3-(3-羟基苯基)丙酸 | 621-54-5

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 中文名称: 3-(3-羟基苯基)丙酸
• 中文别名: 3-(3-羟苯基)丙酸；间羟基苯丙酸
• 英文名称: 3-(3-hydroxyphenyl)-propanoic acid
• 英文别名: 3-(3-hydroxyphenyl)propionic acid；3-hydroxyphenylpropionic acid；3-(3-Hydroxyphenyl)propanoic acid
• CAS: 621-54-5
• 化学式: C₉H₁₀O₃
• 分子量: 166.177
• InChiKey: QVWAEZJXDYOKEH-UHFFFAOYSA-N

物化性质

• 熔点：
  111 °C
• 沸点：
  355℃
• 密度：
  1.260
• 闪点：
  182℃
• 溶解度：
  易溶于氯仿和甲醇。
• 物理描述：
  Solid
• 碰撞截面：
  136.11 Ų [M-H]- [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]
• 稳定性/保质期：
  - 远离氧化物。 - 存在于烟叶、烟气中。

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 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：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

ADMET

代谢

3-(3-羟基苯基)丙酸是3,4-二羟基苯基丙酸的人类已知代谢物。

3-(3-hydroxyphenyl)propanoic acid is a known human metabolite of 3,4-dihydroxyphenylpropionic acid.

来源:NORMAN Suspect List Exchange

安全信息

• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38
• RTECS号：
  MW5340000
• 海关编码：
  2918290000
• WGK Germany：
  3
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  请将存放在密封容器中，并置于阴凉、干燥处。储存位置需远离氧化剂。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-(3-Hydroxyphenyl)propionic acid
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
H303: May be harmful if swallowed
Avoid breathing dust/fume/gas/mist/vapours/spray
P261:
P280: Wear protective gloves/protective clothing/eye protection/face protection
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
P405: Store locked up

---

Section 3. Composition/information on ingredients.
Ingredient name: 3-(3-Hydroxyphenyl)propionic acid
CAS number: 621-54-5

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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.

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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.
Storage: Store in closed vessels.

---

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
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C9H10O3
Molecular weight: 166.2

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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.

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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.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

生物活性
3-(3-羟基苯基)丙酸（m-羟基苯基丙酸，3-羟基肉桂酸）在结肠中是咖啡酸的主要代谢产物之一，也是原花青素被微生物降解的酚类代谢物。

靶点
人类内源性代谢物

化学性质
类白色至白色的结晶。

反应信息

• 作为反应物：
  描述：

  3-(3-羟基苯基)丙酸 在 sodium hydroxide 、 硫酸 、 ammonium acetate 、 sodium 、 potassium carbonate 、 potassium iodide 作用下， 以 甲醇 、 溶剂黄146 、 乙腈 为溶剂， 反应 5.67h， 生成 2-[3-[2-(4,5-diphenyl-2-oxazolyl)ethyl]phenoxy]acetic acid
  参考文献：
  名称：

  非前列腺素前列环素模拟物。2. 4,5-二苯基恶唑衍生物。

  摘要：

  合成了4,5-二苯基-2-恶唑壬酸（18b），发现其抑制ADP诱导的人血小板聚集，IC50为2.5 microM。酸18b以浓度依赖的方式从人血小板膜置换了[3H]伊洛前列素，与18b通过充当前列环素模拟物抑制血小板功能相一致。通过将苯氧基环插入18b的侧链部分并系统地改变取代方式和系链长度，可以鉴定出更有效的血小板聚集抑制剂。证明在侧链中心插入的苯氧基是最佳排列，但是当芳环直接键合到杂环的2位时，观察到显着的活性。作为本研究的一部分，间位取代的顺式（乙烯基苯氧基）乙酸37是最有效的血小板凝集抑制剂，IC50为0.18 microM。酸37从人的血小板膜上置换了[3H]伊洛前列素，IC50为6 nM。作为ADP诱导的血小板凝集抑制剂，37（25p）的反式烯烃异构体弱72倍，但饱和衍生物25w（BMY 42393）的效力中等。以25w为模板进行结构活性研究的重点是侧链苯环与恶唑和羧酸根末端之

  DOI：

  10.1021/jm00097a006
• 作为产物：
  描述：

  3,4-methylenedioxy-trans-cinnamic acid 在 sodium hydroxide 、 aluminum nickel 作用下， 生成 3-(3-羟基苯基)丙酸
  参考文献：
  名称：

  REDUCTIONS WITH NICKEL-ALUMINUM ALLOY AND AQUEOUS ALKALI.¹ PART V. RUPTURE OF THE METHYLENEDIOXYL BRIDGE

  摘要：

  DOI：

  10.1021/jo01179a013
• 作为试剂：
  描述：

  3-(3-羟基苯基)丙酸 、 四正丁基氢氧化膦 、 3-(chloromethyl)-6-cyclopropyl-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl 在 3-(3-羟基苯基)丙酸 、 ice 、 水 、 乙酸乙酯 、 SiO2 、 hexanes 作用下， 以 四氢呋喃 为溶剂， 反应 44.17h， 以to yield a colorless film 13 (0.023 g, 28% yield.) 1H NMR (400 MHz, CDCl3) δ ppm 7.39 (1H, dd, J=8.0, 1.8 Hz), 7.31 (1H, d, J=2.0 Hz), 7.23 (1H, t, J=8.0 Hz), 7.10 (1H, m), 6.99 (1H, d, J=7.8 Hz), 6.90 (5H, m), 5.04 (2H, s), 3.82 (3H, s), 2.95 (2H, t, J=7.8 Hz), 2.72 (2H, m), 1.85 (1H, m), 0.87 (2H, m), 0.68 (2H, m)的产率得到3-(3-(((6-cyclopropyl-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-3-yl)methyl)oxy)phenyl)propanoic acid
  参考文献：
  名称：

  Substituted biphenyl GPR40 modulators

  摘要：

  本发明提供了一些化合物，例如用于治疗受试者代谢紊乱的化合物。这些化合物的一般式为I：其中变量的定义在此处提供。本发明还提供了包括该化合物的组合物以及使用该化合物制备药物和治疗代谢紊乱的方法，例如二型糖尿病。

  公开号：

  US07572934B2

文献信息

• [EN] LEVORPHANOL PRODRUGS AND PROCESSES FOR MAKING AND USING THEM<br/>[FR] PROMÉDICAMENTS DE LEVORANOL ET LEURS PROCÉDÉS DE FABRICATION ET D'UTILISATION
  申请人：KEMPHARM INC

  公开号：WO2018191472A1

  公开（公告）日：2018-10-18

  The presently described technology provides compositions of one or more of oxoacids, polyethylene glycols, and vitamin compounds chemically conjugated to levorphanol ((-)-17-methylmorphinan-3-ol) to form novel prodrugs and compositions of levorphanol.

  目前描述的技术提供了一种或多种羟基酸、聚乙二醇和维生素化合物与左旋吗啡醇((-)-17-甲基吗啡-3-醇)在化学上结合形成新型前药和左旋吗啡的组合物。
• [EN] IONIC LIQUID SOLVENTS<br/>[FR] SOLVANTS LIQUIDES IONIQUES
  申请人：UNIV DUBLIN CITY

  公开号：WO2010097412A1

  公开（公告）日：2010-09-02

  A chiral ionic compound comprising an alkyl substituted imidazolium or pyridinium cationic core having an alkyl ester side chain (-alkyl-C(O)O-) directly linked to the core and an associated counter anion, characterized in that the -O- atom of the ester side chain is linked to an alpha, a beta or a gamma hydroxycarboxylic acid functionality via the alpha, beta or gamma hydroxy of the acid functionality and the hydroxycarboxylic acid functionality has at least one asymmetric carbon, or characterized in that an -N= atom of the alkyl substituted imidazolium or pyridinium cationic core is substituted with an alpha, a beta or a gamma hydroxy group of a alpha, a beta or a gamma hydroxycarboxylic acid functionality and the hydroxycarboxylic acid functionality has at least one asymmetric carbon. The chiral ionic liquids (CILs) may be used as novel solvents, in particular for organic synthesis. The CILs have the potential to induce asymmetry into substrates or catalysts in a variety of organic transformations. A number of the compounds have low antimicrobial and low antifungal toxicities and are also biodegradable CILs.

  一种手性离子化合物，包括具有烷基取代的咪唑或吡啶阳离子核心，其具有直接连接到核心的烷基酯侧链（-烷基-C（O）O-）和相关的对应阴离子，其特征在于酯侧链的-O-原子通过α、β或γ羟基羧酸功能与羧酸功能的α、β或γ羟基相连，且羟基羧酸功能具有至少一个不对称碳，或者其特征在于烷基取代的咪唑或吡啶阳离子核心的-N=原子被α、β或γ羟基羧酸功能的α、β或γ羟基取代，且羟基羧酸功能具有至少一个不对称碳。这种手性离子液体（CILs）可用作新型溶剂，特别适用于有机合成。这些CILs有潜力在各种有机转化中向底物或催化剂引入不对称性。其中一些化合物具有低抗菌和低抗真菌毒性，并且也是可生物降解的CILs。
• A Biocompatible Alkene Hydrogenation Merges Organic Synthesis with Microbial Metabolism
  作者：Gopal Sirasani、Liuchuan Tong、Emily P. Balskus

  DOI：10.1002/anie.201403148

  日期：2014.7.21

  Organic chemists and metabolic engineers use orthogonal technologies to construct essential small molecules such as pharmaceuticals and commodity chemicals. While chemists have leveraged the unique capabilities of biological catalysts for small‐molecule production, metabolic engineers have not likewise integrated reactions from organic synthesis with the metabolism of living organisms. Reported herein

  有机化学家和代谢工程师使用正交技术构建必要的小分子，如药物和商品化学品。虽然化学家利用生物催化剂的独特能力生产小分子，但代谢工程师还没有将有机合成的反应与生物体的代谢相结合。本文报道了一种利用钯催化剂和由活微生物直接产生的氢气进行烯烃加氢的方法。这种生物相容性转化需要催化剂和微生物，并且可以在制备规模上使用，代表了一种结合有机化学和代谢工程的化学合成新策略。
• [EN] COMPOSITIONS FOR THE TREATMENT OF KIDNEY AND/OR LIVER DISEASE<br/>[FR] COMPOSITIONS POUR LE TRAITEMENT D'UNE MALADIE HÉPATIQUE ET/OU RÉNALE
  申请人：VECTUS BIOSYSTEMS LTD

  公开号：WO2016145478A1

  公开（公告）日：2016-09-22

  The present invention relates to novel compounds and their use in the prophylactic and/or therapeutic treatment of kidney and/or liver disease.

  本发明涉及新化合物及其在预防性和/或治疗性治疗肾脏和/或肝脏疾病中的用途。
• 新規リゾホスファチジン酸誘導体
  申请人：田辺三菱製薬株式会社

  公开号：JP2021080183A

  公开（公告）日：2021-05-27

  【課題】本発明は、ＬＰＡ４受容体を特異的に作動する化合物、及びそれを含有する医薬組成物を提供することを目的とする。【解決手段】本発明は、ＬＰＡ４受容体のアゴニスト作用を有し、ＬＰＡ４受容体が関与する血管形成異常を伴う疾患、又は血管障害に伴う疾患、或いはそれに伴う症状の予防及び／又は治療に有用である、新規リゾホスファチジン酸誘導体に関する。また、本発明は、当該リゾホスファチジン酸誘導体を含有する医薬組成物にも関する。【選択図】なし

  本发明旨在提供特异作用于LPA4受体的化合物以及含有该化合物的药物组合物。本发明涉及具有LPA4受体激动剂作用的新型磷脂酰肌醇酸衍生物，对涉及LPA4受体引起的血管形成异常疾病、血管障碍疾病或相关症状的预防和/或治疗具有用处。此外，本发明还涉及含有该磷脂酰肌醇酸衍生物的药物组合物。【选择图】无

表征谱图