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6-エトキシ-2,2,4-トリメチル-1,2-ジヒドロキノリン
6-エトキシ-2,2,4-トリメチル-1,2-ジヒドロキノリン · 2,2,4-トリメチル-6-エトキシ-1,2-ジヒドロキノリン · ノンフレックスAW · サントキン · 酸化防止剤EC · 抗酸化剤EC · 1,2-ジヒドロ-6-エトキシ-2,2,4-トリメチルキノリン · 1,2-ジヒドロ-2,2,4-トリメチル-6-エトキシキノリン
識別子と物理属性
| CAS No. | 63301-91-7 |
|---|---|
| 分子式 | C14H19NO |
| 平均分子量 | 217.31 g/mol |
| 単同位体質量 | 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 |
| 現地名 | 6-エトキシ-2,2,4-トリメチル-1,2-ジヒドロキノリン |
化学・物理的性質
| XLogP | 3.1 |
|---|---|
| 極性表面積 | 21.3 |
| 水素結合供与体数 | 1 |
| 水素結合受容体数 | 2 |
| 回転可能結合数 | 2 |
| 重原子数 | 16 |
| 形式電荷 | 0 |
| 複雑度 | 282 |
| 物質分類 | Other Uses -> Animal Feed AdditivesAntioxidant |
| 農薬 | Plant Growth RegulatorsActive substance -> EU Pesticides database: Not approvedPesticide (Ethoxyquin) -> USDA PDB |
| 食品添加物 | ANTIOXIDANT -> FDA Substance added to food |
| 密度 | 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 |
| 溶解度 | less than 1 mg/mL at 68 °F (NTP, 1992)エタノール: 50 mL/L、透明、茶色<0.1 g/100 mL で 20 ºC |
| 引火点 | 225 °F (NTP, 1992)137 °C |
| Animal Drugs | Pharmaceuticals -> Animal Drugs -> Approved in Taiwan |
| 沸点 | 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 ... . |
| 融点 | less than 32 °F (NTP, 1992)Approximately 0 °C<0°C |
| 蒸気密度 | 7.48 (NTP, 1992) - Heavier than airwill sink (Relative to Air)7.48 (AIR= 1) |
| 蒸気圧 | 0.035Pa at 25℃ |
| 屈折率 | 1.569~1.571 |
| 貯蔵条件 | 2-8°C |
| 外観・状態 | Liquid |
| pKa（酸解離定数） | 5.02±0.70(Predicted) |
| 色 | 黄色から非常に濃い茶色から厚い |
| Merck | 14,3753 |
| BRN | 158223 |
| ヘンリー定数 | 8.0×100 mol/(m3Pa) at 25℃, Ebert et al. (2023) |
| 安定性 | 安定。可燃性。酸化剤および強酸とは相容れない。加熱すると重合する。光や空気にさらされると重合することがある。 |
| 主な用途 | 洗浄剤化粧品食品および飲料パーソナルケア |
| 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（分配係数） | 3.39 |
| CAS データベース | 91-53-2(CAS DataBase Reference) |
| NISTの化学物質情報 | Quinoline, 6-ethoxy-1,2-dihydro-2,2,4-trimethyl-(91-53-2) |
| EPAの化学物質情報 | Ethoxyquin (91-53-2) |
化学的特性
Transparent yellow or brown viscous liquid. Discolors and stains badly. Soluble in benzene, gasoline, ether, ethanol, carbon tetrachloride, acetone, dichloroethane, insoluble in water.
安全性と法規制
| GHS 分類 | 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) |
|---|---|
| 規制情報 | 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 |
| 火災危険 | This chemical is combustible. (NTP, 1992) |
| 火災の可能性 | FIRE HAZARD /IS/ SLIGHT |
| 健康有害性 | 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. |
| 有害性の概要 | 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 要件 | 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. |
| 反応性グループ | Amines, Phosphines, and Pyridines |
| FIFRA 要件 | 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 * |
| 消火 | 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) |
| 応急処置 | 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. |
| 非火災時の漏出対応 | 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. |
| 処分方法 | 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) |
| 相互作用 | 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. |
| 有害作用 | 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 |
| 水環境危害等級（WGK） | 1 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | VB8225000 |
| 輸送番号（UN） | 3082 |
| 毒性 | LD50 orally in rats, mice: 1920, 1730 mg/kg (Piul'skaya) |
| 税関コード | 29334900 |
| 危険文句（R） | 22 |
| 化審法 | (5)-813 |
| 消防法 | 危険物第4類第三石油類(非水溶性) |
| 危険表示 | Xn |
| 安全措置（S） | 24 |
| 危険等級 | 9Acute Tox. 4 Oral |
| 包装等級 | III |
| 貯蔵分類 | 10 - Combustible liquids |
| 有害物質データ | 91-53-2(Hazardous Substances Data) |
用途
用途
天然ゴム,合成ゴムの老化防止剤.耐熱,耐屈曲性にすぐれるほかにオゾン劣化防止性にすぐれる.ほかのアミン系老化防止剤やワックス類と併用して,耐オゾン性ゴム製品に使用される。(有機化合物辞典 (1985))
説明
Ethoxyquin is used as an antioxidant in animal feed and caused contact dermatitis in a worker at an animal feed mill.
使用
Ethoxyquin is an antioxidant used in the preservation of color in chili powder, ground chili, and paprika.
一般的な説明
Clear light yellow to dark brown viscous liquid. Discolors and stains badly. Mercaptan-like odor.
製法・合成法
純化方法
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.]