1-羟基异丁基苯基-1’-甲基丙酸 | 53949-53-4

• 物质功能分类: 分析化学 - 分析试剂 - 离子色谱试剂
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 中文名称: 1-羟基异丁基苯基-1’-甲基丙酸
• 中文别名: 异丁苯丙酸杂质L；1-羟基布洛芬；(9ci)-4-(1-羟基-2-甲基丙基)-alpha-甲基苯乙酸；1-羟基异丁基苯基-1'-甲基丙酸
• 英文名称: 1-hydroxyibuprofen
• 英文别名: 2-[4-(1-hydroxyisobutyl)phenyl]propionic acid；2-[4-(1-Hydroxy-2-methylpropyl)phenyl]propanoic acid
• CAS: 53949-53-4
• 化学式: C₁₃H₁₈O₃
• 分子量: 222.284
• InChiKey: RMOQYHYFRKTDRI-UHFFFAOYSA-N

物化性质

• 熔点：
  80-85°C
• 沸点：
  367.5±22.0 °C(Predicted)
• 密度：
  1.119±0.06 g/cm3(Predicted)
• 溶解度：
  乙腈（微溶）、氯仿（微溶、加热）、甲醇（微溶）
• 碰撞截面：
  154.28 Ų [M+Na]+

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S36
• 危险类别码：
  R22
• WGK Germany：
  3
• 储存条件：
  -20°C冷冻室

SDS

---

Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : 1-Hydroxyibuprofen
CAS-No. : 53949-53-4
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

---

Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008 [EU-GHS/CLP]
Acute toxicity, Oral (Category 4)
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Harmful if swallowed.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
Pictogram
Signal word Warning
Hazard statement(s)
H302 Harmful if swallowed.
Precautionary statement(s) none
Supplemental Hazard none
Statements
According to European Directive 67/548/EEC as amended.
Hazard symbol(s)
R-phrase(s)
R22 Harmful if swallowed.
S-phrase(s)
S36 Wear suitable protective clothing.
Other hazards - none

---

Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Formula : C13H18O3
Molecular Weight : 222,28 g/mol
Component Concentration
1-Hydroxyibuprofen
CAS-No. 53949-53-4 -

---

Section 4. FIRST AID MEASURES
Description of first aid measures
General advice
Consult a physician. Show this safety data sheet to the doctor in attendance.
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician.
In case of skin contact
Wash off with soap and plenty of water. Consult a physician.
In case of eye contact
Flush eyes with water as a precaution.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.
Most important symptoms and effects, both acute and delayed
To the best of our knowledge, the chemical, physical, and toxicological properties have not been thoroughly
investigated.
Indication of any immediate medical attention and special treatment needed
no data available

---

Section 5. FIREFIGHTING MEASURES
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

---

Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure
adequate ventilation. Avoid breathing dust.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed
containers for disposal.
Reference to other sections
For disposal see section 13.

---

Section 7. HANDLING AND STORAGE
Precautions for safe handling
Avoid contact with skin and eyes. Avoid formation of dust and aerosols.
Provide appropriate exhaust ventilation at places where dust is formed.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Specific end uses
no data available

---

Section 8. EXPOSURE CONTROLS/PERSONAL PROTECTION
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at
the end of workday.
Personal protective equipment
Eye/face protection
Safety glasses with side-shields conforming to EN166 Use equipment for eye protection tested and
approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the
standard EN 374 derived from it.
Body Protection
Complete suit protecting against chemicals, The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator.For higher
level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges. Use
respirators and components tested and approved under appropriate government standards such as
NIOSH (US) or CEN (EU).

---

Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Information on basic physical and chemical properties
a) Appearance Form: crystalline
Colour: colourless
b) Odour odourless
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing 90 °C
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evaporation rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density no data available
n) Water solubility no data available
o) Partition coefficient: n- log Pow: 2,06
octanol/water
p) Autoignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

---

Section 10. STABILITY AND REACTIVITY
Reactivity
no data available
Chemical stability
no data available
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Oxidizing agents
Hazardous decomposition products

---

Section 11. TOXICOLOGICAL INFORMATION
Information on toxicological effects
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitization
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation
May be harmful if inhaled. May cause respiratory tract irritation.
Ingestion Harmful if swallowed.
Skin May be harmful if absorbed through skin. May cause skin irritation.
Eyes May cause eye irritation.
Signs and Symptoms of Exposure
To the best of our knowledge, the chemical, physical, and toxicological properties have not been thoroughly
investigated.
Additional Information
RTECS: Not available

---

Section 12. ECOLOGICAL INFORMATION
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
no data available
Other adverse effects
no data available

---

Section 13. DISPOSAL CONSIDERATIONS
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company. Dissolve or mix the material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber.
Contaminated packaging
Dispose of as unused product.

---

Section 14. TRANSPORT INFORMATION
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

---

---

SECTION 15 - REGULATORY INFORMATION
N/A

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

生物活性方面，1-羟基布洛芬是布洛芬的活性代谢物。布洛芬作为COX-1和COX-2的抑制剂，其IC50值分别为13 μM和370 μM，并具有抗炎作用。

反应信息

• 作为产物：
  描述：

  4-((diethoxyphosphoryl)oxy)butyl 2-(4-(1-hydroxy-2-methylpropyl)phenyl)propanoate 在 porcine liver esterase 作用下， 反应 0.5h， 生成 1-羟基异丁基苯基-1’-甲基丙酸
  参考文献：
  名称：

  Phospho-Ibuprofen (MDC-917) Is a Novel Agent against Colon Cancer: Efficacy, Metabolism, and Pharmacokinetics in Mouse Models

  摘要：

  我们开发了一种对传统非甾体抗炎药进行新型化学修饰，以降低其毒性并增强其疗效。磷酸布洛芬 [(PI) 2-(4-异丁基-苯基)-丙酸-4-(二乙氧基-磷酰氧基)-丁基酯 (MDC-917)] 是布洛芬的一种新型衍生物，可强烈抑制人结肠的生长体外癌细胞和裸鼠 SW480 人结肠癌异种移植物。 PI 被培养的细胞最低程度地代谢，但被肝微粒体和小鼠广泛代谢，经历区域选择性氧化产生 1-OH-PI 和羧基-PI，它们可以分别水解为 1-OH-布洛芬和羧基-布洛芬。 PI还可水解释放布洛芬，布洛芬可生成2-OH-布洛芬、羧基布洛芬和布洛芬葡萄糖醛酸苷。单次口服（400mg/kg）PI后，布洛芬和布洛芬葡萄糖醛酸苷是PI的主要血浆代谢物；它们的 C max 分别为 530 和 215 μM，T max 分别为 1 和 2 小时，消除 t 1/2 分别为 7.7 和 5.3 小时，浓度-时间曲线下面积（0-24 小时）分别为 1816 和 832微米×小时。在多种组织中检测到完整的 PI，但在血浆中未检测到；在较高的 PI 剂量（1200 mg/kg）下，PI 血浆水平为 12.4 μM。 PI 在小鼠血浆中产生与传统布洛芬相同的代谢物，但含量低得多，这可能是 PI 安全性增强的原因。 PI 的抗肿瘤作用与血浆布洛芬水平显着相关 (p = 0.016)，但与异种移植物布洛芬水平无关 (p = 0.08)，表明其具有复杂的抗癌作用。这些结果提供了药理学基础，至少部分地解释了这种有前途的化合物的抗癌功效和安全性，并表明 PI 作为抗癌剂值得进一步评估。

  DOI：

  10.1124/jpet.111.180224

文献信息

• Preparation of human drug metabolites using fungal peroxygenases
  作者：Marzena Poraj-Kobielska、Matthias Kinne、René Ullrich、Katrin Scheibner、Gernot Kayser、Kenneth E. Hammel、Martin Hofrichter

  DOI：10.1016/j.bcp.2011.06.020

  日期：2011.10

  organic chemists. Here we report that aromatic peroxygenases (APOs; EC 1.11.2.1) secreted by the agaric fungi Agrocybe aegerita and Coprinellus radians catalyzed the H(2)O(2)-dependent selective monooxygenation of diverse drugs, including acetanilide, dextrorphan, ibuprofen, naproxen, phenacetin, sildenafil and tolbutamide. Reactions included the hydroxylation of aromatic rings and aliphatic side chains

  通过选择性单加氧合成羟基化和O-或N-去烷基化的人类药物代谢产物（HDM）对于合成有机化学家而言仍然是一项艰巨的任务。在这里我们报告说，由琼脂真菌Agrocybe aegerita和Coprinellus radians分泌的芳香过氧化物酶（APOs; EC 1.11.2.1）催化H（2）O（2）依赖的选择性单氧合作用的多种药物，包括对乙酰苯胺，右旋糖酐，布洛芬，萘普生，非那西丁，西地那非和甲苯磺丁酰胺。反应包括芳环和脂族侧链的羟基化，以及O-和N-脱烷基，根据所使用的特定APO表现出不同的区域选择性。充其量，可以以大于80％的产率和高达99％的异构体纯度获得所需的HDM。甲苯磺丁酰胺的氧化，乙苯胺和卡马西平在H（2）（1）（8）O（2）的存在下导致（1）（8）O几乎完全掺入相应的产物中，因此确定这些反应是过氧化反应。非那西丁-d（1）的脱乙基显示观察到的分子内氘同位素效应[（k（H）/ k（D））（obs）]为3
• Photolysis and photocatalysis of ibuprofen in aqueous medium: characterization of by-products via liquid chromatography coupled to high-resolution mass spectrometry and assessment of their toxicities against<i>Artemia Salina</i>
  作者：Júlio César Cardoso da Silva、Janaina Aparecida Reis Teodoro、Robson José de Cássia Franco Afonso、Sérgio Francisco Aquino、Rodinei Augusti

  DOI：10.1002/jms.3320

  日期：2014.2

  The degradation of the pharmaceutical compound ibuprofen (IBP) in aqueous solution induced by direct photolysis (UV-A and UV-C radiation) and photocatalysis (TiO2/UV-A and TiO2/UV-C systems) was evaluated. Initially, we observed that whereas photocatalysis (both systems) and direct photolysis with UV-C radiation were able to cause an almost complete removal of IBP, the mineralization rates achieved for all the photodegradation processes were much smaller (the highest value being obtained for the TiO2/UV-C system: 37.7%), even after an exposure time as long as 120 min. Chemical structures for the by-products formed under these oxidative conditions (11 of them were detected) were proposed based on the data from liquid chromatography coupled to high-resolution mass spectrometry (LC-HRMS) analyses. Taking into account these results, an unprecedented route for the photodegradation of IBP could thus be proposed. Moreover, a fortunate result was achieved herein: tests against Artemia salina showed that the degradation products had no higher ecotoxicities than IBP, which possibly indicates that the photocatalytic (TiO2/UV-A and TiO2/UV-C systems) and photolytic (UV-C radiation) processes can be conveniently employed to deplete IBP in aqueous media. Copyright © 2014 John Wiley & Sons, Ltd.

  我们评估了直接光解（UV-A 和 UV-C 辐射）和光催化（TiO2/UV-A 和 TiO2/UV-C 系统）诱导的水溶液中药物化合物布洛芬（IBP）的降解情况。我们初步观察到，虽然光催化（两种体系）和紫外线-C 辐射直接光解能够几乎完全去除 IBP，但所有光降解过程的矿化率都要小得多（TiO2/UV-C 体系的矿化率最高：37.7%），即使暴露时间长达 120 分钟。根据液相色谱耦合高分辨质谱（LC-HRMS）分析的数据，提出了在这些氧化条件下形成的副产品（检测到 11 种）的化学结构。考虑到这些结果，可以提出一种前所未有的 IBP 光降解途径。此外，本研究还取得了一项幸运的结果：对盐藻的测试表明，降解产物的生态毒性并不比IBP高，这可能表明光催化（TiO2/UV-A和TiO2/UV-C系统）和光解（UV-C辐射）过程可以方便地用于去除水介质中的IBP。Copyright © 2014 John Wiley & Sons, Ltd. All Rights Reserved.
• Abiotic degradation and environmental toxicity of ibuprofen: Roles of mineral particles and solar radiation
  作者：Gayan Rubasinghege、Rubi Gurung、Hom Rijal、Sabino Maldonado-Torres、Andrew Chan、Shishir Acharya、Snezna Rogelj、Menake Piyasena

  DOI：10.1016/j.watres.2017.12.016

  日期：2018.3

  irradiated samples compared to those of dark conditions. Toxicity of primary ibuprofen and its secondary residues were tested on three microorganisms: Bacillus megaterium, Pseudoaltermonas atlantica; and algae from the Chlorella genus. The results from the biological assays show that primary PPCP is more toxic than the mixture of secondary products. Overall, however, biological assays carried out using

  人口不断增长的医疗和个人需求已将药物和个人护理产品释放到我们的自然环境中。这项工作研究了在土壤中主要矿物质（高岭石粘土）存在的情况下特定PPCP布洛芬的非生物降解途径，以及主要化合物及其降解产物的健康影响。这些研究的结果表明，布洛芬降解的速度和程度受粘土颗粒和太阳辐射的存在影响很大。在没有太阳辐射的情况下，观察到主要的反应机理是布洛芬在粘土表面的吸附，而表面硅烷醇基团起着关键作用。相反，在太阳辐射下和粘土颗粒的存在下，布洛芬分解成几个部分。与黑暗条件下相比，被辐照样品的衰减率至少高出6倍。在三种微生物上测试了布洛芬初级化合物及其次级残留物的毒性：巨大芽孢杆菌，大西洋假拟杆菌。和小球藻属的藻类。生物学测定的结果表明，初级PPCP比次级产品的混合物毒性更大。但是，总的来说，仅使用4-乙酰基苯甲酸（含量最高的副产物）进行的生物学分析显示，与其母体化合物相比，藻类具有更高的毒性作用。
• Exploring the Biocatalytic Potential of a Self‐Sufficient Cytochrome P450 from<i>Thermothelomyces thermophila</i>
  作者：Maximilian J. L. J. Fürst、Bianca Kerschbaumer、Claudia Rinnofner、Anna K. Migglautsch、Margit Winkler、Marco W. Fraaije

  DOI：10.1002/adsc.201900076

  日期：——

  CYPs are studied in drug development due to their physiological role at the forefront of metabolic detoxification, but their challenging handling makes them unsuitable for application. CYPs have a great potential for biocatalysis, but often lack appropriate features such as high and soluble expression, self‐sufficient internal electron transport, high stability, and an engineerable substrate scope.

  在自然界的氧化酶库中，细胞色素P450（CYP）催化最具挑战性的反应，即未活化的CH键的羟基化。由于人类CYP在代谢排毒的最前沿具有生理作用，因此已在药物开发中进行了研究，但其具有挑战性的处理方式使其不适合应用。CYP具有巨大的生物催化潜力，但通常缺乏适当的功能，例如高表达和可溶表达，自给自足的内部电子传输，高稳定性和可设计的底物范围。我们已经针对最近描述的源自嗜热真菌嗜热嗜热菌（Thermothelomyces thermophila）（CYP505A30）的CYP探测了这些特征，CYP505A30是巨大芽孢杆菌中著名的P450-BM3的同系物。CYP505A30是一种天然的单加氧酶-还原酶融合体，表达良好，对温度和溶剂的接触具有中等耐受性。尽管总体上具有可比性，但我们发现该酶结构域的稳定性与P450-BM3相反，与血红素结构域相比，还原酶更稳定。对同源性模型进行分析后，我们根据P450
• Visible Light Mediated Chemoselective Hydroxylation of Benzylic Methylenes
  作者：Zhiyong Tan、Tingting Chen、Jinbin Zhu、Wenjun Luo、Daohong Yu、Wei Guo

  DOI：10.1021/acs.joc.3c02683

  日期：2024.2.16

  hydroxylation of benzylic methylenes to secondary alcohols. This approach utilizes low-cost eosin Y as photocatalyst, O2 as green oxidant, and inexpensive triethylamine as inhibitor for overoxidation. The mild reaction conditions enable the production of secondary alcohols with 56–95% yields, making it a promising and environmental-friendly method for the synthesis of secondary alcohols from benzylic methylenes

  我们开发了一种无金属光催化选择性羟基化苄基亚甲基生成仲醇。该方法利用低成本的曙红Y作为光催化剂，O 2作为绿色氧化剂，以及廉价的三乙胺作为过度氧化抑制剂。温和的反应条件使得仲醇的产率达到56-95%，使其成为一种有前途且环境友好的由苄基亚甲基合成仲醇的方法。