2-乙酰基-3-甲基苯甲酸 | 4386-39-4

• 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-乙酰基-3-甲基苯甲酸
• 中文别名: 2-(乙酰氧基)-3-甲基苯甲酸；2-(乙酰基氧基)-3-甲基苯甲酸
• 英文名称: 3-methylaspirin
• 英文别名: 2-acetoxy-3-methylbenzoic acid；2-Acetoxy-3-methyl-benzoesaeure；2-(Acetyloxy)-3-methylbenzoic acid；2-acetyloxy-3-methylbenzoic acid
• CAS: 4386-39-4
• 化学式: C₁₀H₁₀O₄
• mdl: MFCD00085683
• 分子量: 194.187
• InChiKey: XRBMKGUDDJPAMH-UHFFFAOYSA-N

物化性质

• 熔点：
  113 °C
• 沸点：
  324.5±30.0 °C(Predicted)
• 密度：
  1.245±0.06 g/cm3(Predicted)
• 碰撞截面：
  129.1 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2918990090

SDS

Name:	2-(Acetyloxy)-3-methylbenzoic acid 97% Material Safety Data Sheet
Synonym:	2-(Acetoxy)-m-toluic acid
CAS:	4386-39-4

Section 1 - Chemical Product MSDS Name:2-(Acetyloxy)-3-methylbenzoic acid 97% Material Safety Data Sheet
Synonym:2-(Acetoxy)-m-toluic acid

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
4386-39-4	2-(Acetyloxy)-3-methylbenzoic acid	97%	224-499-1

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation. May cause chemical conjunctivitis.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
Causes respiratory tract irritation. May be harmful if inhaled.
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. Wash mouth out with 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.
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 chemical 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. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Minimize dust generation and accumulation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing.
Keep container tightly closed. Avoid ingestion and inhalation. Use with adequate ventilation. Wash clothing before reuse.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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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# 4386-39-4: 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 prevent skin exposure.
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: Solid
Color: white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 115 - 117 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C10H10O4
Molecular Weight: 194

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat.
Incompatibilities with Other Materials:
Strong oxidizing agents, acids, bases.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 4386-39-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2-(Acetyloxy)-3-methylbenzoic 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: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 4386-39-4: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 4386-39-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 4386-39-4 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：

  2-乙酰基-3-甲基苯甲酸 在 氯化亚砜 、 水 、 sodium hydroxide 作用下， 反应 2.0h， 生成 2-amino-8-methyl-4-oxo-4H-1-benzopyran-3-carbonitrile
  参考文献：
  名称：

  Synthesis of novel thiopyrimidines: an investigation of anti-tubercular and antimicrobial activity

  摘要：

  A variety of novel sulfur-containing tricyclic pyrimidine derivatives have been synthesized via the reaction of 2-amino-4-oxo-4H-chromene-3-carbonitriles 3(a-f) with different reagents and characterized by IR, H-1 NMR, C-13 NMR, mass spectrometry and elemental analysis. The anti-tubercular and antimicrobial activities of the synthesized compounds were investigated.[GRAPHICS].

  DOI：

  10.1080/17415993.2010.523894
• 作为产物：
  描述：

  3-甲基水杨酸 、 乙酰氯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.75h， 以85%的产率得到2-乙酰基-3-甲基苯甲酸
  参考文献：
  名称：

  1-羟基-2，5，8-三甲基-9-芴酮的合成方法

  摘要：

  本发明属于天然药物合成领域，首次公开了一种以3‑甲基水杨酸和对二甲苯为原料，先将3‑甲基水杨酸用乙酰氯酰化制得3‑甲基乙酰水杨酸，再以醋酸钯为催化剂，过硫酸钠为氧化剂，N‑乙酰‑L‑异亮氨酸、二甲基亚砜和三氟甲磺酸为络合剂，将3‑甲基乙酰水杨酸与对二甲苯反应合成1‑羟基‑2，5，8‑三甲基‑9‑芴酮的方法。

  公开号：

  CN112574033B

文献信息

• Novel Short-Step Synthesis of Functionalized γ-Phenyl-β-hydroxybutenoates and their Cyclization to 4-Hydroxycoumarins via the <i>N</i>-Hydroxybenzotriazole Methodology
  作者：Olga Igglessi-Markopoulou、Giorgos Athanasellis、Georgia Melagraki、Haralambos Chatzidakis、Antreas Afantitis、Anastasia Detsi、John Markopoulos

  DOI：10.1055/s-2004-829132

  日期：——

  A novel method for the synthesis of functionalized 3- substituted 4-hydroxycoumarins is reported. C-Acylation com- pounds were derived from the reaction of the N-hydroxybenzotri- azole ester of the functionalized acetyl salicylic acids and a variety of active methylene compounds and cyclized to the title com- pounds. The synthesis is simple and the compounds are produced in yields varying from 39 to

  报道了一种合成功能化3-取代4-羟基香豆素的新方法。C-酰化化合物衍生自官能化乙酰水杨酸的 N-羟基苯并三唑酯与多种活性亚甲基化合物的反应，并环化为标题化合物。合成很简单，化合物的产率从 39% 到 80% 不等。文献中首次通过核磁共振光谱对新制备的 C-酰化化合物的结构进行了深入研究。
• Development of methylated cobalt–alkyne complexes with selective cytotoxicity against COX‐positive cancer cell lines
  作者：Daniel Baecker、Jessica Sagasser、Serhat Karaman、Anton Amadeus Hörmann、Ronald Gust

  DOI：10.1002/ardp.202100408

  日期：2022.2

  potency in T-24 cells, which express distinctly fewer COX enzymes (COX-1/COX-2 = 50/1) than HT-29 cells (COX-1/COX-2 = 50/50), and the only marginal activity in COX-negative MCF-7 breast cancer cells point to an interference in the arachidonic acid cascade through COX-2 inhibition as part of the mode of action, especially as the cellular uptake was even higher in MCF-7 cells than in T-24 cells. These findings

  细胞毒性环氧合酶 (COX) 抑制剂 [(prop-2-ynyl)−2-acetoxybenzoate]dicbalhexacarbonyl (Co-ASS) 在乙酰水杨酸 (ASS) 的 3、4、5 或 6 位上具有甲基的衍生物合成支架的目的是提高对 COX-2 的选择性。通过这种修改，预期对表达 COX-2 的肿瘤具有更高的特异性，从而防止 COX-1 介导的副作用。测试了钴-炔烃复合物的 COX 抑制和抗增殖特性以及它们的细胞摄取。甲基化降低了对分离的 COX-1 的影响，而对分离的 COX-2 的影响与 Co-ASS 相比几乎保持不变。在细胞系统中，新化合物对 COX 阳性 HT-29 结肠癌细胞的细胞毒性优于顺铂。T-24 细胞的生长抑制效力降低，其表达的 COX 酶（COX-1/COX-2 = 50/1）明显少于 HT-29 细胞（COX-1/COX-2 = 50/50）， COX
• Synthesis and biological evaluation of CX-659S and its related compounds for their inhibitory effects on the delayed-type hypersensitivity reaction
  作者：Masanori Tobe、Yoshiaki Isobe、Yuso Goto、Fumihiro Obara、Masami Tsuchiya、Junko Matsui、Kosaku Hirota、Hideya Hayashi

  DOI：10.1016/s0968-0896(00)00126-7

  日期：2000.8

  In order to find novel nonsteroidal compounds possessing an inhibitory activity against delayed-type hypersensitivity (DTH) reactions, we conducted random screening using a picryl chloride (PC)-induced contact hypersensitivity reaction (CHR) in mice, and found compound 1 as a lead compound. Then we synthesized and evaluated an extensive series of 5-carboxamidouracil derivatives focused on both the

  为了找到对延迟型超敏反应（DTH）反应具有抑制活性的新型非甾体化合物，我们使用氯化吡啶（PC）诱导的小鼠接触超敏反应（CHR）在小鼠中进行了随机筛选，发现化合物1为铅复合。然后，我们合成并评估了一系列广泛的针对尿嘧啶和抗氧化部分的5-羧酰胺基尿嘧啶衍生物。其中，我们发现受阻酚部分对于展示其活性是必要的。特别地，发现具有维生素E的部分结构的化合物28a-28c通过口服和局部给药都具有针对DTH反应的有效活性。化合物28c对脂质过氧化具有抗氧化活性，IC50为5.9 microM。
• N-ACYL ANTHRANILIC ACID DERIVATIVE OR SALT THEREOF
  申请人：Yokotani Junichi

  公开号：US20110275797A1

  公开（公告）日：2011-11-10

  An N-acyl anthranilic acid derivative represented by general formula (1) or a salt thereof is useful for prevention or treatment of diseases associated with excessive production of collagen. (In the formula, R 1 represents a carboxyl group or the like; R 2 represents a hydrogen atom or the like; R 3 represents an optionally substituted aryl group or the like; X 1 represents a carbonyl group; X 2 represents a bonding hand; X 3 represents a bonding hand; X 4 represents a bonding hand or the like; and A represents an optionally substituted phenyl group or the like.)

  通用公式（1）表示的N-酰基蒽酸衍生物或其盐对预防或治疗与胶原蛋白过度产生相关的疾病具有用处。（在该公式中，R1代表羧基或类似物；R2代表氢原子或类似物；R3代表可选择取代的芳基或类似物；X1代表羰基；X2代表连接手；X3代表连接手；X4代表连接手或类似物；A代表可选择取代的苯基或类似物。）
• Thiazolides as Novel Antiviral Agents. 1. Inhibition of Hepatitis B Virus Replication
  作者：Andrew V. Stachulski、Chandrakala Pidathala、Eleanor C. Row、Raman Sharma、Neil G. Berry、Mazhar Iqbal、Joanne Bentley、Sarah A. Allman、Geoffrey Edwards、Alison Helm、Jennifer Hellier、Brent E. Korba、J. Edward Semple、Jean-Francois Rossignol

  DOI：10.1021/jm200153p

  日期：2011.6.23

  activity against HBV; by contrast, some related salicyloylanilides show a narrower spectrum of activity. The ADME properties of 3 are similar to 1; viz., the O-acetate is an effective prodrug, and the O-aryl glucuronide is a major metabolite. The QSAR study shows a good correlation of observed EC(90) for intracellular virions with thiazolide structural parameters. Finally we discuss the mechanism of action

  我们报告了多种噻唑烷 [即 2-羟基芳酰基-N-（噻唑-2-基）酰胺] 对抗乙型肝炎病毒复制的合成和活性，并对我们的结果进行了 QSAR 分析。原型噻唑啉硝唑尼特 [2-羟基苯甲酰基-N-(5-硝基噻唑-2-基)酰胺，NTZ] 1 是一种广谱抗感染剂，可有效对抗厌氧细菌、病毒和寄生虫。相比之下，2-羟基苯甲酰-N-(5-氯噻唑-2-基)酰胺 3 是一种新型、有效、选择性的乙型肝炎复制抑制剂 (EC(50) = 0.33 μm)，但对厌氧菌无活性。几种 4'- 和 5'-取代的噻唑化物对 HBV 显示出良好的活性；相比之下，一些相关的水杨酰苯胺的活性范围更窄。3 的 ADME 属性与 1 类似；即，O-乙酸酯是一种有效的前药，O-芳基葡糖苷酸是主要代谢物。QSAR 研究显示观察到的 EC(90) 与噻唑啉结构参数的细胞内病毒粒子具有良好的相关性。最后，我们讨论了与当前结果相关的噻唑化物的作用机制。