Ethoxyquin

Modify Date: 2024-01-02 20:38:15

Ethoxyquin Structure
Ethoxyquin structure
 Common Name Ethoxyquin
CAS Number 91-53-2 Molecular Weight 217.307
Density 1.0±0.1 g/cm3 Boiling Point 333.1±42.0 °C at 760 mmHg
Molecular Formula C14H19NO Melting Point <0ºC
MSDS Chinese USA Flash Point 137.8±17.3 °C
Symbol GHS07
GHS07		 Signal Word Warning

 Use of Ethoxyquin


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

 Names

Name Ethoxyquin
Synonym More Synonyms

 Ethoxyquin Biological Activity

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

HSP90

In Vitro Ethoxyquin (EQ) does not block Paclitaxel’s (PTX’s) ability to induce cell death in 4 different breast cancer cell lines. Results demonstrate that only when Hsp90 level is down regulated is neuroprotec-tion provided by Ethoxyquin (EQ) no longer seen[2]. It is found that Ethoxyquin provides neuroprotection with a best efficacy range from 30 to 300 nM. It is interesting to note that higher (μM) concentrations of Ethoxyquin do not provide further neuroprotection and in fact at these higher concentrations Ethoxyquin loses its neuroprotective effects[3].
In Vivo Ethoxyquin (EQ) provides a dose-dependent neuroprotection. Although all 3 doses of Ethoxyquin provide partial neuroprotection against reduction in intraepidermal nerve fiber density, the peak efficacy is with the 75 μg/kg dose[2]. Rats treated with Ethoxyquin (EQ) alone or control vehicle treated rats gain weight as expected under normal physiological conditions[3].
Kinase Assay To evaluate the impact of Ethoxyquin (EQ) on Paclitaxel’s (PTX’s) ability to kill breast cancer cells, conditions for culturing 4 cancer cell lines and measuring the ATP levels are optimized for the 96-well plate format. Briefly, 1,500 cells/well in media are plated in 96-well plates for 24 hours. Constant concentrations of PTX with or without Ethoxyquin are added to the wells for another 24 hours. Cellular ATP levels are measured using kit according tomanufacturer ’s protocol[2].
Cell Assay Briefly, DRGs are harvested from embryonic day 14.5 rats according to standard protocols, then cells are plated onto collagen-coated glass coverslips and allowed to extend neurites for 24 hours in media (Neurobasal medium, 50 mM pencillin-streptomycin (PS), 0.2% FBS, 0.5 mM glutamine, 1×B-27 supplement, 0.2% glucose,10 ng/mL glial cell line-derived neurotrophic factor). Ethoxyquin (EQ) or vehicle control is added to the wells for another 24-hour incubation. DRG cells are fixed with 4% paraformaldehyde and stained with anti-βIII-tubulin antibody to delineate the axons. Axon lengths are measured in multiple fields using a random sampling method[2].
Animal Admin To examine the effect of Ethoxyquin (EQ) on Paclitaxel’s (PTX’s) ability to reduce tumor burden in vivo, a mouse model in which breast cancer cell line SUM-159 (3×106 tumor cells suspended in phosphate-buffered saline in a final volume of 0.15 mL) is injected subcutaneously into adult male nude mice. When the tumor size reaches 5 mm in diameter, the animals are randomly assigned to PTX or PTX with Ethoxyquin groups. Ethoxyquin is given by intraperitoneal administration on a daily basis for 3 weeks. At the end of 3 weeks, animals are euthanized and tumor size and weight are measured (n=5 per group)[2].
References

[1]. Sadikot T, et al. Development of a high-throughput screening cancer cell-based luciferase refolding assay for identifying Hsp90 inhibitors. Assay Drug Dev Technol. 2013 Oct;11(8):478-88.

[2]. Zhu J, et al. Ethoxyquin prevents chemotherapy-induced neurotoxicity via Hsp90 modulation. Ann Neurol. 2013 Dec;74(6):893-904.

[3]. Zhu J, et al. Ethoxyquin provides neuroprotection against cisplatin-induced neurotoxicity. Sci Rep. 2016 Jun 28;6:28861.

 Chemical & Physical Properties

Density 1.0±0.1 g/cm3
Boiling Point 333.1±42.0 °C at 760 mmHg
Melting Point <0ºC
Molecular Formula C14H19NO
Molecular Weight 217.307
Flash Point 137.8±17.3 °C
Exact Mass 217.146667
PSA 21.26000
LogP 3.93
Vapour Pressure 0.0±0.7 mmHg at 25°C
Index of Refraction 1.512
Stability Stable. Combustible. Incompatible with oxidizing agents, strong acids. Polymerizes if heated. May polymerize upon exposure to light and air.
Water Solubility ethanol: 50 mL/L, clear, brown | <0.1 g/100 mL at 20 ºC

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
VB8225000
CHEMICAL NAME :
Quinoline, 6-ethoxy-1,2-dihydro-2,2,4-trimethyl-
CAS REGISTRY NUMBER :
91-53-2
LAST UPDATED :
199710
DATA ITEMS CITED :
17
MOLECULAR FORMULA :
C14-H19-N-O
MOLECULAR WEIGHT :
217.34
WISWESSER LINE NOTATION :
T66 BM CHJ C1 C1 E1 HO2

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
800 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1730 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
200 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
178 mg/kg
TOXIC EFFECTS :
Behavioral - altered sleep time (including change in righting reflex) Behavioral - convulsions or effect on seizure threshold Behavioral - coma
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
14377 mg/kg/3W-C
TOXIC EFFECTS :
Blood - change in clotting factors
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
63 gm/kg/30W-I
TOXIC EFFECTS :
Kidney, Ureter, Bladder - changes in bladder weight Nutritional and Gross Metabolic - weight loss or decreased weight gain
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
122 gm/kg/58W-C
TOXIC EFFECTS :
Kidney, Ureter, Bladder - other changes
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
12 gm/kg/29W-C
TOXIC EFFECTS :
Liver - changes in liver weight Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis) Kidney, Ureter, Bladder - changes in bladder weight

MUTATION DATA

TEST SYSTEM :
Rodent - rat
DOSE/DURATION :
13 gm-kg/4W (Continuous)
REFERENCE :
TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 99,37,1989 *** U.S. STANDARDS AND REGULATIONS *** EPA FIFRA 1988 PESTICIDE SUBJECT TO REGISTRATION OR RE-REGISTRATION FEREAC Federal Register. (U.S. Government Printing Office, Supt. of Documents, Washington, DC 20402) V.1- 1936- Volume(issue)/page/year: 54,7740,1989 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 83809 No. of Facilities: 204 (estimated) No. of Industries: 3 No. of Occupations: 13 No. of Employees: 3572 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 83809 No. of Facilities: 876 (estimated) No. of Industries: 6 No. of Occupations: 14 No. of Employees: 7945 (estimated)

 Safety Information

Symbol GHS07
GHS07
Signal Word Warning
Hazard Statements H302
Precautionary Statements P301 + P312 + P330
Personal Protective Equipment Eyeshields;Faceshields;full-face respirator (US);Gloves;multi-purpose combination respirator cartridge (US);type ABEK (EN14387) respirator filter
Hazard Codes Xn:Harmful
Risk Phrases R22
Safety Phrases S24
RIDADR NONH for all modes of transport
WGK Germany 1
RTECS VB8225000
HS Code 2933499090

 Synthetic Route

2-Phenoxyethanamine structure

2-Phenoxyethanamine

CAS#:156-43-4

Acetone structure

Acetone

CAS#:67-64-1

~48%

Ethoxyquin Structure

Ethoxyquin

CAS#:91-53-2

Literature: Fotie, Jean; Rhodus, Jessica L.; Taha, Hashem A.; Reid, Carolyn S. Heteroatom Chemistry, 2012 , vol. 23, # 6 p. 598 - 604
4-Hydroxy-4-methyl-2-pentanone structure

4-Hydroxy-4-met...

CAS#:123-42-2

2-Phenoxyethanamine structure

2-Phenoxyethanamine

CAS#:156-43-4

~%

Mesityl oxide structure

Mesityl oxide

CAS#:141-79-7

Ethoxyquin Structure

Ethoxyquin

CAS#:91-53-2

Literature: Mutation Research - Genetic Toxicology and Environmental Mutagenesis, , vol. 542, # 1-2 p. 117 - 128

 Customs

HS Code 2933499090
Summary 2933499090. other compounds containing in the structure a quinoline or isoquinoline ring-system (whether or not hydrogenated), not further fused. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

 Articles27

More Articles
Modulation of ethoxyquin genotoxicity by free radical scavengers and DNA damage repair in human lymphocytes.

Toxicol. Lett. 193(2) , 194-9, (2010)

N-tert-butyl-alpha-phenylnitrone (PBN) and its new derivative N-(Pyridine-4-ylmethylidene)-2-carboxy-tert-butylamine N-oxide (PBNC) were synthesized and used to modulate ethoxyquin (1,2-dihydro-6-etho...

Effects of a dietary antioxidant blend and vitamin E on fatty acid profile, liver function, and inflammatory response in broiler chickens fed a diet high in oxidants.

Poult. Sci. 93(7) , 1658-66, (2014)

The aim of the current study was to determine the effects of a dietary antioxidant blend and vitamin E on fatty acid profile, inflammatory response, and liver function. Cobb 500 male broilers (n = 1,2...

Effects of a dietary antioxidant blend and vitamin E on growth performance, oxidative status, and meat quality in broiler chickens fed a diet high in oxidants.

Poult. Sci. 93(7) , 1649-57, (2014)

The aim of the study was to determine the effects of a dietary antioxidant blend (AB) and vitamin E on performance, oxidative status, and meat quality. Cobb 500 male broilers (n = 1,200, d 0) were ran...

 Synonyms

6-Ethoxy-2,2,4-trimethyl-1,2-dihydroquinoline
Quinoline, 6-ethoxy-1,2-dihydro-2,2,4-trimethyl-
EINECS 202-075-7
6-Ethoxy-1,2-dihydro-2,2,4-trimethylquinoline
emq
quinoled
1,2-dihydro-2,2,4-trimethylquinolin-6-yl ethyl ether
UNII-9T1410R4OR
2,2,4-trimethyl-6-ethoxy-1,2-dihydroquinoline
nocracaw
amea100
Santoquin
usafb-24
antageaw
niflex
ETMDQ
1,2-dihydro-6-ethoxy-2,2,4-trimethylQUINOLINE
Santoflex
niflexd
MFCD00023883
Ethoxyquin
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Chemsrc provides Ethoxyquin(CAS#:91-53-2) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of Ethoxyquin are included as well.>> amp version: Ethoxyquin

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