HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Ethoxychin
eq · Ethoxiquin · ethoxyquine · emq · Santoflex · EthoxyQuinoline · 6-ETHOXY-2,2,4-TRIMETHYL-1,2-DIHYDROQUINOLINE · 1,2-dihydro-2,2,4-trimethyl-6-ethoxyquinoline
Identifikatoren & physikalische Daten
| CAS No. | 63301-91-7 |
|---|---|
| Summenformel | C14H19NO |
| Durchschnittliche Molmasse | 217,31 g/mol |
| Monoisotopische Masse | 217,14666423 g/mol |
| SMILES | CCOc1ccc2c(c1)C(C)=CC(C)(C)N2 |
| InChIKey | DECIPOUIJURFOJ-UHFFFAOYSA-N |
| PubChem CID | 3293 |
| ChEMBL | CHEMBL172064 |
| ChEBI | CHEBI:77323 |
| EC No. | 202-075-7 |
| DTXSID | DTXSID9020582 |
| Lokaler Name | Ethoxychin |
Chemische & physikalische Eigenschaften
| XLogP | 3,1 |
|---|---|
| Polarare Oberfläche (TPSA) | 21,3 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 16 |
| Formalladung | 0 |
| Komplexität | 282 |
| Stoffklassen | Other Uses -> Animal Feed AdditivesAntioxidant |
| Pestizide | Plant Growth RegulatorsActive substance -> EU Pesticides database: Not approvedPesticide (Ethoxyquin) -> USDA PDB |
| Lebensmittelzusatzstoffe | ANTIOXIDANT -> FDA Substance added to food |
| Dichte | 1.029 to 1.031 at 77 °F (NTP, 1992)1.029-1.031 AT 25 °C/25 °C1.03 g/mL at 20 °C (lit.) |
| Color/Form | YELLOW LIQUID |
| Löslichkeit | less than 1 mg/mL at 68 °F (NTP, 1992)ethanol: 50 mL/L, clear, brown<0.1 g/100 mL at 20 ºC |
| Flammpunkt | 225 °F (NTP, 1992)137 °C |
| Animal Drugs | Pharmaceuticals -> Animal Drugs -> Approved in Taiwan |
| Siedepunkt | 253 to 257 °F at 2 mmHg (NTP, 1992)123-125 °C AT 2 MM HG123-125°C |
| Decomposition | ... WHEN HEATED TO DECOMP, EMITS TOXIC FUMES ... . |
| Schmelzpunkt | less than 32 °F (NTP, 1992)Approximately 0 °C<0°C |
| Dampfdichte | 7.48 (NTP, 1992) - Heavier than airwill sink (Relative to Air)7.48 (AIR= 1) |
| Dampfdruck | 0.035Pa at 25℃ |
| Brechungsindex | 1.569~1.571 |
| Lagerbedingungen | 2-8°C |
| Aggregatzustand | Liquid |
| pKa (Säurekonstante) | 5.02±0.70(Predicted) |
| Farbe | Yellow to Very Dark Brown |
| Merck | 14,3753 |
| BRN | 158223 |
| Henry-Konstante | 8.0×100 mol/(m3Pa) at 25℃, Ebert et al. (2023) |
| Stabilität | Stable. Combustible. Incompatible with oxidizing agents, strong acids. Polymerizes if heated. May polymerize upon exposure to light and air. |
| Hauptanwendungen | cleaning productscosmeticsfood and beveragespersonal 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 |
| InChIKey | DECIPOUIJURFOJ-UHFFFAOYSA-N |
| SMILES | CCOc1ccc2NC(C)(C)C=C(C)c2c1 |
| LogP (Verteilungskoeffizient) | 3.39 |
| CAS Datenbank | 91-53-2(CAS DataBase Reference) |
| NIST chemische Informationen | Quinoline, 6-ethoxy-1,2-dihydro-2,2,4-trimethyl-(91-53-2) |
| EPA chemische Informationen | Ethoxyquin (91-53-2) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH302: Harmful if swallowed [Warning Acute toxicity, oral]P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]P264, P270, P273, P301+P317, P330, P391, and P501 (click each P-code to see the statement) |
|---|---|
| Regulatorische Informationen | Chemical: Quinoline, 6-ethoxy-1,2-dihydro-2,2,4-trimethyl-Regulation (EC) No 1831/2003 (amended)Ethoxyquin is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)2008/941, 2011/143/EUREACH registered substance: Ethoxyquin (EC: 202-075-7)Ethoxyquin: Does not have an individual approval but may be used under an appropriate group standard |
| Brandgefahren | This chemical is combustible. (NTP, 1992) |
| Brandpotenzial | FIRE HAZARD /IS/ SLIGHT |
| Gesundheitsgefahren | SYMPTOMS: Symptoms of exposure to this compound include skin irritation. It can cause eye irritation. It can also cause skin sensitization (allergic reactions), lacrimation, depression, reproductive effects, liver effects, kidney effects and thyroid effects. Dermatitis may also occur. |
| Gefahrenübersicht | Allergic contact dermatitis reported in a feed mill worker[Kanerva, p. 1793] A skin irritantMay cause reversible changes to the liverReports of contact dermatitis in animal feed employees[HSDB] May polymerize on exposure to light and airA skin and eye irritantMay cause skin sensitization[CAMEO] Strongly associated with cases of occupational contact dermatitisCauses increased liver enzymes in animal experiments[Reference #2] |
| FDA-Anforderungen | 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. |
| Reaktive Gruppe | Amines, Phosphines, and Pyridines |
| FIFRA-Anforderungen | As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Ethoxyquin is found on List A, which contains most food use pesticides and consists of the 194 chemical cases (or 350 individual active ingredients) for which EPA issued registration standards prior to FIFRA, as amended in 1988. Case No: 0003Pesticide type: HerbicideRegistration Standard Date: 03/01/81Case Status: OPP is reviewing data from the pesticide's producers regarding its human health and/or environmental effects, or OPP is determining the pesticide's eligibility for reregistration and developing the Reregistration Eligibility Decision (RED) document.Active ingredient (AI): EthoxyquinData Call-in (DCI) Date(s): 08/20/90, 10/13/95AI Status: The producers of the pesticide has made commitments to conduct the studies and pay the fees required for reregistration, and are meeting those commitments in a timely manner.A tolerance is established for residues of the plant regulator ethoxyquin (1,2-dihydro-6-ethoxy-2,2,4-trimethylquinoline) from preharvest or postharvest use in or on apples and pears. |
| Reactivity Alerts | Polymerizable |
| 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 (NTP, 1992). |
| Air and Water Reactions | Polymerizes and darkens in color on exposure to light and air. Insoluble in water. |
| Hazard Classes and Categories | Acute Tox. 4 (100%)Acute toxicity - category 4Acute toxicity (Oral) - Category 4Acute Tox. 4 * |
| Brandbekämpfung | Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. A water spray may also be used. (NTP, 1992) |
| Erste Hilfe | EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. |
| Freisetung ohne Brand | SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. Then, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. |
| Entsorgungsverfahren | 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. |
| Allowable Tolerances | A tolerance of 3 ppm is established for residues of the plant regulator ethoxyquin (1,2-dihydro -6-ethoxy -2,2,4-trimethylquinoline)from preharvest or postharvest use in or on apples and pears. |
| Personal Protective Equipment (PPE) | RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992) |
| Wechselwirkungen | ELEVATION OF EPOXIDE HYDRATASE ACTIVITY IS OBTAINED BY IP OR ORAL TREATMENT OF MICE WITH ETHOXYQUIN. THIS ELEVATION IS PREVENTED BY CONCOMITANT TREATMENT WITH CYCLOHEXIMIDE.SINGLE ORAL DOSE OF ETHOXYQUIN (200 MG/KG) TO RATS INHIBITED HEPATIC MICROSOMAL HYDROXYLATION OF THIABENDAZOLE, ANILINE & BIPHENYL BY 65, 40 & 40% IN VITRO AT 1 HR AFTER DOSAGE. ORAL ETHOXYQUIN (400 MG/KG) DELAYED ABSORPTION OF & DECR PLASMA CONCN OF THIABENDAZOLE.The effects of dietary administration of ethoxyquin on aflatoxin B1 metabolism, DNA adduct formation and removal and hepatic tumorigenesis were examined in male Fischer rats. Rats were fed a semipurified diet containing 0.4% ethoxyquin for 1 wk, gavaged with 250 ug of aflatoxin B1 per kg 5 times a wk during the next 2 wk, and finally restored to the control diet 1 wk after cessation of dosing. At 4 mo, focal areas of hepatocellular alteration were identified and quantitated by staining sections of liver for gamma-glutamyl transpeptidase. Treatment with ethoxyquin reduced by greater than 95% both area and volume of liver occupied by gamma-glutamyl transpeptidase-positive foci. Utilizing the same multiple dosing protocol, patterns of covalent modifications of DNA by aflatoxin B1 were determined. Ethoxyquin produced a dramatic reduction in the binding of aflatoxin B1 to hepatic DNA: 18-fold initially and 3-fold at the end of the dosing period. Although binding was detectable at 3 and 4 mo postdosing, no effect of ethoxyquin was observed, suggesting that these persistent adducts are not of primary relevance to aflatoxin B1 carcinogenesis. Analysis of nucleic acid bases by high-performance liquid chromatography revealed no qualitative differences in adduct species between treatment groups. The inhibitory effect of ethoxyquin on aflatoxin B1 binding to DNA and tumorigenesis appears related to induction of detoxication enzymes. Rats fed 0.4% ethoxyquin for 7 days showed a 5-fold increase in hepatic cytosolic glutathione S-transferase (GST)-specific activities. Multiple molecular forms of glutathione S-transferase were induced, and concomitant elevations in messenger RNA levels coding for the synthesis of glutathione S-transferase subunits were observed. Correspondingly, billary elimination of aflatoxin B1-glutathione conjugate was increased 4.5-fold in animals on the ethoxyquin diet during the first 2 hr following oral administration of 250 micrograms of aflatoxin B1 per kg. Thus, induction by ethoxyquin of enzymes important to aflatoxin B1 detoxication, such as glutathione S-transferase can lead to enhanced carcinogen elimination, as well as reductions of aflatoxin B1-DNA adduct formation and subsequent expression of preneoplastic lesions, and, ultimately, neoplasia. |
| Unerwünschte Wirkungen | Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation. |
| Ongoing Test Status | The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=91-53-2] |
| Human Toxicity Excerpts | SKIN IRRITANT. MAY PRODUCE REVERSIBLE LIVER CHANGES.CASES OF CONTACT DERMATITIS DUE TO ADDITIVES IN ANIMAL FEED SUBSTANCES ARE DESCRIBED OCCURRING IN ANIMAL FEED WORKERS. THERE ARE 2 CASES OF SENSITIVITY TO ETHOXYQUIN. |
| Carcinogen Classification | No indication of carcinogenicity to humans (not listed by IARC). |
| Non-Human Toxicity Excerpts | ITS CHRONIC TOXICITY IS APPARENTLY LOW, 0.2% IN DIET CAUSING TRANSIENT DEPRESSION IN GROWTH RATE OF RATS. AT AUTOPSY, DAMAGE WAS APPARENT IN KIDNEYS, LIVER & THYROID GLAND IN MANY MALES BUT IN NONE OF FEMALES ... ./IN RATS FED A DIET CONTAINING 0.2% OF SANTOQUIN/ SOME TUMORS WERE FOUND AFTER CONTINUOUS ADMIN ... .ORAL ADMIN OF ETHOXYQUIN TO RATS INCR EPOXIDE HYDRATASE ACTIVITY IN LIVER MICROSOMES. T/2 OF INCR 3-4 DAYS. AN INCR OF THIS ENZYME WAS ALSO PRODUCED IN MICE BY IP ADMIN.DIETARY ADMIN OF 0.5% ETHOXYQUIN MARKEDLY ENHANCED RAT HEPATIC UDP-GLUCURONOSYLTRANSFERASE ACTIVITIES.For more Non-Human Toxicity Excerpts (Complete) data for ETHOXYQUIN (12 total), please visit the HSDB record page. |
| RAIS Toxicity Values | 1OPP0.04 |
| EPA Human Health Benchmarks for Pesticides | Ethoxyquin17000Children0.04200 |
| F | 2-8-10 |
| Wassergefährdungsklasse (WGK) | 1 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | 3082 |
| Zollcode | 29334900 |
| RTECS-Nr. | VB8225000 |
| R-Sätze (R) | 22 |
| Toxizität | LD50 orally in rats, mice: 1920, 1730 mg/kg (Piul'skaya) |
| Gefahrensymbole | Xn |
| Sicherheitshinweise (S) | 24 |
| Gefahrenklasse | 9Acute Tox. 4 Oral |
| Verpackungsgruppe | III |
| Lagerklasse | 10 - Combustible liquids |
| Gefahrstoffdaten | 91-53-2(Hazardous Substances Data) |
Anwendungen & Verwendung
Beschreibung
Ethoxyquin is used as an antioxidant in animal feed and caused contact dermatitis in a worker at an animal feed mill.
Verwenden
Ethoxyquin is an antioxidant used in the preservation of color in chili powder, ground chili, and paprika.