2-羟基马尿酸 | 487-54-7

• 物质功能分类: 化学试剂 - 有机试剂 - 脂肪酸
• 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: 2-羟基马尿酸
• 中文别名: O-羟基马尿酸
• 英文名称: Salicyluric acid
• 英文别名: 2-hydroxyhippuric acid；2-[(2-hydroxybenzoyl)amino]acetic acid
• CAS: 487-54-7
• 化学式: C₉H₉NO₄
• 分子量: 195.175
• InChiKey: ONJSZLXSECQROL-UHFFFAOYSA-N

物化性质

• 熔点：
  164-169 °C
• 沸点：
  331.83°C (rough estimate)
• 密度：
  1.3544 (rough estimate)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）
• 物理描述：
  Solid
• 碰撞截面：
  133.01 Ų [M-H]- [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]
• 稳定性/保质期：
  在常温常压下稳定，应避免与强氧化剂接触。

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  86.6
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S24/25
• 危险类别码：
  R36/37/38
• 海关编码：
  2924299090
• RTECS号：
  MR8160000
• WGK Germany：
  3
• 储存条件：
  密封保存，应储存在阴凉干燥的仓库中。

SDS

Name:	2-Hydroxyhippuric acid 97% Material Safety Data Sheet
Synonym:	Glycine, N-(2-hydroxybenzoyl)-; Glycine, N-salicyloyl-; N-(2-Hydroxybenzoyl)glycine; N-o-Hydroxybenzoylglycine; o-Hydroxyhippuric acid; Salicyloylglycine; Salicyluric acid
CAS:	487-54-7

Section 1 - Chemical Product MSDS Name:2-Hydroxyhippuric acid 97% Material Safety Data Sheet
Synonym:Glycine, N-(2-hydroxybenzoyl)-; Glycine, N-salicyloyl-; N-(2-Hydroxybenzoyl)glycine; N-o-Hydroxybenzoylglycine; o-Hydroxyhippuric acid; Salicyloylglycine; Salicyluric acid

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
487-54-7	2-Hydroxyhippuric acid	97	207-661-6

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

---

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. May be harmful if absorbed through the skin. The toxicological properties of this material have not been fully investigated.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated. May be harmful if swallowed.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. May be harmful if inhaled.
Chronic:
No information found.

---

Section 4 - FIRST AID MEASURES
Eyes: In case of contact, immediately flush eyes with plenty of water for at least 15 minutes. Get medical aid.
Skin:
In case of contact, flush skin with plenty of water. Remove contaminated clothing and shoes. Get medical aid if irritation develops and persists. Wash clothing before reuse.
Ingestion:
If swallowed, do not induce vomiting unless directed to do so by medical personnel. Never give anything by mouth to an unconscious person. Get medical aid.
Inhalation:
If inhaled, remove to fresh air. 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. Dusts at sufficient concentrations can form explosive mixtures with air. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use extinguishing media most appropriate for the surrounding fire.

---

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.

---

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

---

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 process enclosure, local exhaust ventilation, or other engineering controls to control airborne levels.
Exposure Limits CAS# 487-54-7: 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:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

---

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Crystalline powder
Color: light gray
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 167.00 - 169.00 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: C9H9NO4
Molecular Weight: 195.17

---

Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Dust generation.
Incompatibilities with Other Materials:
Strong oxidizing agents, strong bases.
Hazardous Decomposition Products:
Thermal decomposition or combustion may produce carbon monoxide, carbon dioxide, and nitrogen oxides..
Hazardous Polymerization: Has not been reported

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 487-54-7: MR8160000 LD50/LC50:
Not available.
Carcinogenicity:
2-Hydroxyhippuric acid - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

---

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: Not regulated.
Hazard Class:
UN Number:
Packing Group:
IMO
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
RID/ADR
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing group:

---

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# 487-54-7: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 487-54-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 487-54-7 is not listed on the TSCA inventory.
It is for research and development use only.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

生物活性方面，salicyluric acid 是一种内源性代谢产物。

反应信息

• 作为反应物：
  描述：

  2-羟基马尿酸 在 三溴化硼 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 60.0h， 生成 N⁵--N¹,N⁹-bis(2,3-dihydroxybenzoyl)bis(4-aminobutyl)amine
  参考文献：
  名称：

  Flexible synthesis of polyamine catecholamides

  摘要：

  DOI：

  10.1021/jo00335a041
• 作为产物：
  描述：

  柳酸苄酯 在 吡啶 、 palladium on activated charcoal 、 乙二醇甲醚 作用下， 生成 2-羟基马尿酸
  参考文献：
  名称：

  氨基酰胆碱。2. Mitteilung。Bildung vonSalicoyl-aminosäurenaus O-（Cbzo-α-aminoacyl）-salicylsäuren

  摘要：

  水杨基水杨基中的邻苯二甲氧基邻苯二甲氧基羰基-α-氨酰基）-水杨基苯胺基苯。在Zimmertemperatur的中性染料oder schwach saurerLösung（Methylcellosolve，Eisessig）中死于Einlagerung erfolgt。

  DOI：

  10.1002/hlca.19570400644

文献信息

• Structural effects of N-aromatic acyl-amino acid conjugates on their deconjugation in the cecal contents of rats: implication in design of a colon-specific prodrug with controlled conversion rate at the target site
  作者：Hyesik Kong、Hyunjeong Kim、Heejeong Do、Yonghyun Lee、Sungchae Hong、Jeong-Hyun Yoon、Yunjin Jung、Young Mi Kim

  DOI：10.1002/bdd.763

  日期：2011.9

  N-aromatic acyl-amino acid conjugates was examined in the cecal contents. On incubation of conjugates with glycine, D or/and L forms of alanine or phenylalanine in the cecal contents, the conjugates with D amino acids were not hydrolysed. The other conjugates are susceptible to the hydrolysis, the rates of which decreased as the size of the substituent on the 2-position of the amino acids increased. The conjugates

  N-芳族酰基-氨基酸缀合物具有靶向结肠的特性，这意味着此类缀合物是稳定的并且在到达大肠之前不被吸收，在大肠中它们被微生物转化（水解）为具有治疗活性的母体药物。为了研究N-芳族酰基-氨基酸缀合物对大肠去结合的结构影响，在盲肠内容物中检查了各种N-芳族酰基-氨基酸缀合物的水解。在将共轭物与甘氨酸，盲肠内容物的D或/和L形式的丙氨酸或苯丙氨酸一起孵育后，具有D氨基酸的共轭物不被水解。其他缀合物易于水解，其速率随着氨基酸2-位上取代基大小的增加而降低。具有甘氨酸和牛磺酸的烷基类似物（2-4个碳原子）的结合物具有抗水解性，而牛磺酸和甘氨酸的结合物则被有效地水解。N-芳族酰基-甘氨酸缀合物的水解通过芳族酰基部分上的吸电子基团的对位取代而得到增强，反之亦然。尽管邻位上的甲基，甲氧基或氯基阻止了水解，但位上的羟基却加速了水解。我们的数据可能为设计大肠内转化率受控的结肠特异性前药提供有用的信息。N-芳族酰基
• [EN] INHIBITORS OF HCV NS5B POLYMERASE<br/>[FR] INHIBITEURS DE LA POLYMERASE NS5B DU VHC
  申请人：UPJOHN CO

  公开号：WO2004002977A1

  公开（公告）日：2004-01-08

  The present invention porivdes compounds of Formula I, compositons and methods that are useful for treating viral infections and associated diseases, particularly HCV infections and associated diseases.

  本发明提供了式I化合物、组合物及方法，这些化合物、组合物及方法对于治疗病毒感染及相关疾病具有效用，特别是HCV感染及相关疾病。
• Synthesis of Cyclic Depsipeptides and Peptidesvia Direct Amide Cyclization
  作者：Jos� M. Villalgordo、Heinz Heimgartner

  DOI：10.1002/hlca.19970800312

  日期：1997.5.12

  depsipeptides and peptides derived from salicylic acids 6 and anthranilic acid 19, respectively (Schemes 2--4 and 5, resp.). The combination of the ‘azirine/oxazolone method’ for the synthesis of linear peptides containing α,α-disubstituted α-amino acids and the acid-catalyzed amide cyclization in DMF at 60° proved to be an excellent preparative route to ten-membered cyclic depsipeptides and peptides. In the

  2,2-二取代的2 H -azirin-3-amines 7（2,2-二取代的3-amino-2 H -azirines）被用作氨基酸合成子，用于制备中等大小的环二肽和水杨酸6和邻氨基苯甲酸19分别（方案2--4和5）。事实证明，将“叠氮基/恶唑酮法”用于合成含有α，α-二取代α-氨基酸的线性肽和酸催化的酰胺在DMF中于60°环化是一种极好的制备十元环的方法十肽和肽。在邻氨基苯甲酸衍生物的情况下，观察到跨环闭环反应（24 25）。较大的环被证明对水解极其敏感。
• Evaluation of aspirin metabolites as inhibitors of hypoxia-inducible factor hydroxylases
  作者：Benoit M. Lienard、Ana Conejo-García、Ineke Stolze、Christoph Loenarz、Neil J. Oldham、Peter J. Ratcliffe、Christopher J. Schofield

  DOI：10.1039/b814440k

  日期：——

  Known and potential aspirinmetabolites were evaluated as inhibitors of oxygen-sensing hypoxia-inducible transcription factor (HIF) hydroxylases; some of the metabolites were found to stabilise HIF-α in cells.

  已知和潜在的阿司匹林代谢物被评估为氧感应缺氧诱导转录因子（HIF）羟化酶的抑制剂；一些代谢物被发现能在细胞中稳定HIF-α。
• Hydrophobicity and glutathione peroxidase-like activity of substituted salicyloyl-5-seleninic acids: Re-investigations on aromatic selenium compounds based on their hydrophobicity
  作者：Sun-Chol Yu、Dong-Myong Ri、Hartmut Kühn

  DOI：10.1016/j.jorganchem.2018.02.045

  日期：2018.5

  salicylic acid derivatives exhibit glutathione peroxidase (GPx)-like activities higher than or equal to ebselen [Yu et al., Chem. Eur. J., 2008, 14, 7066; Org. Biomol. Chem., 2010, 8, 828]. For understanding the absence of GPx-like activity of the homologue of 5-seleninic anhydride of salicyloylglycine with a loger side chain, we have further synthesized 19 new derivatives (5-seleninic acids of methyl

  先前我们已经表明，一些5-硒化水杨酸衍生物表现出的谷胱甘肽过氧化物酶（GPx）样活性高于或等于依伯硒仑[Yu et al。，Chem。欧元。J.，2008，14，7066; 单位 生物分子 化学 ，2010，8，828]。为了解不存在具有loger侧链的水杨酰甘氨酸5-硒酸酐的同系物没有GPx样活性的情况，我们进一步合成了19种新衍生物（甲基或苯基水杨酸酯的5-硒酸，N-水杨酰ω-羧烷基胺或ñ-水杨酰基烷基/苯基胺，及其一些二硒化物）。某些带有长侧链或环己基的5-硒酸，无论其衍生自ω-羧烷基胺还是简单的烷基胺，都没有GPx样的活性。缺乏类似GPx的活性，使我们可以定量地将上述3个系列同源物的GPx活性与其疏水性（ClogP）相关联，在每个系列中均显示出令人满意的相关性。然后将分子疏水性广泛应用于包括二芳基二硒化物和依布硒仑衍生物在内的各种已知的芳香族硒GPx模拟物，以相对定量的方式解释其G

表征谱图