2-氨基-3-(4-羟基-3-甲氧基苯基)丙酸 | 7636-26-2

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 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: 2-氨基-3-(4-羟基-3-甲氧基苯基)丙酸
• 中文别名: 3-(4-羟基-3-甲氧基苯基)丙氨酸；3-甲氧基酪氨酸；3-O-甲基多巴
• 英文名称: 3-methoxy-DL-tyrosine
• 英文别名: 3-methoxytyrosine；4-Hydroxy-3-methoxy-phenylalanin；2-azaniumyl-3-(4-hydroxy-3-methoxyphenyl)propanoate
• CAS: 7636-26-2
• 化学式: C₁₀H₁₃NO₄
• 分子量: 211.218
• InChiKey: PFDUUKDQEHURQC-UHFFFAOYSA-N

物化性质

• 熔点：
  268 °C (decomp)
• 沸点：
  407.3±45.0 °C(Predicted)
• 密度：
  1.321
• 溶解度：
  酸水溶液（微溶），水（微溶，加热）
• 物理描述：
  Solid
• 碰撞截面：
  153.2 Ų [M+H]+ [CCS Type: DT, Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  92.8
• 氢给体数：
  3
• 氢受体数：
  5

ADMET

毒理性

• 毒性总结

甲氧基酪氨酸是芳香族L-氨基酸脱羧酶缺乏的主要生化标志物之一，这是一种影响血清素和生物合成的新型代谢错误。3-甲氧基酪氨酸在脑脊液、血浆和尿液中升高。儿茶酚-O-甲基转移酶是负责3-甲氧基酪氨酸形成的酶，它由许多器官中的L-DOPA产生。然而，它的半衰期（大约15小时）比L-DOPA的半衰期（大约1小时）要长。这意味着在患有帕金森病等慢性L-DOPA治疗的患者中，它会在血浆和大脑中积累。3-甲氧基酪氨酸对与L-DOPA相关的运动功能障碍、抑制纹状体对酪氨酸的摄取、与L-DOPA竞争血脑屏障转运系统以及抑制多巴胺释放都有一定的影响。3-甲氧基酪氨酸会增加同型半胱氨酸水平，这种氨基酸会导致心血管疾病和神经元损伤。其他一些毒性效应可能包括氧化DNA损伤，可能导致细胞死亡、活动能力下降和线粒体膜电位降低。（维基百科）

Methoxytyrosine is one of the main biochemical markers for aromatic L-amino acid decarboxylase deficiency, an inborn error of metabolism that affects serotonin and dopamine biosynthesis. 3-Methoxytyrosine is elevated in CSF, plasma, and urine. Catechol-O-methyl transferase is the enzyme in charge of 3-methoxytyrosine formation, which is produced from L-DOPA in many organs. Nevertheless, its half-life (15 hours approximately) is longer than the L-DOPA 's half-life, which is about one hour. This means that it is accumulated in the plasma and the brain of chronic L-DOPA therapy patients such as people suffering from Parkinson's disease. 3-Methoxytyrosine has some effects on L-DOPA related motor dysfunction, inhibition of striatal uptake of tyrosine, competition with L-DOPA for the blood–brain barrier transporter system and inhibition of dopamine release. 3-Methoxytyrosine increases homocysteine levels, and this amino acid induces cardiovascular disease and neuronal damage. Some other toxic effects could be oxidative DNA damage which can cause cell death, a decrease in locomotor activities and diminishment in mitochondrial membrane potential. (Wikipedia)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 致癌物分类

对人类不具有致癌性（未被国际癌症研究机构IARC列名）。

No indication of carcinogenicity to humans (not listed by IARC).

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 健康影响

3-甲氧基酪氨酸长期高水平与芳香族L-氨基酸脱羧酶缺乏症相关。

Chronically high levels of 3-methoxytyrosine are associated with Aromatic L-Amino acid Decarboxylase Deficiency.

来源:Toxin and Toxin Target Database (T3DB)

安全信息

• 安全说明：
  S22,S26,S36/37/39
• 危险类别码：
  R22,R36/37/38
• WGK Germany：
  3

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-Methoxy-DL-tyrosine
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: 3-Methoxy-DL-tyrosine
CAS number: 7636-26-2

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels, refrigerated.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C10H13NO4
Molecular weight: 211.2

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  3-甲氧基-L-酪氨酸	3-O-methyldopa	300-48-1	C10H13NO4	211.218
  4-羟基-3-甲氧基苯基丙酮酸	vanilpyruvic acid	1081-71-6	C10H10O5	210.186
  ——	3-(4-hydroxy-3-methoxy-phenyl)-2-thioxo-propionic acid	5438-45-9	C10H10O4S	226.253
  ——	2-hydroxyimino-3-(4-hydroxy-3-methoxy-phenyl)-propionic acid	5447-36-9	C10H11NO5	225.201
  ——	5-vanillyl-imidazolidine-2,4-dione	62682-19-3	C11H12N2O4	236.227
  ——	4-Acetoxy-3-methoxyphenylacetaldehyde	6391-59-9	C11H12O4	208.214
  乙酸丁香酚酯	eugenol acetate	93-28-7	C12H14O3	206.241

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	tert-butyl 2-amino-3-(4-hydroxy-3-methoxyphenyl)propanoate	1352293-13-0	C14H21NO4	267.325
  ——	2-[(tert-butoxycarbonyl)amino]-3-(4-hydroxy-3-methoxyphenyl)propanoic acid	129048-72-2	C15H21NO6	311.335
  ——	(R)-N-acetyl-(4-acetoxy-3-methoxyphenyl)alanine	30948-27-7	C14H17NO6	295.292

反应信息

• 作为反应物：
  描述：

  2-氨基-3-(4-羟基-3-甲氧基苯基)丙酸 在 sodium hydroxide 、 乙酸酐 作用下， 生成 (R)-N-acetyl-(4-acetoxy-3-methoxyphenyl)alanine
  参考文献：
  名称：

  Process for L-dopa

  摘要：

  描述了一种制备(S)-或L-3-(3,4-二羟基苯基)丙氨酸(L-dopa)的过程。该过程利用水作为反应过程溶剂，通过形成一个中间体，在极性溶剂中可以动力学地分离出所需异构体的前体，其中不需要的异构体可以高效地进行消旋以供再利用。

  公开号：

  US04716246A1
• 作为产物：
  描述：

  4-羟基-3-甲氧基苯基丙酮酸 在 水 、 甲酸铵 、 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 反应 15.0h， 生成 2-氨基-3-(4-羟基-3-甲氧基苯基)丙酸
  参考文献：
  名称：

  嗜热酪氨酸苯酚酶和L-乳酸氧化酶的偶合合成L-酪氨酸衍生物

  摘要：

  一锅生物级联反应由l-乳酸氧化酶（AvLOX）和设计的嗜热酪氨酸-苯酚裂解酶（TTPL）突变体催化的两个酶促步骤用于合成l-酪氨酸衍生物，其中丙酮酸是由AvLOX从现成的生物基升-乳。

  DOI：

  10.1002/ejoc.202000061

文献信息

• C-terminal modified oxamyl dipeptides as inhibitors of the ICE-ced-3 family of cysteine proteases
  申请人：——

  公开号：US20020042376A1

  公开（公告）日：2002-04-11

  This invention is directed to novel oxamyl dipeptide ICE/ced-3 family inhibitor compounds. The invention is also directed to pharmaceutical compositions containing these compounds, as well as to the use of such compositions in the treatment of patients suffering inflammatory, autoimmune and neurodegenerative diseases, for the prevention of ischemic injury, and for the preservation of organs that are to undergo a transplantation procedure.

  这项发明涉及新型的oxamyl二肽ICE/ced-3家族抑制剂化合物。该发明还涉及含有这些化合物的药物组合物，以及在治疗患有炎症性、自身免疫和神经退行性疾病的患者中使用这些组合物，用于预防缺血性损伤，并用于保存即将进行移植手术的器官。
• Amino acid derived prodrugs of propofol, compositions and uses thereof
  申请人：Gallop A. Mark

  公开号：US20050004381A1

  公开（公告）日：2005-01-06

  The present invention provides propofol prodrugs, methods of making propofol prodrugs, pharmaceutical compositions of propofol prodrugs and methods of using propofol prodrugs and pharmaceutical compositions thereof to treat or prevent diseases or disorders such as migraine headache pain and post-chemotherapy or post-operative surgery nausea and vomiting.

  本发明提供了丙泊酚前药、制备丙泊酚前药的方法、丙泊酚前药的药物组合物以及使用丙泊酚前药和药物组合物治疗或预防偏头痛疼痛、化疗后或手术后恶心和呕吐等疾病或失调的方法。
• [EN] PRODRUGS OF OXAZOLIDINONE CETP INHIBITORS<br/>[FR] PROMÉDICAMENTS D'INHIBITEURS DE CETP À BASE D'OXAZOLIDINONE
  申请人：MERCK SHARP & DOHME

  公开号：WO2010039474A1

  公开（公告）日：2010-04-08

  The compounds of Formula I are prodrugs of CETP inhibitors having a central oxazolidinone ring. The compounds cyclize by the elimination of HX to form an oxazolidinone ring after administration to a patient.

  公式I的化合物是CETP抑制剂的前药，具有中心噁唑烷酮环。这些化合物在给药后通过消除HX而环化，形成噁唑烷酮环。
• Inhibition of inflammation using interleukin-1beta-converting enzyme (ICE)/CED-3 family inhibitors
  申请人：Idun Pharmaceuticals, Inc.

  公开号：US20020123522A1

  公开（公告）日：2002-09-05

  The present invention provides methods for expanding and increasing survival of hematopoietic cell populations, for prolonging viability of an organ for transplantation, and enhancing bioproduction, using interleukin-1&bgr;-converting enzyme (ICE)/CED-3 family inhibitors. Exemplary compounds useful in the methods of the invention are provided herein.

  本发明提供了一种使用白细胞介素-1β转化酶（ICE）/CED-3家族抑制剂来扩展和增加造血细胞群体的存活、延长移植器官的存活能力和增强生物生产的方法。本发明中提供了可用于该方法中的典型化合物。
• TREATMENT OF INFECTIOUS DISEASE USING INTERLEUKIN-1BETA-CONVERTING ENZYME (ICE)/CED-3 FAMILY INHIBITORS
  申请人：Idun Pharmaceuticals, Inc.

  公开号：US20020128306A1

  公开（公告）日：2002-09-12

  The present invention provides methods and compositions for treating infectious disease or suppressing inflammation associated therewith or ameliorating symptoms thereof by the suppression of the activity of a member of the interleukin-1&bgr;-converting enzyme (ICE)/CED-3 family of proteases. Also provided are compositions useful for these purposes. Exemplary compounds useful in the methods of the invention are provided herein.

  本发明提供了一种通过抑制白细胞介素-1β转化酶（ICE）/CED-3家族蛋白酶的活性来治疗传染病、抑制相关炎症或缓解症状的方法和组合物。还提供了用于这些目的的组合物。本发明方法中有用的示例化合物在此提供。