHFFFAOYSA-N

InChi Code

InChI=1S/C14H19NO/c1-5-16-11-6-7-13-12(8-11)10(2)9-14(3,4)15-13/h6-9,15H,5H2,1-4H3

SMILES Code

CC1=CC(C)(C)NC2=C1C=C(OCC)C=C2

Appearance

Liquid or Viscous Liquid

Purity

>90% (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

>2 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:

Ethoxyquin is an antioxidant which has been used in animal feed for many years and also an inhibitor of heat shock protein 90 (Hsp90).

In vitro activity:

This study validated the screening results with ethoxyquin and its derivatives and showed that they prevented paclitaxel-induced peripheral neuropathy without blocking paclitaxel's ability to kill tumor cells. Furthermore, this study demonstrated that ethoxyquin acts by modulating the chaperone activity of heat shock protein 90 (Hsp90) and blocking the binding of 2 of its client proteins, ataxin-2 and Sf3b2. Ethoxyquin-induced reduction in levels of both of these proteins resulted in prevention of axonal degeneration caused by paclitaxel. Reference: Ann Neurol. 2013 Dec;74(6):893-904. https://pubmed.ncbi.nlm.nih.gov/23955554/

In vivo activity:

Following 7 weeks of treatment, small unmyelinated fibers density was assessed in sweat glands (SGNFD) and epidermis (IENFD). db/+-vehicle control group IENFD was 61.96 ± 3.1 fibers/mm while vehicle-treated db/db mice had reduced IENFD at 24.85 ± 2.3 fiber/mm. This distal axon loss was partially prevented in EQ-treated db/db mice, which had an IENFD of 46.74 ± 3.0 fiber/mm. A similar pattern of neuroprotection was observed in SGNFD. In db/+ vehicle treated control mice, SGNFD was 27.1 ± 1.7 m/mm3 but it was reduced to 7.36 ± 1.46 m/mm3 in db/db-vehicle treated mice. In EQ treated db/db-EQ mice, the SGNFD was partially rescued to 12.64 ± 1.6 m/mm3. These findings suggest that in db/db mice, there is both somatic and autonomic denervation of distal targets and that this is partially ameliorated with EQ treatment (Fig 2). Reference: Sci Rep. 2021; 11: 10749. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8144207/

	Solvent	mg/mL	mM
Solubility
	DMSO	40.0	184.07
	DMF	30.0	138.05
	Ethanol	30.0	138.05
	Ethanol:PBS (pH 7.2) (1:3)	0.3	1.15

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 217.31 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. Zhu J, Carozzi VA, Reed N, Mi R, Marmiroli P, Cavaletti G, Hoke A. Ethoxyquin provides neuroprotection against cisplatin-induced neurotoxicity. Sci Rep. 2016 Jun 28;6:28861. doi: 10.1038/srep28861. PMID: 27350330; PMCID: PMC4924091. 2. Zhu J, Chen W, Mi R, Zhou C, Reed N, Höke A. Ethoxyquin prevents chemotherapy-induced neurotoxicity via Hsp90 modulation. Ann Neurol. 2013 Dec;74(6):893-904. doi: 10.1002/ana.24004. PMID: 23955554. 3. Liu Y, Sun Y, Ewaleifoh O, Wei J, Mi R, Zhu J, Hoke A, Polydefkis M. Ethoxyquin is neuroprotective and partially prevents somatic and autonomic neuropathy in db/db mouse model of type 2 diabetes. Sci Rep. 2021 May 24;11(1):10749. doi: 10.1038/s41598-021-89781-5. PMID: 34031437; PMCID: PMC8144207. 4. Zhu J, Carozzi VA, Reed N, Mi R, Marmiroli P, Cavaletti G, Hoke A. Ethoxyquin provides neuroprotection against cisplatin-induced neurotoxicity. Sci Rep. 2016 Jun 28;6:28861. doi: 10.1038/srep28861. PMID: 27350330; PMCID: PMC4924091.

In vitro protocol:

In vivo protocol:

1. Liu Y, Sun Y, Ewaleifoh O, Wei J, Mi R, Zhu J, Hoke A, Polydefkis M. Ethoxyquin is neuroprotective and partially prevents somatic and autonomic neuropathy in db/db mouse model of type 2 diabetes. Sci Rep. 2021 May 24;11(1):10749. doi: 10.1038/s41598-021-89781-5. PMID: 34031437; PMCID: PMC8144207. 2. Zhu J, Carozzi VA, Reed N, Mi R, Marmiroli P, Cavaletti G, Hoke A. Ethoxyquin provides neuroprotection against cisplatin-induced neurotoxicity. Sci Rep. 2016 Jun 28;6:28861. doi: 10.1038/srep28861. PMID: 27350330; PMCID: PMC4924091.

1: Zhu J, Carozzi VA, Reed N, Mi R, Marmiroli P, Cavaletti G, Hoke A. Ethoxyquin provides neuroprotection against cisplatin-induced neurotoxicity. Sci Rep. 2016 Jun 28;6:28861. doi: 10.1038/srep28861. PubMed PMID: 27350330; PubMed Central PMCID: PMC4924091. 2: Zhu J, Chen W, Mi R, Zhou C, Reed N, Höke A. Ethoxyquin prevents chemotherapy-induced neurotoxicity via Hsp90 modulation. Ann Neurol. 2013 Dec;74(6):893-904. doi: 10.1002/ana.24004. PubMed PMID: 23955554. 3: Papadopoulou ES, Tsachidou B, Sułowicz S, Menkissoglu-Spiroudi U, Karpouzas DG. Land Spreading of Wastewaters from the Fruit-Packaging Industry and Potential Effects on Soil Microbes: Effects of the Antioxidant Ethoxyquin and Its Metabolites on Ammonia Oxidizers. Appl Environ Microbiol. 2015 Nov 20;82(2):747-55. doi: 10.1128/AEM.03437-15. PubMed PMID: 26590271; PubMed Central PMCID: PMC4711131. 4: Błaszczyk A, Augustyniak A, Skolimowski J. Ethoxyquin: An Antioxidant Used in Animal Feed. Int J Food Sci. 2013;2013:585931. doi: 10.1155/2013/585931. Epub 2013 Apr 30. Review. PubMed PMID: 26904606; PubMed Central PMCID: PMC4745505. 5: Ørnsrud R, Arukwe A, Bohne V, Pavlikova N, Lundebye AK. Investigations on the metabolism and potentially adverse effects of ethoxyquin dimer, a major metabolite of the synthetic antioxidant ethoxyquin in salmon muscle. J Food Prot. 2011 Sep;74(9):1574-80. doi: 10.4315/0362-028X.JFP-10-547. PubMed PMID: 21902931. 6: Aoki Y, Kotani A, Miyazawa N, Uchida K, Igarashi Y, Hirayama N, Hakamata H, Kusu F. Determination of ethoxyquin by high-performance liquid chromatography with fluorescence detection and its application to the survey of residues in food products of animal origin. J AOAC Int. 2010 Jan-Feb;93(1):277-83. PubMed PMID: 20334189. 7: Skolimowski JJ, Cieślińska B, Zak M, Osiecka R, Błaszczyk A. Modulation of ethoxyquin genotoxicity by free radical scavengers and DNA damage repair in human lymphocytes. Toxicol Lett. 2010 Mar 15;193(2):194-9. doi: 10.1016/j.toxlet.2010.01.006. Epub 2010 Jan 20. PubMed PMID: 20093172. 8: Błaszczyk A, Skolimowski J. Apoptosis and cytotoxicity caused by ethoxyquin and two of its salts. Cell Mol Biol Lett. 2005;10(1):15-21. PubMed PMID: 15809676. 9: Lauridsen C, Jakobsen K, Hansen TK. The influence of dietary ethoxyquin on the vitamin E status in broilers. Arch Tierernahr. 1995;47(3):245-54. PubMed PMID: 7668984. 10: Masui T, Tsuda H, Inoue K, Ogiso T, Ito N. Inhibitory effects of ethoxyquin, 4,4'-diaminodiphenylmethane and acetaminophen on rat hepatocarcinogenesis. Jpn J Cancer Res. 1986 Mar;77(3):231-7. PubMed PMID: 3084413. 11: Błaszczyk A, Skolimowski J, Materac A. Genotoxic and antioxidant activities of ethoxyquin salts evaluated by the comet assay. Chem Biol Interact. 2006 Sep 25;162(3):268-73. Epub 2006 Jul 31. PubMed PMID: 16959229. 12: Burka LT, Sanders JM, Matthews HB. Comparative metabolism and disposition of ethoxyquin in rat and mouse. II. Metabolism. Xenobiotica. 1996 Jun;26(6):597-611. PubMed PMID: 8810031. 13: Henson KL, Stauffer G, Gallagher EP. Induction of glutathione S-transferase activity and protein expression in brown bullhead (Ameiurus nebulosus) liver by ethoxyquin. Toxicol Sci. 2001 Jul;62(1):54-60. PubMed PMID: 11399793. 14: Lundebye AK, Hove H, Måge A, Bohne VJ, Hamre K. Levels of synthetic antioxidants (ethoxyquin, butylated hydroxytoluene and butylated hydroxyanisole) in fish feed and commercially farmed fish. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2010 Dec;27(12):1652-7. doi: 10.1080/19440049.2010.508195. PubMed PMID: 20931417. 15: Shah AG, Pierson JA, Pavlostathis SG. Fate and effect of the antioxidant ethoxyquin on a mixed methanogenic culture. Water Res. 2005 Oct;39(17):4251-63. Epub 2005 Sep 30. PubMed PMID: 16199076. 16: Kumar S, Engman L, Valgimigli L, Amorati R, Fumo MG, Pedulli GF. Antioxidant profile of ethoxyquin and some of its S, Se, and Te analogues. J Org Chem. 2007 Aug 3;72(16):6046-55. Epub 2007 Jun 29. PubMed PMID: 17602530. 17: Hard GC, Neal GE. Sequential study of the chronic nephrotoxicity induced by dietary administration of ethoxyquin in Fischer 344 rats. Fundam Appl Toxicol. 1992 Feb;18(2):278-87. PubMed PMID: 1601228. 18: Skaare JU. Studies of the biliary excretion and metabolites of the antioxidant ethoxyquin, 6-ethoxy-2,2,4-trimethyl-1,2-dihydroquinoline in the rat. Xenobiotica. 1979 Nov;9(11):659-68. PubMed PMID: 532215. 19: Cabel MC, Waldroup PW, Shermer WD, Calabotta DF. Effects of ethoxyquin feed preservative and peroxide level on broiler performance. Poult Sci. 1988 Dec;67(12):1725-30. PubMed PMID: 3241778. 20: Perfetti GA, Joe FL Jr, Fazio T. Reverse phase high pressure liquid chromatography and fluorescence detection of ethoxyquin in milk. J Assoc Off Anal Chem. 1983 Sep;66(5):1143-7. PubMed PMID: 6630128.