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ヒドロキノン

ヒドロキノン 化学構造式
123-31-9
CAS番号.
123-31-9
化学名:
ヒドロキノン
别名:
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;キノール;テノックスHQ;4-ヒドロキシフェノール;1,4-ベンゼンジオール;p-ジヒドロキシベンゼン;p-ヒドロキノン;1,4-ジヒドロキシベンゼン;p-ヒドロキシフェノール;エルドパク;エルドキン;アルトラ;ハイドロキノン
英語化学名:
Hydroquinone
英語别名:
HQ;he5;HE 5;Artra;diak5;QUINOL;Diak 5;Melanex;tenoxhq;Phiaquin
CBNumber:
CB6717931
化学式:
C6H6O2
分子量:
110.11
MOL File:
123-31-9.mol

ヒドロキノン 物理性質

融点 :
172-175 °C(lit.)
沸点 :
285 °C(lit.)
比重(密度) :
1.32
蒸気密度:
3.81 (vs air)
蒸気圧:
1 mm Hg ( 132 °C)
屈折率 :
1.6320
闪点 :
165 °C
貯蔵温度 :
Store below +30°C.
溶解性:
H2O: 50 mg/mL, clear
外見 :
Needle-Like Crystals or Crystalline Powder
酸解離定数(Pka):
10.35(at 20℃)
色:
White to off-white
水溶解度 :
70 g/L (20 ºC)
Sensitive :
Air & Light Sensitive
Merck :
14,4808
BRN :
605970
Henry's Law Constant:
(x 10-9 atm?m3/mol): <2.07 at 20 °C (approximate - calculated from water solubility and vapor pressure)
暴露限界値:
NIOSH REL: 15-min ceiling 2, IDLH 50; OSHA PEL: TWA 2; ACGIH TLV: TWA 2 (adopted).
安定性::
Stable. Combustible. Incompatible with strong oxidizing agents, strong bases, oxygen, ferric salts. Light and air-sensitive. Discolours in air.
InChIKey:
QIGBRXMKCJKVMJ-UHFFFAOYSA-N
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)
IARC:
3 (Vol. 15, Sup 7, 71) 1999
EPAの化学物質情報:
Hydroquinone (123-31-9)
安全性情報
  • リスクと安全性に関する声明
  • 危険有害性情報のコード(GHS)
主な危険性  Xn,N
Rフレーズ  22-40-41-43-50-68-R68-R50-R43-R41-R40-R22
Sフレーズ  26-36/37/39-61-S61-S36/37/39-S26
RIDADR  2662
WGK Germany  3
RTECS 番号 MX3500000
自然発火温度 930 °F
TSCA  Yes
国連危険物分類  9
容器等級  III
HSコード  29072210
有毒物質データの 123-31-9(Hazardous Substances Data)
毒性 LD50 orally in rats: 320 mg/kg (Woodard)
化審法 (3)-543 優先評価化学物質
安衛法 変異原性物質
PRTR法 第一種指定化学物質
絵表示(GHS)
注意喚起語 Danger
危険有害性情報
コード 危険有害性情報 危険有害性クラス 区分 注意喚起語 シンボル P コード
H302 飲み込むと有害 急性毒性、経口 4 警告 P264, P270, P301+P312, P330, P501
H317 アレルギー性皮膚反応を起こすおそれ 感作性、皮膚 1 警告 P261, P272, P280, P302+P352,P333+P313, P321, P363, P501
H318 重篤な眼の損傷 眼に対する重篤な損傷性/眼刺激 性 1 危険 P280, P305+P351+P338, P310
H341 遺伝性疾患のおそれの疑い 生殖細胞変異原性 2 警告 P201,P202, P281, P308+P313, P405,P501
H351 発がんのおそれの疑い 発がん性 2 警告 P201, P202, P281, P308+P313, P405,P501
H400 水生生物に強い毒性 水生環境有害性、急性毒性 1 警告 P273, P391, P501
H410 長期的影響により水生生物に非常に強い毒性 水生環境有害性、慢性毒性 1 警告 P273, P391, P501
注意書き
P201 使用前に取扱説明書を入手すること。
P273 環境への放出を避けること。
P280 保護手袋/保護衣/保護眼鏡/保護面を着用するこ と。
P305+P351+P338 眼に入った場合:水で数分間注意深く洗うこと。次にコ ンタクトレンズを着用していて容易に外せる場合は外す こと。その後も洗浄を続けること。
P308+P313 暴露または暴露の懸念がある場合:医師の診断/手当てを 受けること。
P501 内容物/容器を...に廃棄すること。

ヒドロキノン 価格 もっと(50)

メーカー 製品番号 製品説明 CAS番号 包装 価格 更新時間 購入
富士フイルム和光純薬株式会社(wako) W01W0108-0123 ヒドロキノン 99.0+% (Titration)
Hydroquinone 99.0+% (Titration)
123-31-9 500g ¥4600 2021-03-23 購入
富士フイルム和光純薬株式会社(wako) W01CHDASB-00008358 ハイドロキノン
Hydroquinone
123-31-9 1g ¥18000 2021-03-23 購入
東京化成工業 H0186 ヒドロキノン >99.0%(T)
Hydroquinone >99.0%(T)
123-31-9 25g ¥1600 2021-03-23 購入
東京化成工業 H0186 ヒドロキノン >99.0%(T)
Hydroquinone >99.0%(T)
123-31-9 500g ¥3900 2021-03-23 購入
関東化学株式会社(KANTO) 12091-3A ヒドロキノン
Hydroquinone
123-31-9 10kg ¥58000 2021-03-23 購入

ヒドロキノン 化学特性,用途語,生産方法

外観

白色〜ほとんど白色, 結晶〜結晶性粉末

定義

本品は、次の化学式で表される芳香族化合物である。

溶解性

熱水、エタノール及びジエチルエーテルに溶けやすく、冷水にやや溶けやすい。水, エタノール, エーテルに可溶 : 冷べンゼンに難溶.

解説

1,4-benzenediol.C6H6O2(110.11).C6H4(OH)2.キノールともいう.ベンゾキノンを還元すると得られる.結晶.融点169 ℃,沸点287 ℃(97 kPa).d20"1.332.285 ℃ で昇華する.λmax 225,293 nm(log ε 3.71,3.43).pKa1 9.91,pKa2 12.04(30 ℃,水).水,エタノール,エーテルなどに易溶.水溶液は還元性が強く,写真の現像薬として用いられる.また,同じ理由で,酸化防止剤,重合防止剤ともなる.種々の合成中間体のほか,分析試薬として,リン,ヒ素,ケイ酸の定量にも用いられる.[CAS 123-31-9]
森北出版「化学辞典(第2版)

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

白黒写真現像液の材料。

用途

写真用、分析用還元剤。

用途

電球、軽合金のメッキ

化粧品の成分用途

還元剤、毛髪着色剤、皮膚ブリーチ剤、酸化防止剤、香料

効能

皮膚漂白作用, チロシナーゼ阻害薬

使用上の注意

空気中で次第に着色する。

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.

化学的特性

white needle-like crystals or crystalline powder

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.

物理的性質

Colorless to pale brown, odorless, hexagonal crystals

Originator

Quinnone,Dermohr,US,1980

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.

使用

Photographic reducer and developer; antioxidant; stabilizing agent for some polymers; intermediate in the manufacturing of some dyes and pigments; in cosmetic formulations.

使用

Use as photographic reducer and developer; as reagent in the determination of small quantities of phosphate; as antioxidant. Depigmentor

使用

K channel agonist, antihypertensive

使用

reducing agent prevents polymerization of resin monomers lightens darkened skin, light sensitive

定義

ChEBI: A benzenediol comprising benzene core carrying two hydroxy substituents para to each other.

適応症

Hydroquinone interferes with the production of the pigment melanin by epidermal melanocytes through at least two mechanisms: it competitively inhibits tyrosinase, one of the principal enzymes responsible for converting tyrosine to melanin, and it selectively damages melanocytes and melanosomes (the organelles within which melanin is stored).

調製方法

There are three current manufacturing processes for 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.

Manufacturing Process

Into a pressure reactor there was charged 100 ml of methanol and 1 g of diruthenium nonacarbonyl. The reactor was closed, cooled in solid carbon dioxide/acetone, and evacuated. Acetylene, to the extent of 1 mol (26 g), was metered into the cold reactor. Carbon monoxide was then pressured into this vessel at 835-980 atmospheres, during a period of 16.5 hours; while the reactor was maintained at 100°C to 150°C. The reactor was then cooled to room temperature and opened.
The reaction mixture was removed from the vessel and distilled at a pressure of 30-60 mm, and a bath temperature of 30°C to 50°C until the methanol had all been removed. The extremely viscous tarry residue remaining in the still pot was given a very crude distillation, the distillate boiling at 82°C to 132°C/2 mm. In an attempt to purify this distillate by a more careful distillation, 5.3 g of a liquid distilling from 53°C to 150°C/5 mm was collected. At this point, much solid sublimate was noted not only in this distillate but in the condenser of the still. 7 g of the solid sublimate was scraped out of the condenser of the still. Recrystallization of the sublimate from ethyl acetate containing a small amount of petroleum ether gave beautiful crystals melting at 175°C to 177°C (5 g). Infrared analysis confirmed that this compound was hydroquinone (9% conversion).

brand name

Aida;Ambi- skin tone;Black and white;Creme des 3 fleur d'orient;Eldopaque forte;Eldoquin forte 4% cream;Epocler;Esoterica facial;Esoterica regular;Esoterica sensitive skin;Esoterica sunscreen;Melanex topical sollution;Melpaque hp;Melqui hp;Neostrata aha gel;Neostrata hq;Nuquin hp;Pigmanorm;Porcelana;Sinquin;Solaquin forte sun bleaching;Superfade age spot;Ultraquin plaine.

Therapeutic Function

Depigmentor

世界保健機関(WHO)

Hydroquinone was introduced in 1965 as a topical depigmenting agent for hyperpigmentation. At high concentrations hydroquinone is corrosive and in most countries has been restricted to the level of approximately 2% and limited to the period of less than 2 months. Additional consideration for restrictive action is that animal experiments have also demonstrated carcinogenic and mutagenic potential of hydroquinone.

Synthesis Reference(s)

Chemistry Letters, 14, p. 731, 1985
The Journal of Organic Chemistry, 50, p. 1722, 1985
Tetrahedron Letters, 22, p. 2337, 1981 DOI: 10.1016/S0040-4039(01)82900-2

一般的な説明

Light colored crystals or solutions. May irritate the skin, eyes and mucous membranes. Mildly toxic by ingestion or skin absorption.

空気と水の反応

Darkens on exposure to air and light. Miscible in water. Solutions become brown in air due to oxidation. Oxidation is very rapid in the presence of alkali.

反応プロフィール

Hydroquinone is a slight explosion hazard when exposed to heat. Incompatible with strong oxidizing agents. Also incompatible with bases. Hydroquinone reacts with oxygen and sodium hydroxide. Reacts with ferric salts . Hot and/or concentrated NaOH can cause Hydroquinone to decompose exothermically at elevated temperature. (NFPA Pub. 491M, 1975, 385)

危険性

Toxic by ingestion and inhalation, irritant. Questionable carcinogen.

健康ハザード

Exposures to hydroquinone in large quantities by accidental oral ingestion produce toxicity and poisoning. The symptoms of poisoning include, but are not limited to, blurred speech, tinnitus, tremors, sense of suffocation, vomiting, muscular twitching, headache, convul- sions, dyspnea and cyanosis from methemoglobinemia, coma, and collapse from respira- tory failure. Occupational workers should be allowed to work with protective clothing and dust masks with full-face or goggles to protect the eyes, and under proper management.

健康ハザード

Hydroquinone is very toxic; the 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.

火災危険

Dust cloud may explode if ignited in an enclosed area. Hydroquinone can react with oxidizing materials and is rapidly oxidized in the presence of alkaline materials. Oxidizes in air.

接触アレルゲン

Hydroquinone is used in photography developers (black and white, X-ray, and microfilms), in plastics, in hair dyes as an antioxidant and hair colorant. Hydroquinone is found in many skin bleaching creams.

臨床応用

Hydroquinone is applied topically to treat disorders characterized by excessive melanin in the epidermis, such as melasma. In the United States, nonprescription skin-lightening products contain hydroquinone at concentrations of 2% or less; higher concentrations are available by prescription.

副作用

The incidence of adverse effects with hydroquinone increases in proportion to its concentration. A relatively common side effect is local irritation, which may actually exacerbate the discoloration of the skin being treated. Allergic contact dermatitis occurs less commonly. A rare but more serious complication is exogenous ochronosis, in which a yellow-brown pigment deposited in the dermis results in blue-black pigmentation of the skin that may be permanent.

Carcinogenicity

No case reports of cancer associated with HQ exposure have been published.

Source

Hydroquinone occurs naturally in strawberry tree leaves, pears, blackberries, Chinese alpenrose, bilberries, blackberries, hyacinth flowers, anise, cowberries, and lingonberries (Duke, 1992).

環境運命予測

Biological. In activated sludge, 7.5% mineralized to carbon dioxide after 5 d (Freitag et al., 1985). Under methanogenic conditions, inocula from a municipal sewage treatment plant digester degraded hydroquinone to phenol prior to being mineralized to carbon dioxide and methane (Young and Rivera, 1985). In various pure cultures, hydroquinone degraded to the following intermediates: benzoquinone, 2-hydroxy-1,4-benzoquinone, and β-ketoadipic acid. Hydroquinone also degraded in activated sludge but no products were identified (Harbison and Belly, 1982). Heukelekian and Rand (1955) reported a 5-d BOD value of 0.74 g/g which is 39.2% of the ThOD value of 1.89 g/g. In activated sludge inoculum, following a 20-d adaptation period, 90.0% COD removal was achieved. The average rate of biodegradation was 54.2 mg COD/g?h (Pitter, 1976).
Photolytic. A carbon dioxide yield of 53.7% was achieved when hydroquinone adsorbed on silica gel was irradiated with light (λ >290 nm) for 17 h (Freitag et al., 1985). Chemical/Physical. Ozonolysis products reported are p-quinone and dibasic acids (Verschueren, 1983). Moussavi (1979) studied the autoxidation of hydroquinone in slightly alkaline (pH 7 to 9) aqueous solutions at room temperature. The oxidation of hydroquinone by oxygen followed first-order kinetics that yielded hydrogen peroxide and p-quinone as products. At pH values of 7.0, 8.0, and 9.0, the calculated half-lives of this reaction were 111, 41, and 0.84 h, respectively (Moussavi, 1979).
Chlorine dioxide reacted with hydroquinone in an aqueous solution forming p-benzoquinone (Wajon et al., 1982). Kanno et al. (1982) studied the aqueous reaction of hydroquinone and other substituted aromatic hydrocarbons (aniline, toluidine, 1- and 2-naphthylamine, phenol, cresol, pyrocatechol, resorcinol, and 1-naphthol) with hypochlorous acid in the presence of ammonium ion. They reported that the aromatic ring was not chlorinated as expected but was cleaved by chloramine forming cyanogen chloride. As the pH was lowered, the amount of cyanogen chloride formed increased (Kanno et al., 1982).
At influent concentrations of 1.0, 0.1, 0.01, and 0.001 mg/L, the GAC adsorption capacities were 160, 90, 51, and 29 mg/g, respectively (Dobbs and Cohen, 1980).

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.]

Toxicity evaluation

Benzene, phenol, and hydroquinone are metabolized in vivo to benzoquinone and excreted as the mercapturate, N-acetyl-S- (2,5-dihydroxyphenyl)-L-cysteine. Hydroquinone is a reducing cosubstrate for peroxidase enzymes, and the resultant semiquinone and p-benzoquinone may bind to DNA.

ヒドロキノン 上流と下流の製品情報

原材料

準備製品

抱水クロラール tert-ブチルヒドロキノン 4-クロロ-2,5-ジメトキシアニリン 3,3-ジメチル-4-ペンテン酸エチル フルアジホップ-P-ブチル標準品 アクリル酸ヒドロキシプロピル (2-ヒドロキシプロピルエステル, 2-ヒドロキシ-1-メチルエチルエステル混合物) 4-クロロ-8-(トリフルオロメチル)キノリン t-ブチルヒドロキシアニソール α-シアノアクリル酸ブチル ピレノキシン 2-ジシクロヘキシルホスフィノ-2',4',6'-トリイソプロピルビフェニル 3-メチルスルホレン 2,6-ジクロロ-4-ニトロ-4'-[2-シアノエチル(2-アセトキシエチル)アミノ]アゾベンゼン 1,2,4-トリメトキシベンゼン クロロ(1,5-シクロオクタジエン)イリジウム(I) (ダイマー) 3-スルホレン 2-[4-[[5-(トリフルオロメチル)-2-ピリジニル]オキシ]フェノキシ]プロパン酸ブチル メタクリル酸2-ヒドロキシエチル 2,2-ジメチル-3-(2-メチル-1-プロペニル)シクロプロパン-1-カルボン酸メチル アクリル酸ノニル アゾイックジアゾコンポーネント20 (ベース) 2,3-ジメチル-1,3-ブタジエン 2,5-ジヒドロキシ安息香酸 4-フェノキシフェノール 1,4-ジメトキシベンゼン 1,4-ジアセトキシベンゼン 2,5-ジメトキシアニリン 2,5-ジ-tert-ブチルヒドロキノン 2,2-ジメチル-3-(2-メチル-1-プロペニル)シクロプロパン カルボン酸 エチル キザロホップ-P-エチル標準品 1,2-ナフタル酸無水物 ヘキサン酸アリル 酢酸4-ビニルフェニル

ヒドロキノン 生産企業

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123-31-9(ヒドロキノン)キーワード:


  • 123-31-9
  • Hydroquinone, 99.5%, 99.5%
  • HYDROXYQUINOL
  • HYDROCHINONE
  • HYDROQUINONE
  • AKOS BBS-00004220
  • hydroquinone--1,4-benzenediol
  • Idrochinone
  • Melanex
  • NCI-C55834
  • para-dihydroxybenzene
  • paradioxybenzene
  • para-dioxybenzene
  • para-hydroquinone
  • p-Benzenediol
  • p-dihydroxy-benzen
  • p-Dioxobenzene
  • Phiaquin
  • p-Hydroxybenzene
  • p-Hydroxyphenol
  • p-quinol
  • pyrogentisticacid
  • Solaquin forte
  • Tecquinol
  • Tecquinol tech. grade
  • Tenox HQ
  • tenoxhq
  • Tequinol
  • USAF ek-356
  • usafek-356
  • Hydrochinone 0
  • 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
  • キノール
  • テノックスHQ
  • 4-ヒドロキシフェノール
  • 1,4-ベンゼンジオール
  • p-ジヒドロキシベンゼン
  • p-ヒドロキノン
  • 1,4-ジヒドロキシベンゼン
  • p-ヒドロキシフェノール
  • エルドパク
  • エルドキン
  • アルトラ
  • ハイドロキノン
  • 1,4-ベンゼンジオ-ル
  • ハイドロキノン, 99%
  • p-ベンゼンジオール
  • レドックス触媒 (分子状酸素による酸化)
  • 酸化反応 (分子状酸素による酸化)
  • 有機合成化学
  • 昆虫不妊剤
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