26046-90-2

• 常用中文名：3-(甲基硒基)-L-丙氨酸
• 常用英文名：Methylselenocysteine
• CAS号：26046-90-2
• 分子式：C₄H₉NO₂Se
• 分子量：182.080
• 相关类别： 生物化工 氨基酸及其衍生物 丙氨酸类衍生物
• 发布时间：2018-05-25 08:00:00
• 更新时间：2024-01-03 21:46:54
• Se-Methylselenocysteine,甲基硒的前体,具有强大的癌症化学预防活性和抗氧化活性。Se-Methylselenocysteine 具有口服生物活性,可诱导细胞凋亡 (apoptosis)。

名称

• 中文名: 3-(甲基硒基)-L-丙氨酸
• 英文名: (2R)-2-amino-3-methylselanylpropanoic acid
• 中文别名: 3-甲基硒代-L-丙氨酸; 甲基硒代半胱氨酸; 3-甲基硒代-L-D-Α-氨基羧酸
• 英文别名: Selenium-methylselenocystine; L-Alanine, 3-(methylseleno)-; 3-(Methylselanyl)-L-alanine; Methylselenocysteine; Se-Methylseleno-L-Cysteine; Se-Methyl-seleno-L-cysteine; L-Se-methylselenocysteine; 3-(Methylseleno)-L-alanine; Se-methylselenocysteine; Se-methyl selenocystein; (R)-2-Amino-3-(methylselanyl)propanoic acid; Se-Methyl-L-selenocysteine; MFCD00800565

物化性质

• 沸点: 314.1±37.0 °C at 760 mmHg
• 熔点: 177 °C(dec.)
• 分子式: C₄H₉NO₂Se
• 分子量: 182.080
• 闪点: 143.7±26.5 °C
• 精确质量: 182.979858
• PSA: 63.32000
• LogP: -0.89
• 外观性状: 白色至略黄色粉末
• 蒸汽压: 0.0±1.4 mmHg at 25°C
• 储存条件:

  -20℃

• 计算化学:

  1.疏水参数计算参考值（XlogP）:无

  2.氢键供体数量:2

  3.氢键受体数量:3

  4.可旋转化学键数量:3

  5.互变异构体数量:无

  6.拓扑分子极性表面积63.3

  7.重原子数量:8

  8.表面电荷:0

  9.复杂度:86.1

  10.同位素原子数量:0

  11.确定原子立构中心数量:1

  12.不确定原子立构中心数量:0

  13.确定化学键立构中心数量:0

  14.不确定化学键立构中心数量:0

  15.共价键单元数量:1

• 更多:

  1. 性状：粉末

  2. 密度（g/mL,25/4℃）：未确定

  3. 相对蒸汽密度（g/mL,空气=1）：未确定

  4. 熔点（ºC）：未确定

  5. 沸点（ºC,常压）：未确定

  6. 沸点（ºC,5.2kPa）：未确定

  7. 折射率：未确定

  8. 闪点（ºC）：未确定

  9. 比旋光度（º）：未确定

  10. 自燃点或引燃温度（ºC）：未确定

  11. 蒸气压（kpa,20ºC）：未确定

  12. 饱和蒸气压（kPa,60ºC）：未确定

  13. 燃烧热（KJ/mol）：未确定

  14. 临界温度（ºC）：未确定

  15. 临界压力（KPa）：未确定

  16. 油水（辛醇/水）分配系数的对数值：未确定

  17. 爆炸上限（%,V/V）：未确定

  18. 爆炸下限（%,V/V）：未确定

  19. 溶解性：未确定

生物活性

• 描述: Se-Methylselenocysteine,甲基硒的前体,具有强大的癌症化学预防活性和抗氧化活性。Se-Methylselenocysteine 具有口服生物活性,可诱导细胞凋亡 (apoptosis)。
• 相关类别:
  信号通路 >> 细胞凋亡 >> 细胞凋亡
  研究领域 >> 癌症
• 体外研究: 硒-甲基硒代半胱氨酸(100-400μM；3天)诱导SKOV-33细胞凋亡[1]。硒-甲基硒代半胱氨酸(100-400μM；3天)诱导caspase-3介导的细胞凋亡[1]。细胞凋亡分析[1]细胞系：SKOV-3细胞浓度：100、200、400μM孵育时间：3天结果：导致亚G1期的积累明显增加,这与SeMSC浓度和培养时间有关。Western Blot分析[1]细胞株：SKOV-3细胞浓度：100、200、400μM孵育时间：3d结果：导致32kda型前蛋白酶-3表达减少。
• 体内研究: 硒-甲基硒代半胱氨酸(0.2 mg/小鼠；p.o.；每日14天)增强人FaDu和A253头颈部异种移植瘤裸鼠体内CDDP和环磷酰胺的抗肿瘤活性[2]。阿尔茨海默病(AD)小鼠在饮用水中用硒-甲基硒代半胱氨酸(0.75 mg/kg BW/天)治疗10个月。硒甲基硒半胱氨酸降低氧化应激和神经炎症；Se Methylselenocysteine调节几种金属离子的分布和水平；硒甲基硒半胱氨酸通过抑制其前体蛋白APP和β-分泌酶(BAE1)的表达降低淀粉样β肽(Aβ)的生成；并通过促进蛋白磷酸酶2A(PP2A)活性来减弱tau高磷酸化和神经纤维缠结(NFT)的形成,从而保留突触蛋白和神经元活性,最终改善AD模型小鼠的空间学习记忆缺陷[3]。动物模型：雌性裸鼠(携带人A253和FaDu鳞状细胞癌异种移植瘤)[2]剂量：0.2 mg/小鼠给药：p.o.；每日14天(环磷酰胺或CDDP前7天和后7天共14天)结果：
• 参考文献:

  [1]. Yeo JK, et al. Se-methylselenocysteine induces apoptosis through caspase activation and Bax cleavage mediated by calpain in SKOV-3 ovarian cancer cells. Cancer Lett. 2002 Aug 8;182(1):83-92.

  [2]. Cao S, et al. Se-methylselenocysteine offers selective protection against toxicity and potentiates the antitumour activity of anticancer drugs in preclinical animal models. Br J Cancer. 2014 Apr 2;110(7):1733-43.

  [3]. Xie Y, et al. Se-Methylselenocysteine Ameliorates Neuropathology and Cognitive Deficits by Attenuating Oxidative Stress and Metal Dyshomeostasis in Alzheimer Model Mice. Mol Nutr Food Res. 2018 Jun;62(12):e1800107.

MSDS

Name: SE-Methylseleno-L-Cysteine Material Safety Data Sheet Synonym: 2-Amino-3-Methylselanyl Propionic Acid; 3-(Methylseleno)-L-Alanine CAS: 26046-90-2 Section 1 - Chemical Product MSDS Name:SE-Methylseleno-L-Cysteine Material Safety Data Sheet Synonym:2-Amino-3-Methylselanyl Propionic Acid; 3-(Methylseleno)-L-Alanine Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS CAS# Chemical Name content EINECS# 26046-90-2 SE-Methylseleno-L-Cysteine ca. 100% unlisted Hazard Symbols: T Risk Phrases: 23/25 33 Section 3 - HAZARDS IDENTIFICATION EMERGENCY OVERVIEW Toxic by inhalation and if swallowed. Danger of cumulative effects.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: Effects may be delayed. 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. 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: Never give anything by mouth to an unconscious person. Get medical aid. Get medical aid immediately. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water. 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: Treat symptomatically and supportively. 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. Containers may explode when heated. Non-combustible, substance itself does not burn but may decompose upon heating to produce irritating, corrosive and/or toxic fumes. Runoff from fire control or dilution water may cause pollution. Extinguishing Media: Use water spray to cool fire-exposed containers. Do NOT get water inside containers. For small fires, use dry chemical, carbon dioxide, or water spray. For large fires, use water spray, fog or regular foam. Section 6 - ACCIDENTAL RELEASE MEASURES General Information: Use proper personal protective equipment as indicated in Section 8. Spills/Leaks: Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions. Provide ventilation. Section 7 - HANDLING and STORAGE Handling: Wash thoroughly after handling. Use only in a well-ventilated area. Minimize dust generation and accumulation. Do not breathe dust, vapor, mist, or gas. Do not get in eyes, on skin, or on clothing. Keep container tightly closed. Do not ingest or inhale. Use only in a chemical fume hood. Discard contaminated shoes. Storage: Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION Engineering Controls: Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low. Exposure Limits CAS# 26046-90-2: 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. Section 9 - PHYSICAL AND CHEMICAL PROPERTIES Physical State: Solid Color: white Odor: Not available. pH: Not available. Vapor Pressure: Not available. Viscosity: Not available. Boiling Point: Not available. Freezing/Melting Point: Not available. Autoignition Temperature: Not applicable. Flash Point: Not applicable. Explosion Limits, lower: Not available. Explosion Limits, upper: Not available. Decomposition Temperature: Solubility in water: Specific Gravity/Density: Not available. Molecular Formula: C4H9NO2Se Molecular Weight: 182.0285 Section 10 - STABILITY AND REACTIVITY Chemical Stability: Stable at room temperature in closed containers under normal storage and handling conditions. Conditions to Avoid: Incompatible materials, dust generation, excess heat, strong oxidants. Incompatibilities with Other Materials: Oxidizing agents. Hazardous Decomposition Products: Carbon monoxide, oxides of nitrogen, irritating and toxic fumes and gases, carbon dioxide, selenium/selenium oxides. Hazardous Polymerization: Has not been reported Section 11 - TOXICOLOGICAL INFORMATION RTECS#: CAS# 26046-90-2 unlisted. LD50/LC50: Not available. Carcinogenicity: SE-Methylseleno-L-Cysteine - Not listed by ACGIH, IARC, or NTP. Section 12 - ECOLOGICAL INFORMATION Section 13 - DISPOSAL CONSIDERATIONS Dispose of in a manner consistent with federal, state, and local regulations. Section 14 - TRANSPORT INFORMATION IATA Shipping Name: SELENIUM COMPOUND, N.O.S. Hazard Class: 6.1 UN Number: 3283 Packing Group: III IMO Shipping Name: SELENIUM COMPOUND, N.O.S. Hazard Class: 6.1 UN Number: 3283 Packing Group: III RID/ADR Shipping Name: SELENIUM COMPOUND, N.O.S. Hazard Class: 6.1 UN Number: 3283 Packing group: III Section 15 - REGULATORY INFORMATION European/International Regulations European Labeling in Accordance with EC Directives Hazard Symbols: T Risk Phrases: R 23/25 Toxic by inhalation and if swallowed. R 33 Danger of cumulative effects. Safety Phrases: S 20/21 When using do not eat, drink or smoke. 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# 26046-90-2: No information available. Canada None of the chemicals in this product are listed on the DSL/NDSL list. CAS# 26046-90-2 is not listed on Canada's Ingredient Disclosure List. US FEDERAL TSCA CAS# 26046-90-2 is not listed on the TSCA inventory. It is for research and development use only. SECTION 16 - ADDITIONAL INFORMATION N/A

安全

• 危害码 (欧洲): T: Toxic;N: Dangerous for the environment;
• 风险声明 (欧洲): R23/25;R33;R50/53
• 安全声明 (欧洲): S20/21-S28-S45-S60-S61
• 危险品运输编码: UN 3283
• WGK德国: 3
• 海关编码: 2922499990

合成路线

7101-31-7 51887-89-9 ~% 26046-90-2

文献：Sami Labs Limited Patent: US6794537 B1, 2004 ; Location in patent: Page column 5-6 ;

7101-31-7 32345-44-1 ~% 26046-90-2

文献：Sami Labs Limited Patent: US6794537 B1, 2004 ; Location in patent: Page column 5 ;

1464-43-3 74-88-4 ~% 26046-90-2

文献：Andreadou; Menge; Commandeur; Worthington; Vermeulen Journal of Medicinal Chemistry, 1996 , vol. 39, # 10 p. 2040 - 2046

上下游产品

上游产品  5
7101-31-7 51887-89-9 32345-44-1 1464-43-3
74-88-4
下游产品  2
127-17-3 2574-71-2

海关

海关编码	2922499990
中文概述	2922499990 其他氨基酸及其酯及它们的盐（含有一种以上含氧基的除外）. 增值税率:17.0% 退税率:9.0% 监管条件:AB(入境货物通关单,出境货物通关单) 最惠国关税:6.5% 普通关税:30.0%
申报要素	品名, 成分含量, 用途, 乙醇胺及其盐应报明色度, 乙醇胺及其盐应报明包装
监管条件	A.入境货物通关单 B.出境货物通关单
检验检疫	P.进境动植物、动植物产品检疫 Q.出境动植物、动植物产品检疫 R.进口食品卫生监督检验 S.出口食品卫生监督检验 M.进口商品检验 N.出口商品检验
Summary	HS:2922499990 other amino-acids, other than those containing more than one kind of oxygen function, and their esters; salts thereof VAT:17.0% Tax rebate rate:9.0% Supervision conditions:AB(certificate of inspection for goods inward,certificate of inspection for goods outward) MFN tariff:6.5% General tariff:30.0%