4-乙酰基-3-羟基乙酸苯酯 | 42059-48-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4-乙酰基-3-羟基乙酸苯酯
• 英文名称: acetic acid 4-acetyl-3-hydroxyphenyl ester
• 英文别名: 4-acetoxy-2-hydroxyacetophenone；4-Acetyl-3-hydroxyphenyl acetate；(4-acetyl-3-hydroxyphenyl) acetate
• CAS: 42059-48-3
• 化学式: C₁₀H₁₀O₄
• mdl: MFCD00092225
• 分子量: 194.187
• InChiKey: XBBMROOTCQXGMR-UHFFFAOYSA-N

物化性质

• 熔点：
  73,5-74,5°C
• 沸点：
  331.2±32.0 °C(Predicted)
• 密度：
  1.236±0.06 g/cm3(Predicted)
• 溶解度：
  溶于甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 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,S36/37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2915390090
• 储存条件：
  室温

SDS

Name:	4-Acetyl-3-hydroxyphenyl acetate 95+% Material Safety Data Sheet
Synonym:	4-Acetoxy-2-hydroxyacetophenon
CAS:	42059-48-3

Section 1 - Chemical Product MSDS Name:4-Acetyl-3-hydroxyphenyl acetate 95+% Material Safety Data Sheet
Synonym:4-Acetoxy-2-hydroxyacetophenon

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
42059-48-3	4-Acetyl-3-hydroxyphenyl acetate	95+%	unlisted

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.
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:
Not available.

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Section 4 - FIRST AID MEASURES
Eyes: 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.
Ingestion:
Get medical aid. 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.
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.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
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# 42059-48-3: Personal Protective Equipment Eyes: Not available.
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: tan
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 57 - 59 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:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents, acids, bases.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide, acrid smoke and fumes.
Hazardous Polymerization: Not available.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 42059-48-3 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
4-Acetyl-3-hydroxyphenyl acetate - 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
No information available.
IMO
No information available.
RID/ADR
No information available.

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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# 42059-48-3: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 42059-48-3 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 42059-48-3 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：

  4-乙酰基-3-羟基乙酸苯酯 在 sodium hydroxide 、 三氯氧磷 作用下， 以 甲醇 为溶剂， 生成 7-羟基-4-氧代-4H-1-苯并吡喃-3-羧醛
  参考文献：
  名称：

  Inhibition of Alzheimer’s BACE-1 by 2,6-dialkyl-4-chromon-3-yl-1,4-dihydropyridine-3,5-dicarboxylates

  摘要：

  Alzheimer's disease is the most common cause of dementia in the elderly, and no disease-modifying therapy is yet available for this devastating pathology. Deposition of different physicochemical forms of amyloid-beta peptides is a critical phase in the pathogenesis of Alzheimer's disease. beta-Site amyloid precursor protein cleaving enzyme 1 (BACE-1) is a major enzyme responsible for amyloid-beta production; therefore, inhibition of this enzyme represents a promising approach for the discovery of amyloid-beta-lowering agents. In this study, a series of novel 2,6-dialkyl-4-chromon-3-yl-1,4-dihydropyridine-3,5-dicarboxylates (14-23) were synthesized and assessed as BACE-1 inhibitors using the Forster resonance energy transfer-based enzyme assay. Synthesized dihydropyridines exhibited weak-to-relatively-good BACE-1 inhibitory activities. Enzyme inhibitory activities ranged from 6.84 +/- A 6.62 (23) to 51.32 +/- A 1.04 (14) percent enzyme inhibitions at the concentration of 10 mu M. The structure-activity relationship study showed that the presence of 4-[7-(ethanoyloxy)-4-oxo-4H-chromen-3-yl] moiety at C4 position of dihydropyridine ring (14, 16 and 18) confers higher activity compared with other substitutions at this position. Docking simulation predicted a key H-bond interaction between Asp32 residue and dihydropyridine NH group. Moreover, all docked dihydropyridines made good hydrophobic contacts with S1 and S2 subpockets of BACE-1. A good correlation between estimated binding affinities (pK(i)) and experimental BACE-1 inhibitory activities at 10 mu M was obtained (R (2) = 0.639). The findings of this study suggested that 2,6-dialkyl-4-chromon-3-yl-1,4-dihydropyridine-3,5-dicarboxylates could be promising scaffolds for the discovery of novel BACE-1 inhibitors for management of Alzheimer's disease.

  DOI：

  10.1007/s00044-015-1367-z
• 作为产物：
  描述：

  2,4-diacetoxy acetophenone 在 三氟化硼乙醚 作用下， 以 1,4-二氧六环 为溶剂， 以93%的产率得到4-乙酰基-3-羟基乙酸苯酯
  参考文献：
  名称：

  BF3·OEt2 mediated regioselective deacetylation of polyacetoxyacetophenones and its application in the synthesis of natural products

  摘要：

  We have developed an efficient method to regioselectively deacetylate polyacetoxyacetophenones using BF(3)center dot OEt(2) in excellent yields and demonstrated the application of the procedure in the synthesis of natural products. (C) 2008 Elsevier Ltd All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.05.020

文献信息

• Palladium-Catalyzed Asymmetric Conjugate Addition of Arylboronic Acids to Heterocyclic Acceptors
  作者：Jeffrey C. Holder、Alexander N. Marziale、Michele Gatti、Bin Mao、Brian M. Stoltz

  DOI：10.1002/chem.201203643

  日期：2013.1.2

  Flava Flavanone: Asymmetric conjugate additions to chromones and 4‐quinolones are reported utilizing a single catalyst system formed in situ from Pd(OCOCF3)2 and (S)‐tBuPyOX. Notably, these reactions are performed in wet solvent under ambient atmosphere, and employ readily available arylboronic acids as the nucleophile, thus providing ready access to these asymmetric heterocycles (see scheme).

  Flava 黄烷酮：据报道，使用由 Pd(OCOCF 3 ) 2和 ( S ) -t BuPyOX原位形成的单一催化剂体系，不对称共轭加成到色酮和 4-喹诺酮。值得注意的是，这些反应是在环境气氛下在湿溶剂中进行的，并使用容易获得的芳基硼酸作为亲核试剂，从而提供了对这些不对称杂环的快速访问（参见方案）。
• Ac2O–Py/basic alumina as a versatile reagent for acetylations in solvent-free conditions under microwave irradiation
  作者：Satya Paul、Puja Nanda、Rajive Gupta、André Loupy

  DOI：10.1016/s0040-4039(02)00732-3

  日期：2002.6

  Acetic anhydride–pyridine over basic alumina has been used in order to carry out acetylations of hydroxy, thiol and amino groups in solvent-free conditions under microwave irradiation. The technique can be extended for selective acetylations by regulation of irradiation time.

  为了在无溶剂条件下在微波辐射下进行羟基，硫醇和氨基的乙酰化反应，已使用碱性氧化铝上的乙酸酐-吡啶进行乙酰化。该技术可通过调节照射时间扩展到选择性乙酰化。
• Synthesis and evaluation of c-Src kinase inhibitory activity of pyridin-2(1H)-one derivatives
  作者：Karam Chand、Suchita Prasad、Rakesh K. Tiwari、Amir N. Shirazi、Sumit Kumar、Keykavous Parang、Sunil K. Sharma

  DOI：10.1016/j.bioorg.2014.02.001

  日期：2014.4

  Src kinase, a prototype member of the Src family of kinases (SFKs), is over-expressed in various human tumors, and has become a target for anticancer drug design. In this perspective, a series of eighteen 2-pyridone derivatives were synthesized and evaluated for their c-Src kinase inhibitory activity. Among them, eight compounds exhibited c-Src kinase inhibitory activity with IC50 value of less than

  Src激酶是Src激酶家族（SFKs）的原型成员，在各种人类肿瘤中均过表达，已成为抗癌药物设计的目标。从这个角度出发，合成了一系列十八个2-吡啶酮衍生物，并评估了它们的c-Src激酶抑制活性。其中，八种化合物表现出c-Src激酶抑制活性，IC 50值小于25μM。化合物1- [2-（二甲基氨基）乙基] -5-（2-羟基-4-甲氧基苯甲酰基）吡啶-2（1H）-一（36）表现出最高的c-Src激酶抑制作用，IC 50值为12.5μM 。此外，化合物36的激酶抑制活性研究人员针对EGFR，MAPK和PDK进行了研究，但在最高测试浓度（300μM）下未观察到明显的活性。这些结果为进一步优化该支架以设计下一代2-吡啶酮衍生物作为候选Src激酶抑制剂提供了见识。
• Lipase-catalyzed regioselective protection of hydroxyl groups in aromatic dihydroxyaldehydes and ketones
  作者：Giovanni Nicolisi、Mario Piattelli、Claudia Sanfilippo

  DOI：10.1016/s0040-4020(01)89897-5

  日期：1993.4

  Pseudomonas cepacia lipase catalyzes the acetylation in organic solvent of dihydroxyaldehydes and ketones using vinyl acetate as acyl donor. The method is completely regioselective and allows to obtain partially acetylated compounds different from those obtained by enzymic hydrolysis of polyacetoxy arylaldehydes and ketones.

  假单胞菌洋葱脂肪酶在乙酸乙烯酯作为酰基供体的情况下催化二羟基醛和酮在有机溶剂中的乙酰化。该方法是完全区域选择性的，并允许获得部分乙酰化的化合物，该化合物与通过酶水解聚乙酰氧基芳基醛和酮获得的化合物不同。
• [EN] PROCESS FOR THE PREPARATION OF 4-ALKYL RESORCINOL ESTERS<br/>[FR] PROCEDE DE PREPARATION D'ESTERS DE 4-ALKYLRESORCINOL
  申请人：UNILEVER PLC

  公开号：WO2004052827A1

  公开（公告）日：2004-06-24

  A process for the preparation of one or more esters of 4-alkyl resorcinol comprising the steps of: (i) reacting resorcinol or a pre-cursor thereof with an esterifying agent which comprises at least one of an organic acid, anhydride or chloride having a maximum carbon chain length of 18, at a temperature of 10 to 250 °C; and (ii) reducing the products from step (i) at a pH of 6.5 to 7.5 in the presence of a catalyst in an alcoholic medium.

  制备一种或多种4-烷基间苯二酚酯的方法包括以下步骤：(i)将间苯二酚或其前体与至少含有一种有机酸、酐或氯化物的酯化剂在10至250°C的温度下反应；以及(ii)在酒精介质中，在pH值为6.5至7.5的条件下，在存在催化剂的情况下还原步骤(i)中的产物。