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Ethoxyquin ( CASNO:91-53-2 )

Identification and Related Records
Name:
Ethoxyquin
CAS Registry number:
91-53-2
Synonyms:
6-Ethoxy-2,2,4-trimethylquinoline
6-Ethoxy-1,2-dihydro-2,2,4-trimethylquinoline
Anti-oxidizing quinoline
1,2-dihydro-2,2,4-trimethyl-6-ethoxyquinoline
2,2,4-trimethyl-6-ethoxy-1,2-di hydroquinoline
6-ethoxy-1,2-dihydro-2,2,4-trimethyl-quinolin
6-Ethoxyl-2,2,4-trimethyl-1,2-dihydrquinoline
amea100
antageaw
AntioxidantAW
antioxidantec
Ethoxy Quinoline
EINECS(EC#):
202-075-7
Molecular Formula:
C14H19NO
Molecular Weight:
217.31
Inchi:
InChI=1/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
InChIKey:
DECIPOUIJURFOJ-UHFFFAOYSA-N
Canonical SMILES:
CCOC1=CC2=C(C=C1)NC(C=C2C)(C)C
Chemical and Physical Properties
Appearance:
yellow to red-brown liquid
Density:
1.03
Melting Point:
<0℃
Boiling Point:
123-125℃
Refractive Index:
1.569~1.571
Flash Point:
137 °C
Water:
Water Solubility:
Solubilities:
< 1 mg/ ml at 20 C
Color/Form:
YELLOW LIQUID
Stability:
Stable. Combustible. Incompatible with oxidizing agents, strong acids. Polymerizes if heated. May polymerize upon exposure to light and air.
Storage temp:
0-6°C
Spectral properties:
INDEX OF REFRACTION: 1.569-1.672 AT 25 DEG C/D
MAX ABSORPTION: 354 NM
Intense mass spectral peaks: 202 m/z (100%), 108 m/z (53%), 174 m/z (48%), 137 m/z (36%)
Computed Properties:
Molecular Weight:217.30676 [g/mol]
Molecular Formula:C14H19NO
XLogP3-AA:3.1
H-Bond Donor:1
H-Bond Acceptor:2
Rotatable Bond Count:2
Exact Mass:217.146664
MonoIsotopic Mass:217.146664
Topological Polar Surface Area:21.3
Heavy Atom Count:16
Formal Charge:0
Complexity:283
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:1
Feature 3D Donor Count:1
Feature 3D Cation Count:1
Feature 3D Hydrophobe Count:1
Feature 3D Ring Count:2
Effective Rotor Count:2.4
Conformer Sampling RMSD:0.6
CID Conformer Count:4
Safety and Handling
Hazard Codes:
Xn:Harmful
Risk Statements:
R22
Safety Statements:
S24
Skin, Eye, and Respiratory Irritations:
SKIN IRRITANT.
Transport:
200kgs
Fire Potential:
FIRE HAZARD /IS/ SLIGHT
Formulations/Preparations:
USEPA/OPP Pesticide Code 055501; Trade Names: Stop-scald.
Emulsifiable concentrate
Exposure Standards and Regulations:
Ethoxyquin is a food additive permitted for direct addition to food for human consumption, as long as 1) the quantity added to food does not exceed the amount reasonably required to accomplish its intended physical, nutritive, or other technical effect in food, and 2) when intended for use in or on food it is of appropriate food grade and is prepared and handled as a food ingredient.
Ethoxyquin in animal feeds may be safely used in accordance with conditions prescribed in 21 CFR Part 573.
Ethoxyquin in certain dehydrated forage crops may be safely used in accordance with conditions prescribed in 21 CFR Part 573.
Reactivities and Incompatibilities:
Can react with oxidizing materials.
Protective Equipment and Clothing:
SKIN IRRITANT.
Specification:
The Ethoxyquin with the cas number 91-53-2, is also called 6-ethoxy-2,2,4-trimethyl-1H-quinolinenamed by IUPAC. There are also other names such as (1)6-Ethoxy-2,2,4-trimethyl-1,2-dihydrochinolin ; (2)6-ethoxy-2,2,4-trimethyl-1,2-dihydroquinoline ; (3)quinoline, 6-ethoxy-1,2-dihydro-2,2,4-trimethyl- ; (4)Santoflex. It belongs to the following product categories: (1)Industrial/Fine Chemicals; (2)Inorganic & Organic Chemicals; (3)Antioxidant; (4)Biochemistry; (5)Amines; (6)Aromatics; (7)Heterocycles. Besides, it is stable, but combustible and incompatible with oxidizing agents, strong acids. And it will polymerizes if heated or may polymerize upon exposure to light and air. Physical properties about this chemical are: (1)ACD/LogP: 3.93 ; (2)# of Rule of 5 Violations: 0 ; (3)ACD/LogD (pH 5.5): 3.57 ; (4)ACD/LogD (pH 7.4): 3.92 ; (5)ACD/BCF (pH 5.5): 247.56 ; (6)ACD/BCF (pH 7.4): 559.1 ; (7)ACD/KOC (pH 5.5): 1420.5 ; (8)ACD/KOC (pH 7.4): 3208.1 ; (9)#H bond acceptors: 2 ; (10)#H bond donors: 1 ; (11)#Freely Rotating Bonds: 2 ; (12)Polar Surface Area: 12.47??2 ; (13)Index of Refraction: 1.511 ; (14)Molar Refractivity: 66.71 cm3 ; (15)Molar Volume: 222.4 cm3 ; (16)Polarizability: 26.44 ×10-24cm3 ; (17)Surface Tension: 29.7 dyne/cm ; (18)Density: 0.976 g/cm3 ; (19)Flash Point: 137.8 °C ; (20)Enthalpy of Vaporization: 57.59 kJ/mol ; (21)Boiling Point: 333.1 °C at 760 mmHg ; (22)Vapour Pressure: 0.00014 mmHg at 25°C Uses of Ethoxyquin: Ethoxyquin is a quinoline-based antioxidant used as a food preservative (E324) and a pesticide (under commercial names such as "Stop-Scald"). It is commonly used as a preservative in pet foods to prevent the rancidification of fats. Besides, Ethoxyquin is also commonly used in spices to prevent color loss due to oxidation of the natural carotenoid pigments. You can still convert the following datas into molecular structure :
(1) SMILES: O(c2ccc1c(\C(=C/C(N1)(C)C)C)c2)CC
(2) InChI: InChI=1/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 Toxic information of Ethoxyquin can be showed as follows:
Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 200mg/kg (200mg/kg) ? National Technical Information Service. Vol. AD277-689,
mouse LD50 intravenous 178mg/kg (178mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: COMA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Journal of Agricultural and Food Chemistry. Vol. 7, Pg. 203, 1959.
mouse LD50 oral 1584mg/kg (1584mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Toksikologicheskii Vestnik. Vol. (6), Pg. 29, 1997.
rat LD50 oral 800mg/kg (800mg/kg) ? Rubber Chemistry and Technology. Vol. 45, Pg. 627, 1972.

?
Disposal Methods:
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Use and Manufacturing
Use and Manufacturing:
Methods of Manufacturing

/BY PASSING ACETONE VAPOR INTO P-PHENETIDINE CONTAINING 1% OF IODINE @ 120-130 DEG C & SEPARATING BY DISTILLATION/
Usage:
Antioxidant in feed and food; antidegradation agent for rubber.
Biomedical Effects and Toxicity
Therapeutic Uses:
(VET): Ethoxyquin is added to animal feeds at 0.015% as an antioxidant ... to help prevent encephalomalacia in growing chickens.
(VET): SANTOQUIN HAS BEEN SUCCESSFULLY USED WITH VITAMIN E IN TREATMENT OF WHITE MUSCLE DISEASE IN LAMBS.
Vitamin E and also several synthetic antioxidants, such as ... ethoxyquin, have modified tumor induction by certain carcinogens in a number of target organs. However, inhibition was achieved at high doses at which induction of biotransformation enzymes also occurs with the synthetics and, therefore, inhibition may not be due solely to antioxidant effects.
Biomedical Effects and Toxicity:
FEEDING TRIAL IN COWS WAS CONDUCTED TO DETERMINE WHETHER ETHOXYQUIN OR ITS RESIDUES ARE TRANSFERRED FROM FEED TO MILK WHEN ADDED TO COW FEED AT 0.015% OF DRY MATTER INTAKE. LESS THAN 7 UG ETHOXYQUIN/L WAS DETECTED IN MILK BY FLUORIMETRY & BY THIN-LAYER CHROMATOGRAPHY. [DUNKLEY WL ET AL; J DAIRY SCI 51 (8): 1215-8 (1968)] PubMed Abstract
(14)C-ETHOXYQUIN WAS DISTRIBUTED THROUGHOUT MOST TISSUES & BLOOD AT 0.5 HR AFTER ADMIN TO RATS. HIGHEST RADIOACTIVITY THROUGHOUT EXPERIMENT WAS OBSERVED IN LIVER, KIDNEY, GI TRACT & ADIPOSE TISSUE. THERE WAS NO ACTIVITY IN CNS. OF DOSE INGESTED BY RAT 2.2 & 0.2% WERE FOUND IN LIVER AT 0.5 HR & 6 DAYS RESPECTIVELY FOLLOWING DOSE. HEPATIC PEAK IN RADIOACTIVITY WAS MEASURED AT 8 HR; & AFTER 6 DAYS 7.5% OF THIS LEVEL WAS STILL PRESENT IN LIVER. 6 DAYS AFTER ADMIN TO RATS RESIDUES OF ETHOXYQUIN & METABOLITES WERE PRESENT IN KIDNEY CORTEX, INTESTINES, LUNG, VARIOUS ADIPOSE TISSUES & BLOOD.
The compound is readily absorbed, metabolized, and excreted in urine and feces.
Ethoxyquin residue levels in the mouse tissue were determined by the HPLC-fluorometric detection method. Mice were given powdered feed containing 0, 0.125, and 0.5% ethoxyquin hydrochloric acid and the ethoxyquin residue levels in liver kidney, lung, and brain tissues were determined after 2, 4, 6, 10, and 14 wk (4 mice/group). The tissue samples were homogenized in 10 volumes (w/v) of acetonitrile-water (7:3 v/v) centrifuged and the supernatants were stored in a freezer for 2-3 hr or until the two layers separated; then the clear upper layers were analyzed. The mean ethoxyquin residue levels in the tissue ranged 0.84-4.58 ug ethoxyquin/g liver and 0.11-0.92 ug ethoxyquin/g brain. The relative weight of the liver (5.21-7.07% body weight) and the hepatic glutathione level (5.99-7.83 uM GSH/g tissue) of mice that received ethoxyquin were significantly higher than those of the controls (4.67-5.05% body weight and 4.30-5.78 uM GSH/g tissue, respectively). The mean hepatic mitochondrial glutathione levels of the higher ethoxyquin feeding group following dietary administration of ethoxyquin for 14 wk, was approximately twofold (1.68 nM GSH/mg protein) of both the control and the lower ethoxyquin feeding groups (0.83 and 0.74 nM GSH/mg protein, respectively. [Kim HL; J Toxicol Environ Health 33 (21): 229-36 (1991)] PubMed Abstract
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