N-Ethylmaleimide N-乙基马来酰亚胺

CAS 128-53-0 MFCD00005509

化学结构图

128-53-0
SMILES: CCN1C(=O)C=CC1=O

化学属性

Mol. FormulaC6H7NO2
Mol. Weight125.13
Boiling Point210 °C at 760 mmHg
Melting Point43-46°C
Flash Point73°(163°F)
TSCAYes
Solubility1 G/L (20 ºC)
Density1.207
Stability对光敏感

别名和识别编码

Chemical NameN-Ethylmaleimide
CAS Number128-53-0
Synonym N-Ethylmaleimide {LY} N-Ethylmaleimide {} {LY} N-Ethylmaleimide {} {} {LY} N-Ethylmaleimide {} {} {} {LY} N-Ethylmaleimide {} {} {} {} {LY} N-Ethylmaleimide {} {} {} {} {} {LY} N-Ethylmaleimide {} {} {} {} {} {} {LY} N-Ethylmaleimide {} {} {} {} {} {} {} {LY} N-Ethylmaleimide {} {} {} {} {} {} {} {} {LY} N-Ethylmaleimide {} {} {} {} {} {} {} {} {} {LY} N-Ethylmaleimide {} {} {} {} {} {} {} {} {} {} {LY} N-Ethylmaleimide {} {} {} {} {} {} {} {} {} {} {} {LY} N-Ethylmaleimide {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {LY} N-Ethylmaleimide {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} N-Ethylmaleimide {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} N-Ethylmaleimide {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} N-Ethylmaleimide {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {
MDL NumberMFCD00005509
PubChem Substance ID4362
EC Number204-892-4
Beilstein Registry Number112448
Merck Number3822
Reaxys-RN112448
Chemical Name TranslationN-乙基马来酰亚胺
Wiswesser Line NotationT5VNVJ B2
LabNetwork Molecule IDLN00194741
InChIInChI=1S/C6H7NO2/c1-2-7-5(8)3-4-6(7)9/h3-4H,2H2,1H3
Canonical SMILESO=C(C=C1)N(CC)C1=O
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分类

  • {SNA} Bioactive Small Molecules, E,
  • {SNA} Apoptosis Inhibitors, Apoptosis and Cell Cycle, Core Bioreagents, Enzyme Inhibitors, Research Essentials, 细胞信号转导和神经科学, 细胞生物学
  • {SNA} Core Bioreagents, Enzyme Inhibitors, Research Essentials
  • Heterocycles
  • {SNA} Apoptosis Inhibitors, Apoptosis and Cell Cycle, Bioactive Small Molecules, Cell Biology, Cell Signaling and Neuroscience, Core Bioreagents, E, Enzyme Inhibitors, Research Essentials
  • {SNA} A to C, Apoptosis Enzymes, Apoptosis Inhibitors, Apoptosis and Cell Cycle, Application Index, Broa

产品应用

  • 1、蛋白质半胱氨酸残基的共价修饰试剂。
  • 2、巯基烷化试剂，使依赖于NADP的异柠檬酸脱氢酶和许多的内切酶失活。
  • 3、在交感神经元中增加来自于M-通道的电流，并作为KCNQ2, KCNQ4 和 KCNQ5通道的开放者（opener）行施作用。

相关文献及参考

  • [2]. Hatase O , et al. Specific inhibition of phosphate transport in mitochondria by N-ethylmaleimide. Journal of Bioenergetics, 1973, 5(1):1-15.
  • [3]. Choo YS, et al. Detection of protein ubiquitination. J Vis Exp. 2009;(30):1293. Published 2009 Aug 19. doi:10.3791/1293
  • Merck: 14,3822
  • Merck: 14,3822 Beilstein:21,399
  • Reactive dienophile and dipolarophile. Reagent for modification of sulfhydryl groups of cysteine residues in proteins: Methods Enzymol., 25, 449 (1972); Eur. J. Biochem., 145, 245 (1984).
  • Sheehan, M., et al.: J. Cell Biol., 106, 1
  • [1]. Wu KH, et al. Cys32 and His105 are the critical residues for the calcium-dependent cysteine proteolyticactivity of CvaB, an ATP-binding cassette transporter. J Biol Chem. 2004 Jan 9;2
  • [1]. Wu KH, et al. Cys32 and His105 are the critical residues for the calcium-dependent cysteine proteolyticactivity of CvaB, an ATP-binding cassette transporter. J Biol Chem. 2004 Jan 9;279(2):901-9.

安全信息

GHS Symbol
WGK Germany3
Hazard statements
  • H314 Causes severe skin burns and eye damage 导致严重的皮肤灼伤和眼睛损伤
  • H317 May cause an allergic skin reaction 可能导致皮肤过敏
  • H311 Toxic in contact with skin 皮肤接触中毒
  • H300 Fatal if swallowed 吞食致命
Personal Protective Equipment Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
RTECSUX9625000
Precautionary statements
  • 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。
  • P303+P361+P353+P310+P363
  • P301+P310+P330
  • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
  • 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
  • P303+P361+P353
  • P405 Store locked up. 上锁保管。
  • P304+P340
  • P272 Contaminated work clothing should not be allowed out of the workplace. 污染的工作服不得带出工作场所。
Signal word
Safety Statements
Packing GroupII
UN Number
Risk Statements
  • R34 Causes burns 会导致灼伤
  • R43 May cause sensitisation by skin contact 皮肤接触会产生过敏反应
  • R20/21 Harmful by inhalation and in contact with skin 吸入及与皮肤接触有害
  • R28 Very toxic if swallowed 吞咽极毒
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
Hazard Codes T+
Storage condition 2-8°C, protect from light {LY} 2-8°C, protect from light Light Sensitive {} {LY} 2-8°C, protect from light {} {} {LY} 2-8°C, protect from light {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C,
Hazard Class6.1/8 
TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 25 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   NTIS** National Technical Information Service.  (Springfield, VA 22161)
   Formerly U.S. Clearinghouse for Scientific & Technical Information.
   Volume(issue)/page/year: AD277-689

TYPE OF TEST            : LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE       : Intracerebral
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 1669 ug/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   JMCMAR Journal of Medicinal Chemistry.  (American Chemical Soc.,
   Distribution Office Dept. 223, POB POB 57136, West End Stn., Washington, DC
   20037)  V.6-    1963-  Volume(issue)/page/year: 15,534,1972

TYPE OF TEST            : LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 17 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   JMCMAR Journal of Medicinal Chemistry.  (American Chemical Soc.,
   Distribution Office Dept. 223, POB POB 57136, West End Stn., Washington, DC
   20037)  V.6-    1963-  Volume(issue)/page/year: 15,534,1972

TYPE OF TEST            : DNA inhibition
TEST SYSTEM             : Rodent - rat Liver
DOSE/DURATION           : 2 umol
REFERENCE :
   MAGDA3 Mechanisms of Ageing and Development.  (Elsevier Science Pub. Co.,
   Inc., 52 Vanderbilt Ave., New York, NY 10017)  V.1-    1972-
   Volume(issue)/page/year: 8,363,1978

TYPE OF TEST            : DNA inhibition
TEST SYSTEM             : Rodent - mouse Cells - not otherwise specified
DOSE/DURATION           : 300 umol/L
REFERENCE :
   BBRCA9 Biochemical and Biophysical Research Communications.  (Academic
   Press, Inc., 1 E. First St., Duluth, MN 55802)  V.1-    1959-
   Volume(issue)/page/year: 106,1448,1982

TYPE OF TEST            : DNA inhibition
TEST SYSTEM             : Human HeLa cell
DOSE/DURATION           : 750 nmol/L
REFERENCE :
   32YWA5 "Radiation Research, Biomedical, Chemical, and Physical Perspectives,
   Proceedings of the International Congress of Radiation Research, 5th,
   Seattle, 1974,"  Nygaard, O.F., et al., eds., New York, Academic Press,
   Inc., 1975  Volume(issue)/page/year: -,742,1975

TYPE OF TEST            : Sex chromosome loss and nondisjunction
TEST SYSTEM             : Mold - Aspergillus nidulans
DOSE/DURATION           : 30 umol/L
REFERENCE :

TYPE OF TEST            : DNA inhibition
TEST SYSTEM             : Human Cells - not otherwise specified
DOSE/DURATION           : 6 umol/L
REFERENCE :
   CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut
   Sts., Philadelphia, PA 19106)  V.1-    1941-  Volume(issue)/page/year:
   40,1414,1980

TYPE OF TEST            : DNA inhibition
TEST SYSTEM             : Rodent - mouse Cells - not otherwise specified
DOSE/DURATION           : 6 umol/L
REFERENCE :
   CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut
   Sts., Philadelphia, PA 19106)  V.1-    1941-  Volume(issue)/page/year:
   40,1414,1980

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其他信息

  • MOL 文件:128-53-0.mol
  • F:19
  • 外观性质:无色结晶，易溶于醇及醚，微溶于水。有刺激性，催泪。 溶解度:1 g/l 水(20°C)，1115 g/l 甲苯(20°C)。熔点：46℃ 沸点: 210℃ 乙醇中溶解度：50 mg/ml. 水中溶解度：>50 mg /4 ml；然而，水溶液不稳定。水解速率准一级，并且显著依赖于pH值。
  • Acros Organics:N-乙基马来酰亚胺 N-Ethylmaleimide, 99+%(128-53-0)
  • 易溶于醇及醚，微溶于水。有刺激性，催泪。
  • 存储注意事项:氮气保护
  • 用途一:1、蛋白质半胱氨酸残基的共价修饰试剂。2、巯基烷化试剂，使依赖于NADP的异柠檬酸脱氢酶和许多的内切酶失活。3、在交感神经元中增加来自于M-通道的电流，并作为KCNQ2, KCNQ4 和 KCNQ5通道的开放者（opener）行施作用。
  • TCI Shanghai:N-乙基顺丁烯二酰亚胺 N-Ethylmaleimide,>;98.0%(N)(128-53-0)
  • Alfa Aesar:N-乙基马来酰亚胺,99+% N-Ethylmaleimide, 99+%(128-53-0)
  • N-乙基马来酰亚胺价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2011/08/23 30087232 N-乙基顺丁烯二酰亚胺(+4℃) 5g 165元 2011/04/16 E0136 N-乙基顺丁烯二酰亚胺 N-Ethylmaleimide 1G 187元 2011/04/16 E0136 N-乙基顺丁烯二酰亚胺 N-Ethylmaleimide 25G 1020元
  • Sigma Aldrich:128-53-0(sigmaaldrich)
  • 上游原料:马来酸酐 --> 乙胺 --> 石蜡油

系列性分类

  1. Life Science 生命科学
  2. Cell Biology 细胞生物学
  3. Bioactive Small Molecules - Cell Biology
  4. E - Bioactive Small Molecules
  1. Life Science 生命科学
  2. Cell Biology 细胞生物学
  3. Cell Signaling and Neuroscience - Cell Biology
  4. Apoptosis and Cell Cycle - Cell Signaling and Neuroscience
  5. Apoptosis Inhibitors - Apoptosis and Cell Cycle
  1. Life Science 生命科学
  2. Cell Biology 细胞生物学
  3. Cell Signaling and Neuroscience - Cell Biology
  4. Apoptosis and Cell Cycle - Cell Signaling and Neuroscience
  5. Apoptosis Inhibitors - Apoptosis and Cell Cycle
  1. Chemical Synthesis 化学合成
  2. Synthetic Reagents 合成试剂
  3. Inorganic Salts - Synthetic Reagents
  4. Magnesium - Inorganic Salts
  1. Analytical & Chromatography 分析化学与色谱
  2. Inorganic Salts
  3. Lithium
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Dry Powder Media
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Enzymes, Inhibitors, and Substrates
  4. Cell Signaling Enzymes
  5. Apoptosis Enzymes
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Enzymes, Inhibitors, and Substrates
  4. Cell Signaling Enzymes
  5. Proteasome, Calpain and Lysosomal Proteases
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Enzymes, Inhibitors, and Substrates
  4. Enzyme Inhibitors
  5. Protease Inhibitors
  6. Broad Spectrum Inhibitors of Proteolytic Enzyme Classes
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Enzymes, Inhibitors, and Substrates
  4. Proteolytic Enzymes and Substrates
  5. Protease Inhibitors
  6. Broad Spectrum Inhibitors of Proteolytic Enzyme Classes
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Cell Signaling and Neuroscience
  4. Apoptosis and Cell Cycle
  5. Apoptosis Detection
  6. Reagents
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Cell Signaling and Neuroscience
  4. Peptides and Proteins
  5. Proteins for Cell Biology
  6. Apoptosis and Cell Cycle Proteins
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Cell Signaling and Neuroscience
  4. Signal Transduction Research Tools
  5. Protease Inhibitors
  6. Broad Spectrum Inhibitors of Proteolytic Enzyme Classes
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Enzymes, Inhibitors, and Substrates
  4. Cell Signaling Enzymes
  5. Proteasome, Calpain and Lysosomal Proteases
  6. Proteasomes
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Enzymes, Inhibitors, and Substrates
  4. Enzyme Inhibitors
  5. Enzyme Inhibitors by Enzyme
  6. Calmodulin-regulated enzymes
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Enzymes, Inhibitors, and Substrates
  4. Enzyme Inhibitors
  5. Enzyme Inhibitors by Enzyme
  6. Carboxypeptidase B
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Enzymes, Inhibitors, and Substrates
  4. Enzyme Inhibitors
  5. Protease Inhibitors
  6. Broad Spectrum Inhibitors of Proteolytic Enzyme Classes
  7. Serine Protease Inhibitors
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Enzymes, Inhibitors, and Substrates
  4. Proteolytic Enzymes and Substrates
  5. Protease Inhibitors
  6. Broad Spectrum Inhibitors of Proteolytic Enzyme Classes
  7. Serine Protease Inhibitors
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Cell Signaling and Neuroscience
  4. Peptides and Proteins
  5. Apoptosis and Cell Cycle Proteins
  6. Apoptosis Detection
  7. Reagents
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Cell Signaling and Neuroscience
  4. Signal Transduction Research Tools
  5. Protease Inhibitors
  6. Broad Spectrum Inhibitors of Proteolytic Enzyme Classes
  7. Serine Protease Inhibitors
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Proteins and Derivatives
  4. Proteins for Cell Biology
  5. Apoptosis and Cell Cycle Proteins
  6. Apoptosis Detection
  7. Reagents
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Proteomics
  4. Protein Structural Analysis
  5. Protein Modification
  6. Specific Amino Acid Modification
  7. Reagents for arginine modification
  1. Medical Research Areas
  2. Metabolism
  3. Cathepsin  (组织蛋白酶)

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