化工社化工社 化学情報印刷レポート · 研究参考用
ヒドロキノン
ヒドロキノン · ヒドロキノール · ベンゼン-1,4-ジオール · テキノール · 1,4-ヒドロキノン · ヒドロキシキノン · エルドパケ · ブラックアンドホワイトブリーチングクリーム
識別子と物理属性
| CAS No. | 123-31-9 |
|---|---|
| 分子式 | C6H6O2 |
| 平均分子量 | 110.11 g/mol |
| 単同位体質量 | 110.03677943 g/mol |
| SMILES | Oc1ccc(O)cc1 |
| InChIKey | QIGBRXMKCJKVMJ-UHFFFAOYSA-N |
| PubChem CID | 785 |
| ChEMBL | CHEMBL537 |
| ChEBI | CHEBI:17594 |
| EC No. | 204-617-8 |
| DTXSID | DTXSID7020716 |
| 現地名 | ヒドロキノン |
化学・物理的性質
| XLogP | 0.6 |
|---|---|
| 極性表面積 | 40.5 |
| 水素結合供与体数 | 2 |
| 水素結合受容体数 | 2 |
| 回転可能結合数 | 0 |
| 重原子数 | 8 |
| 形式電荷 | 0 |
| 複雑度 | 54.9 |
| 物質分類 | Hazardous Air Pollutants (HAPs)Other Classes -> PhenolsAntioxidant |
| 医薬品 | Pharmaceuticals -> Listed in ZINC15 |
| 化粧品 | Cosmetic ingredients (Hydroquinone) -> CIR (Cosmetic Ingredient Review)AntioxidantReducingBleachingHair dyeing |
| SpringerMaterials Properties | 13C nuclear magnetic resonance spectrum |
| 農薬 | Pesticide -> EPA IRISEnvironmental transformation -> Pesticide transformation products (metabolite, successor) |
| LogP（分配係数） | log Kow = 0.590.61 |
| 臭い | Odorless無臭 |
| 味 | A slightly bitter taste in aqueous solutions |
| 密度 | 1.332 at 59 °F (EPA, 1998) - Denser than waterwill sink1.330 g/cu cm at 20 °CDensity of "saturated" air = 1.011 (150 °C) (air = 1) ... Crystals remain relatively stable in air if dry ... Reacts with molecular oxygen undergoing autooxidation in aqueous mediaRelative density (water = 1): 1.31.358 @ 20°C1.32 |
| Color/Form | White crystalsMonoclinic prisms (sublimation)needles from waterprisms from methanolLight-tan, light-gray, or colorless crystals |
| 溶解度 | 10 to 50 mg/mL at 68 °F (NTP, 1992)6.72g/L at 20 deg CIn water, 72,000 mg/L at 25 °CIn water, 6.72 g/L at 20 °C. Also water solubility = 3.85 g/L at 0 °C5.12 g/L at 10 °C5.40 g/L at 15 °C8.76 g/L at 30 °C11.5 g/L at 40 °C25/9 g/L at 60 °C46.8 g/L at 80 °C66.4 g/L at 100 °C7% soluble in water at 25 °CGrams of hydroquinone per 100 g solvent (30 °C)ethanol 46.4acetone 28.4water 8.3benzene 0.06tetrachloromethane 0.01H2O: 50 mg/mL、透明70g/l (20℃) |
| 引火点 | 329 °F (EPA, 1998)329 °F (CLOSED CUP)165 °C (329 °F) (Closed cup)329 °F (165 °C) (Closed cup) |
| 融点 | 172-175 °C(lit.) |
| 沸点 | 285 °C(lit.) |
| 蒸気密度 | 3.81 (vs air) |
| 蒸気圧 | 1 mm Hg ( 132 °C) |
| 屈折率 | 1.6320 |
| 貯蔵条件 | Store below +30°C. |
| pKa（酸解離定数） | 10.35(at 20℃) |
| 外観・状態 | 針状結晶または結晶性粉末 |
| 色 | ホワイトからオフホワイト |
| 由来生物 | synthetic |
| 比熱容量 | Cp(crystal): 1.24 J/(g·K), at 25℃ |
| Merck | 14,4808 |
| BRN | 605970 |
| ヘンリー定数 | (x 10-9 atmm3/mol): <2.07 at 20 °C (approximate - calculated from water solubility and vapor pressure) |
| 安定性 | 安定。可燃性。強酸化剤、強塩基、酸素、鉄塩とは相容れない。光や空気に敏感。空気中の変色。 |
| 化粧品成分の機能 | 香料ヘアカラーリング還元剤抗酸化物質漂白 |
| InChI | 1S/C6H6O2/c7-5-1-2-6(8)4-3-5/h1-4,7-8H |
| InChIKey | QIGBRXMKCJKVMJ-UHFFFAOYSA-N |
| SMILES | Oc1ccc(O)cc1 |
| LogP（分配係数） | 0.59 at 20℃ |
| CAS データベース | 123-31-9(CAS DataBase Reference) |
| NISTの化学物質情報 | Hydroquinone(123-31-9) |
| EPAの化学物質情報 | Hydroquinone (123-31-9) |
化学的特性
Hydroquinone, a colorless, hexagonal prism, has been reported to be a good antimitotic and tumor-inhibiting agent. It is a reducing agent used in a photographic developer, which polymerizes in the presence of oxidizing agents. In the manufacturing industry it may occur include bacteriostatic agent, drug, fur processing, motor fuel, paint, organic chemicals, plastics, stone coating, and styrene monomers.
安全性と法規制
| GHS 分類 | DangerH302: Harmful if swallowed [Warning Acute toxicity, oral]P203, P261, P264, P264+P265, P270, P272, P273, P280, P301+P317, P302+P352, P305+P354+P338, P317, P318, P321, P330, P333+P317, P362+P364, P391, P405, and P501 (click each P-code to see the statement)This chemical does not meet GHS hazard criteria for < 0.1% (1 of 2485) of reports.H302+H312 (17.7%): Harmful if swallowed or in contact with skin [Warning Acute toxicity, oralacute toxicity, dermal] |
|---|---|
| 規制情報 | Chemical: 1,4-BenzenediolHazard Traits - CarcinogenicityCommission Regulation (EC) No 1490/20021,4-Benzenediol is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,4-Benzenediol are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 05-05-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/14417Hydroquinone: HSNO Approval: HSR003003 Approved with controls |
| その他の安全情報 | IMAP assessments - 1,4-Benzenediol: Human health tier II assessment |
| 輸送ラベル（DOT） | Class 9 Poison |
| 火災危険 | Dust cloud may explode if ignited in an enclosed area. It can react with oxidizing materials and is rapidly oxidized in the presence of alkaline materials. Oxidizes in air. (EPA, 1998)Combustible. Finely dispersed particles form explosive mixtures in air. |
| 火災の可能性 | Fire hazard: slight, when exposed to heat or flamecan react with oxidizing materials. |
| 健康有害性 | This material is very toxicthe probable oral lethal dose for humans is 50-500 mg/kg, or between 1 teaspoon and 1 ounce for a 150 lb. person. It is irritating but not corrosive. Fatal human doses have ranged from 5-12 grams, but 300-500 mg have been ingested daily for 3-5 months without ill effects. Death is apparently initiated by respiratory failure or anoxia. (EPA, 1998) |
| 有害性の概要 | Hydroquinone is used as a developing agent in photography and as an antioxidant in rubber and food. Tinnitus (ringing in the ears), dizziness, headache, nausea, vomiting, dyspnea, erosion of the gastric mucosa, edema of internal organs, cyanosis, convulsions, delirium, and collapse may result from the ingestion of a large amount of hydroquinone in humans. Hydroquinone is also a skin irritant in humans. Chronic (long-term) occupational exposure to hydroquinone dust can result in eye irritation, corneal effects, and impaired vision. No information is available on the reproductive, developmental, or carcinogenic effects of hydroquinone in humans. There was some evidence of carcinogenic activity in orally-exposed rodents. Increased skin tumor incidence has been reported in mice treated dermally. EPA has not classified hydroquinone for carcinogenicity.Workers exposed to high concentrations developed corneal ulcers. [ACGIH] Animals exposed to lethal doses have convulsions and methemoglobinemia. [HSDB] Can cause leukoderma (depigmentation of skin)[LaDou, p. 328] Allergic contact dermatitis in photographers[Marks] Allergic contact dermatitis reported in developers of photographs, x-rays, and microfilmsalso reported in dental technicians[Kanerva, p. 1802] Severe eye irritant[ICSC] Induces genetic damage in germ cells of humans or animals (3A)[MAK] |
| 輸送番号・ガイド（DOT） | 2662 153 |
| FDA 要件 | Hydroquinone is an indirect food additive for use only as a component of adhesives. |
| 反応性グループ | Phenols and Cresols |
| EC 分類 | Symbol: Xn, NR: 22-40-41-43-50-68S: (2)-26-36/37/39-61 |
| UN 分類 | UN Hazard Class: 6.1UN Pack Group: III |
| 消火 | Wear self-contained (positive pressure if available) breathing apparatus and full protective clothing.Use water spray, powder, foam, carbon dioxide. |
| 応急処置措置 | Fresh air, rest. Artificial respiration may be needed. Refer for medical attention.Remove contaminated clothes. Rinse and then wash skin with water and soap.First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.Rinse mouth. Induce vomiting (ONLY IN CONSCIOUS PERSONS!). Refer for medical attention . |
| 応急処置 | Signs and Symptoms of Acute Hydroquinone Exposure: Signs and symptoms of acute exposure to hydroquinone may be severe and include dyspnea (shortness of breath), a sense of suffocation, increased respiratory rate, and respiratory failure. Pallor (paleness of the skin), cyanosis (blue tint to skin and mucous membranes), and cardiovascular collapse may occur. Neurologic effects include headache, tinnitus (ringing in the ears), dizziness, delirium, muscle twitching, tremor, and convulsions. Nausea, vomiting, and the production of green to brown-green urine may also occur. Hydroquinone may be irritating and corrosive to the skin, eyes, and mucous membranes. Jaundice (yellow tint to skin) may be noticed.(General first aid procedures) |
| 安全保管 | Separated from strong bases and food and feedstuffs. |
| Firefighting Hazards | Special hazards arising from the substance or mixture: Carbon oxides |
| 消火手順 | To fight fire, use water, carbon dioxide, dry chem ... .If material on fire or involved in fire: Extinguish fire using agent suitable for type of surrounding fire (Material itself does not burn or burns with difficulty). Use water in flooding quantities as fog. Apply water from as far a distance as possible. Keep run-off water out of sewers and water sources.Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.Advice for firefighters: Wear self contained breathing apparatus for fire fighting if necessary. |
| 保管条件 | Keep well closed and protected from light.Plug tight and store in a place away from direct sunlight.Conditions for safe storage, including any incompatibilities: Keep container tightly closed in a dry and well-ventilated place. Air and light sensitive. |
| 清掃方法 | Environmental Considerations: Land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. Cover solids with a plastic sheet to prevent dissolving in rain or fire fighting water. Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash, cement powder, or commercial sorbents. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./Environmental Considerations: Water spill: Use natural barriers or oil spill control booms to limit spill travel. Use natural deep water pockets, excavated lagoons, or sand bag barriers to trap material at bottom. Remove trapped material with suction hoses.Environmental Considerations: Air spill: Apply water spray or mist to knock down vapors.Accidental Release Measures. Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Methods and materials for containment and cleaning up: Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal. |
| 非火災時の漏出対応 | Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: |
| 処分方法 | SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air qualitypotential migration in soil or watereffects on animal and plant lifeand conformance with environmental and public health regulations.The following wastewater treatment technologies have been investigated for Hydroquinone: Concentration process: Reverse osmosis.The following wastewater treatment technologies have been investigated for Hydroquinone: Concentration process: Activated carbon.Hydroquinone is a waste chemical stream constituent which may be subjected to ultimate disposal by controlled incineration.For more Disposal Methods (Complete) data for HYDROQUINONE (6 total), please visit the HSDB record page. |
| 漏出処分 | Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into covered sealable containers. Carefully collect remainder. Then store and dispose of according to local regulations. |
| Preventive Measures | Work clothing that becomes wet or significantly contaminated should be removed and replaced.Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premises.The worker should immediately wash the skin when it becomes contaminated.SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.For more Preventive Measures (Complete) data for HYDROQUINONE (11 total), please visit the HSDB record page. |
| 体内負荷 | During an environmental benzene exposure assessment for parent-child pairs in Rouen, France, hydroquinone, a urinary metabolite of benzene, was detected in urine samples collected from a group of parents and their children. The parent's urine samples (n = 22) contained a mean hydroquinone concentration of 2.50 mg/L while the children's samples (n = 21) contained a mean concentration of 1.11 mg/L(1). |
| 相互作用 | Possible interactions between hydroquinone and phenol, two known benzene metabolites, in inducing micronuclei in mouse bone marrow cells were investigated. Hydroquinone and phenol administered alone gave weak and negative results, at the doses tested. However, simultaneous administration of both compounds caused a considerable increase in the induction of micronuclei as well as an increase in bone marrow toxicity. Using 3 different statistical methods, it was shown that the observed joint effect was significantly higher than additive interaction, and was close to multiplicative interaction. These findings bring further support to the hypothesis that the toxic and genotoxic effects of benzene are produced by several metabolites acting synergistically.Phenol, when administered together with (14)C hydroquinone, significantly stimulated the covalent binding of (14)C hydroquinone oxidation products to blood (p< 0.001) and bone marrow (p< 0.05) macromolecules, but had no significant effect on covalent binding of (14)C hydroquinone oxidation products to liver and kidney macromolecules (p> 0.05). Catechol, on the other hand, had no effect on the binding of (14)C hydroquinone oxidation products in either bone marrow, kidney or liver (p> 0.05). When hydroquinone was administered together with (14)C phenol, a stimulation of the covalent binding of phenol oxidation products to bone marrow macromolecules also occurred (p< 0.05).Modifying effects of catechol resorcinol and hydroquinone on second stage hepato- and renal carcinogenesis was investigated in rats pretreated with N-ethyl-N-hydroxyethyl-nitrosamine (EHEN). Groups of twenty 6-week-old Wistar/Crj male rats were treated with 0.1% N-ethyl-N-hydroxyethyl-nitrosamine in the drinking water for 3 weeks. Starting 1 week after the termination of N-ethyl-N-hydroxyethyl-N-nitrosamine treatment they were given a diet containing 0.8% catechol, 0.8% resorcinol or 0.8% hydroquinone or basal diet for 36 weeks. Further groups of 15 rats were each treated with the same doses of phenolic compounds or basal diet alone without N-ethyl-N-hydroxyethyl-N-nitrosamine pretreatment. ... At the end of week 40 histopathological assessment revealed significant reduction of the numbers per rat of hepatocellular adenonas and hepatocellular carcinomas by resorcinol whereas hydroquinone significantly enhanced the numbers per rat of renal microadenomas and renal cell tumors. On the other hand the number of alpha 2u-globulin positive tubules in the animals treated with hydroquinone was significantly lower than controls without any alteration in bromodeoxyuridine incorporation. Lipid peroxidation as evaluated by thiobarbituric acid reactive substance was at control levels in the kidneys of rats treated with hydroquinone throughout the experiment. The results showed that the known renal carcinogen hydroquinone potently enhances the second stage of N-ethyl-N-hydroxyethyl-N-nitrosamine-induced renal carcinogenesis, while its isomer resorcinol inhibited hepatocarcinogenesis.The effects of diethylnitrosamine on hydroquinone induced hepatic enzyme altered foci were studied. Male Sprague-Dawley-rats were injected with 40 mg/kg diethylnitrosamine followed 24 to 48 hr later by a single dose by gavage of hydroquinone. The presence of foci positive for glutathione-S-transferase-P activity was determined after 1 week by immunohistochemistry. Hepatocytes isolated from rats that had been treated with diethylnitrosamine, hydroquinone, and phenobarbital were immunostained for gamma-glutamyl-transpeptidase activity. For studies of enzyme induction rats were treated daily with hydroquinone for 3 days and the activities of several oxidative enzymes measured. Treatment with diethylnitrosamine andhydroquinone resulted in a dose dependent increase in the area ofenyme altered foci and a dose independent increase in the number of enzyme altered foci. Diethylnitrosamine and hydroquinone treatment also resulted in a decrease in the number of glutathione-S-transferase-P positive cells. The toxicity of hydroquinone was potentiated in-vitro by pretreatment with diethylnitrosamine. A glutathione and dose dependent increase in the percentage of gamma-glutamyl-transpeptidase positive cells as a function of time was seen. Hydroquinone demonstrated only minor effects in the induction of oxidative enzymes. These results support a synergistic effect of hydroquinone and diethylnitrosamine on the reduction of enzyme altered foci precursor cells but they do not support selective damage of enzyme altered foci cells by hydroquinone. |
| 標的器官 | Eyes, skin, respiratory system, central nervous system |
| 生態毒性値 | EC50Species: Chlorococcales (Green algae)Conditions: freshwater, staticConcentration: 17000 ug/L for 24 hrEffect: physiologyassimilation efficiency /formulation/Species: Dunaliella tertiolecta (Green algae)Conditions: freshwater, static, 24 °C, pH 6.8, salinity 2.348%,Concentration: 29250 ug/L for 24 hrEffect: population, decreased photosynthesis /formulation/Species: Selenastrum capricormutum (algae)Concentration: 0.335 mg/L for 72 hrEffect: growth /Conditions of bioassay not specified in source examined/Species: Daphnia magna (Water flea) age 6-24 hrConditions: freshwater, static, 20 °C, pH > or =7.0Concentration: 320 ug/L for 24 hr (95% confidence interval: 270-380 ug/L)Effect: intoxication, immobilization /formulation/For more Ecotoxicity Values (Complete) data for HYDROQUINONE (22 total), please visit the HSDB record page. |
| 環境中動態 | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 240(SRC), determined from a strucure estimation method(2), indicates that hydroquinone is expected to have moderate mobility in soil(SRC). Volatilization of hydroquinone from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.7X10-11 atm-cu m/mole(SRC), derived from its vapor pressure, 2.4X10-5 mm Hg(3), and water solubility, 7.2X10+4 mg/L(4). Hydroquinone is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). The compound may be removed from soil by oxidation processes(5,6) or by direct photolysis on the surface(7,8). In a survey of standardized tests, hydroquinone was found to biodegrade in the coupled units test, the Zahn-Wellens test, the MITI test, the Sturm test, the AFNOR test, the OECD screening test and the closed bottle test, although its biodegradation is likely to be strongly concentration-dependent. It may be inhibitory at high concentration(9,10).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 240(SRC), determined from a structure estimation method(2), indicates that hydroquinone is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 4.7X10-11 atm-cu m/mole(SRC), derived from its vapor pressure, 2.4X10-5 mm Hg(4), and water solubility, 7.2X10+4 mg/L(5). According to a classification scheme(6), an estimated BCF of 3(SRC), from its log Kow(7) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). In a survey of standardized tests, hydroquinone was found to biodegrade in the coupled units test, the Zahn-Wellens test, the MITI test, the Sturm test, the AFNOR test, the OECD screening test and the closed bottle test, although its biodegradation is likely to be strongly concentration-dependent. It may be inhibitory at high concentration(8,9).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), hydroquinone, which has a vapor pressure of 2.4X10-5 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase hydroquinone is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC)the half-life for this reaction in air is estimated to be 17 hrs(SRC), calculated from its rate constant of 2.3X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase hydroquinone may be removed from the air by wet and dry deposition(SRC). The water solubility of hydroquinone, 72,000 mg/L at 25 °C(4), indicates that it may undergo atmospheric removal by wet deposition processes(SRC). It may also be removed from the atmosphere by a gas-phase reaction with nitrate radicals, an important nighttime oxidant(3). Hydroquinone contains chromophores that absorb at wavelengths >290 nm(5) and, therefore, may be susceptible to direct photolysis by sunlight(SRC). |
| 食品調査値 | Hydroquinone is present in several foods such as wheat products, fruits, and beverages including coffee, teas, beer, and wine(1). Hydroquinone was detected in trace amounts in a mixture of extractable organic substances from New Zealand honeys from unifloral manuka (Leptospermum scoparium) and nodding thistle (Carduus nutans)(2,3). |
| 有害作用 | Methemoglobinemia - The presence of increased methemoglobin in the bloodthe compound is classified as secondary toxic effectAdverse Effects Include |
| 暴露経路 | The substance can be absorbed into the body by inhalation, through the skin and by ingestion.inhalation, ingestion, skin and/or eye contact |
| 毒性の概要 | The CIR Expert Panel concluded that hydroquinone is safe at concentrations of less than or equal to 1% for cosmetic formulations designed for discontinuous, brief use followed by rinsing from the skin and hair. Hydroquinone is safe for use in nail adhesives and in artificial nail coatings, as a polymerization inhibitor, that are cured by LED light. Hydroquinone is unsafe for use in other leave-on cosmetic products.The ingredient is unsafe for use in cosmeticsIDENTIFICATION AND USE: Hydroquinone (HQ) is an aromatic compound in the form of light tan to gray crystals. It is a high-volume commodity chemical used as a reducing agent, antioxidant, polymerization inhibitor, chemical stabilizer, chemical intermediate, and photographic reducer and developer. It is also used in skin lighteners, in cosmetics, hair dye, glue, and a medication to treat dyschromias. HUMAN EXPOSURE: A great deal of research has been conducted with HQ because it is a metabolite of benzene. In workers engaged in the manufacture, HQ dust oxidizes to brown benzoquinone. This material causes pigmentation of the eye and, in some cases, permanent corneal damage. There are reported cases of keratitis and discoloration of the conjunctiva among men exposed to concentrations ranging from 10 to 30 mg of vapor or dust of HQ per cubic meter of air. Ingestion of 1 g by an adult has caused dizziness, sense of suffocation, increased rate of respiration, vomiting, pallor, muscular twitching, headache, dyspnea, cyanosis and collapse and eventually death due to respiratory failure. Upon ingestion urine is green or brownish-green in color and continues to darken on standing. Five hundred forty-four (544) crewmen aboard a large USA Navy vessel developed GI disease characterized by acute onset of nausea, vomiting, abdominal cramps, and diarrhea which was found to be due to hydroquinone contamination of the chilled water system by automatic photo developing machines on the ship. HQ is only weakly positive in in vivo chromosomal assays when expected human exposure routes are used. Chromosomal effects are increased significantly when parenteral or in vitro assays are used. Hydroquinone impairs several leukocyte cell functions, which alter the immune response. It evokes pro-inflammatory properties in endothelial cells that are triggered by the enhancement of NF-kappaB nuclear translocation-dependent gene transcription. Parenteral administration of HQ is associated with changes in several hematopoietic and immunologic endpoints. This toxicity is more severe when combined with parenteral administration of phenol. It is likely that oxidation of HQ within the bone marrow compartment to the semiquinone or p-benzoquinone (BQ), followed by covalent macromolecular binding, and is critical to these effects. Bone marrow and hematologic effects are generally not characteristic of HQ exposures in animal studies employing routes of exposure other than parenteral. Enhanced Ras signaling increases both hydroquinone-mediated growth inhibition in yeast and genotoxicity in mammalian hematopoietic suggesting that HQ toxicity is modulated by Ras signaling and individuals with abnormal Ras signaling could be more vulnerable to developing myeloid diseases after exposure. Hydroquinone also increases proliferation of CFU-GM progenitor cells in mice with Nf1 null bone marrow relative to WT, the same cell type associated with benzene-associated leukemia. It is confirmed animal carcinogen with unknown relevance to humans. ANIMAL STUDIES: In cancer bioassays, HQ has reproducibly produced renal adenomas in male rats. The mechanism of tumorigenesis is unclear but probably involves a species-, strain-, and sex-specific interaction between renal tubule toxicity and an interaction with the chronic progressive nephropathy that is characteristic of aged male rats. Mouse liver tumors (adenomas) and mononuclear cell leukemia (female rat) have also been reported following HQ exposure, but their significance is uncertain. Various tumor initiation/promotion assays with HQ have shown generally negative results. In two-year studies in rats of each sex given hydroquinone in deionized water by gavage, nearly all male rats and most female rats in all vehicle control and dosed groups had nephropathy. The severity of this disease was judged to be greater in high dose male rats. The data on the effect of HQ on development are conflicting, with several studies reporting minimal to no treatment -related effects on duration of gestation, mean litter size, fetal viability, or lactation index in rats fed diets containing HQ. However, one study reports that female rats fed 0.5 g of hydroquinone in their diet during pregnancy had higher rates of fetal resorption than controls (100% versus 41% of the dams), and a greater number of the total implantations were resorbed (27% versus 11%). HQ was not mutagenic in Salmonella typhimurium strains TA98, TA100, TA1535, or TA1537 with or without exogenous metabolic activation. It induced trifluorothymidine resistance in mouse L5178Y/TK lymphoma cells in the presence or absence of metabolic activation, and induced sister chromatid exchanges in Chinese hamster ovary cells both with or without exogenous metabolic activation and caused chromosomal aberrations in the presence of activation. HQ also induced aneuploidy in yeast by delaying the cell cycle at the G2/M transition. |
| 生態毒性抜粋 | /AQUATIC SPECIES/ Sea bass (Dicentrarchus labrax) were injected intraperitoneally once (single dose) or three times (fractionated dose) with phenol or OH-phenols (hydroquinone, resorcinol, and pyrocatechol). On the basis of the lethal doses, OH-phenols were more toxic than phenol, and pyrocatechol was the most powerful compound. Hematological, metabolic and antioxidant blood parameters were measured 3 days after the end of the treatment. Metabolic variations as specific effects on erythrocytes were revealed and differences between single and fractionated doses were observed. OH-phenols-treated fish showed disorders in the metabolic toxicity indicators as hypoglycemia, low blood urea nitrogen level (BUN) and decrease of alkaline phosphatase activity (ALP). |
| Plant Concentrations | Hydroquinone occurrence in foods(1).[Table#1672] |
| Animal Concentrations | Hydroquinone may play an important part in the defense mechanisms of a number of insects, including the bombadier beetle (Carabidae) and the earwig (Forficula auricularia)(1). |
| TSCA 要件 | Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Hydroquinone is included on this list. Effective date 10/04/84Sunset date: 10/04/94. |
| 大気基準 | This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Hydroquinone is produced, as an intermediate or final product, by process units covered under this subpart.Listed as a hazardous air pollutant (HAP) generally known or suspected to cause serious health problems. The Clean Air Act, as amended in 1990, directs EPA to set standards requiring major sources to sharply reduce routine emissions of toxic pollutants. EPA is required to establish and phase in specific performance based standards for all air emission sources that emit one or more of the listed pollutants. Hydroquinone is included on this list. |
| CERCLA 報告数量 | Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 100 lb or 45.4 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. Hydroquinone is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 500 or 10,000 lbs. Extremely hazardous substances that are solids are subject to either of two threshold planning quantities ... The lower quantity applies only if the solid exists in powdered form and has a particle size less than 100 micronsor is handled in solution or in molten formor meets the criteria for a National Fire Protection Association (NFPA) rating of 2, 3 or 4 for reactivity. If the solid does not meet any of these criteria, it is subject to the upper ... threshold planning quantity ... . |
| 州飲料水ガイドライン | (FL) FLORIDA 280 ug/L |
| 職業暴露限界（OEL） | Ceiling: 2 mg/m3 [15-minute] |
| 水環境危害等級（WGK） | 3 |
| 生命健康即時危険濃度 | 50 mg/m3 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | MX3500000 |
| 輸送番号（UN） | 2662 |
| 毒性 | LD50 orally in rats: 320 mg/kg (Woodard) |
| PRTR法 | 第一種指定化学物質 |
| 税関コード | 29072210 |
| 危険文句（R） | 22-40-41-43-50-68-R68-R50-R43-R41-R40-R22 |
| 化審法 | (3)-543 優先評価化学物質 |
| 安衛法 | 変異原性物質 |
| 危険表示 | Xn,N |
| 安全措置（S） | 26-36/37/39-61-S61-S36/37/39-S26 |
| 危険等級 | 9Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1Carc. 2Eye Dam. 1Muta. 2Skin Sens. 1B |
| 包装等級 | III |
| 自然発火温度 | 930 °F |
| 環境リスク評価 | ヒドロキノン(123-31-9) |
| 貯蔵分類 | 11 - Combustible Solids |
| 有害物質データ | 123-31-9(Hazardous Substances Data) |
用途
解説
二価フェノールの一つ。ハイドロキノン、キノールともよばれる。ヒドロキノンの名は、キノンに水素（2原子）がついた組成をもつことを意味している。カテコールやレゾルシンはヒドロキシ基-OHの位置が異なる異性体である。分子式C6H6O2、分子量110.1。以前はアニリンを酸化してp(パラ)-ベンゾキノンにしたのちに、亜硫酸により還元して製造していたが、現在ではベンゼンとプロピレンからジイソプロピルベンゼン法により製造している。この方法では、ヒドロキノンとレゾルシン（m(メタ)-ジヒドロキシベンゼン）の両方ができる（図）。無色の針状結晶。熱水、エタノール（エチルアルコール）、エーテルなどにはよく溶けるが、冷水には100ミリリットルに対して5.8グラムしか溶けない。還元性をもち、とくにアルカリ性水溶液は還元性が強い。写真現像剤、酸化防止剤としての用途をもつ。医薬部外品であり、クリーム・軟膏(なんこう)として使われているが、発癌(はつがん)性が疑われていて、2％以上の高濃度の配合は制限されている。［廣田 穰 2015年7月21日］
用途
白黒写真現像液の材料。
用途
写真用、分析用還元剤。
用途
写真現像薬、ゴム酸化防止剤、染料等の中間合成原料
用途
写真用、有機合成原料、重合防止剤。
用途
電球、軽合金のメッキ
説明
Hydroquinone (HQ) is produced by the oxidation of aniline or phenol, by the reduction of quinone, or from a reaction of acetylene and carbon monoxide. Hydroquinone occurs naturally as a glucose ether, also known as arbutin, in the leaves of many plants and in fruits, as well as one of the agents used in the defense mechanism of the bombardier beetle, family Carabidae.
使用
hydroquinone is a pigment-lightening agent used in bleaching creams. Hydroquinone combines with oxygen very rapidly and becomes brown when exposed to air. Although it occurs naturally, the synthetic version is the one commonly used in cosmetics. Application to the skin may cause allergic reaction and increase skin sun sensitivity. Hydroquinone is potentially carcinogenic and is associated with causing ochronosis, a discoloration of the skin. The u.S. FDA has banned hydroquinone from oTC cosmetic formulations, but allows 4 percent in prescription products. Its use in cosmetics is prohibited in some european countries and in Australia.
製法・合成法
調製方法
There are three current manufacturing processes for Hydroquinone (HQ): oxidative cleavage of diisopropylbenzene, oxidation of aniline, and hydroxylation of phenol.Diisopropylbenzene is air oxidized to the intermediate diisopropylbenzene bishydroperoxide. This hydroperoxide is purified by extraction and reacted further to form hydroquinone. The purified product is isolated by filtration and packaged. The process can be almost entirely closed, continuous, computer-controlled, and monitored.HQcan also be prepared by oxidizing aniline to quinone in the presence of manganese dioxide and sulfuric acid. p-Benzoquinone is then reduced to HQ using iron oxide. The resulting hydroquinone is crystallized and dried. The process occurs in a closed system.HQis also manufactured by hydroxylation of phenol using hydrogen peroxide as a hydroxylation agent. The reaction is catalyzed by strong mineral acids or ferrous or cobalt salts.
合成方法
Hock法
純化方法
Crystallise quinol from acetone, *benzene, EtOH, EtOH/*benzene, water or acetonitrile (25g in 30mL), preferably under nitrogen. Dry it under vacuum. [Wolfenden et al. J Am Chem Soc 109 463 1987, Beilstein 6 H 836, 6 IV 5712.]