Z-脱氢丙氨酸 | 39692-63-2

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 丙氨酸类衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: Z-脱氢丙氨酸
• 英文名称: 2-benzyloxycarbonylamino-acrylic acid
• 英文别名: N-Benzyloxycarbonyl-dehydroalanin；2-Benzyloxycarbonylamino-acrylsaeure；2-benzyloxycarbonylaminopropenoic acid；Z-dehydro-Ala-OH；2-(phenylmethoxycarbonylamino)prop-2-enoic acid
• CAS: 39692-63-2
• 化学式: C₁₁H₁₁NO₄
• mdl: MFCD00056722
• 分子量: 221.213
• InChiKey: QCHJVTWVRPQBBU-UHFFFAOYSA-N

物化性质

• 稳定性/保质期：

  常规情况下不会分解，没有危险反应。<?xml:namespace prefix = o ns = "urn:schemas-microsoft-com:office:office" />

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• WGK Germany：
  3
• 储存条件：
  密封，在-15°C下保存

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : Z-dehydro-Ala-OH
CAS-No. : 39692-63-2
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
Not a hazardous substance or mixture according to Regulation (EC) No. 1272/2008.
This substance is not classified as dangerous according to Directive 67/548/EEC.
Label elements
The product does not need to be labelled in accordance with EC directives or respective national laws.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Synonyms : Z-dehydroalanine
Formula : C11H11NO4
Molecular Weight : 221,21 g/mol

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Section 4. FIRST AID MEASURES
Description of first aid measures
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration.
In case of skin contact
Wash off with soap and plenty of water.
In case of eye contact
Flush eyes with water as a precaution.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water.
Most important symptoms and effects, both acute and delayed
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Indication of any immediate medical attention and special treatment needed
no data available

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Section 5. FIREFIGHTING MEASURES
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, nitrogen oxides (NOx)
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, protective equipment and emergency procedures
Avoid dust formation. Avoid breathing vapors, mist or gas.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Sweep up and shovel. Keep in suitable, closed containers for disposal.
Reference to other sections
For disposal see section 13.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Provide appropriate exhaust ventilation at places where dust is formed.Normal measures for preventive fire
protection.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Specific end uses
no data available

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Section 8. EXPOSURE CONTROLS/PERSONAL PROTECTION
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
General industrial hygiene practice.
Personal protective equipment
Eye/face protection
Use equipment for eye protection tested and approved under appropriate government standards
such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Body Protection
Choose body protection in relation to its type, to the concentration and amount of dangerous
substances, and to the specific work-place., The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Respiratory protection is not required. Where protection from nuisance levels of dusts are desired,
use type N95 (US) or type P1 (EN 143) dust masks. Use respirators and components tested and
approved under appropriate government standards such as NIOSH (US) or CEN (EU).

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Information on basic physical and chemical properties
a) Appearance Form: powder
Colour: white
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing no data available
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evaporation rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density no data available
n) Water solubility no data available
o) Partition coefficient: n- no data available
octanol/water
p) Autoignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

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Section 10. STABILITY AND REACTIVITY
Reactivity
no data available
Chemical stability
no data available
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available

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Section 11. TOXICOLOGICAL INFORMATION
Information on toxicological effects
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitization
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation
May be harmful if inhaled. May cause respiratory tract irritation.
Ingestion May be harmful if swallowed.
Skin May be harmful if absorbed through skin. May cause skin irritation.
Eyes May cause eye irritation.
Signs and Symptoms of Exposure
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Additional Information
RTECS: Not available

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Section 12. ECOLOGICAL INFORMATION
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
no data available
Other adverse effects
no data available

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Section 13. DISPOSAL CONSIDERATIONS
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company.
Contaminated packaging
Dispose of as unused product.

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Section 14. TRANSPORT INFORMATION
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

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SECTION 15 - REGULATORY INFORMATION
N/A

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

Z-脱氢-丙氨酸-OH是一种丙氨酸衍生物。

反应信息

• 作为反应物：
  描述：

  Z-脱氢丙氨酸 在 乙醚 、 五氯化磷 作用下， 生成 4-methyleneoxazolidine-2,5-dione
  参考文献：
  名称：

  Studies on Dehydroalanine Derivatives. I. Synthesis ofN-Carboxy-dehydroalanine Anhydride

  摘要：

  N-Carboxy dehydroalanine anhydride 首先是由 carbobenzoxy dehydroalanine 合成的。通过分析 N-羧基酸酐的红外光谱和研究其化学行为，确认了其结构。将 N-羧基酸酐的水解反应与 N-羧基 Dl-丙氨酸酸酐的水解反应进行了比较，推测脱氢丙氨酸氨基甲酸可能在常温下稳定地存在于二氧六环中。

  DOI：

  10.1246/bcsj.32.13
• 作为产物：
  描述：

  N-(benzyloxycarbonyl)-S-methyl-L-cysteine 在 sodium hydroxide 、 甲酸 作用下， 反应 2.0h， 生成 Z-脱氢丙氨酸
  参考文献：
  名称：

  Nonenzymatic Cleavages of Peptide Chains at the Cysteine and Serine Residues through Their Conversion to Dehydroalanine (DHAL). II. The Specific Chemical Cleavage of Cysteinyl Peptides

  摘要：

  DOI：

  10.1021/ja01060a050

文献信息

• Microstructural investigation of four kinds of γ′–Fe₄N nitrides in ion-nitrided pure iron
  作者：Z. Q. Liu、Z. K. Hei、D. X. Li

  DOI：10.1557/jmr.2002.0380

  日期：2002.10

  Conventional and high-resolution electron microscopies were used to investigate the microstructure and precipitation mechanism of four kinds of γ′–Fe₄N nitrides, formed at the surface during nitriding of polycrystalline pure iron sheet. γ′ nitrides in the top columnar compound layer were thin plates (3–12 nm), which precipitated from ε–Fe₂₋₃N grains with orientation relationship of (111)γ′//(0001)ε and [011]γ′//[1210]ε. Those in the transition compound layer remained as equiaxed grains (1–1.5 μm), which grew from the α–Fe substrate during nitriding. In the diffusion layer, striated γ′ nitrides nucleated from α″–Fe₁₆N₂ nitrides with orientation relationship of (100)γ′// (110)α″ and [011]γ′//[111]α″ while unstriated γ′ nitrides precipitated from the α–Fe substrate with the orientation relationship of (100)γ′//(110)α and [011]γ′//[111]α.

  采用传统电子显微镜和高分辨率电子显微镜研究了多晶纯铁板氮化过程中表面形成的四种γ′-Fe4N氮化物的显微结构和析出机理。顶部柱状化合物层中的γ′氮化物为薄板（3-12 nm），由取向关系为（111）γ′//（0001）ε和[011]γ′//[1210]ε的ε-Fe2-3N晶粒析出。过渡化合物层中的晶粒仍为等轴晶粒（1-1.5 μm），它们是在氮化过程中从α-Fe基底上长出来的。在扩散层中条纹状γ′氮化物由α″-Fe16N2 氮化物成核，取向关系为(100)γ′//(110)α″和[011]γ′//[111]α″。而从α-Fe基底析出的非条状γ′氮化物的取向关系为(100)γ′//(110)α和[011]γ′//[111]α。
• 1,3,2‐Diazaphospholenes Catalyze the Conjugate Reduction of Substituted Acrylic Acids
  作者：John H. Reed、Nicolai Cramer

  DOI：10.1002/cctc.202000662

  日期：2020.9.4

  nucleophilicity and remarkably low basicity of 1,3,2‐diazaphospholenes (DAPs) is exploited in a catalytic, metal‐free 1,4‐reduction of free α,β‐unsaturated carboxylic acids. Notably, the reduction occurs without a prior deprotonation of the carboxylic acid moiety and hence does not consume an additional hydride equivalent. This highlights the excellent nucleophilic character and low basicity of DAP‐hydrides

  1,3,2-二氮杂磷烯（DAP）的强亲核性和极低的碱性被用于催化的，无金属的1,4-还原的游离α，β-不饱和羧酸的催化作用。值得注意的是，还原反应是在没有羧酸部分预先去质子化的情况下发生的，因此不消耗额外的氢化物当量。这突出了DAP氢化物的出色的亲核特性和低碱度。在DAP催化过程中，对传统的过渡金属催化剂可能存在问题的Cbz基团或卤代烷等官能团具有很好的耐受性。此外，该转变的特征在于催化剂负载低，在环境温度下温和的反应条件以及快速的反应时间和高产率。描述了催化对映体选择形式的原理证明。
• [EN] AMIDINO COMPOUNDS AS CYSTEINE PROTEASE INHIBITORS<br/>[FR] COMPOSES AMIDINO SERVANT D'INHIBITEURS DE PROTEASES A CYSTEINE
  申请人：AXYS PHARMACEUTICALS

  公开号：WO2004108661A1

  公开（公告）日：2004-12-16

  The present invention is directed to compounds that are inhibitors of cysteine proteases, in particular, cathepsins B, K, L, F, and S and are therefore useful in treating diseases mediated by these proteases. The present invention is directed to pharmaceutical compositions comprising these compounds and processes for preparing them.

  本发明涉及一种抑制半胱氨酸蛋白酶的化合物，特别是包括B、K、L、F和S半胱氨酸蛋白酶，因此在治疗由这些蛋白酶介导的疾病方面具有用处。本发明涉及包含这些化合物的药物组合物以及其制备方法。
• Hydantoin formation from alaninamide derivatives. Reactions with 5-amino-5-methylhydantoin
  作者：Giancarlo Zanotti、Francesco Pinnen

  DOI：10.1002/jhet.5570180829

  日期：1981.12

  The influence of the α-substitution on hydantoin formation from urethan protected alaninamide derivatives is investigated. Several 5-methyl-5-substituted hydantoins, obtained from 5-amino-5-methylhydantoin, are described.

  研究了α-取代对由氨基甲酸乙酯保护的丙氨酸酰胺衍生物形成乙内酰脲的影响。描述了得自5-氨基-5-甲基乙内酰脲的几种5-甲基-5-取代的乙内酰脲。
• Dehydrooligopeptides. I. The Facile Coupling of α-Amino Acids with α-Dehydroamino Acids to Dehydrodipeptides
  作者：Yasuchika Yonezawa、Chung-gi Shin、Yuji Ono、Juji Yoshimura

  DOI：10.1246/bcsj.53.2905

  日期：1980.10

  N-Cbz- or N-Tos-α-dehydroamino acid (DHA) and its ester were prepared by the condensation of 2-oxo carboxylic acid or ester with benzyl carbamate or p-toluenesulfonamide. Subsequently, the N-protected DHA and its N-free ester thus obtained were coupled with several L-α-amino acid esters and N-protected (Boc or Cbz)-L-α-amino acid respectively by the usual peptide synthetic methods to give a number

  N-Cbz-或N-Tos-α-脱氢氨基酸（DHA）及其酯是通过2-氧代羧酸或酯与氨基甲酸苄酯或对甲苯磺酰胺缩合制备的。随后，将由此获得的 N-保护的 DHA 及其无 N-酯分别与几种 L-α-氨基酸酯和 N-保护的（Boc 或 Cbz）-L-α-氨基酸通过通常的肽合成方法偶联到给出许多不同类型的脱氢二肽。获得的所有新 DHA 和脱氢二肽的构型均显示为 (Z)-几何。