N-Acetyl-4-hydroxyaniline 对乙酰胺基苯酚

CAS 103-90-2 MFCD00002328

化学结构图

103-90-2
SMILES: CC(=O)Nc1ccc(O)cc1

化学属性

Mol. FormulaC8H9NO2
Mol. Weight151.16
Melting Point168-172°C
Density1.293
TSCAYes
Solubility溶于水(14 g/l at 20 °C), 乙醇 (100 mM), 二甲基亚砜(100 mM), 甲醇(50 mg/ml), and 二甲基甲酰胺.
Stability对光敏感
Boiling Point273.17 °C at 760 mmHg

别名和识别编码

Chemical NameN-Acetyl-4-hydroxyaniline
Synonym Acetaminophen {LY} Acetaminophen {} {LY} Acetaminophen {} {} {LY} Acetaminophen {} {} {} {LY} Acetaminophen {} {} {} {} {LY} Acetaminophen {} {} {} {} {} {LY} Acetaminophen {} {} {} {} {} {} {LY} Acetaminophen {} {} {} {} {} {} {} {LY} Acetaminophen {} {} {} {} {} {} {} {} {LY} Acetaminophen {} {} {} {} {} {} {} {} {} {LY} Acetaminophen {} {} {} {} {} {} {} {} {} {} {LY} Acetaminophen {} {} {} {} {} {} {} {} {} {} {} {LY} Acetaminophen {} {} {} {} {} {} {} {} {} {} {} {} {LY} Acetaminophen {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Acetaminophen {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Acetaminophen {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Acetaminophen {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Acetaminophen {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {}
Beilstein Registry Number13,460
CAS Number103-90-2
EC Number203-157-5
MDL NumberMFCD00002328
Reaxys-RN2208089
Merck Number47
PubChem Substance ID1983
Chemical Name Translation对乙酰胺基苯酚
Wiswesser Line NotationQR DMV1
LabNetwork Molecule IDLN00195030
InChIInChI=1S/C8H9NO2/c1-6(10)9-7-2-4-8(11)5-3-7/h2-5,11H,1H3,(H,9,10)
Canonical SMILESO=C(C)NC1=CC=C(O)C=C1
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分类

  • {SNA} Analytical Standards, Analytical/Chromatography, Chromatography, Pharmaceutical Standards, Pharmacopeia Standards, USP Standards, USP Standards A - B
  • {SNA} Analytical Standards,
  • {SNA} APIs & Metabolites, APIs (Active Pharmaceutical Ingredients) & Metabolites, Acetaminophen / Paracetamol,
  • Analytical Standards, Analytical/Chromatography, Chromatography, Pharmaceutical Secondary Standards, Pharmaceutical Standards
  • {SNA} Analytical Standards, Chromatography, Pharmaceutical Standards, Pharmacopeia Standards, USP Standards, USP Standards A - B, 分析/色谱
  • {SNA} APIs & Metabolites, APIs (Active Pharmaceutical Ingredients) & Metabolites, Acetaminophen / Paracetamol, Ad

产品应用

  • 有机合成中间体,过氧化氢的稳定剂,照相化学药品,非抗炎解热镇痛药。

相关文献及参考

  • [2]. Dini? M, et al. Lactobacillus fermentum Postbiotic-induced Autophagy as Potential Approach for Treatment ofAcetaminophen Hepatotoxicity. Front Microbiol. 2017 Apr 6;8:594.
  • [3]. Uchida NS, et al. Hepatoprotective Effect of Citral on Acetaminophen-Induced Liver Toxicity in Mice. Evid Based Complement Alternat Med. 2017;2017:1796209.
  • [4]. Rothen JP, et al. Acetaminophen is an inhibitor of hepatic N-acetyltransferase 2 in vitro and in vivo. Pharmacogenetics. 1998 Dec;8(6):553-9.
  • Merck:14,47
  • Merck:14,47 Beilstein:13,460
  • [1]. Hinz, B, et al. Acetaminophen (paracetamol) is a selective cyclooxygenase-2 inhibitor in man. FASEB J, 2008. 22(2): p. 383-90.
  • [1]. Hinz, B, et al. Acetaminophen (paracetamol) is a selective cyclooxygenase-2 inhibitor in man. FASEB J, 2008. 22(2): p. 383-90.
  • [2]. Dini? M, et al. Lactobacillus fermentum Postbiotic-induced Autophagy as Potential Approach for Treatment ofAcetaminophen Hepatotoxicity. F

安全信息

Precautionary statements
  • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
  • P260 Do not breathe dust/fume/gas/mist/vapours/spray. 不要吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P305+P351+P338
  • P280 Wear protective gloves/protective clothing/eye protection/face protection. 戴防护手套/防护服/眼睛的保护物/面部保护物。
  • P273 Avoid release to the environment. 避免释放到环境中。
  • P302+P352
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
  • P405 Store locked up. 上锁保管。
  • P270 Do not eat, drink or smoke when using this product. 使用本产品时不要吃东西,喝水或吸烟。
  • P391 Collect spillage. Hazardous to the aquatic environment 收集对水环境有危害的泄漏物。
  • P301+P312+P330
  • P308+P311
  • P201 Obtain special instructions before use. 使用前获取专门指示。
  • P281 Use personal protective equipment as required. 使用所需的个人防护装备。
  • P202 Do not handle until all safety precautions have been read and understood. 已阅读并理解所有的安全预防措施之前,切勿操作。
GHS Symbol
WGK Germany1
Signal word
Hazard statements
  • H315 Causes skin irritation 会刺激皮肤
  • H335 May cause respiratory irritation 可能导致呼吸道刺激
  • H302 Harmful if swallowed 吞食有害
  • H319 Causes serious eye irritation 严重刺激眼睛
RTECSAE4200000
UN Number 3077
Safety Statements
  • S37/39 Wear suitable gloves and eye/face protection 穿戴适当的手套和眼睛/面保护;
  • S36 Wear suitable protective clothing 穿戴适当的防护服;
  • S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 眼睛接触后,立即用大量水冲洗并征求医生意见;
  • S61 Avoid release to the environment. Refer to special instructions/safety data sheet 避免释放到环境中,参考特别指示/安全收据说明书;
Risk Statements
  • R52/53
  • R22 Harmful if swallowed 吞咽有害
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
  • R36/38 Irritating to eyes and skin 对眼睛和皮肤有刺激性
Personal Protective Equipment dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes Xn
Packing GroupIII
Storage condition Store at room temperature {LY} Store at room temperature {} {LY} Store at room temperature {} {} {LY} Store at room temperature {} {} {} {LY} Store at room temperature {} {} {} {} {LY} Store at room temperature {} {} {} {} {} {LY} Store at room temperature {} {} {} {} {} {} { {} {} {} {} {} {} {LY} Store at room temperature {} {} {} {} {} {} {} {LY} Store at room temperature {} {} {} {} {} {} {} {} {LY} Store at room temperature {} {} {} {} {} {} {} {} {} {LY} Store at room temperature {} {} {} {} {} {} {} {} {} {} {LY} Store at room temperature {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {LY} Store at room temperature {} {} {} {} {} {} {} {} {} {} {} {} {LY} Store at room temperature {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Store at room temperature {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Store at room temperature {} {} {} {} {} {} {} {} {} {}
Hazard Class9
TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 164 gm/kg/78W-C
TOXIC EFFECTS :
   Tumorigenic - Carcinogenic by RTECS criteria
   Kidney, Ureter, Bladder - tumors
REFERENCE :
   ACPADQ Acta Pathologica, Microbiologica et Immunologica Scandinavica,
   Section A: Pathology. (Munksgaard International Pub., POB 2148, DK-1016
   Copenhagen K, Denmark)  V.90-95, 1982-87.  Volume(issue)/page/year:
   93,367,1985

TYPE OF TEST            : TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 270 gm/kg/77W-C
TOXIC EFFECTS :
   Tumorigenic - equivocal tumorigenic agent by RTECS criteria
   Liver - tumors
   Endocrine - other changes
REFERENCE :
   CRNGDP Carcinogenesis (London). (Oxford Univ. Press, Pinkhill House,
   Southfield Road, Eynsham, Oxford OX8 1JJ, UK)  V.1-    1980-
   Volume(issue)/page/year: 4,363,1983

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 135 gm/kg/77W-C
TOXIC EFFECTS :
   Tumorigenic - Carcinogenic by RTECS criteria
   Liver - hepatitis (hepatocellular necrosis), zonal
   Liver - tumors
REFERENCE :
   CRNGDP Carcinogenesis (London). (Oxford Univ. Press, Pinkhill House,
   Southfield Road, Eynsham, Oxford OX8 1JJ, UK)  V.1-    1980-
   Volume(issue)/page/year: 4,363,1983

TYPE OF TEST            : TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 329 gm/kg/78W-C
TOXIC EFFECTS :
   Tumorigenic - Carcinogenic by RTECS criteria
   Liver - tumors
REFERENCE :
   ACPADQ Acta Pathologica, Microbiologica et Immunologica Scandinavica,
   Section A: Pathology. (Munksgaard International Pub.,

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 310 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   HUTODJ Human Toxicology.  (Macmillan Press Ltd., Houndmills, Basingstoke,
   Hants., RG 21 2XS, UK) V.1-    1981-  Volume(issue)/page/year: 3,13S,1984

TYPE OF TEST            : LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Human - child
DOSE/DURATION           : 50 mg/kg
TOXIC EFFECTS :
   Cardiac - other changes
   Lungs, Thorax, or Respiration - acute pulmonary edema
   Kidney, Ureter, Bladder - changes in tubules (including acute renal failure,
   acute tubular necrosis)
REFE

TYPE OF TEST            : LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Human - man
DOSE/DURATION           : 714 mg/kg
TOXIC EFFECTS :
   Liver - other changes
REFERENCE :
   HUTODJ Human Toxicology.  (Macmillan Press Ltd., Houndmills, Basingstoke,
   Hants., RG 21 2XS, U

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Human - child
DOSE/DURATION           : 801 mg/kg
TOXIC EFFECTS :
   Behavioral - general anesthetic
   Gastrointestinal - nausea or vomiting
   Liver - other changes
REFERENCE :
   PEDIAU Pediatrics.  (American Academy of Pediatrics, P.O. Box 1034,
   Evanston, IL 60204) V.1-    1948-  Volume(issue)/page/year: 61,68,1978

TYPE OF TEST            : LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Human
DOSE/DURATION           : 357 mg/kg
TOXIC EFFECTS :
   Behavioral - anorexia (human)
   Behavioral - coma
   Gastrointestinal - nausea or vomit

TYPE OF TEST            : LD50 -

TYPE OF TEST            : Mutation in microorganisms
TEST SYSTEM             : Bacteria - Salmonella typhimurium
DOSE/DURATION           : 100 ug/disc
REFERENCE :
   JNUDAT Journal of Nihon University School of Dentistry.  (Nihon University
   School of Dentistry, 1-8-13 Surugadai, Kanda, Chiyoda-ku, Tokyo, 101, Japan)
    V.1-    1958-  Volume(issue)/page/year: 34,183,1992

TYPE OF TEST            : DNA inhibition
TEST SYSTEM             : Human Lymphocyte
DOSE/DURATION           : 300 umol/L
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 261,1,1991

TYPE OF TEST            : Cytogenetic analysis
ROUTE OF EXPOSURE       : Oral
TEST SYSTEM             : Human
DOSE/DURATION           : 42860 ug/

TYPE OF TEST            : Micronucleus test
ROUTE OF EXPOSURE       : Intraperitoneal
TEST SYSTEM             : Rodent - mouse
DOSE/DURATION           : 100 mg/kg
REFERENCE :
   JPMSAE Journal of Pharmaceutical Sciences.  (American Pharmaceutical Assoc.,
   2215 Constitution Ave., NW, Washington, DC 20037)  V.50-    1961-
   Volume(issue)/page/year: 80,761,1991

TYPE OF TEST            : Micronucleus test
ROUTE OF EXPOSURE       : Oral
TEST SYSTEM             : Human
DOSE/DURATION           : 42857 ug/kg/8H (Intermittent)
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 227,147,1989

TYPE OF TEST            : Unscheduled DNA synthesis
TEST SYSTEM             : Rodent - mouse Liver
DOSE/DURATION           : 7500 umol/L
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 164,167,1986

TYPE OF TEST            : Mutation test systems - not otherwi

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Human - woman
DOSE                    : 417 mg/kg
SEX/DURATION            : female 20 week(s) after conception
TOXIC EFFECTS :
   Reproductive - Specific Developmental Abnormalities - craniofacial
   (including nose and tongue)
   Reproductive - Specific Developmental Abnormalities - hepatobiliary system
REFERENCE :
   BJOGAS British Journal of Obstetrics and Gynaecology.  (Blackwell Scientific
   Pub. Ltd., POB 88, Oxford, UK)  V.82-    1975- Volume(issue)/page/year:
   91,286,1984

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - mouse
DOSE                    : 600 mg/kg
SEX/DURATION            : male 1 day(s) pre-mating
TOXIC EFFECTS :
   Reproductive - Paternal Effects - spermatogenesis (incl. genetic material,
   sperm morphology, motility, and count)
   Reproductive - Paternal Effects - testes, epididymis, sperm duct
REFERENCE :
   TOXID9 Toxicologist.  (Soc. of Toxicology, Inc., 475 Wolf Ledge Parkway,
   Akron, OH 44311) V.1-    1981-  Volume(issue)/page/year: 4,170,1984

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSUR

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 1500 mg/kg
SEX/DURATION            : female 8-19 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Fertility - post-implantation mortality (e.g. dead and/or
   resorbed implants per total number of implants)
   Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death,
   e.g., stunted fetus)
REFERENCE :
   JPMSAE Journal of Pharmaceutical Sciences.  (American Pharmaceutical Assoc.,
   2215 Constitution Ave., NW, Washington, DC 20037)  V.50-    1961-
   Volum

其他信息

  • 上游原料:盐酸 --> 乙酸 --> 乙酐 --> 铁粉 --> 亚硫酸氢钠 --> 活性炭 --> 氧化镁 --> 焦亚硫酸钠 --> 4-氨基苯酚 --> 对羟基苯乙酮 --> 二苯甲酮腙
  • 图谱信息:N-乙酰对氨基酚(103-90-2)红外图谱(IR1) N-乙酰对氨基酚(103-90-2)核磁图( 13 CNMR) N-乙酰对氨基酚(103-90-2)质谱(MS) N-乙酰对氨基酚(103-90-2)Raman光谱 N-乙酰对氨基酚(103-90-2)核磁图( 1 HNMR) N-乙酰对氨基酚(103-90-2)红外图谱(IR2)
  • Acros Organics:对乙酰氨基酚 4-Acetamidophenol, 98%(103-90-2)
  • 用途三:有机合成中间体,过氧化氢的稳定剂,照相化学药品,非抗炎解热镇痛药。
  • Alfa Aesar:4-乙酰胺基苯酚,98% 4-Acetamidophenol, 98%(103-90-2)
  • 海关编码:29242930
  • MSDS 信息:4-Acetamidophenol(103-90-2).msds
  • 用途一:用作解热、镇痛、抗风湿药
  • N-乙酰对氨基酚价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2011/08/23 30001224 4-乙酰氨基酚 25g 35元 2011/04/16 H0190 4'-羟基乙酰苯胺 4'-Hydroxyacetanilide 25G 155元 2011/04/16 H0190 4'-羟基乙酰苯胺 4'-Hydroxyacetanilide 500G 567元
  • 用途二:该品为解热镇痛药,国际非专有药名为Paracetamol。它是最常用的非抗炎解热镇痛药,解热作用与阿司匹林相似,镇痛作用较弱,无抗炎抗风湿作用,是乙酰苯胺类药物中最好的品种。特别适合于不能应用羧酸类药物的病人。用于感冒、牙痛等症。对乙酰氨基酚也是有机合成中间体,过氧化氢的稳定剂,照相化学药品。
  • 水中溶解度: 14 g/l (20°C) 溶于乙醇、丙酮、甲醇、DMF, 二氯乙烷和乙酸乙酯,实际上不溶于石油醚、戊烷和苯。
  • TCI Shanghai:4-羟基乙酰苯胺 4'-Hydroxyacetanilide,>;98.0%(LC)(N)(103-90-2)
  • Sigma Aldrich:103-90-2(sigmaaldrich)
  • 下游产品:(6R,7R)-3-[[(1-甲基-1H-四唑-5-基)硫]甲基]-7-[(R)-2-(4-乙基-2,3-二氧代-1-哌嗪甲酰氨基)-2-对羟基苯基-乙酰氨基]-8-氧代-5-硫杂-1-氮杂双环[4.2.0]辛-2-烯-2-甲酸 --> 非那西丁 --> 奥苯达唑 --> 地芬尼泰 --> 5-苄氧基吲哚-2-甲酸乙酯 --> 硝硫氰醚 --> 3-[(对乙酰氨基)苯氧基]-1,2-环氧丙烷 --> 氯乙酸-4-乙酰氨基苯酯 --> 6-(乙酰氨基)-2,3-二氢-4H-1-苯并吡喃-4酮 --> 6-氟-4-二氢色原酮
  • 方法一:对氨基酚乙酰化而得。方法1:将对氨基酚加入稀乙酸中,再加入冰醋酸,升温至150℃反应7h,加入乙酐,再反应2h,检查终点,合格后冷却至25℃以下,甩滤,水洗至无乙酸味,甩干,得粗品。方法2:将对氨基酚、冰醋酸及含酸50%以上的酸母液一起蒸馏,蒸出稀酸的速度为每小时馏出总量的十分之一,待内温升至130℃以上,取样检查对氨基酚残留量低于2.5%,加入稀酸(含量50%以上),冷却结晶。甩滤,先用少量稀酸洗涤,再用大量水洗至滤液接近无色,得粗品。方法1的收率为90%,方法2的收率为90-95%。精制方法:将水加热至近沸时投入粗品。升温至全溶,加入用水浸泡过的活性炭,用稀乙酸调节至pH=4.2-4.6,沸腾10min。压滤,滤液加少量重亚硫酸钠。冷却至20℃以下,析出结晶。甩滤,水洗,干燥得原料药扑热息痛成品。其他的生产方法还有:(1)在冰醋酸中用锌还原对硝基苯酚,同时乙酰化得到对乙酰氨基酚;(2)将对羟基苯乙酮生成的腙,置于硫酸酸性溶液中,加入亚硝酸钠,转位生成对乙酰氨基酚。
  • 常规方法:密闭保存。
  • MOL 文件:1

系列性分类