Ethoxyquin

Ethoxyquin Basic information
Product Name:Ethoxyquin
Synonyms:1,2-dihydro-2,2,4-trimethyl-6-ethoxyquinoline;2,2,4-trimethyl-6-ethoxy-1,2-dihydroquinoline;6-ethoxy-1,2-dihydro-2,2,4-trimethyl-quinolin;6-Ethoxyl-2,2,4-trimethyl-1,2-dihydrquinoline;amea100;antageaw;AntioxidantAW;antioxidantec
CAS:91-53-2
MF:C14H19NO
MW:217.31
EINECS:202-075-7
Product Categories:C11 to C30;Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks;Quinolines;Amines;Aromatics;Heterocycles;Antioxidant;Biochemistry;Industrial/Fine Chemicals;INORGANIC & ORGANIC CHEMICALS;91-53-2
Mol File:91-53-2.mol
Ethoxyquin Structure
Ethoxyquin Chemical Properties
Melting point <0°C
Boiling point 123-125°C
density 1.03 g/mL at 20 °C (lit.)
vapor pressure 0.035Pa at 25℃
refractive index 1.569~1.571
Fp 137 °C
storage temp. 2-8°C
solubility ethanol: 50 mL/L, clear, brown
pka5.02±0.70(Predicted)
form neat
color Yellow to Very Dark Brown
Water Solubility <0.1 g/100 mL at 20 ºC
Merck 14,3753
BRN 158223
Stability:Stable. Combustible. Incompatible with oxidizing agents, strong acids. Polymerizes if heated. May polymerize upon exposure to light and air.
InChIKeyDECIPOUIJURFOJ-UHFFFAOYSA-N
LogP3.39
CAS DataBase Reference91-53-2(CAS DataBase Reference)
NIST Chemistry ReferenceQuinoline, 6-ethoxy-1,2-dihydro-2,2,4-trimethyl-(91-53-2)
EPA Substance Registry SystemEthoxyquin (91-53-2)
Safety Information
Hazard Codes Xn
Risk Statements 22
Safety Statements 24
RIDADR 3082
WGK Germany 1
RTECS VB8225000
2-8-10
HazardClass 9
PackingGroup III
HS Code 29334900
Hazardous Substances Data91-53-2(Hazardous Substances Data)
ToxicityLD50 orally in rats, mice: 1920, 1730 mg/kg (Piul'skaya)
MSDS Information
Ethoxyquin Usage And Synthesis
DescriptionEthoxyquin is used as an antioxidant in animal feed and caused contact dermatitis in a worker at an animal feed mill.
Chemical PropertiesTransparent yellow or brown viscous liquid. Discolors and stains badly. Soluble in benzene, gasoline, ether, ethanol, carbon tetrachloride, acetone, dichloroethane, insoluble in water.
UsesAntioxidant in feed and food; antidegradation agent for rubber.
UsesEthoxyquin is an antioxidant used in the preservation of color in chili powder, ground chili, and paprika.
DefinitionChEBI: Ethoxyquin is a quinoline that is 1,2-dihydroquinoline bearing three methyl substituents at position 2, 2 and 4 as well as an ethoxy substituent at position 6. It has a role as a herbicide, an UDP-glucuronosyltransferase activator, a neuroprotective agent, a Hsp90 inhibitor, a genotoxin, a food antioxidant, a geroprotector and an antifungal agrochemical. It is a member of quinolines and an aromatic ether.
General DescriptionClear light yellow to dark brown viscous liquid. Discolors and stains badly. Mercaptan-like odor.
Air & Water ReactionsPolymerizes and darkens in color on exposure to light and air. Insoluble in water.
Reactivity ProfileEthoxyquin may undergo a hazardous polymerization at temperatures above 320° F. Tends to polymerize and darken in color on exposure to light and air. Not compatible with oxidizing agents and with strong acids .
HazardToxic by ingestion.
Fire HazardEthoxyquin is combustible.
Agricultural UsesInsecticide, Fungicide, Plant growth regulator, Ingredient in other products: Used for preharvest or postharvest preservation of color in apples and pears. It is used as an antioxidant to preserve color in paprika and ground and powdered chili. Ethoxyquin is also a chemical preservative used in animal feed to prevent ingredients from reacting with oxygen and becoming rancid. It has been known to cause birth defects in pet birds and dogs. Not approved for use in EU countries[ 115]. Registered for use in the U.S.
Trade nameCHEMLEY®[C]; DECCOQUIN 305®; EMQ®; EQ®; NIFLEX®; NIX-SCALD®[C]; SANTOFLEX A®; SANTOFLEX AW®; SANTOQUIN®; SANTOQUINE®; STOP-SCALD®
Contact allergensEthoxyquin is used as an antioxidant in animal feed and caused contact dermatitis in a worker at an animal feed mill
Safety ProfilePoison by intraperitoneal route. Moderately toxic by ingestion. Mutation data reported. Combustible when exposed to heat or flame; can react with oxidizing materials. When heated to decomposition it emits toxic fumes of NOx.
Potential ExposureQuinoline insecticide, fungicide and plant growth regulator. Also and ingredient in other products. Used for preharvest or postharvest preservation of color in apples and pears. It is used as an anti-oxidant to preserve color in paprika and ground and powdered chili. Ethoxyquin also is a chemical preservative used in animal feed to prevent ingredients from reacting with oxygen and becoming rancid. It has been known to cause birth defects in pet birds and dogs
ShippingUN3082 Environmentally hazardous substances, liquid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required
Purification MethodsPurify Ethoxyquin by fractional distillation in vacuo whereby the distillate solidifies to a glass. [Knoevenagel Chem Ber 54 1723, 1730 1921.] The methiodide has m 179o (from EtOH), and the 1-phenylcarbamoyl derivative has m 146-147o (from EtOH). [Beaver et al. J Am Chem Soc 79 1236 1957, Beilstein 21 III/IV 95.]
IncompatibilitiesPolymerization can occur on contact with strong light and/or water. Decomposes in temperatures above 150℃. Keep away from oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); strong acids.
Waste DisposalDo not discharge into drains or sewers. Dispose of waste material as hazardous waste using a licensed disposal contractor to an approved landfill. Consult with environmental regulatory agencies for guidance on acceptable disposal practices. If allowed, Incineration with effluent gas scrubbing is recommended. Containers must be disposed of properly by following package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office
Ethoxyquin Preparation Products And Raw materials
Raw materialsAcetone-->PARA TOLUENE-->Benzenesulfonic acid-->Phenetidine
Preparation ProductsMesityl oxide-->2,2,4-TRIMETHYL-1,2-DIHYDRO-QUINOLIN-6-OL
N-[(1Z)-8-ETHOXY-4,4-DIMETHYL-4,5-DIHYDRO-1H-[1,2]DITHIOLO[3,4-C]QUINOLIN-1-YLIDENE]-N-PHENYLAMINE AKOS BBS-00005649 5-[(2-CHLOROPHENOXY)ACETYL]-8-ETHOXY-4,4-DIMETHYL-4,5-DIHYDRO-1H-[1,2]DITHIOLO[3,4-C]QUINOLINE-1-THIONE 8-ETHOXYQUINOLINE-5-SULFONIC ACID SODIUM SALT HEMIHYDRATE AKOS BBS-00005643 AKOS BBS-00005645 AKOS BBS-00005379 Ethoxyguin Ethoxyquin TOSLAB 501211 Quinaldine AKOS BBS-00005641 AKOS BBS-00005642 (8-ETHOXY-4,4-DIMETHYL-1-THIOXO-1H-[1,2]DITHIOLO[3,4-C]QUINOLIN-5(4H)-YL)(NAPHTHALEN-1-YL)METHANONE AKOS BBS-00005644 acetic acid, triethoxy-, ethyl ester AKOS BBS-00005656 6-ETHOXY-2,2,4-TRIMETHYL-1,2-DIHYDROQUINOLINE HYDROCHLORIDE

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