6-Hydroxycoumarin
(Synonyms: 6-羟基香豆素) 目录号 : GC61660
6-Hydroxycoumarin是一种香豆素。香豆素具有抗炎，解热，抗氧化，支气管扩张，血管扩张，抗菌，抗真菌，抑菌和抗肿瘤活性。
Cas No.:6093-68-1
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
6-Hydroxycoumarin is a coumarin which has anti-inflammatory, anti-pyretic, anti-oxidant, vasodilator, anti-amoebic, anti-bacterial, anti-fungal, bacteriostatic and antitumor activity[1].
[1]. Farooq S, et al. Isolation, cytotoxicity evaluation and HPLC-quantification of the chemical constituents from Prangos pabularia. PLoS One. 2014 Oct 14;9(10):e108713.
| Cas No. | 6093-68-1 | SDF | |
| 别名 | 6-羟基香豆素 | ||
| Canonical SMILES | O=C1C=CC2=CC(O)=CC=C2O1 | ||
| 分子式 | C9H6O3 | 分子量 | 162.14 |
| 溶解度 | DMSO: 250 mg/mL (1541.88 mM) | 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 | 6.1675 mL | 30.8375 mL | 61.6751 mL |
| 5 mM | 1.2335 mL | 6.1675 mL | 12.335 mL |
| 10 mM | 0.6168 mL | 3.0838 mL | 6.1675 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。
Structural, vibrational and electronic spectroscopic study of 6-Hydroxycoumarin using experimental and theoretical methods
Spectrochim Acta A Mol Biomol Spectrosc 2020 Mar 15;229:117930.PMID:31931406DOI:10.1016/j.saa.2019.117930.
Understanding the photochemical behavior of structural isomers of hydroxycoumarin (HC) having different properties of consequence in biological activities demand spectroscopic information of this class of compounds. Barring 6-Hydroxycoumarin (6-HC), other isomers of HC's are well studied spectroscopically. To understand and compare the photochemical activity of 6-HC with other isomers, a detailed study of this molecule has been taken up. For this purpose, electronic, vibrational and structural properties of 6-HC have been studied using ultraviolet absorption and Infrared spectroscopy techniques. Quantum chemical calculations have been performed at DFT/B3LYP level of theory to get the optimized geometry and vibrational frequencies of normal modes to support and analyze experimental data. The detailed vibrational assignments were made on the basis of potential energy distributions. Chemical activity, molecular orbital energies, band gap and hyper-polarizability information have been computed from quantum chemical simulations. NBO analysis helped in understanding the stability of the molecule arising from hyper-conjugative interaction and charge delocalization. UV-Visible spectrum of the compound was recorded in the region 300-600 nm helped in obtaining band gap data of the compound. Molecular Electrostatic Potentials (MESP) were plotted and the respective centers of electrophilic and nucleophilic attacks were predicted with the help of Fukui functions calculations. Further, it was observed that the negative electrostatic potential regions are mainly localized over the oxygen atoms and the positive regions are localized over the benzene ring. Details of the results and analysis of experimental and theoretical spectroscopy studies are presented in this paper.
Synthesis and biological evaluation of novel isoxazoles and triazoles linked 6-Hydroxycoumarin as potent cytotoxic agents
Bioorg Med Chem Lett 2014 Sep 1;24(17):4243-6.PMID:25088398DOI:10.1016/j.bmcl.2014.07.031.
A new series of diverse isoxazoles and triazoles linked 6-Hydroxycoumarin (1) were synthesized using click chemistry approach. All the derivatives were subjected to 3-(4,5-dimethylthiazol-yl)-diphenyl tetrazoliumbromide (MTT) cytotoxicity screening against a panel of five different human cancer cell lines viz. prostate (PC-3), colon (HCT-116 and Colo-205), leukemia (HL-60) and lung (A-549) to check their cytotoxic potential. Interestingly, among the tested molecules, some of the analogs displayed better cytotoxic activity than the parent 6-Hydroxycoumarin (1). Of the synthesized isoxazoles, compounds 10 and 13 showed the best activity with IC50 of 8.2 and 13.6 μM against PC-3 cancer cell line, while as, among the triazoles, compounds 23 and 25 were the most active with the IC50 of 10.2 and 12.6 μM against A-549 cancer cell line. The other derivatives showed almost comparable activity with that of the parent molecule. The present study resulted in identification of ortho substituted isoxazole and triazole derivatives of 6-Hydroxycoumarin as effective cytotoxic agents against prostate (PC-3) and lung (A-549) cancer cell lines, respectively.
Photoprotective effect of coumarin and 3-hydroxycoumarin in sea urchin gametes and embryonic cells
J Photochem Photobiol B 2015 May;146:44-51.PMID:25795999DOI:10.1016/j.jphotobiol.2015.02.024.
Ultraviolet radiation B (UVB) represents 5% of all solar UV radiation and chronic exposure can induce harmful biological responses, including skin cancer. Prospection of new drugs with photoprotective properties and less toxic effects is constant and natural products have been the main options in this field. Coumarins are a group of natural phenolic compounds that shows several pharmacological activities. The aim of present work was to investigate the effect of coumarin and six derivatives in sea urchin gametes and zygotes exposed to UVB. Embryonic development assay was used to monitor UVB embryotoxicity. Firstly, we demonstrated that coumarin inhibited first embryonic cell division from 5 μM (EC50 = 52.9 μM) and its derivatives showed an embryotoxic effect ten times higher. Then, gametes or zygotes were treated with coumarin compounds before or after UVB exposure (UVB doses ranged from 0.056 to 0.9 kJm(-2)). Pretreatment of gametes or zygotes with coumarin or 3-hydroxycoumarin (1 μM, both) decreased UVB embryotoxic effect. Protective effect of the compounds was observed only when cells were treated previous to UVB exposure. Coumarin derivatives 4-hydroxycoumarin, 6-Hydroxycoumarin, 7-hydroxycoumarin, 6,7-dihydroxycoumarin and 6-methoxy-7-hydroxycoumarin did not exhibit photoprotective activity. Our data provides evidences that coumarin and 3-hydroxycoumarin can be a promising class of photoprotective drugs.
The First Step of Biodegradation of 7-Hydroxycoumarin in Pseudomonas mandelii 7HK4 Depends on an Alcohol Dehydrogenase-Type Enzyme
Int J Mol Sci 2021 Feb 4;22(4):1552.PMID:33557119DOI:10.3390/ijms22041552.
Coumarins are well known secondary metabolites widely found in various plants. However, the degradation of these compounds in the environment has not been studied in detail, and, especially, the initial stages of the catabolic pathways of coumarins are not fully understood. A soil isolate Pseudomonas mandelii 7HK4 is able to degrade 7-hydroxycoumarin (umbelliferone) via the formation of 3-(2,4-dihydroxyphenyl)propionic acid, but the enzymes catalyzing the α-pyrone ring transformations have not been characterized. To elucidate an upper pathway of the catabolism of 7-hydroxycoumarin, 7-hydroxycoumarin-inducible genes hcdD, hcdE, hcdF, and hcdG were identified by RT-qPCR analysis. The DNA fragment encoding a putative alcohol dehydrogenase HcdE was cloned, and the recombinant protein catalyzed the NADPH-dependent reduction of 7-hydroxycoumarin both in vivo and in vitro. The reaction product was isolated and characterized as a 7-hydroxy-3,4-dihydrocoumarin based on HPLC-MS and NMR analyses. In addition, the HcdE was active towards 6,7-dihydroxycoumarin, 6-Hydroxycoumarin, 6-methylcoumarin and coumarin. Thus, in contrast to the well-known fact that the ene-reductases usually participate in the reduction of the double bond, an alcohol dehydrogenase catalyzing such reaction has been identified, and, for P. mandelii 7HK4, 7-hydroxycoumarin degradation via a 7-hydroxy-3,4-dihydrocoumarin pathway has been proposed.
Inhibitory effects of 6-alkoxycoumarin and 7-alkoxycoumarin derivatives on lipopolysaccharide/interferon γ-stimulated nitric oxide production in RAW264 cells
Biol Pharm Bull 2012;35(6):963-6.PMID:22687539DOI:10.1248/bpb.35.963.
Coumarin and its derivatives are well known for their anti-inflammatory and anti-oxidative effects. In this study, we synthesized 32 coumarin derivatives from commercially available 6-Hydroxycoumarin (6HC) and 7-hydroxycoumarin (7HC) and examined their effects on lipopolysaccharide/interferon γ (LPS/IFNγ)-stimulated nitric oxide (NO) production in murine macrophage RAW264 cells. Among these derivatives, 6HC-8 (6-(3-phenylpropoxy)coumarin), 6HC-14 (6-(2-octynyloxy)coumarin), 7HC-14 (7-(2-octynyloxy)coumarin), and 7HC-16 (7-(3,5-dimethoxybenzyloxy)coumarin) markedly suppressed NO production at low concentration (25 µM). These synthesized coumarin derivatives also markedly inhibited inducible NO synthase (iNOS) protein and mRNA expression, as assessed by western blotting and quantitative real time-polymerase chain reaction (RT-PCR).