N-乙酰基卞基半胱氨酸 | 19542-77-9

• 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-乙酰基卞基半胱氨酸
• 中文别名: N-乙酰基-s-苄基-l-半胱氨酸
• 英文名称: N-acetyl-S-benzyl-L-cysteine
• 英文别名: N-acetyl-S-benzyl cysteine；(2R)-2-acetamido-3-benzylsulfanylpropanoic acid
• CAS: 19542-77-9
• 化学式: C₁₂H₁₅NO₃S
• 分子量: 253.322
• InChiKey: BJUXDERNWYKSIQ-NSHDSACASA-N

物化性质

• 熔点：
  144-146°C
• 沸点：
  506.2±50.0 °C(Predicted)
• 密度：
  1.2516 (rough estimate)
• 溶解度：
  DMSO（微溶）、乙醇（微溶）、甲醇（微溶）
• 稳定性/保质期：
  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  91.7
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险品标志：
  T
• 海关编码：
  2930909090
• 危险类别：
  6.1(a)
• 安全说明：
  S28,S28A,S36/37,S45,S61
• 危险类别码：
  R23/24/25,R52/53,R33
• 包装等级：
  II
• 危险品运输编号：
  1711
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  存放于0-6°C的阴凉干燥处

SDS

Name:	n-Acetyl-s-phenyl-l-cysteine methyl ester Material Safety Data Sheet
Synonym:
CAS:	19542-77-9

Section 1 - Chemical Product MSDS Name:n-Acetyl-s-phenyl-l-cysteine methyl ester Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
19542-77-9	N-acetyl-s-phenyl-l-cysteine methyl es	100.0	unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid immediately.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
If victim is conscious and alert, give 2-4 cupfuls of milk or water.
Never give anything by mouth to an unconscious person. Get medical aid immediately.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or appropriate foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Sweep up or absorb material, then place into a suitable clean, dry, closed container for disposal. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Keep refrigerated. (Store below 4C/39F.)

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 19542-77-9: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Crystalline powder
Color: white to light yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 139-143 C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C12H15NO3S
Molecular Weight: 253.32

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Irritating and toxic fumes and gases.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 19542-77-9 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
N-acetyl-s-phenyl-l-cysteine methyl ester - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 7/8 Keep container tightly closed and dry.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 19542-77-9: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 19542-77-9 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 19542-77-9 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  N-乙酰基卞基半胱氨酸 在 盐酸 、 1,1,2,3-四甲基胍 、 氨 、 sodium amide 作用下， 以 二甲基亚砜 、 乙酸乙酯 为溶剂， 生成 N-acetyl-L-cysteine N'-methylamide
  参考文献：
  名称：

  铁硫蛋白活性位点的合成类似物。VI。四核簇（Fe4S4（SR）4）.2-的光谱和氧化还原特性。

  摘要：

  DOI：

  10.1021/ja00820a017
• 作为产物：
  描述：

  S-苄基-L-半胱氨酸 生成 N-乙酰基卞基半胱氨酸
  参考文献：
  名称：

  Stekol, Journal of Biological Chemistry, 1946, vol. 164, p. 651,652

  摘要：

  DOI：
• 作为试剂：
  描述：

  1-脱氧-1-(7,8-二甲基-2,4-二氧代-1,3,4,5-四氢苯并[g]蝶啶-10(2H)-基)-5-O-膦酰戊糖醇 在 N-乙酰基卞基半胱氨酸 、 氧气 、 alkylcysteine sulfoxide C−S monooxygenase CmoJ 作用下， 以 aq. buffer 为溶剂， 生成 FMN-N5-oxide
  参考文献：
  名称：

  烷基半胱氨酸亚砜 C-S 单加氧酶使用黄素依赖性 Pummerer 重排

  摘要：

  黄素酶用途广泛，参与多种反应的催化，包括含硫化合物代谢中的关键反应。 S-烷基半胱氨酸主要由亲电子解毒过程中产生的S-烷基谷胱甘肽降解形成。最近发现的 S-烷基半胱氨酸补救途径使用两种黄素酶（CmoO 和 CmoJ）使土壤细菌中的这种代谢物脱烷基化。 CmoO 催化立体定向磺化氧化，CmoJ 在未知机制的新反应中催化其中一个亚砜 C-S 键的断裂。在本文中，我们研究了 CmoJ 的机制。我们提供了消除碳负离子和自由基中间体的实验证据，并得出结论，该反应是通过前所未有的酶介导的修饰普默勒重排进行的。 CmoJ机制的阐明为含硫天然产物的黄酮酶学添加了新的基序，并展示了酶催化C-S键断裂的新策略。

  DOI：

  10.1021/jacs.3c03545

文献信息

• Initial Intraorgan Formation of Mercapturic Acid.
  作者：Kazumi SANO、Yoji IKEGAMI、Takashi UESUGI

  DOI：10.1248/bpb.24.1324

  日期：——

  The disposition of S-benzyl-glutathione (BSG) in male Wistar rats was evaluated by the HPLC method to examine whether the kidney and liver contributed independently to the biosynthesis of S-benzyl-N-acetylcysteine (BNAc), a mercapturic acid (Chart 1). After intravenous injection, BSG was rapidly transported in both the kidney and the liver at a ratio of about 7:3. Simultaneously, a large amount of BNAc was found in both the kidney and the liver. In the kidney, S-benzyl-cysteine (BCys) reached a maximum concentration (Cmax) at 2 min after BSG injection, whereas BNAc reached Cmax within 3 to 5 min. The generation of BNAc was also observed in the liver. While renal BNAc reached Cmax within 3 to 5 min, hepatic BNAc reached Cmax around 5 min after BSG injection. Moreover, the elimination half-life of the BNAc after intravenous injection of the BSG was equivalent to that observed after intravenous injection of the BNAc itself. These results demonstrate that the kidney contributes to the initial intraorgan generation of BNAc and that this mercapturic acid is also synthesized in the liver and preferentially excreted into urine.

  采用高效液相色谱法评估雄性Wistar大鼠体内S-苄基谷胱甘肽(BSG)的代谢情况，以检验肾脏和肝脏是否独立参与合成S-苄基-N-乙酰半胱氨酸(BNAc)（图1：硫醚氨酸）。静脉注射后，BSG在肾脏和肝脏中的转运速率约为7:3。同时，在肾脏和肝脏中发现了大量的BNAc。在肾脏中，S-苄基-半胱氨酸(BCys)在BSG注射后2分钟达到最大浓度(Cmax)，而BNAc在3至5分钟内达到Cmax。BNAc的生成也在肝脏中得到了观察。虽然肾脏中的BNAc在3至5分钟内达到Cmax，但肝脏中的BNAc在BSG注射后约5分钟达到Cmax。此外，静脉注射BSG后BNAc的消除半衰期与静脉注射BNAc本身的观察结果相当。这些结果表明，肾脏对BNAc的初始体内生成有贡献，这种硫醚氨酸也在肝脏中合成并优先排入尿液。
• Cobalt assisted cleavage of SS bonds and a base-free synthesis of mercapturic acids
  作者：Shantanu Chowdhury、Sujit Roy

  DOI：10.1016/s0040-4039(97)00268-2

  日期：1997.3

  Base free transformation of PhSSPh to sulfides, PhSR (R= alkyl, benzyl, allyl, acyl) and N-acetyl-L-cystine to mercapturic acids [AcNHCH(COOH)CH2SR, R= alkyl, benzyl, allyl, acyl] have been achieved using Zn/cat. CoCl2/organic halide in MeCN at room temperature.

  PhSSPh的无碱转化为硫化物，PhSR（R =烷基，苄基，烯丙基，酰基）和N-乙酰基-L-胱氨酸转化为巯基酸[AcNHCH（COOH）CH 2 SR，R =烷基，苄基，烯丙基，酰基]使用锌/催化剂已经实现。室温下在MeCN中的CoCl 2 /有机卤化物。
• Native Serine Peptide Assembly – Scope and Utility
  作者：Michael C. Pirrung、Ryan S. Schreihans

  DOI：10.1002/ejoc.201601148

  日期：2016.12

  serine peptide assembly (SPA), which complements and contrasts with classic native chemical ligation (NCL). Advances in reagent-less peptide bond formation have been applied to serine (and serine models) and a range of C-terminal amino acids, including bulky residues that are not amenable to NCL. The particular appeal of SPA is preparative-scale segment condensations with zero racemization risk and

  这项工作开发了丝氨酸肽组装 (SPA)，它与经典的天然化学连接 (NCL) 形成了互补和对比。无试剂肽键形成方面的进展已应用于丝氨酸（和丝氨酸模型）和一系列 C 端氨基酸，包括不适合 NCL 的庞大残基。SPA 的特别吸引力在于具有零外消旋风险和有利的过程质量强度 (PMI) 的制备级段缩合。机理研究支持先前提出的通过初始酯交换步骤的反应途径。对有利于该途径的因素的理解依赖于硬-软酸碱理论，其中具有最大羰基正电荷的温和活化酯与羟基胺的反应性最强。
• BTEX METABOLITES DERIVATIZATION KIT AND COMPOSITION
  申请人：Board of Regents, The University of Texas System

  公开号：US20190346449A1

  公开（公告）日：2019-11-14

  A kit or composition for in situ simultaneously derivatization of 14 phenol and carboxylic acid metabolites of benzene, toluene, ethylbenzene, and xylene (BTEX) in a urine sample is disclosed. The derivatization imparts a positive charge to phenol and carboxylic acid for subsequent LC-MS analysis. Limit of detection reached part-per-trillion levels for o-Cresol and part-per-billion levels for the remaining BTEX metabolites. BTEX metabolites can be detected in less than 35 mins according to one embodiment of the invention. Methods, kits and compositions disclosed herein can be used for in situ simultaneous derivatization of phenol and carboxylic acid in aqueous solution in general.

  本文介绍了一种针对尿样中苯、甲苯、乙苯和二甲苯（BTEX）的14种酚和羧酸代谢物的原位同时衍生化试剂盒或组合物。衍生化使酚和羧酸带有正电荷，以便进行后续的LC-MS分析。对于o-甲酚，检测限达到了每万亿级别，对于其余的BTEX代谢物，检测限达到了每十亿级别。根据本发明的一种实施方式，BTEX代谢物可以在不到35分钟内被检测到。本文所披露的方法、试剂盒和组合物可用于一般水溶液中酚和羧酸的原位同时衍生化。
• [EN] INHIBITION OF AMINOACYLASE 3 (AA3) IN THE TREATMENT OF CANCER<br/>[FR] INHIBITION DE L'AMINOACYLASE 3 (AA3) DANS LE TRAITEMENT DU CANCER
  申请人：UNIV CALIFORNIA

  公开号：WO2019055825A1

  公开（公告）日：2019-03-21

  The current methods and compositions provide for therapeutic approaches to treating hepatocellular carcinoma (HCC) and other types of cancer including, for example, pancreatic and colon cancer. Accordingly, certain aspects of the disclosure relates to methods and compositions for treating HCC, pancreatic and colon cancer using one or more small molecule inhibitors disclosed herein. In certain embodiments, the small molecule inhibitor is a benzothiazine, a sulfonamide, a thiazolidinone or other chemical compound.

  目前的方法和组合物提供了治疗肝细胞癌（HCC）和其他类型癌症的治疗方法，包括胰腺癌和结肠癌等。因此，本公开的某些方面涉及使用本文所披露的一种或多种小分子抑制剂治疗HCC、胰腺癌和结肠癌的方法和组合物。在某些实施例中，小分子抑制剂是苯并噻唑、磺酰胺、噻唑烷酮或其他化学化合物。