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Ethoxyquin structure
Ethoxyquin structure

Ethoxyquin

Iupac Name:6-ethoxy-2,2,4-trimethyl-1H-quinoline
CAS No.: 91-53-2
Molecular Weight:217.312
Modify Date.: 2022-04-20 07:10
Introduction: Ethoxyquin is used as an antioxidant in animal feedand caused contact dermatitis in a worker at an animalfeed mill. View more+
1. Names and Identifiers
1.1 Name
Ethoxyquin
1.2 Synonyms

1,2-dihydro-2,2,4-trimethyl-6-ethoxyquinoline 1,2-dihydro-2,2,4-trimethylquinolin-6-yl ethyl ether 1,2-dihydro-6-ethoxy-2,2,4-trimethylQUINOLINE 2,2,4-trimethyl-6-ethoxy-1,2-dihydroquinoline 6-ethoxy-1,2-dihydro-2,2,4-trimethyl-quinolin 6-Ethoxy-1,2-dihydro-2,2,4-trimethylquinoline 6-Ethoxy-2,2,4-trimethyl-1,2-dihydroquinoline 6-Ethoxyl-2,2,4-trimethyl-1,2-dihydrquinoline amea100 antageaw AntioxidantAW antioxidantec EINECS 202-075-7 emq ETMDQ MFCD00023883 niflex niflexd nocracaw quinoled Quinoline, 6-ethoxy-1,2-dihydro-2,2,4-trimethyl- Santoflex Santoquin UNII-9T1410R4OR usafb-24

1.3 CAS No.
91-53-2
1.4 CID
3293
1.5 EINECS(EC#)
202-075-7
1.6 Molecular Formula
C14H19NO (isomer)
1.7 Inchi
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
1.8 InChkey
DECIPOUIJURFOJ-UHFFFAOYSA-N
1.9 Canonical Smiles
CCOC1=CC2=C(C=C1)NC(C=C2C)(C)C
1.10 Isomers Smiles
CCOC1=CC2=C(C=C1)NC(C=C2C)(C)C
2. Properties
3.1 Density
1.03
3.1 Melting point
<0℃
3.1 Boiling point
less than 32° F (NTP, 1992)
3.1 Refractive index
1.569~1.571
3.1 Flash Point
225° F (NTP, 1992)
3.1 Vapour pressure
1.82e-05 mm Hg at 32° F ; 0.000256 mm Hg at 77° F (NTP, 1992)
3.1 Precise Quality
217.14700
3.1 PSA
21.26000
3.1 logP
3.83070
3.1 Solubility
ethanol: 50?mL/L, clear, brown
3.2 VaporDensity
7.48 (AIR= 1)
3.3 AnalyticLaboratory Methods
METHOD OF CHOICE IS FLUORESCENCE ASSAY WITH ISOOCTANE; SOLVENT, APPLICABLE TO MILK & TISSUE; EXCITATION WAVELENGTH APPROX 365 NM WITH BLUE FLUORESCENCE. /FROM TABLE/
3.4 Appearance
yellow to red-brown liquid
3.5 Chemical Properties
Yellow liquid.Discolors and stains badly.
3.6 Color/Form
YELLOW LIQUID
3.7 Contact Allergens
Ethoxyquin is used as an antioxidant in animal feedand caused contact dermatitis in a worker at an animalfeed mill
3.8 Decomposition
... WHEN HEATED TO DECOMP, EMITS TOXIC FUMES ... .
3.9 Physical
PHYSICAL DESCRIPTION: Clear light yellow to dark brown viscous liquid. Discolors and stains badly. Mercaptan-like odor. (NTP, 1992)
3.10 pKa
5.02±0.70(Predicted)
3.11 Water Solubility
ethanol: 50?mL/L, clear, brown | <0.1 g/100 mL at 20 oC
3.12 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%)
3.13 Stability
Stable. Combustible. Incompatible with oxidizing agents, strong acids. Polymerizes if heated. May polymerize upon exposure to light and air.
3.14 StorageTemp
2-8°C
3. Use and Manufacturing
4.1 Agricultural Uses
Insecticide, Fungicide, Plant growth regulator,Ingredient in other products: Used for preharvest or postharvest preservation ofcolor in apples and pears. It is used as an antioxidant topreserve color in paprika and ground and powdered chili.Ethoxyquin is also a chemical preservative used in animalfeed to prevent ingredients from reacting with oxygen andbecoming rancid. It has been known to cause birth defectsin pet birds and dogs. Not approved for use in EU countries[115]. Registered for use in the U.S.
4.2 Definition
ChEBI: 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.
4.3 General Description
Clear light yellow to dark brown viscous liquid. Discolors and stains badly. Mercaptan-like odor.
4.4 GHS Classification
Signal: Warning
GHS Hazard Statements
H302: Harmful if swallowed [Warning Acute toxicity, oral]

Precautionary Statement Codes
P264, P270, P301+P312, P330, and P501
4.5 Methods of Manufacturing
/BY PASSING ACETONE; VAPOR INTO P-PHENETIDINE; CONTAINING 1% OF IODINE; @ 120-130 DEG C & SEPARATING BY DISTILLATION/
4.6 Potential Exposure
Quinoline insecticide, fungicide andplant growth regulator. Also and ingredient in other products. Used for preharvest or postharvest preservation ofcolor in apples and pears. It is used as an anti-oxidant topreserve color in paprika and ground and powdered chili.Ethoxyquin also is a chemical preservative used in animalfeed to prevent ingredients from reacting with oxygen andbecoming rancid. It has been known to cause birth defectsin pet birds and dogs
4.7 Purification Methods
Purify 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.]
4.8 Shipping
UN3082 Environmentally hazardous substances,liquid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required
4.9 Usage
Antioxidant in feed and food; antidegradation agent for rubber.
4.10 Waste Disposal
Do not discharge into drainsor sewers. Dispose of waste material as hazardous wasteusing a licensed disposal contractor to an approved landfill.Consult with environmental regulatory agencies forguidance 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 yourregional EPA office Ethoxyquin Preparation Products And Raw materials Raw materials
4. Safety and Handling
5.1 Symbol
GHS07
5.1 Hazard Codes
Xn
5.1 Signal Word
Warning
5.1 Risk Statements
R22
5.1 Safety Statements
S24
5.1 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.
5.2 Packing Group
III
5.2 Fire Hazard
Ethoxyquin is combustible.
5.3 Hazard Class
9
5.3 Hazard Declaration
H302
5.3 DisposalMethods
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.
5.4 RIDADR
200kgs
5.4 FirePotential
FIRE HAZARD /IS/ SLIGHT
5.5 Safety Profile
Poison 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.
5.6 Caution Statement
P301 + P312 + P330
5.6 Formulations/Preparations
USEPA/OPP Pesticide Code 055501; Trade Names: Stop-scald.
Emulsifiable concentrate
5.7 WGK Germany
1
5.7 RTECS
VB8225000
5.7 Protective Equipment and Clothing
SKIN IRRITANT.
5.8 Reactivities and Incompatibilities
Can react with oxidizing materials.
5.9 Skin, Eye, and Respiratory Irritations
SKIN IRRITANT.
5.10 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.

?

5.11 Toxicity

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)
5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Warning

Hazard statement(s)

H302 Harmful if swallowed

Precautionary statement(s)
Prevention

P264 Wash ... thoroughly after handling.

P270 Do not eat, drink or smoke when using this product.

Response

P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell.

P330 Rinse mouth.

Storage

none

Disposal

P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

7. Precursor and Product
8. Other Information
8.0 Merck
14,3753
8.1 BRN
158223
8.2 Description
Ethoxyquin is used as an antioxidant in animal feed and caused contact dermatitis in a worker at an animal feed mill.
8.3 Chemical Properties
Yellow liquid.Discolors and stains badly.
8.4 Chemical Properties
Transparent yellow or brown viscous liquid.
8.5 Uses
Antioxidant in feed and food; antidegradation agent for rubber.
8.6 Uses
Antifungal
8.7 Uses
Ethoxyquin is an antioxidant used in the preservation of color in chili powder, ground chili, and paprika.
8.8 Definition
ChEBI: 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.
8.9 General Description
Clear light yellow to dark brown viscous liquid. Discolors and stains badly. Mercaptan-like odor.
8.10 Air & Water Reactions
Polymerizes and darkens in color on exposure to light and air. Insoluble in water.
8.11 Reactivity Profile
Ethoxyquin 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 .
8.12 Hazard
Toxic by ingestion.
8.13 Fire Hazard
Ethoxyquin is combustible.
8.14 Agricultural Uses
Insecticide, 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.
8.15 Trade name
CHEMLEY?[C]; DECCOQUIN 305?; EMQ?; EQ?; NIFLEX?; NIX-SCALD?[C]; SANTOFLEX A?; SANTOFLEX AW?; SANTOQUIN?; SANTOQUINE?; STOP-SCALD?
8.16 Safety Profile
Poison 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.
8.17 Potential Exposure
Quinoline 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
8.18 Shipping
UN3082 Environmentally hazardous substances, liquid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required
8.19 Purification Methods
Purify 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.]
8.20 Incompatibilities
Polymerization 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.
8.21 Waste Disposal
Do 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
9. Computational chemical data
  • Molecular Weight: 217.312g/mol
  • Molecular Formula: C14H19NO
  • Compound Is Canonicalized: True
  • XLogP3-AA: 3.1
  • Exact Mass: 217.146664230
  • Monoisotopic Mass: 217.146664230
  • Complexity: 283
  • Rotatable Bond Count: 2
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 2
  • Topological Polar Surface Area: 21.3
  • Heavy Atom Count: 16
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count: 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 1
  • CACTVS Substructure Key Fingerprint: AAADceByIAAAAAAAAAAAAAAAAAAAAAAAAAAwQAAAAAAAAACBAAAAHgAQAAAADIyhmAIyxoLABACAAiRCQACCCAAhIgAIiAAGbIgMJiLEsZuGOCjk0BHI6AewwLAOAEABAAACAAAAgAIAAAQAAAAAAAAAAA==
11. Realated Product Infomation