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对苯二酚 | 123-31-9

中文名称
对苯二酚
中文别名
醌醇;1,4-二羟基苯;几奴尼;对羟基苯;;氢醌;孔奴尼;1,4-苯二酚;鸡纳酚;对羟基苯
英文名称
hydroquinone
英文别名
1,4-dihydroxybenzene;1,4-benzenediol;1,4-hydroquinone;quinol;benzene-1,4-diol;p-diphenol;4-hydroxyphenol;p-benzoquinone;p-hydroquinone;4-oxoniophenolate
对苯二酚化学式
CAS
123-31-9
化学式
C6H6O2
mdl
MFCD00002339
分子量
110.112
InChiKey
QIGBRXMKCJKVMJ-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 熔点:
    172-175 °C(lit.)
  • 沸点:
    285 °C(lit.)
  • 密度:
    1.32
  • 蒸气密度:
    3.81 (vs air)
  • 闪点:
    165 °C
  • 溶解度:
    在水中的溶解度50 mg/mL,澄清
  • 暴露限值:
    NIOSH REL: 15-min ceiling 2, IDLH 50; OSHA PEL: TWA 2; ACGIH TLV: TWA 2 (adopted).
  • LogP:
    0.59 at 20℃
  • 物理描述:
    Hydroquinone appears as light colored crystals or solutions. May irritate the skin, eyes and mucous membranes. Mildly toxic by ingestion or skin absorption.
  • 颜色/状态:
    White crystals
  • 气味:
    Odorless
  • 味道:
    A slightly bitter taste in aqueous solutions
  • 蒸汽密度:
    3.81 (EPA, 1998) (Relative to Air)
  • 蒸汽压力:
    1.9X10-5 mm Hg at 25 °C
  • 稳定性/保质期:
    1. 可燃,在空气中见光容易变成褐色,碱性溶液中氧化更快。

    2. 中等毒性。在动物实验中,反复给予30-50毫克/千克剂量可引起急性黄色肝萎缩,除了严重损伤肾脏外,并能导致异常的色素沉着。因此,有时用它涂在人体局部可以去除雀斑。服用1克对苯二酚会引起食道刺激,产生耳鸣、恶心、呕吐、腹痛和虚脱;服用5克则可致死。此外,长期接触对二苯酚蒸气、粉尘或烟雾会刺激皮肤、黏膜,并可能引起眼晶体浑浊。操作现场空气中最高允许浓度为2毫克/立方米。生产设备应封闭,操作人员需穿戴好防护用具。

    3. 在动物试验中,反复给予30~50毫克/千克剂量时,则可引起急性黄色肝萎缩,除了导致严重的肝损伤外,并能引发异常的色素沉着。服用1克本品时,会刺激食道,引起耳鸣、恶心、呕吐、腹痛和虚脱;服用5克则可能致死。

    4. 氢醌有毒且可燃。氢醌还原性很强,极易被氧化成对苯醌氢醌可通过皮肤引起中毒。动物经口致死量为0.08~0.2克/千克。人若口服1克以上会出现急性中毒症状;59克则可能致命。

    5. 稳定。

    6. 禁配物:酰基、酸酐、碱、强氧化剂、强酸。

    7. 避免接触的条件:光照、空气接触。

    8. 聚合危害:不会聚合。

  • 自燃温度:
    960 °F (516 °C)
  • 燃烧热:
    -2.74X10+3 kJ/mol
  • 电离电位:
    7.95 eV
  • 折光率:
    Index of refraction = 1.632 at 25 °C
  • 解离常数:
    pKa = 10.85 at 25 °C
  • 碰撞截面:
    128.79 Ų [M+H]+ [CCS Type: DT, Method: stepped-field]
  • 保留指数:
    1334;1327;1334

计算性质

  • 辛醇/水分配系数(LogP):
    0.6
  • 重原子数:
    8
  • 可旋转键数:
    0
  • 环数:
    1.0
  • sp3杂化的碳原子比例:
    0.0
  • 拓扑面积:
    40.5
  • 氢给体数:
    2
  • 氢受体数:
    2

ADMET

代谢
氢醌通过皮肤吸收,并在体内主要代谢成硫酸盐和葡萄糖醛酸苷结合物,这些结合物通过尿液排出。[DHHS/NTP: 提名档案 氢醌]
Hydroquinone is absorbed through the skin and metabolized primarily to sulfate and glucuronide conjugates, which are excreted in the urine.[DHHS/NTP: Nomination Profile Hydroquinone
来源:Hazardous Substances Data Bank (HSDB)
代谢
大约45 ng(18%)的苯作为微囊代谢产物的对苯二酚绝对回收率已确定。
Absolute recovery of approximately 45 ng (18%) of hydroquinone as microsomal metabolite of benzene was determined.
来源:Hazardous Substances Data Bank (HSDB)
代谢
这项研究调查了氢醌在未经处理和预先处理过的雄性Sprague-Dawley大鼠体内的代谢情况。将(14)C氢醌通过灌胃单次给予5、30或200 mg/kg剂量的未经处理大鼠。将氢醌反复通过灌胃给予雄性大鼠,剂量为200 mg/kg,连续4天,随后单次给予200 mg/kg的(14)C氢醌。在单独的研究中,大鼠在饮食中摄入了5.6%未标记的氢醌,持续2天,或者通过灌胃给予311 mg/kg的(14)C氢醌。单次或多次给药的大鼠(14)C氢醌及其代谢物的排泄模式相似。单次给予200 mg/kg的(14)C氢醌的大鼠在2-4天内通过尿液排出了剂量的91.9%;3.8%通过粪便排出,大约0.4%通过呼出的空气排出,1.2%残留在尸体中。放射性物质广泛分布在整个组织中,肝和肾中的浓度较高。从48小时到96小时,(14)C组织浓度有所下降。尿液中唯一的放射性标记化合物是氢醌(剂量的1.1-8.6%)、氢醌硫酸盐(25-42%)和氢醌葡萄糖醛酸苷(56-66%)。对于通过饲料给予氢醌的大鼠,也观察到了类似的结果。与对照组相比,反复给予200 mg/kg氢醌的大鼠的绝对或相对肝重量、肝微粒体蛋白浓度、细胞色素b-5、细胞色素P450或细胞色素c还原酶活性没有显著增加。与对照组相比,反复给予氢醌的大鼠的细胞色素P450值略有但显著降低。
/This study/ investigated the metabolism of hydroquinone in naive and hydroquinone pretreated male Sprague-Dawley rats. (14)C hydroquinone was administered by gavage in single doses of 5, 30, or 200 mg/kg to naive rats. Hydroquinone was given repeatedly by gavage to male rats at 200 mg/kg for 4 consecutive days followed by a single dose with 200 mg/kg of (14)C hydroquinone. In separate studies rats were fed 5.6% unlabeled hydroquinone in the diet for 2 days or were dosed by gavage with 311 mg/kg (14)C hydroquinone. The excretion patterns of (14)C hydroquinone and its metabolites were similar for rats dosed singly or repeatedly. Rats given a single dose of 200 mg/kg of (14)C hydroquinone excreted 91.9% of the dose in the urine within 2-4 days; 3.8% was excreted in the feces, about 0.4% was excreted in expired air, and 1.2% remained in the carcass. Radioactivity was widely distributed throughout the tissues with higher concentrations in the liver and kidneys. A decrease in (14)C tissue concentrations occurred from 48 to 96 hr. The only radiolabeled compounds in the urine were hydroquinone (1.1-8.6% of the dose), hydroquinone monosulfate (25-42%), and hydroquinone monoglucuronide (56-66%). Similar findings were observed for rats given hydroquinone in the feed. There were no significant increases from controls for absolute or relative liver weights, liver microsomal protein concentrations, cytochrome b-5, cytochrome P450 or cytochrome c reductase activity in rats dosed repeatedly with 200 mg/kg hydroquinone. Cytochrome P450 values were slightly but significantly decreased in rats dosed repeatedly with hydroquinone compared with controls.
来源:Hazardous Substances Data Bank (HSDB)
代谢
当含有苯或的微粒体培养混合物中加入谷胱甘肽时,会形成代谢物2-(S-谷胱甘肽基)氢醌。这个代谢物来源于氢醌的氧化产物苯醌与谷胱甘肽的结合。然而,无论是在体内代谢苯、氢醌的过程中,都没有发现谷胱甘肽结合物或其巯基尿酸生物,N-乙酰-S-(2,5-二羟基苯基)-L-半胱氨酸。为了确定是否在体内产生了羟基化的巯基尿酸,我们用苯(600毫克/千克)、(75毫克/千克)或氢醌(75毫克/千克)处理雄性Sprague-Dawley大鼠,并收集24小时的尿液。高效液相色谱与电化学检测相结合,确认了存在一种与N-乙酰-S-(2,5-二羟基苯基)-L-半胱氨酸在色谱和电化学上相同的代谢物。从尿样中分离出代谢物,并用重氮甲烷处理形成N-乙酰-S-(2,5-二甲氧基苯基)-L-半胱氨酸甲酯衍生物。从这些样品中获得的质谱与该衍生物的真实样品的质谱相同。这些实验的结果表明,苯、氢醌在体内被代谢成苯醌,并以巯基尿酸,N-乙酰-S-(2,5-二羟基苯基)-L-半胱氨酸的形式排出体外。
The metabolite 2-(S-glutathionyl)hydroquinone is formed when a microsomal incubation mixture containing either benzene or phenol is supplemented with glutathione. This metabolite is derived from the conjugation of benzoquinone, an oxidation product of hydroquinone. However, neither the glutathione conjugate or its mercapturate, N-acetyl-S-(2,5-dihydroxyphenyl)-L-cysteine, have been identified as metabolites resulting from in vivo metabolism of benzene, phenol, or hydroquinone. To determine if a hydroxylated mercapturate is produced in vivo, we treated male Sprague-Dawley rats with either benzene (600 mg/kg), phenol (75 mg/kg), or hydroquinone (75 mg/kg) and collected the urine for 24 hr. HPLC coupled with electrochemical detection confirmed the presence of a metabolite that was chromatographically and electrochemically identical to N-acetyl-S-(2,5-dihydroxyphenyl)-L-cysteine. The metabolite was isolated from the urine samples and treated with diazomethane to form the N-acetyl-S-(2,5-dimethoxyphenyl)-L-cysteine methyl ester derivative. The mass spectra obtained from these samples were identical to that of an authentic sample of the derivative. The results of these experiments indicate that benzene, phenol, and hydroquinone are metabolized in vivo to benzoquinone and excreted as the mercapturate, N-acetyl-S-(2,5-dihydroxyphenyl)-L- cysteine.
来源:Hazardous Substances Data Bank (HSDB)
代谢
氢醌的人类已知代谢物。
Hydroquinone is a known human metabolite of phenol.
来源:NORMAN Suspect List Exchange
毒理性
  • 毒性总结
识别和使用:氢醌(HQ)是一种具有从浅棕到灰色晶体形态的芳香化合物。它是一种高产量商品化学品,用作还原剂、抗氧化剂、聚合抑制剂化学稳定剂、化学中间体,以及摄影减量和显影剂。它还用于皮肤增白剂、化妆品、染发剂、胶和治疗色素异常的药物。人类暴露:由于HQ是苯的代谢物,因此进行了大量研究。在从事制造工作的工人中,HQ粉尘氧化成棕色的苯醌。这种材料会导致眼睛色素沉着,在某些情况下,还会造成永久性角膜损伤。有报道称,暴露于每立方米空气中含有10至30毫克HQ蒸汽或粉尘的男性出现了角膜炎和结膜变黑的情况。成年人摄入1克HQ会导致头晕、窒息感、呼吸频率增加、呕吐、苍白、肌肉抽搐、头痛、呼吸困难、发绀和衰竭,最终因呼吸衰竭而死亡。摄入后尿液呈绿色或棕绿色,并在静置时颜色会变深。在一艘大型美国海军舰艇上的544名船员出现了急性发作的恶心、呕吐、腹痛和腹泻,这些症状被发现是由于舰艇上的自动照片冲洗机污染了冷系统中的氢醌。当使用预期的人类暴露途径时,HQ在体内染色体分析中仅呈弱阳性。当使用parenteral或体外分析时,染色体的效果显著增加。氢醌损害了几种白细胞细胞功能,改变了免疫反应。它在内皮细胞中引发促炎症特性,这是通过增强NF-kappaB核易位依赖性基因转录触发的。HQ的parenteral给药与几种造血和免疫终点的变化有关。当与的parenteral给药结合使用时,这种毒性更为严重。HQ在骨髓室中氧化成半醌或p-苯醌(BQ),随后与共价大分子结合,这是这些效果的关键。在动物研究中,使用非parenteral暴露途径的骨髓和造血效应通常不是HQ暴露的特征。增强Ras信号既增加了酵母中氢醌介导的生长抑制,也增加了哺乳动物造血中的遗传毒性,表明HQ的毒性受到Ras信号的调节,异常Ras信号的个人在暴露后可能更容易发展髓系疾病。氢醌还增加了小鼠Nf1空骨 marrow 中CFU-GM祖细胞的增殖,与WT相比,与苯相关的白血病相同的细胞类型。它是一种已确认的动物致癌物,对人类的相关性未知。动物研究:在癌症生物分析中,HQ可靠地产生了雄性大鼠的肾腺瘤。肿瘤发生机制尚不清楚,但可能涉及物种、品系和性别特异性的肾小管毒性以及与老年雄性大鼠特有的慢性进行性肾病之间的相互作用。还有报道称,在暴露于HQ后,小鼠肝脏肿瘤(腺瘤)和雌性大鼠的单核细胞白血病,但它们的意义尚不确定。各种使用HQ的肿瘤启动/促进分析通常显示出阴性结果。在每性别的大鼠中,通过灌胃给予去离子中的氢醌,几乎所有雄性大鼠和大多数雌性大鼠在所有载体对照和给药组中都有肾病。这种疾病的严重程度在高剂量雄性大鼠中被认为是更大的。关于HQ对发育影响的数据是相互矛盾的,有几项研究报告称,在饮食中含有HQ的大鼠在怀孕期间、平均窝产仔数、胎儿存活率或哺乳指数方面几乎没有或没有治疗相关的影响。然而,一项研究报告称,在怀孕期间饮食中添加0.5克氢醌的雌性大鼠的胎儿吸收率高于对照组(100%对41%的母体),并且更多的总着床被吸收(27%对11%)。在存在或不存在外源代谢激活的情况下,HQ在鼠伤寒沙门氏菌TA98、TA100、TA1535或TA1537株中不具有诱变性。它在存在或不存在代谢激活的情况下,诱导小鼠L5178Y/TK淋巴瘤细胞对三氟胸苷的抗性,并诱导中国仓鼠卵巢细胞姐妹染色单体交换,在激活的情况下引起染色体畸变。HQ还通过延迟细胞周期在G2/M转变,诱导酵母的非整倍体。
IDENTIFICATION 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.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 致癌性证据
评估:对于氢醌在人类中的致癌性,证据不足。在实验动物中,氢醌的致癌性证据有限。总体评估:氢醌的致癌性对人体不可分类(第3组)。
Evaluation: There is inadequate evidence in humans for the carcinogenicity of hydroquinone. There is limited evidence in experimental animals for the carcinogenicity of hydroquinone. Overall evaluation: Hydroquinone is not classifiable as to its carcinogenicity to humans (Group 3).
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 致癌性证据
A3;已确认对动物有致癌性,但对人类的相关性未知。
A3; Confirmed animal carcinogen with unknown relevance to humans.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 致癌物分类
国际癌症研究机构致癌物:氢醌
IARC Carcinogenic Agent:Hydroquinone
来源:International Agency for Research on Cancer (IARC)
毒理性
  • 致癌物分类
国际癌症研究机构(IARC)致癌物分类:第3组:对其对人类的致癌性无法分类
IARC Carcinogenic Classes:Group 3: Not classifiable as to its carcinogenicity to humans
来源:International Agency for Research on Cancer (IARC)
吸收、分配和排泄
氢醌的毒理学评估报告中提到,有几份报告表明氢醌通过口服途径相对快速地被吸收,包括一项涉及大鼠摄入含有3%氢醌的显影液的研究。此外,在给予CD和F344大鼠350毫克/千克的剂量后,血液中的吸收率超过90%,在1小时内观察到峰值平。[DHHS/NTP: 氢醌提名简介]
A toxicology review of hydroquinone noted several reports indicating relatively rapid absorption of hydroquinone via the oral route, including a study involving rats that ingested 3% hydroquinone in developer solution. In addition, in CD and F344 rats dosed with 350 mg/kg, >90% absorption was measured in blood levels, with peak levels observed within 1 hr.[DHHS/NTP: Nomination Profile Hydroquinone
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
静脉(iv)给药放射性标记的氢醌后,在大鼠的骨髓和胸腺中在2小时内检测到放射性(氢醌或其代谢物),给予1.2-12 mg/kg。在大鼠的肝脏和骨髓中,放射性可持续检测到24小时。无论是单次还是重复口服给药,放射性在大鼠的各种组织中都有发现,其中肝脏和肾脏的浓度最高。在狗中静脉给药放射性标记的氢醌后,在皮肤、肝脏和肠道中发现了放射性。当小鼠通过腹腔(ip)注射给予75 mg/kg的放射性标记的氢醌时,放射性在肝脏、肾脏、血液和骨髓中的蛋白质上以共价键结合的形式被检测到,肝脏的特定活性比骨髓高10倍...[DHHS/NTP: 氢醌提名简介]
Following intravenous (iv) administration of radiolabeled hydroquinone, radioactivity (either hydroquinone or a metabolite) was detected within 2 hr in bone marrow and thymus of rats given 1.2-12 mg/kg. Radioactivity was also detected in the liver and bone marrow of these rats up to 24 hr. Whether given in single or repeated oral doses, radioactivity was found in various rat tissues, with the highest concentrations in the liver and kidneys. Following i.v. administration of radiolabeled hydroquinone in dogs, radioactivity was found in the skin, liver, and intestine. When mice were administered 75 mg/kg radiolabeled hydroquinone by intraperitoneal (ip) injection, radioactivity was detected covalently bound to proteins in the liver, kidneys, blood, and bone marrow, with 10-fold higher specific activity in the liver than in the bone marrow...[DHHS/NTP: Nomination Profile Hydroquinone
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
当2%[(14)C]-氢醌以未指定的乳膏形式施用于人类前臂(n = 4名男性)时,氢醌迅速并持续地进入角质层,并且在0.5小时内就能在血浆样本中检测到放射性标记。在8小时的血浆采样期间,氢醌平在4小时时达到峰值(0.04当量/mL)。在6名男性志愿者的额头上应用2%乳膏24小时后,尿液中氢醌的回收率为45.3%(标准差= 11.2%)。[DHHS/NTP:氢醌提名档案]
When 2% [(14)C]-hydroquinone was administered to human forearms (n = 4 males) in an unspecified cream, hydroquinone moved rapidly and continuously into the stratum corneum and radiolabel was detected in plasma samples within 0.5 hr. Over an 8 hr plasma sampling period, hydroquinone levels peaked at 4 hr (0.04 equivalents/ mL). Following application of the 2% cream on the foreheads of 6 male volunteers for 24 hr, the recovery of hydroquinone in urine was 45.3% (SD = 11.2%).[DHHS/NTP: Nomination Profile Hydroquinone
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
人体对氢醌的吸收在局部应用时比口服给药效率低。当以尿液排出形式测量氢醌的吸收时,在志愿者(每种制剂6名男性)的前额涂抹24小时的2.0%酒精溶液后,报告的平均透皮吸收率为57%(标准差=11%),在12小时内达到排泄高峰,5天内完全排泄。添加防晒霜(3.0% Escalol 507)显著降低了吸收率(26%,标准差=14%),而添加渗透增强剂(0.5% Azone)在防晒霜存在与否的情况下均未显著增加吸收(分别为35%,标准差=17%和66%,标准差=13%)。[DHHS/NTP:氢醌提名档案]
Human absorption of hydroquinone upon topical application is less efficient than with oral administration. When absorption was measured as elimination 10 of hydroquinone via urine following application (2.0% in alcohol) to the foreheads of human volunteers (6 males per preparation) for 24 hr, the average percutaneous absorption reported was 57% (SD = 11%) with peak elimination within 12 hr and complete elimination by 5 days. The addition of a sunscreen (3.0% Escalol 507) significantly decreased the absorption (26%, SD = 14%), and the addition of a penetration enhancer (0.5% Azone) did not significantly increase absorption in the presence or absence of the sunscreen (35%, SD = 17% and 66%, SD = 13%, respectively).[DHHS/NTP: Nomination Profile Hydroquinone
来源:Hazardous Substances Data Bank (HSDB)

安全信息

  • 职业暴露限值:
    Ceiling: 2 mg/m3 [15-minute]
  • TSCA:
    Yes
  • 危险等级:
    9
  • 立即威胁生命和健康浓度:
    50 mg/m3
  • 危险品标志:
    Xn
  • 安全说明:
    S26,S36/37/39,S61
  • 危险类别码:
    R40,R43,R22,R68,R50,R41
  • WGK Germany:
    3
  • 海关编码:
    2907221000
  • 危险品运输编号:
    2662
  • 危险类别:
    9
  • RTECS号:
    MX3500000
  • 包装等级:
    III
  • 危险标志:
    GHS05,GHS07,GHS08,GHS09
  • 危险性描述:
    H302,H317,H318,H341,H351,H410
  • 危险性防范说明:
    P201,P273,P280,P305 + P351 + P338 + P310,P308 + P313
  • 储存条件:
    1. 采用聚乙烯塑料袋包装,每袋5kg,4袋装一木箱;或使用圆木箱内衬塑料袋包装,每桶50kg。应存放在阴凉、干燥处,避免日光直射和潮湿,防潮并注意防热。根据有毒物品的规定进行运输与储存。 2. 储存时请注意:存放于阴凉且通风良好的仓库中,并远离火源和热源。包装需密封,确保不与空气接触。应将该物质与其他氧化剂、酸类、碱类及食用化学品分开存放,避免混合存储。同时配备相应的消防设备,并在储区准备合适材料以处理泄漏情况。

SDS

SDS:ef5e7cfadb7d631cdeb6fec7a8f4d99a
查看
国标编号: 61725
CAS: 123-31-9
中文名称: 1,4-苯二
英文名称: p-Dihydroxybenzene;p-Hydroquinone
别 名: 对苯二酚氢醌
分子式: C 6 H 6 O 2 ;HOC 6 H 4 OH
分子量: 110.11
熔 点: 170.5℃
密 度: 相对密度(=1)1.33;
蒸汽压: 165℃
溶解性: 溶于,易溶于乙醇乙醚
稳定性: 稳定
外观与性状: 白色结晶
危险标记: 15(毒害品)
用 途: 制取黑白显影剂、蒽醌染料、偶氮染料、橡胶防老剂、稳定剂和抗氧剂


2.对环境的影响:

一、健康危害

侵入途径:吸入、食入、经皮吸收。 健康危害:毒性比大,对皮肤、粘膜有强烈的腐蚀作用,可抑制中枢神经系统或损害肝、皮肤功能。 急性中毒:吸入高浓度蒸气,可致头痛、头昏、乏力、视物模糊、肺肿等;误服可出现头痛、头晕、耳鸣、苍白、紫绀、恶心、呕吐、腹育、呼吸困难、心动过速、尺厥、谵妄和虚脱 ,严重者呕血、血尿、溶血性黄疸,甚至可致死。 慢性影响:长期低浓度吸入,可致头痛、头晕、咳嗽、食欲减退、恶心、呕吐等。皮肤可引起皮炎。

二、毒理学资料及环境行为

急性毒性:LD50 320mg/kg(大鼠经口);人经口5000mg/kg,死亡。 刺激性:人经皮:250mg (24小时),轻度刺激。 亚急性和慢性毒性:动物亚急性中毒表现为溶血性黄疸、贫血、白细胞增多、红细胞脆性增加、低血糖、皮毛无光泽和明显的恶病质。 致突变性:微生物致突变性:鼠伤寒沙门氏菌2umol/皿。微核试验:人淋巴细胞75umol/L。性染色体缺失和不分离:人淋巴细胞6mg/kg。DNA损伤:人骨髓500mol/L。 生殖毒性:大鼠经口最低中毒剂量(TDL0):2500mg/kg(孕1~22天),致植入后的死亡率(51天,雄性),影响睾丸、附睾、输精管、前列腺、精囊等,对雄性生育指数有影响。 致癌性:IARC致癌性评论:动物不明确,人类无可靠数据。

危险特性:遇明火、高热可燃。与强氧化剂可发生反应。受高热分解放出有毒的气体。 燃烧(分解)产物:一氧化碳二氧化碳


3.现场应急监测方法:
4.实验室监测方法:

气相色谱法,参照《分析化学手册》(第四分册,色谱分析),化学工业空气中:样品经滤器收集后,用酸洗脱,再用高压液相色谱法测定(NIOSH法)高效液相色谱法测定焦化废中的酚类化合物[刊]/张万让等//新疆环境保护1989,(1).-49~52


5.环境标准:
前苏联(1975) 作业环境空气中有害物质的允许浓度 2mg/m 3
前苏联(1978) 地面中最高容许浓度 0.2mg/L
前苏联(1975) 排放标准 0.5mg/L
中嗅觉阈浓度 5mg/L


6.应急处理处置方法:

一、泄漏应急处理

隔离泄漏污染区,周围设警标志,建议应急处理人员戴好防毒面具,穿化学防护服。不要直接接触泄漏物,避免扬尘,用清洁的铲子收集于干燥净洁有盖的容器中,运至废物场所。也可以用大量冲洗,经稀释的洗放入废系统。如大量泄漏,收集回收或无害处理后废弃。 废弃物处置方法:用焚烧法。焚烧炉排出的气体通过洗涤器除去有害成份。

二、防护措施

呼吸系统防护:空气中浓度超标时,必须佩带防毒面具。紧急事态抢救或逃生时,佩带自给式呼吸器。 眼睛防护:戴化学安全防护眼镜。 防护服:穿相应的防护服。 手防护:戴防化学品手套。 其它:工作现场禁止吸烟、进食和饮。工作后,彻底清洗。单独存入被毒物污染的衣服,洗后再用。注意个人清洁卫生。

三、急救措施

皮肤接触:立即脱去污染的衣着,用甘油、聚乙烯乙二醇或聚乙烯乙二醇酒精混合液(7:3)抹擦。然后用彻底冲洗。或立即用冲洗至少15分钟。就医。 眼睛接触:立即提起眼睑,用流动清或生理盐冲洗至少15分钟。就医。 吸入:迅速脱离现场至空气新鲜处。保持呼吸道通畅。呼吸困难时给输氧。呼吸停止时,立即进行人工呼吸。就医。 食入:患者清醒时立即给饮植物油15~30ml。催吐,尽快彻底洗胃。就医。

灭火方法:雾状、泡沫、二氧化碳、干粉、砂土。

废弃物处置方法:用焚烧法。焚烧炉排出的气体通过洗涤器除去有害成份。


制备方法与用途

化学性质

对苯二酚又称氢醌或1.4-苯二,分子式C6H6O2,分子量为110.11。无色或白色结晶,在空气中暴露易变色;其溶液在空气中能氧化成褐色,碱性介质中氧化速度更快。熔点为170~171℃,沸点为285~287℃,相对密度为1.33215,在中UVλmax为288nm。对苯二酚易溶于热乙醇乙醚,微溶于苯。它化学性质活泼,容易被氧化,并可发生酯化和取代等反应。

用途

对苯二酚是一种重要的有机显影剂,需在较强碱性溶液中才能发挥作用。其还原速度较米吐尔缓慢,但影像一旦显现,则密度增长迅速,能获得较大反差。27~29℃温度下显影最快,低于15℃时变缓,低于5℃则几乎停止。多用可使照片产生暖色调。主要用于普通照相显影剂、物理显影及再显影还原剂,并常与菲尼酮米吐尔混合使用。

用途

对苯二酚除草剂喹禾灵吡氟禾草灵噻唑禾草灵噁唑禾草灵禾草灵乳氟禾草灵的中间体,也是医药和染料中间体。对苯二酚及其烷基化物广泛用作单体贮运过程中的阻聚剂,常用浓度约为200ppm。对苯二酚甲醚是食用油抗氧剂BHA的中间体;对苯二酚甲醚用作染料有机颜料香料的中间体;而对苯二酚乙醚则用于制备感光色素染料,还用于合成N,N'-二苯基对苯二胺,后者是橡胶及汽油的抗氧剂和抗臭剂。

用途

除了上述应用,对苯二酚还可用于比色法测定等元素;在的极谱法和容量法中测定其含量;作为杂多酸的还原剂;的还原剂;检验磷酸盐、酸盐、硝酸盐亚硝酸盐等物质;用作显影剂及抗氧剂,用于化肥工业中的脱硫剂以及尿素增效剂。

生产方法

对苯二酚传统上采用苯胺法生产,但目前工业上还发展了邻苯二酚联产法、异丙苯法和双酚A法。我国当前主要使用苯胺法进行工业化生产。具体步骤如下:首先在硫酸介质中用二氧化锰氧化苯胺生成对苯醌;然后经铁粉还原产生对苯二酚,随后通过浓缩、脱色、结晶及干燥工序最终制得成品。工业级对苯二酚含量需≥99%,而照相级的则要求≥99.5%。

生产方法
  1. 硝基苯为原料,进行加氢反应,并加热制备得到。
  2. 利用苯酚双氧水氧化合成邻苯二酚对苯二酚,再分别分离出这两种化合物。
类别

有毒物品

  • 毒性分级:高毒
  • 急性毒性
    • 大鼠口服LD50: 320 毫克/公斤;
    • 小鼠口服LD50: 245 毫克/公斤
  • 刺激数据
    • 皮肤接触(人):5%浓度导致重度刺激
燃烧与储存特性

可燃性危险特性

  • 明火下可燃,遇氧化剂或氢氧化钠反应;燃烧时释放出刺激性烟雾

储运特性

  • 应存放在通风、低温和干燥的仓库中
  • 须与氧化剂及食品添加剂分开存放
灭火方法

使用二氧化碳、泡沫灭火器、干粉灭火器、砂土或雾状进行扑灭。

职业健康标准
  • 时间加权平均浓度(TWA):2 毫克/立方米
  • 短时间接触极限(STEL):4 毫克/立方米

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量
  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

点击查看最新优质反应信息

文献信息

  • Additives and products including oligoesters
    申请人:——
    公开号:US20030199593A1
    公开(公告)日:2003-10-23
    The present invention relates to oligoesters and their use or the creation of additives. Oligoester containing additives and/or oligoesters themselves may be used for formulating pharmaceutical preparations, cosmetics or personal care products such as shampoos and conditioners. These oligoesters are particularly useful for the creation of multi-purpose additives that can impart conditioning, long substantivity and/or UV protection. Individual oligoesters and oligoester mixtures are described.
    本发明涉及寡酯及其用途或添加剂的制备。含有寡酯的添加剂和/或寡酯本身可用于配制药物制剂、化妆品或个人护理产品,如洗发和护发素。这些寡酯对于制备能够赋予调理、长效性和/或紫外线保护的多功能添加剂特别有用。描述了单独的寡酯和寡酯混合物。
  • Deoxygenation of Polyhydroxybenzenes:  An Alternative Strategy for the Benzene-Free Synthesis of Aromatic Chemicals
    作者:Chad A. Hansen、J. W. Frost
    DOI:10.1021/ja0176346
    日期:2002.5.1
    e requires 2 enzyme-catalyzed and 2 chemical steps. By contrast, synthesis of hydroquinone using the shikimate pathway and intermediacy of quinic acid requires 18 enzyme-catalyzed steps and 1 chemical step. Methylation of triacetic acid lactone, cyclization, and regioselective deoxygenation of phloroglucinol methyl ether affords resorcinol. Given the ability to synthesize triacetic acid lactone from
    葡萄糖和芳香族化学品(如连苯三对苯二酚间苯二酚)之间建立了新的合成联系。这种方法的核心是从 1,2,3,4-四羟基苯、羟基氢醌间苯三酚甲基醚中去除一个氧原子,分别形成连苯三氢醌间苯二酚。脱氧是通过起始多羟基苯的 Rh 催化氢化,然后是推定的二氢中间体的酸催化脱来完成的。连苯三合成包括将葡萄糖转化为肌醇,氧化为肌 2-肌糖,脱为 1,2,3,4-四羟基苯,以及脱氧形成连苯三。通过 myo-2-inosose 合成连苯三需要 4 个酶催化和 2 个化学步骤。为了比较,通过没食子酸中间体和莽草酸途径从葡萄糖合成连苯三需要至少 20 个酶催化步骤。一种新的对苯二酚的无苯合成采用将葡萄糖转化为 2-脱氧青蟹肌糖,将该肌糖为羟基氢醌,然后脱氧形成对苯二酚。通过 2-脱氧青蟹肌糖合成氢醌需要 2 个酶催化和 2 个化学步骤。相比之下,使用莽草酸途径和奎尼酸中间体合成对苯二酚需要
  • [EN] PREPARATION AND USES OF REACTIVE OXYGEN SPECIES SCAVENGER DERIVATIVES<br/>[FR] PRÉPARATION ET UTILISATIONS DE DÉRIVÉS PIÉGEURS D'ESPÈCES RÉACTIVES DE L'OXYGÈNE
    申请人:XW LAB INC
    公开号:WO2019033330A1
    公开(公告)日:2019-02-21
    Compounds of Formula (I) a or (I) b: including certain quinone derivatives, and the corresponding pharmaceutical compositions, which may serve to modulate ferroptosis in a subject. Also disclosed herein are the preparations of these compounds and pharmaceutical compositions and their potential uses in the manufacture of a medicament in reducing reactive oxygen species (ROS) in a cell and for preventing, treating, ameliorating certain related disorder or a disease.
    公式(I) a或(I) b的化合物:包括某些醌衍生物,以及相应的药物组合物,可以用于调节受试者中的死亡。本文还披露了这些化合物和药物组合物的制备方法,以及它们在制造药物中用于减少细胞中的活性氧化物(ROS)并预防、治疗、改善某些相关疾病或疾病的潜在用途。
  • New Drug Delivery System for Crossing the Blood Brain Barrier
    申请人:Lipshutz H. Bruce
    公开号:US20070203080A1
    公开(公告)日:2007-08-30
    New ubiquinol analogs are disclosed, as well as methods of using these compounds to deliver drug moieties to the body.
    新的泛醌类似物被披露,以及利用这些化合物将药物基团输送到人体的方法。
  • Efficient synthesis of α-substituted-α-arylmethyl phosphonates using trichloroacetimidate C C coupling method
    作者:Walid Fathalla、Pavel Pazdera、Samir El-Rayes、Ibrahim.A.I. Ali
    DOI:10.1016/j.tet.2018.02.033
    日期:2018.4
    A simple convenient protocol for the synthesis of diethyl α,α-diaryl methylphosphonate derivatives 5a-f, 6b-f, 7a-f and 8a-f, diethyl α-alkenyl α-aryl methylphosphonates 9a-d and 10a-d and α-(oxoalkyl) α-aryl methylphosphonate 11a-d and 12a-d is described. Trichloroacetimidates 3a-d were treated with activated arenes, styrene, allyltrimethylsilane or silylenol ethers C-nucleophiles in the presence
    用于合成α,α-二芳基甲基膦酸二乙酯生物5a-f,6b-f,7a-f和8a-f,二乙基α-烯基α-芳基甲基膦酸酯9a-d和10a-d和α-的简单便捷方案描述了(氧代烷基)α-芳基甲基膦酸酯11a-d和12a-d。Trichloroacetimidates 3a-d中,用活化的芳烃苯乙烯,烯丙基三甲基硅烷或silylenol醚处理Ç -nucleophiles在存在加入TMSOTf,得到良好的产率和较短的反应时间所需产物。
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表征谱图

  • 氢谱
    1HNMR
  • 质谱
    MS
  • 碳谱
    13CNMR
  • 红外
    IR
  • 拉曼
    Raman
hnmr
mass
cnmr
ir
raman
  • 峰位数据
  • 峰位匹配
  • 表征信息
Shift(ppm)
Intensity
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Assign
Shift(ppm)
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测试频率
样品用量
溶剂
溶剂用量
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