| Identification | More | [Name]
Ethoxyquin | [CAS]
91-53-2 | [Synonyms]
1,2-DIHYDRO-6-ETHOXY-2,2,4-TRIMETHYLQUINOLINE
6-ETHOXY-1,2-DIHYDRO-2,2,4-TRIMETHYLQUINOLINE
6-ETHOXY-2,2,4-TRIMETHYL-1,2-DIHYDROQUINOLINE
ETHOXYQUIN
RALUQUIN (R)
SANTOQUIN
SANTOQUIN(R)
STOP-SCALD
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
ariesantox
dawe’snutrigard
emq
eq | [EINECS(EC#)]
202-075-7 | [Molecular Formula]
C14H19NO | [MDL Number]
MFCD00023883 | [Molecular Weight]
217.31 | [MOL File]
91-53-2.mol |
| Chemical Properties | Back Directory | [Appearance]
Transparent yellow or brown viscous liquid. | [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. ]
0-6°C | [solubility ]
ethanol: 50 mL/L, clear, brown
| [form ]
neat | [pka]
5.02±0.70(Predicted) | [color ]
Yellow to Very Dark Brown to Thick | [Stability:]
Stable. Combustible. Incompatible with oxidizing agents, strong acids. Polymerizes if heated. May polymerize upon exposure to light and air. | [Water Solubility ]
<0.1 g/100 mL at 20 ºC | [Usage]
Antioxidant in feed and food; antidegradation agent for rubber. | [Merck ]
3753 | [BRN ]
158223 | [Henry's Law Constant]
8.0×100 mol/(m3Pa) at 25℃, Ebert et al. (2023) | [Major Application]
cleaning products
cosmetics
food and beverages
personal care | [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 | [Contact allergens]
Ethoxyquin is used as an antioxidant in animal feed
and caused contact dermatitis in a worker at an animal
feed mill | [InChIKey]
DECIPOUIJURFOJ-UHFFFAOYSA-N | [SMILES]
CCOc1ccc2NC(C)(C)C=C(C)c2c1 | [LogP]
3.39 | [Uses]
Ethoxyquin is an antioxidant used in the preservation of color in
chili powder, ground chili, and paprika. | [CAS DataBase Reference]
91-53-2(CAS DataBase Reference) | [NIST Chemistry Reference]
Quinoline, 6-ethoxy-1,2-dihydro-2,2,4-trimethyl-(91-53-2) | [EPA Substance Registry System]
Ethoxyquin (91-53-2) |
| Hazard Information | Back Directory | [Chemical Properties]
Yellow Liquid | [Uses]
Antifungal | [Uses]
Antioxidant in feed and food; antidegradation agent for rubber. | [Definition]
ChEBI: Ethoxyquin(91-53-2) 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 Description]
Clear light yellow to dark brown viscous liquid. Discolors and stains badly. Mercaptan-like odor. | [Reactivity Profile]
ETHOXYQUIN(91-53-2) 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 . | [Air & Water Reactions]
Polymerizes and darkens in color on exposure to light and air. Insoluble in water. | [Hazard]
Toxic by ingestion. | [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 | [Fire Hazard]
This chemical is combustible. | [First aid]
If this chemical gets into the eyes, remove any
contact lenses at once and irrigate immediately for at least
15 minutes, occasionally lifting upper and lower lids. Seek
medical attention immediately. If this chemical contacts the
skin, remove contaminated clothing and wash immediately
with soap and water. Seek medical attention immediately.
If this chemical has been inhaled, remove from exposure,
begin rescue breathing (using universal precautions) if
breathing has stopped, and CPR if heart action has stopped.
Transfer promptly to a medical facility. When this chemical
has been swallowed, get medical attention. Give large
quantities of water and induce vomiting. Do not make an
unconscious person vomit | [Shipping]
UN3082 Environmentally hazardous substances,
liquid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required | [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. | [Description]
Ethoxyquin is used as an antioxidant in animal feed
and caused contact dermatitis in a worker at an animal
feed mill. | [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 | [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. | [Trade name]
CHEMLEY®[C]; DECCOQUIN
305®; EMQ®; EQ®; NIFLEX®; NIX-SCALD®[C];
SANTOFLEX A®; SANTOFLEX AW®; SANTOQUIN®;
SANTOQUINE®; STOP-SCALD® | [Mechanism of action]
Anti-oxidant effecting plant growth. Ethoxyquin may also inhibit heat shock protein 90 (Hsp90), a molecular chaperone involved in protein folding and stress responses | [Synthesis]
The general procedure for the synthesis of ethoxyquinoline from p-ethoxyaniline and acetone was as follows: 100 kg of p-aminoanisole, 30 kg of the solvent acetic anhydride and 5 kg of the catalyst cuprous chloride were added to the reaction tank and mixed thoroughly. Subsequently, the reaction mixture was heated to 130°C, and the titration rate of acetone was controlled by a rotameter at atmospheric pressure, and a total of 210 kg of acetone was titrated. The reaction lasted for 12 hours, during which the content of ethoxyquinoline in the reaction mixture was determined periodically. When the content of ethoxyquinoline reached 90% or higher, the reaction mixture was cooled to 75°C. Water and unreacted acetone produced during the reaction were recovered by condensation and the acetone was recycled. | [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.] | [References]
[1] Heteroatom Chemistry, 2012, vol. 23, # 6, p. 598 - 604
[2] Chemische Berichte, 1921, vol. 54, p. 1723,1730
[3] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 21, p. 5081 - 5085
[4] Patent: CN104961679, 2016, B. Location in patent: Paragraph 0023; 0044-0053
[5] European Journal of Pharmaceutical Sciences, 2018, vol. 118, p. 67 - 79 | [Pesticide Type]
Fungicide; Veterinary substance |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H302 | [Precautionary statements ]
P301+P312+P330 | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed. | [Safety Statements ]
S24:Avoid contact with skin . | [RIDADR ]
3082 | [WGK Germany ]
1
| [RTECS ]
VB8225000
| [F ]
2-8-10 | [TSCA ]
TSCA listed | [REACH Registrations]
Inactive | [HazardClass ]
9 | [PackingGroup ]
III | [HS Code ]
29334900 | [Storage Class]
10 - Combustible liquids | [Hazard Classifications]
Acute Tox. 4 Oral | [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. | [Hazardous Substances Data]
91-53-2(Hazardous Substances Data) | [Toxicity]
LD50 orally in rats, mice: 1920, 1730 mg/kg (Piul'skaya) |
|
| Company Name: |
J & K SCIENTIFIC LTD.
|
| Telephone: |
18210857532 18210857532 |
| Website: |
https://www.jkchemical.com |
| Company Name: |
Energy Chemical
|
| Telephone: |
400-0056266 |
| Website: |
www.energy-chemical.com |
| Company Name: |
China Langchem Inc.
|
| Telephone: |
0086-21-58956006 |
| Website: |
www.chemicalbook.com/ShowSupplierProductsList19141/0_EN.htm |
| Company Name: |
Maya High Purity Chemicals
|
| Telephone: |
+86 (573) 82222445 (0)18006601000 452520369 |
| Website: |
www.chemicalbook.com/ShowSupplierProductsList15221/0_EN.htm |
| Company Name: |
Spectrum Chemical Manufacturing Corp.
|
| Telephone: |
021-021-021-67601398-809-809-809 15221380277 |
| Website: |
www.spectrumchemical.com/oa_html/index.jsp?minisite=10020&respid=22372&language=us |
|