N-乙酰基-D-半胱氨酸 | 26117-28-2

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 半胱氨酸类衍生物
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: N-乙酰基-D-半胱氨酸
• 中文别名: 乙酰-D-半胱氨酸
• 英文名称: (S)-N-acetylcysteine
• 英文别名: N-acetylcysteine；NAC；N-Acetyl-D-cysteine；(2S)-2-acetamido-3-sulfanylpropanoic acid
• CAS: 26117-28-2
• 化学式: C₅H₉NO₃S
• 分子量: 163.197
• InChiKey: PWKSKIMOESPYIA-SCSAIBSYSA-N

物化性质

• 熔点：
  104-107°C
• 沸点：
  407.7±40.0 °C(Predicted)
• 密度：
  1.294±0.06 g/cm3(Predicted)
• 溶解度：
  DMSO（少许）、甲醇（少许）、水（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  67.4
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 海关编码：
  2930909090
• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  存于室温、密闭且干燥的环境中。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: N-Acetyl-D-cysteine
Synonyms: (2S)-2-Acetamido-3-sulfanylpropanoic acid

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: N-Acetyl-D-cysteine
CAS number: 26117-28-2

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C5H9NO3S
Molecular weight: 163.2

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides, sulfur oxides.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

生物活性

N-乙酰半胱氨酸具有抗氧化活性，通过与巯基反应清除ROS，但不能进入谷胱甘肽代谢途径。

体外研究

在体外实验中，20 mM N-乙酰半胱氨酸（1小时预处理，12小时后）并未增加细胞内谷胱甘肽水平，而谷胱甘肽单酯可以。D-乙酰半胱氨酸不能增强缺氧诱导的细胞凋亡。这表明是谷胱甘肽而不是D-乙酰半胱氨酸或N-乙酰半胱氨酸负责增强缺氧诱导的细胞凋亡。

反应信息

• 作为反应物：
  描述：

  N-乙酰基-D-半胱氨酸 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 9.0h， 生成 [2-hydroxy-3-(2-methoxyphenoxy)propyl] (2S)-2-acetamido-3-sulfanylpropanoate
  参考文献：
  名称：

  COMPOSITIONS AND METHODS FOR THE TREATMENT OF COUGH

  摘要：

  该发明涉及公式I的化合物或其药用可接受的盐，以及其多晶型、溶剂合物、对映体、立体异构体和水合物。包括有效量的公式I化合物的药物组合物，以及用于治疗或预防咳嗽的方法可以制备为口服、颊内、直肠、局部、经皮、经粘膜、静脉、肠道给药、糖浆或注射。这种组合物可用于治疗急性呼吸道感染、哮喘、痛风、纤维肌痛、促进受孕、促进呼吸系统中的次级粘膜分泌、肌肉松弛剂、过敏、哮喘、慢性阻塞性肺疾病、痉挛、呼吸和神经系统疾病。

  公开号：

  US20150133533A1
• 作为产物：
  描述：

  N-乙酰基-L-半胱氨酸 生成 N-乙酰基-D-半胱氨酸
  参考文献：
  名称：

  l-methionine related l-amino acids by acylase cleavage of their corresponding

  摘要：

  Acylase I from Aspergillus oryzae is an even more useful enzyme than suggested so far. Besides standard amino acids such as L-Met, L-VaI and L-Phe, a number of additional sulfur-and selenium-containing amino acids can be obtained at useful reaction rates and in very high enantiomeric purity by kinetic resolution of the respective N-acety-DL-amino acids. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00400-x
• 作为试剂：
  描述：

  1-(4-azido-2,5-dideoxy-2-fluoro-5-iodo-β-D-arabino-furanosyl)uracil 、 苯甲酰氯 在 N-甲基吗啉 、 4-二甲氨基吡啶 、 N-乙酰基-D-半胱氨酸 作用下， 以 四氢呋喃 为溶剂， 以0.98 g的产率得到1-(4'-azido-3'-O-benzoyl-2'-deoxy-2'-fluoro-5'-iodo-β-D-arabinofuranosyl)uracil
  参考文献：
  名称：

  The Design, Synthesis, and Antiviral Activity of Monofluoro and Difluoro Analogues of 4′-Azidocytidine against Hepatitis C Virus Replication: The Discovery of 4′-Azido-2′-deoxy-2′-fluorocytidine and 4′-Azido-2′-dideoxy-2′,2′-difluorocytidine

  摘要：

  The discovery of 4'-azidocytidine (3) (R1479) (J. Biol. Chem. 2006, 281, 3793; Bioorg. Med. Chem. Lett. 2007, 17, 2570) as a potent inhibitor of RNA synthesis by NS5B (EC50 = 1.28 mu M), the RNA polymerase encoded by hepatitis C virus (HCV), has led to the synthesis and biological evaluation of several monofluoro and difluoro derivatives of 4'-azidocytidine. The most potent compounds in this series were 4'-azido-2'-deoxy-2',2'-difluorocytidine and 4'-azido-2'-deoxy-2'-fluoroarabinocytidine with antiviral EC50 of 66 nM and 24 nM in the HCV replicon system, respectively. The structure-activity relationships within this series were discussed. which led to the discovery of these novel nucleoside analogues with the most potent compound, showing more than a 50-fold increase in antiviral potency as compared to 4'-azidocytidine (3).

  DOI：

  10.1021/jm801595c

文献信息

• Reactivity of a cationic square-planar palladium(II) chloro complex containing bis[2-(diphenylphosphino)ethyl]amine: chloro substitutions by anionic ligands and formation of neutral digold(I) compounds possessing linear PAuX fragments. The X-Ray crystal structure of Au2[Ph2P(CH2)2N(NO)(CH2)2PPh2]Cl2
  作者：M. Inés García-Seijo、Abraha Habtemariam、Simon Parsons、R. O. Gould、M. Esther García-Fernández

  DOI：10.1039/b109675n

  日期：2002.5.22

  tetrachloropalladate(II) with the potentially tridentate aminophosphine bis[2-(diphenylphosphino)ethyl]amine (PNHP) in 1∶1 molar ratio leads to the formation of the four-coordinate complex [Pd(PNHP)Cl]Cl (1). Complex 1 undergoes chloro substitution reactions with NaX (X=Br, I), CuCl, AgNO3, the amino acid N-acetyl-L-cysteine (AcCysSH) and the tripeptide reduced glutathione (γ-L-Glu-L-Cys-Gly, GSH) affording [Pd(PNHP)X]X′

  四氯palladate（II）与潜在的三齿的相互作用氨基膦双[2-（二苯基膦基）乙基]胺（PNHP）以1∶1的摩尔比导致形成四配位络合物[Pd（PNHP）Cl] Cl（1）。配合物1与NaX（X = Br，I），CuCl，AgNO 3，氨基酸N-乙酰基-L-半胱氨酸（AcCysSH）和三肽还原型谷胱甘肽（γ-L-Glu-L-Cys-Gly，GSH），得到[Pd（PNHP）X] X'[X = X' = Br（2），I（3），NO 3 （4）；X = Cl，X' = CuCl 2 （1a）；X' ＝Cl，X ＝RS ＝AcCysS（8），GS（9）]。但是，金（I）导致抽象氨基膦由离子络合物1和2生成中性化合物Au 2（PNHP）X 2 [X = Cl（5），Br（6）]。双核络合物Au 2（PN（NO）P）Cl 2 （5a），含有配体双[2-（二苯基膦基）乙基]亚硝胺是由4与金（I）在微量痕
• [EN] COMPOSITIONS AND METHODS FOR THE TREATMENT OF COUGH<br/>[FR] COMPOSITIONS ET MÉTHODES DE TRAITEMENT DE LA TOUX
  申请人：KANDULA MAHESH

  公开号：WO2013167988A1

  公开（公告）日：2013-11-14

  The invention relates to the compounds of formula (I) or its pharmaceutical acceptable salts, as well as polymorphs, solvates, enantiomers, stereoisomers and hydrates thereof. The pharmaceutical compositions comprising an effective amount of compounds of formula (I), and methods for treating or preventing cough may be formulated for oral, buccal, rectal, topical, transdermal, transmucosal, intravenous, parenteral administration, syrup, or injection. Such compositions may be used to treatment of acute respiratory tract infections, asthma, gout, fibromyalgia, facilitating conception, promoies secondary mucosal secretions in the respiratory system, muscle relaxant, allergy, asthma, chronic obstructive pulmonary disorders, spasms, respiratory and neurological diseases.

  该发明涉及式(I)的化合物或其药用可接受的盐，以及其多晶型、溶剂合物、对映体、立体异构体和水合物。包括式(I)化合物的有效量的药物组合物，以及用于口服、颊部、直肠、局部、经皮、经粘膜、静脉、肠道给药、糖浆或注射的治疗或预防咳嗽的方法可以制备。这种组合物可用于治疗急性呼吸道感染、哮喘、痛风、纤维肌痛、促进受孕、促进呼吸系统中的次级粘膜分泌、肌肉松弛剂、过敏、哮喘、慢性阻塞性肺疾病、痉挛、呼吸和神经系统疾病。
• Drugs for diabetes
  申请人：——

  公开号：US20040023890A1

  公开（公告）日：2004-02-05

  Use for the diabetes treatment of compounds or salts thereof, having the following general formula (I): A-(B) b0 —(C) c0 —NO 2 wherein A contains the radical of a drug having an antiiflammatory or analgesic activity, B is a bivalen: linking group wherein the precursor must meet the tests described in the application, C is a a bivalent linking group as defined in the invention.

  用于治疗糖尿病的化合物或其盐，具有如下通用公式（I）：A-(B) b0 —(C) c0 —NO 2 其中A含有具有抗炎或镇痛活性的药物的自由基，B是一个双价连接基团，其中前体必须符合本申请中描述的测试，C是如发明中定义的双价连接基团。
• Use of (S)-N-tert-butoxycarbonylaziridine-2-carboxylate derivatives for α-amino acid synthesis
  作者：Jack E. Baldwin、Christopher N. Farthing、Andrew T. Russell、Christopher J. Schofield、Alan C. Spivey

  DOI：10.1016/0040-4039(96)00676-4

  日期：1996.5

  (S)-tert-Butyl-N-tert-butoxycarbonylaziridine-2-carboxylate and (S)-tert-butyl-N-tert-butoxycarbonylaziridine-2-carboxamide were synthesised and found to react with copper ‘catalysed’ Grignard reagents to give protected α-amino acids in moderate to good yields.

  （小号） -叔丁基- ñ -叔-butoxycarbonylaziridine -2-甲酸乙酯和（小号） -叔丁基- ñ -叔-butoxycarbonylaziridine -2-甲酰胺的合成和发现与铜反应“催化的”格氏试剂，得到以中等到良好的产率保护α-氨基酸。
• Reversing Reactivity: Stereoselective Desulfurative 1,2-<i>trans</i>-<i>O</i>-Glycosylation of Anomeric Thiosugars with Carboxylic Acids under Copper or Cobalt Catalysis
  作者：Nedjwa Bennai、Amélie Chabrier、Maha I. Fatthalla、Christine Tran、Expédite Yen-Pon、Mohamed Belkadi、Mouâd Alami、Laurence Grimaud、Samir Messaoudi

  DOI：10.1021/acs.joc.0c00766

  日期：2020.7.17

  We have discovered a new mode of reactivity of 1-thiosugars in the presence of Cu(II) or Co(II) for a stereoselective O-glycosylation reaction. The process involves the use of a catalytic amount of Cu(acac)2 or Co(acac)2 and Ag2CO3 as an oxidant in α,α,α-trifluorotoluene. Moreover, this protocol turned out to have a broad scope, allowing the preparation of a wide range of complex substituted O-glycoside

  我们已经发现在立体选择性O-糖基化反应的Cu（II）或Co（II）存在下1-硫糖的反应性的新模式。该方法涉及使用催化量的Cu（acac）2或Co（acac）2和Ag 2 CO 3作为α，α，α-三氟甲苯中的氧化剂。而且，该方案证明具有广泛的范围，允许以良好的至优异的产率和排他的1,2-反式选择性制备多种复杂的取代的O-糖苷酯。还证明了通过这种方法对药物进行后期修饰。为了更深入地了解反应机理，进行了循环伏安法。

表征谱图