(R)-2-氨基-3-羟基-3-甲基丁酸 | 2280-28-6

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 其他氨基酸衍生物
• 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: (R)-2-氨基-3-羟基-3-甲基丁酸
• 中文别名: (R,s)-2-氨基-3-羟基-3-甲基丁酸；3-甲基苏氨酸；2-氨基-3-羟基-3-甲基丁酸；(R,S)-2-氨基-3-羟基-3-甲基丁酸
• 英文名称: 3-hydroxy-DL-valine
• 英文别名: 3-Hydroxy-DL-valin；2-amino-3-hydroxy-3-methylbutyric acid；2-azaniumyl-3-hydroxy-3-methylbutanoate
• CAS: 2280-28-6
• 化学式: C₅H₁₁NO₃
• 分子量: 133.147
• InChiKey: LDRFQSZFVGJGGP-UHFFFAOYSA-N

物化性质

• 熔点：
  200-202 °C
• 沸点：
  245.66°C (rough estimate)
• 密度：
  1.2510 (rough estimate)
• 溶解度：
  PBS（pH 7.2）：2 mg/ml

计算性质

• 辛醇/水分配系数(LogP)：
  -2.8
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  83.6
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 安全说明：
  S24/25
• 海关编码：
  2922509090

SDS

Name:	(R S)-2-Amino-3-hydroxy-3-methylbutanoic acid 99+% Material Safety Data Sheet
Synonym:	3-Hydroxyvaline
CAS:	2280-28-6

Section 1 - Chemical Product MSDS Name:(R S)-2-Amino-3-hydroxy-3-methylbutanoic acid 99+% Material Safety Data Sheet
Synonym:3-Hydroxyvaline

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
2280-28-6	(R,S)-2-Amino-3-hydroxy-3-methylbutano	>99	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 gastrointestinal irritation with nausea, vomiting and diarrhea.
Inhalation:
May cause respiratory tract irritation.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Immediately 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. 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. Do NOT use mouth-to-mouth resuscitation.
Notes to Physician:
Treat symptomatically and supportively.

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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:
Vacuum or sweep up material and place into a suitable disposal container. Avoid generating dusty conditions. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Use with adequate ventilation.
Avoid breathing dust.
Storage:
Store in a cool, dry place. Keep container closed when not in use.
Store in a cool, dry, well-ventilated area away from incompatible substances.

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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# 2280-28-6: 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 minimize contact with skin.
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: Powder
Color: white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 200 - 202 deg C
Autoignition Temperature: Not available.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C5H11NO3
Molecular Weight: 133.15

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Dust generation, excess heat.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, oxides of nitrogen, carbon dioxide.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 2280-28-6 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(R,S)-2-Amino-3-hydroxy-3-methylbutanoic acid - 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 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 2280-28-6: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 2280-28-6 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 2280-28-6 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：

  (R)-2-氨基-3-羟基-3-甲基丁酸 在 sodium hydroxide 作用下， 生成 (+/-)-N-Benzoyl-β-hydroxyvalinmethylester
  参考文献：
  名称：

  β-羟基缬氨酸的合成、拆分和构型

  摘要：

  DL-β-羟基缬氨酸是由β,β-二甲基缩水甘油酸钠通过苯甲胺氨解，然后氢解合成的。N-苯甲酰基-DL-β-羟基缬氨酸通过使用 (-)-α-甲基苄胺进行拆分，得到 (-)-N-苯甲酰基-β-羟基缬氨酸。VI 的构型通过将其转化为 N-苯甲酰基-β-氯缬氨酸甲酯 (I) 和随后的 I 氢解得到 (-) 甲基 N-苯甲酰基缬氨酸 (II) 来确定。从II，水解后获得光学纯的D-(-)-缬氨酸。

  DOI：

  10.1246/bcsj.39.2287
• 作为产物：
  描述：

  Dimethyl-3,3 diethoxycarbonyl-1,2 aziridine 在 氢氧化钾 作用下， 生成 (R)-2-氨基-3-羟基-3-甲基丁酸
  参考文献：
  名称：

  A Novel Synthesis of β-Hydroxyvaline

  摘要：

  从乙基β,β-二甲基丙烯酸酯经过1,2-二(乙氧羰基)-3,3-二甲基环氧乙烷作为中间体合成β-羟基缬氨酸，展示了一种新的合成该氨基酸的方法。

  DOI：

  10.1139/v71-430

文献信息

• Synthesis of α-amino-β-hydroxy acids using -bis(trimethylsilyl)aminoketene bis(trimethylsilyl) acetal or its -methyl--trimethylsilyl analog
  作者：Torsten Hvidt、Olivier R. Martin、Walter A. Szarek

  DOI：10.1016/s0040-4039(00)83885-x

  日期：1986.1

  Condensation of the title compounds with aldehydes and ketones in the presence of trimethylsilyl triflate provided the corresponding α-amino-β-hydroxy acids in fair to good yields as a mixture of diastereomers.

  在三氟甲磺酸三甲基甲硅烷基酯的存在下，标题化合物与醛和酮的缩合以非对映异构体混合物的形式以相当高的收率提供了相应的α-氨基-β-羟基酸。
• Etude par la modélisation moléculaire de la régiosélectivité de l'Ouverture des acides glycidiques par les amines aliphatiques
  作者：F. Grosjean、M. Huché、M. Larchevêque、J.J. Legendre、Y. Petit

  DOI：10.1016/s0040-4020(01)85509-5

  日期：——

  A model for glycidic acids opening reaction by ammonia and amines has been suggested from semi-empiric orbital calculations. It provides a way for evaluating the different interactions between the incoming nucleophile and the oxirane substituents. Steric and coulombic interactions of the carboxylate in staggered conformation (cis substitution) has a major influence to rationalize experimental regioselectivity

  从半经验轨道计算中已经提出了由氨和胺引起的缩水甘油酸打开反应的模型。它提供了一种评估传入的亲核试剂与环氧乙烷取代基之间不同相互作用的方法。交错构象（顺式取代）中羧酸盐的立体和库仑相互作用对合理化实验区域选择性具有重大影响。
• β-Lactam synthesis: Chemospecific sulfonation and cyclization of the β-hydroxyvaline nucleus
  作者：W.A Slusarchyk、T Dejneka、J Gougoutas、W.H Koster、D.R Kronenthal、M Malley、M.G Perri、F.L Routh、J.E Sundeen、E.R Weaver、R Zahler、J.D Godfrey、R.H Mueller、D.J Von Langen

  DOI：10.1016/s0040-4039(00)84643-2

  日期：1986.1

  intramolecular cyclization of “hydroxamate” using Mitsunobu conditions was inefficient for the formation and isolation of the C-4 dimethyl monobactam . However, chemospecific O-sulfonation of 1 and subsequent cyclization with base provides a useful method for β-lactam synthesis from a sterically hindered β-hydroxy amino acid. Competitive rearrangement of also occurs during cyclization providing isomeric

  使用Mitsunobu条件的“异羟肟酸酯”的分子内环化对于形成和分离C-4二甲基单bactam效率低下。然而，1的化学特异性O磺化以及随后的碱环化为从位阻β-羟基氨基酸合成β-内酰胺提供了一种有用的方法。在环化过程中也会发生竞争性重排，提供异构体β-内酰胺。
• Zur Synthese von β-Oxy-valin. Vereinfachte Darstellung der α-Brom-β-methoxy-isovaleriansäure
  作者：K. Rüfenacht

  DOI：10.1002/hlca.19520350309

  日期：1952.5.2

  1. Zur Zinkbestimmung in Cadmium-Zink-Legierungen mit 0,05 bis 10% Zn wird eine funkenspektrographische Methode beschrieben mit Verwendung eines reinen Cadmiumstabes als Gegenelektrode.

  1.为了测定锌含量为0.05％到10％的镉锌合金中的锌，描述了一种使用纯镉棒作为对电极的火花光谱法。
• Behrens et al., Journal of Biological Chemistry, 1948, vol. 175, p. 771,778
  作者：Behrens et al.

  DOI：——

  日期：——