L-蛋氨酸亚砜 | 3226-65-1

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 蛋氨酸类衍生物
• 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: L-蛋氨酸亚砜
• 中文别名: L-2-氨基-4-(甲基磺酰基)丁酸
• 英文名称: L-methionine sulfoxide
• 英文别名: methionine sulfoxide；L-methionine S-oxide；(2S)-2-azaniumyl-4-methylsulfinylbutanoate
• CAS: 3226-65-1
• 化学式: C₅H₁₁NO₃S
• 分子量: 165.213
• InChiKey: QEFRNWWLZKMPFJ-YGVKFDHGSA-N

物化性质

• 熔点：
  234-235°C
• 沸点：
  434.3±40.0 °C(Predicted)
• 密度：
  1.385±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于酸性水溶液（轻微）、水（轻微）
• 物理描述：
  Solid
• 稳定性/保质期：
  温度敏感，易吸潮

计算性质

• 辛醇/水分配系数(LogP)：
  -4.1
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  99.6
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• WGK Germany：
  3
• 海关编码：
  2930909090
• 危险标志：
  GHS07
• 危险性描述：
  H319
• 危险性防范说明：
  P305 + P351 + P338
• 储存条件：
  2-8°C

SDS

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Section 1. Chemical Product and Company Identification
L-Methionine Sulfoxide
Common Name/
Trade Name
Manufacturer
Commercial Name(s)
Synonym
Chemical Name
Chemical Family
L-Methionine Sulfoxide

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Section 4. First Aid Measures
Eye Contact Check for and remove any contact lenses. In case of contact, immediately flush eyes with plenty of water for at
least 15 minutes. Cold water may be used. Get medical attention if irritation occurs.
Skin Contact Wash with soap and water. Cover the irritated skin with an emollient. Get medical attention if irritation develops.
Cold water may be used.
Serious Skin Contact Not available.
Inhalation If inhaled, remove to fresh air. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get
medical attention.
Serious Inhalation Not available.
Ingestion Do NOT induce vomiting unless directed to do so by medical personnel. Never give anything by mouth to an
unconscious person. If large quantities of this material are swallowed, call a physician immediately. Loosen tight
clothing such as a collar, tie, belt or waistband.
Serious Ingestion Not available.

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Section 5. Fire and Explosion Data
Flammability of the Product May be combustible at high temperature.
Auto-Ignition Temperature Not available.
Flash Points Not available.
Flammable Limits Not available.
These products are carbon oxides (CO, CO2), nitrogen oxides (NO, NO2...).
Products of Combustion
Fire Hazards in Presence of Slightly flammable to flammable in presence of heat.
Various Substances Non-flammable in presence of shocks.
Explosion Hazards in Presence Slightly explosive in presence of open flames and sparks.
of Various Substances Non-explosive in presence of shocks.
Fire Fighting Media SMALL FIRE: Use DRY chemical powder.
and Instructions LARGE FIRE: Use water spray, fog or foam. Do not use water jet.
Special Remarks on As with most organic solids, fire is possible at elevated temperatures
Fire Hazards
Special Remarks on Explosion Fine dust dispersed in air in sufficient concentrations, and in the presences of an ignition source is a potential dust
Hazards explosion hazard.

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Section 6. Accidental Release Measures
Small Spill Use appropriate tools to put the spilled solid in a convenient waste disposal container. Finish cleaning by
spreading water on the contaminated surface and dispose of according to local and regional authority
requirements.
Large Spill
Use a shovel to put the material into a convenient waste disposal container. Finish cleaning by spreading water
on the contaminated surface and allow to evacuate through the sanitary system.
L-Methionine Sulfoxide

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Section 7. Handling and Storage
Precautions Keep away from heat. Keep away from sources of ignition. Do not breathe dust. Keep away from incompatibles
such as oxidizing agents, acids, alkalis.
Storage Keep container tightly closed. Keep container in a cool, well-ventilated area.

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Section 8. Exposure Controls/Personal Protection
Engineering Controls Use process enclosures, local exhaust ventilation, or other engineering controls to keep airborne levels below
recommended exposure limits. If user operations generate dust, fume or mist, use ventilation to keep exposure to
airborne contaminants below the exposure limit.
Personal Protection
Safety glasses. Lab coat. Dust respirator. Be sure to use an approved/certified respirator or equivalent. Gloves.
Personal Protection in Case of Splash goggles. Full suit. Dust respirator. Boots. Gloves. A self contained breathing apparatus should be used
a Large Spill to avoid inhalation of the product. Suggested protective clothing might not be sufficient; consult a specialist
BEFORE handling this product.
Exposure Limits Not available.

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Section 9. Physical and Chemical Properties
Physical state and appearance Solid. (Powdered solid.) Odor Characteristic.
Taste Not available.
Molecular Weight 165.21 g/mole
Color White. Off-white.
pH (1% soln/water) Not available.
Boiling Point Not available.
Melting Point Not available.
Critical Temperature Not available.
Not available.
Specific Gravity
Vapor Pressure Not applicable.
Vapor Density Not available.
Volatility Not available.
Odor Threshold Not available.
Not available.
Water/Oil Dist. Coeff.
Ionicity (in Water) Not available.
See solubility in water.
Dispersion Properties
Solubility Soluble in cold water.

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Section 10. Stability and Reactivity Data
Stability The product is stable.
Not available.
Instability Temperature
Conditions of Instability Excess heat, incompatible materials, dust generation
Incompatibility with various Reactive with oxidizing agents, acids, alkalis.
substances
Corrosivity Not available.
L-Methionine Sulfoxide
Special Remarks on Not available.
Reactivity
Special Remarks on Not available.
Corrosivity
Polymerization Will not occur.

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Section 11. Toxicological Information
Routes of Entry Inhalation. Ingestion.
Toxicity to Animals LD50: Not available.
LC50: Not available.
Chronic Effects on Humans Not available.
Other Toxic Effects on Slightly hazardous in case of skin contact (irritant), of ingestion, of inhalation.
Humans
Special Remarks on Not available.
Toxicity to Animals
Special Remarks on
Not available.
Chronic Effects on Humans
Special Remarks on other Acute Potential Health Effects:
Toxic Effects on Humans Skin: May cause skin irritation.
Eyes: May cause eye irritation.
Inhalation: May cause respiratory tract irritation.
Ingestion: May cause gastrointestinal tract irritation.
The toxicological properties of this substance have not been fully investigated.

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Section 12. Ecological Information
Ecotoxicity Not available.
BOD5 and COD Not available.
Products of Biodegradation Possibly hazardous short term degradation products are not likely. However, long term degradation products may
arise.
Toxicity of the Products The product itself and its products of degradation are not toxic.
of Biodegradation
Special Remarks on the Not available.
Products of Biodegradation

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Section 13. Disposal Considerations
Waste Disposal Waste must be disposed of in accordance with federal, state and local environmental
control regulations.

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Section 14. Transport Information
DOT Classification Not a DOT controlled material (United States).
Identification Not applicable.
Not applicable.
Special Provisions for
Transport
L-Methionine Sulfoxide
DOT (Pictograms)

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Section 15. Other Regulatory Information and Pictograms
No products were found.
Federal and State
Regulations
California
Proposition 65
Warnings
Other Regulations EINECS: This product is on the European Inventory of Existing Commercial Chemical Substances.
WHMIS (Canada) Not controlled under WHMIS (Canada).
Other Classifications
DSCL (EEC) This product is not classified according S24/25- Avoid contact with skin and eyes.
to the EU regulations.
Health Hazard
HMIS (U.S.A.) 1 National Fire Protection
1 Flammability
1 Association (U.S.A.)
Fire Hazard
1 0 Reactivity
Health
Reactivity
0
Specific hazard
Personal Protection
E
WHMIS (Canada)
(Pictograms)
DSCL (Europe)
(Pictograms)
TDG (Canada)
(Pictograms)
ADR (Europe)
(Pictograms)
Protective Equipment
Gloves.
Lab coat.
Dust respirator. Be sure to use an
approved/certified respirator or
equivalent.
L-Methionine Sulfoxide

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

生物活性 L-甲硫氨酸亚砜（H-Met(O)-OH），作为甲硫氨酸的代谢产物，能够诱导M1/classical巨噬细胞极化，并调节氧化应激和嘌呤能信号传递参数。

靶点

人类内源性代谢物

反应信息

• 作为反应物：
  描述：

  L-蛋氨酸亚砜 在 双氧水 作用下， 以 ammonium molybdate 、 水 、 乙腈 为溶剂， 反应 2.0h， 生成 L-蛋氨酸砜
  参考文献：
  名称：

  来自东加勒比海蓝细菌 Lyngbya majuscula 收集的卤代脂肪酸酰胺和环缩肽†

  摘要：

  东加勒比收集的Lyngbya majuscula的亲脂性提取物产生了两种新的卤代脂肪酸酰胺，手榴弹胺 B ( 1 ) 和 C ( 2 )，以及两种新的缩肽，依曲酰胺 A ( 3 ) 和 B ( 4 )，以及已知的化合物八氯环素和脱乙酰八氯环素。最近报道的缩酚肽 carriebowmide ( 5 ) 也存在于提取物中，并作为其砜类人工制品被分离 ( 6 )。化合物1 - 4通过光谱方法鉴定。3 , 4 , 6氨基酸残基的构型通过酸水解产物的非对映异构衍生物的 LC-MS 分析（高级 Marfey 方法）确定。基于6的构型分析，与真正的carriebowmide ( 5 )直接比较，提出了对5的微小结构修正。化合物1和2对甜菜夜蛾（Spodoptera exigua）显示出边际活性。化合物1 - 4和6进行了评估在人胚胎肾（HEK293）细胞一般小区毒性。只有依曲酰胺 B ( 4 ) 显示出显着的细胞毒性，IC

  DOI：

  10.1021/np900173d
• 作为产物：
  描述：

  L-蛋氨酸 在 5-ethyl-3-methyl-4a-hydroxy-4a,5-dihydrolumiflavin 、 一水合肼 作用下， 以 2,2,2-三氟乙醇 为溶剂， 35.0 ℃ 、101.33 kPa 条件下， 反应 4.0h， 以95%的产率得到L-蛋氨酸亚砜
  参考文献：
  名称：

  5-乙基-4a-羟基异恶嗪的绿色制备及其在催化需氧氧化中的应用

  摘要：

  异咯嗪环系统存在于自然界中的黄素辅因子中，模拟它们的氧化还原催化是开发可持续催化氧化反应的重要任务。尽管 5-乙基-4a-羟基异恶嗪是用于此类目的的最有希望的催化剂候选者之一，但到目前为止，它们在实验室和工业合成化学中的应用非常有限，大概是由于缺乏容易、安全的制备方法，而且价格便宜。在本次交流中，我们介绍了一种从 3,7,8,10-四甲基异恶嗪 (1) 制备 5-乙基-4a-羟基-3,7,8,10-四甲基异恶嗪 (1EtOH) 的环境友好且实用的制备方法，其中常规合成要求，包括 (i) 在惰性条件下操作，(ii) 危险或昂贵的化学品，(iii) 不稳定中间体的分离，已全部溶解。此外，我们还提出了 1EtOH 可以作为 Baeyer-Villiger 氧化以及在合适条件下以分子氧 (O2) 作为末端氧化剂的磺化氧化的有效催化剂，这是第一份关于 5-烷基催化的有氧氧化的报道。 4a-羟基异恶嗪。

  DOI：

  10.1002/ejoc.201801865

文献信息

• Continuous-flow protocol for the synthesis of enantiomerically pure intermediates of anti epilepsy and anti tuberculosis active pharmaceutical ingredients
  作者：Renata M. Aguiar、Raquel A. C. Leão、Alejandro Mata、David Cantillo、C. Oliver Kappe、Leandro S. M. Miranda、Rodrigo O. M. A. de Souza

  DOI：10.1039/c8ob03088j

  日期：——

  role in the development of building blocks for Active Pharmaceutical Ingredients (APIs), being α-amino acids and their derivatives widely applied as building blocks. In this work we developed two different strategies for the synthesis of intermediates used on the synthesis of levetiracetam/brivaracetam and ethambutol. The results obtained show that methionine methyl ester can be continuously converted

  手性中间体的连续流生产在活性药物成分（API）的基础材料的开发中起着重要作用，因为α-氨基酸及其衍生物被广泛用作基础材料。在这项工作中，我们开发了两种用于合成左乙拉西坦/溴乙酰胺和乙胺丁醇的中间体的合成策略。获得的结果表明，通过RANEY®镍脱硫/还原策略，蛋氨酸甲酯可连续转化为所需的乙胺丁醇中间体，而RANEY®镍（无H 2）和Pd / C–H 2均可合成左乙拉西坦/溴乙酰胺中间体。途径或通过光化学脱硫。
• Isotope-labeled differential profiling of metabolites using<i>N</i>-benzoyloxysuccinimide derivatization coupled to liquid chromatography/high-resolution tandem mass spectrometry
  作者：Michel Wagner、Leanne B. Ohlund、Tze Chieh Shiao、Amélie Vézina、Borhane Annabi、René Roy、Lekha Sleno

  DOI：10.1002/rcm.7264

  日期：2015.9.30

  An isotopic labeling strategy based on derivatizing amine‐containing metabolites has been developed using light (12C6) and heavy (13C6) N‐benzoyloxysuccinimide reagents for semi‐targeted metabolomic applications.

  已经开发了一种基于衍生化含胺代谢物的同位素标记策略，该方法使用轻（12 C 6）和重（13 C 6）N-苯甲酰氧基琥珀酰亚胺试剂进行半靶向代谢组学研究。
• Chemoselective Electrophilic Oxidation of Heteroatoms by Hydroperoxy Sultams
  作者：Feyissa Gadissa Gelalcha、Bärbel Schulze

  DOI：10.1021/jo0202841

  日期：2002.11.1

  of the latter with acidified H2O2. Kinetic studies of the reaction of 1c with 1,4-thioxane 12f suggest that the reaction follows the second-order kinetics, first order in substrate and first order in oxidant with the second-order rate constant several orders of magnitude larger than that of the corresponding reaction with hydrogen peroxide and tert-butyl hydroperoxide without the need for any acid

  描述了新型氢过氧阿马酸1b-d的合成及其作为非水介质中广泛的氮，硫和磷杂原子的可再生化学选择性亲电子氧化剂的潜力。1b，c与仲胺10f，g的反应产生羟基磺酰胺2b，c和硝酮11f或自由基11g，这取决于底物和化学计量，而叔胺10a-d给出氧化胺11a-d。化合物1c，d将各种硫醚12a-g平滑地氧化为亚砜13a-g，其通过色谱法以接近定量的产率分离。通过用酸化的H 2 O 2处理2c，从1c再生出1c。1c与1,4-噻吨12f反应的动力学研究表明，该反应遵循二级动力学，底物上的第一级和氧化剂中的第一级，其第二级速率常数比与过氧化氢和叔丁基氢过氧化物的相应反应的速率大几个数量级，而无需任何酸或重金属催化剂。膦14a，b也被1c容易地以定量收率氧化成各自的膦氧化物15a，b。反应可以在环境温度或更低的温度下进行，并且似乎是通过非自由基机理进行的。反应对空间和电子因素均敏感。b容易获得定量产量。
• Iodonitrene in Action: Direct Transformation of Amino Acids into Terminal Diazirines and ¹⁵N₂-Diazirines and Their Application as Hyperpolarized Markers
  作者：Thomas Glachet、Hamid Marzag、Nathalie Saraiva Rosa、Johannes F. P. Colell、Guannan Zhang、Warren S. Warren、Xavier Franck、Thomas Theis、Vincent Reboul

  DOI：10.1021/jacs.9b07035

  日期：2019.8.28

  terminal diazirines has been developed using phenyliodonium diacetate (PIDA) and ammonia. This PIDA mediated transformation occurs via three consecutive reactions and involves an iodonitrene intermediate. This method is tolerant to most functional groups found on the lateral chain of amino acids, it is operationally simple, and can be scaled up to provide multigram quantities of diazirine. Interestingly

  已经使用二乙酸苯基碘鎓 (PIDA) 和氨开发了一种将未受保护的氨基酸一锅无金属转化为末端二氮丙啶的方法。这种 PIDA 介导的转化通过三个连续的反应发生，并涉及碘化氮中间体。这种方法可以耐受氨基酸侧链上的大多数官能团，操作简单，可以放大以提供数克数量的二氮嗪。有趣的是，我们还证明了这种转化可以应用于没有外消旋化的二肽。此外，可以获得 14N2 和 15N2 同位素异构体，这强调了使用 15NH3 时的关键转亚胺化步骤。此外，我们报告了直接产生不对称碳的 14N/15N 同位素异构体的首次实验观察。最后，
• Selective synthesis of sulfoxides and sulfones <i>via</i> controllable oxidation of sulfides with <i>N</i>-fluorobenzenesulfonimide
  作者：Xiaobo Xu、Leyu Yan、Shengqiang Wang、Panpan Wang、A-Xiu Yang、Xiaolong Li、Hao Lu、Zhong-Yan Cao

  DOI：10.1039/d1ob01632f

  日期：——

  A practical and mild method for the switchable synthesis of sulfoxides or sulfones via selective oxidation of sulfides using cheap N-fluorobenzenesulfonimide (NFSI) as the oxidant has been developed. These highly chemoselective transformations were simply achieved by varying the NFSI loading with H2O as the green solvent and oxygen source without any additives. The good functional group tolerance makes

  已经开发出一种实用且温和的方法，通过使用廉价的N-氟苯磺酰亚胺(NFSI) 作为氧化剂选择性氧化硫化物来切换合成亚砜或砜。这些高度化学选择性的转化是通过改变 NFSI 负载而实现的，H 2 O 作为绿色溶剂和氧源，没有任何添加剂。良好的官能团耐受性使该策略具有价值。