D-4-甲氧基扁桃酸甲酯 | 20714-89-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: D-4-甲氧基扁桃酸甲酯
• 中文别名: (R)-4-甲氧基扁桃酸；D-4-甲氧基扁桃酸；(R)-4-甲氧基扁桃酸甲酯
• 英文名称: (R)-p-methoxymandelic acid
• 英文别名: (D)-p-methoxymandelic acid；(R)-4-methoxymandelic acid；(R)-(-)-2-hydroxy-2-(4-methoxyphenyl)acetic acid；(R)-2-Hydroxy-2-(4-methoxyphenyl)acetic acid；(2R)-2-hydroxy-2-(4-methoxyphenyl)acetic acid
• CAS: 20714-89-0
• 化学式: C₉H₁₀O₄
• 分子量: 182.176
• InChiKey: ITECRQOOEQWFPE-MRVPVSSYSA-N

物化性质

• 熔点：
  102-104 °C
• 沸点：
  370.4±32.0 °C(Predicted)
• 密度：
  1.309

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2918990090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  存储条件：室温、密封、干燥

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: (R)-4-Methoxymandelic acid
Synonyms:

---

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

---

Section 3. Composition/information on ingredients.
Ingredient name: (R)-4-Methoxymandelic acid
CAS number: 20714-89-0

---

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.

---

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.

---

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.

---

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.
Storage:

---

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.

---

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: C9H10O4
Molecular weight: 182.2

---

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

---

Section 11. Toxicological information
No data.

---

Section 12. Ecological information
No data.

---

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.

---

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

---

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.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  D-4-甲氧基扁桃酸甲酯 在 sodium hydroxide 、 1-羟基苯并三唑 、 臭氧 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 (S)-5,5-Difluoro-3-{(S)-2-[(R)-2-hydroxy-2-(4-methoxy-phenyl)-acetylamino]-4-methyl-pentanoylamino}-2-oxo-pentanoic acid
  参考文献：
  名称：

  Capped dipeptide α-Ketoacid inhibitors of the HCV NS3 protease

  摘要：

  The N-terminal aminoacid of alpha-ketotripeptide inhibitors of the hepatitis C virus NS3 protease can be replaced with an alpha-hydroxy acid, leading to capped dipeptide inhibitors such as 20 with an IC50 value of 3.0 muM. The importance of the lipophilic side chain interactions at S3 of the protease and the requirement of the capping residue with R configuration have been explained by molecular modeling studies. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00691-1
• 作为产物：
  描述：

  对甲氧基苯乙醛酸 在 (R)-ketoacid reductase from Saccharomyces cerevisiae ZJB₅₀₇₄ 、 甘油 作用下， 以 aq. phosphate buffer 为溶剂， 以99.9%的产率得到
  参考文献：
  名称：

  通过串联生物催化氧化和还原反应对一锅一锅的2-羟基酸进行一步脱硫。

  摘要：

  通过将产生（S）-羟酸脱氢酶的微生物的静止细胞与（ R）-产生酮酸还原酶的微生物。

  DOI：

  10.1039/c3cc46240d

文献信息

• Azacyclosteroid histamine-3 receptor ligands
  申请人：Zhao Chen

  公开号：US20050227953A1

  公开（公告）日：2005-10-13

  Azacyclosteroid histamine-3 receptor ligands, pharmaceutical compositions comprising such compounds, and methods for using such compounds and compositions are described herein.

  阿扎环状类固醇组胺-3受体配体、包含该化合物的药物组合物以及使用这些化合物和组合物的方法在本文件中进行了描述。
• PROCESS FOR STRAIGHTENING KERATIN FIBRES WITH A HEATING MEANS AND DENATURING AGENTS
  申请人：Philippe Michel

  公开号：US20100028280A1

  公开（公告）日：2010-02-04

  The invention relates to a process for straightening keratin fibres, comprising: (i) a step in which a straightening composition containing at least two denaturing agents is applied to the keratin fibres, (ii) a step in which the temperature of the keratin fibres is raised, using a heating means, to a temperature of between 110 and 250° C.

  该发明涉及一种直发角蛋白纤维的拉直过程，包括：(i)将至少两种变性剂含有的拉直组合物涂抹到角蛋白纤维上的步骤，(ii)使用加热装置将角蛋白纤维的温度升高至110至250°C的步骤。
• Microbial Deracemization of α-Substituted Carboxylic Acids:  Substrate Specificity and Mechanistic Investigation
  作者：Dai-ichiro Kato、Satoshi Mitsuda、Hiromichi Ohta

  DOI：10.1021/jo034253x

  日期：2003.9.1

  A new enzymatic method for the preparation of optically active alpha-substituted carboxylic acids is reported. This technique is called deracemization reaction, which provides us with a route to obtain the enantiomerically pure compounds, theoretically in 100% yield starting from the racemic mixture. This means that the synthesis of a racemate is almost equal to the synthesis of the optically active

  报道了一种用于制备旋光的α-取代的羧酸的新的酶促方法。这项技术称为脱硝反应，它为我们提供了从外消旋混合物开始，理论上以100％的收率获得对映体纯化合物的途径。这意味着外消旋体的合成几乎与旋光化合物的合成相同，并且该概念与不对称合成中通常被接受的概念完全不同。使用不断增长的诺卡氏夜蛾诺卡氏菌JCM3208的细胞系统，可以使2-芳基-和2-芳基氧基丙酸的外消旋物顺利脱硫，并以高化学收率（> 50％）回收富含（R）-形式的产物。此外，使用旋光性起始化合物和氘代衍生物以及抑制剂，
• Highly Efficient Deracemization of Racemic 2-Hydroxy Acids in a Three-Enzyme Co-Expression System Using a Novel Ketoacid Reductase
  作者：Ya-Ping Xue、Chuang Wang、Di-Chen Wang、Zhi-Qiang Liu、Yu-Guo Zheng

  DOI：10.1007/s12010-018-2760-0

  日期：2018.11

  coli (HADH-LlKAR-GDH) co-expressing 2-hydroxyacid dehydrogenase, LlKAR, and glucose dehydrogenase was constructed for efficient deracemization of racemic 2-HAs. Most of the racemic 2-HAs were deracemized to their (R)-isomers at high yields and enantiomeric purity. In the case of racemic 2-chloromandelic acid, as much as 300 mM of substrate was completely transformed into the optically pure (R)-2-chloromandelic

  对映纯2-羟基酸（2-HAs）是合成药物和精细化学品的重要中间体。外消旋2-HA脱硫成相应的单个对映体代表了一种工业上合成手性2-HA的经济高效的方法。在这项工作中，通过基因组挖掘发现了一种来自乳酸乳球菌（LlKAR）的新的酮酸还原酶，该酶具有更高的活性和对芳香族α-酮酸的底物耐受性，然后对其酶学性质进行了表征。因此，构建了共表达2-羟酸脱氢酶，LlKAR和葡萄糖脱氢酶的工程化大肠杆菌（HADH-L1KAR-GDH），以有效地消旋外消旋2-HA。大部分外消旋2-HA均以高收率和对映体纯度脱硫为它们的（R）异构体。
• Enantioseparation of chiral mandelic acid derivatives by supercritical fluid chromatography
  作者：Jiawei Ding、Ming Zhang、Huixue Dai、Chunmian Lin

  DOI：10.1002/chir.23018

  日期：2018.12

  Mandelic acid and its derivatives are important chiral analogs which are widely used in the pharmaceutical synthetic industry. The present study investigated the enantiomeric separation of six mandelic acids (mandelic acid, 2‐chloromandelic acid, 3‐chloromandelic acid, 4‐chloromandelic acid, 4‐bromomandelic acid, 4‐methoxymandelic acid) on the Chiralpak AD‐3 column by supercritical fluid chromatography

  扁桃酸及其衍生物是重要的手性类似物，广泛用于药物合成工业中。本研究研究了通过超临界流体在Chiralpak AD-3色谱柱上对6种扁桃酸（扁桃酸，2-氯扁桃酸，3-氯扁桃酸，4-氯扁桃酸，4-溴扁桃酸，4-甲氧基扁桃酸）的对映体分离层析。研究了三氟乙酸的体积分数，改性剂的类型和百分比，柱温和背压对分离效率的影响。并确定对映体的洗脱顺序。结果表明，对于给定的改性剂，保留因子，分离因子和分离分辨率随改性剂体积比的增加而逐渐降低。在相同体积比的改性剂下，除3-氯扁桃酸外，扁桃酸及其衍生物的保留因子按甲醇，乙醇和异丙醇的顺序增加。分离系数和分离分辨率随柱温的升高而降低（低于温度极限）。背压影响对映体分离过程：随着背压增加，保留因子相应降低。在相同的手性柱条件下，与HPLC方法相比，SFC方法显示出更快，更有效的分离和更好的对映选择性。分离因子和分离分辨率随柱温的升高而降低（低于温度极限）。背压影响