Coumarin-3-carboxylic Acid
(Synonyms: 香豆素-3-羧酸; 2-Oxochromene-3-carboxylic acid) 目录号 : GC38238
Coumarin-3-carboxylic acid is used as a detector for hydroxyl radicals (.OH) in aqueous solution.
Cas No.:531-81-7
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Coumarin-3-carboxylic acid is used as a detector for hydroxyl radicals (.OH) in aqueous solution.
| Cas No. | 531-81-7 | SDF | |
| 别名 | 香豆素-3-羧酸; 2-Oxochromene-3-carboxylic acid | ||
| Canonical SMILES | O=C(O1)C(C(O)=O)=CC2=C1C=CC=C2 | ||
| 分子式 | C10H6O4 | 分子量 | 190.15 |
| 溶解度 | Soluble in DMSO | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 5.259 mL | 26.295 mL | 52.5901 mL |
| 5 mM | 1.0518 mL | 5.259 mL | 10.518 mL |
| 10 mM | 0.5259 mL | 2.6295 mL | 5.259 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Coumarin-3-carboxylic Acid
Acta Crystallogr C 1996 Dec 15;52 ( Pt 12):3081-3.PMID:9015897DOI:10.1107/s0108270196010852.
In the structure of the title compound, C10H6O4, there is a single intramolecular hydrogen bond. In addition, there are a number of significant intermolecular C-H...O attractive interactions. These interactions account in part for the rather high density for an ordinary monocarboxylic acid, 1.522 Mg m(-3).
The complex photochemistry of Coumarin-3-carboxylic Acid in acetonitrile and methanol
Photochem Photobiol Sci 2022 Aug;21(8):1481-1495.PMID:35578152DOI:10.1007/s43630-022-00238-8.
Irradiation of Coumarin-3-carboxylic Acid in acetonitrile and methanol solutions at 355 nm results in complex multistep photochemical transformations, strongly dependent on the solvent properties and oxygen content. A number of reaction intermediates, which themselves undergo further (photo)chemical reactions, were identified by steady-state and transient absorption spectroscopy, mass spectrometry, and NMR and product analyses. The triplet excited compound in acetonitrile undergoes decarboxylation to give a 3-coumarinyl radical that traps molecular oxygen to form 3-hydroxycoumarin as the major but chemically reactive intermediate. This compound is oxygenated by singlet oxygen, produced by Coumarin-3-carboxylic Acid sensitization, followed by a pyrone ring-opening reaction to give an oxalic acid derivative. The subsequent steps lead to the production of salicylaldehyde, carbon monoxide, and carbon dioxide as the final products. When 3-coumarinyl radical is not trapped by oxygen in degassed acetonitrile, it abstracts hydrogen from the solvent and undergoes triplet-sensitized [2 + 2] cycloaddition. The reaction of 3-coumarinyl radical with oxygen is largely suppressed in aerated methanol as a better H-atom donor, and coumarin is obtained as the primary product in good yields. Because coumarin derivatives are used in many photophysical and photochemical applications, this work provides detailed and sometimes surprising insights into their complex phototransformations.
A new bioactive cocrystal of Coumarin-3-carboxylic Acid and thiourea: detailed structural features and biological activity studies
Acta Crystallogr C Struct Chem 2022 Mar 1;78(Pt 3):192-200.PMID:35245216DOI:10.1107/S205322962200081X.
Cocrystallization is a phenomenon widely used to enhance the biological and physicochemical properties of active pharmaceutical ingredients (APIs). The present study deals with the synthesis of a cocrystal of Coumarin-3-carboxylic Acid (2-oxochromene-3-carboxylic acid, C10H6O4), a synthetic analogue of the naturally occurring antioxidant coumarin, with thiourea (CH4N2S) using the neat grinding method. The purity and homogeneity of the coumarin-3-carboxylic acid-thiourea (1/1) cocrystal was confirmed by single-crystal X-ray diffraction, FT-IR analysis and thermal stability studies based on differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA). Detailed geometry analysis via density functional theory (DFT) demonstrated that the 1:1 cocrystal stoichiometry is sustained by N-H...O hydrogen bonding between the amine (-NH2) groups of thiourea and the carbonyl group of coumarin. The synthesized cocrystal exhibited potent antioxidant activity (IC50 = 127.9 ± 5.95 µM) in a DPPH radical scavenger assay in vitro in comparison with the standard N-acetyl-L-cysteine (IC50 = 111.6 ± 2.4 µM). The promising results of the present study highlight the significance of cocrystallization as a crystal engineering tool to improve the efficacy of pharmaceutical ingredients.
Molecular-Level Release of Coumarin-3-carboxylic Acid and Warfarin-Derivatives from BSA-Based Hydrogels
Pharmaceutics 2021 Oct 11;13(10):1661.PMID:34683955DOI:10.3390/pharmaceutics13101661.
This investigation aimed at developing BSA hydrogels as a controlled release system to study the release behavior of spin-labeled Coumarin-3-carboxylic Acid (SL-CCS) and warfarin (SL-WFR). The release profiles of these spin-labeled (SL-) pharmaceuticals from BSA hydrogels prepared with different procedures are compared in detail. The mechanical properties of the gels during formation and release were studied via rheology, while a nanoscopic view on the release behavior was achieved by analyzing SL-drugs-BSA interaction using continuous wave electron paramagnetic resonance (CW EPR) spectroscopy. The influence of type of drug, drug concentration, duration of gel formation, and gelation methods on release behavior were characterized by CW EPR spectroscopy, EPR imaging (EPRI), and dynamic light scattering (DLS), which provide information on the interaction of BSA with SL-drugs, the percentage of drug inside the hydrogel and the nature and size of the released structures, respectively. We found that the release rate of SL-CCS and SL-WFR from BSA hydrogels is tunable through drug ratios, hydrogel incubation time and gelation procedures. All of the results indicate that BSA hydrogels can be potentially exploited in controlled drug delivery applications.
Establishment of an HPLC Method for Determination of Coumarin-3-carboxylic Acid Analogues in Rat Plasma and a Preliminary Study on Their Pharmacokinetics
J Chromatogr Sci 2022 Sep 3;60(7):642-647.PMID:34491317DOI:10.1093/chromsci/bmab103.
A simple high performance liquid chromatography (HPLC) method was developed and validated for the determination of Coumarin-3-carboxylic Acid analogues (C3AA) in rat plasma and a preliminary study on pharmacokinetics. Ferulic acid (FA) was used as the internal standard substance, and Coumarin-3-carboxylic Acid (C3A) was used as a substitute for quantitative C3AA. After protein precipitation with methanol, the satisfactory separation was achieved on an ODS2 column when the temperature was maintained at 30 ± 2°C. The correlation coefficient r in the C3A linear equation is equal to 0.9990. Pharmacokinetic parameters for t1/2, Tmax, Cmax, area under the curve (AUC)0-t, average residence time (MRT), apparent volume of distribution (V z/F) and clearance (Cl/F) were 1.89 ± 0.03 h, 0.39 ± 0.14 h, 1.81 ± 0.10 g· mL-1 ·h, 7.88 ± 0.24 g·mL-1·h, 3.23 ± 0.14 h, 0.43 ± 0.03 (mg·kg-1)·(g·mL-1)-1·h-1, respectively. The high performance liquid chromatography-photo diode array detector (HPLC-PDA) method established in this study can be used to separate and determine the content of C3AA in plasma of rats after 60% ethanol extraction by gavage. The plasma concentration-time curve and pharmacokinetic parameters reflect the absorption of C3AA in rat blood after oral administration to some extent.