3-Hydroxycoumarin
(Synonyms: 3-羟基香豆素) 目录号 : GC49364
A coumarin with diverse biological activities
Cas No.:939-19-5
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >97.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
3-Hydroxycoumarin is a coumarin that has been found in A. reinwardtii and has diverse biological activities.1,2,3 It inhibits 15-lipoxygenase-1 (15-LO-1; IC50 = 9.5 µM).1 3-hydroxycoumarin scavenges DPPH radicals in a cell-free assay (IC50 = 0.61 mM) and inhibits lipid peroxidation in vitro (IC50 = 69.07 mM).2 It is protective against UVB-induced embryotoxicity in sea urchins (E. lucunter).3
1.Alavi, S.J., Sadeghian, H., Seyedi, S.M., et al.A novel class of human 15-LOX-1 inhibitors based on 3-hydroxycoumarinChem. Biol. Drug Des.91(6)1125-1132(2017) 2.Rattanapan, J., Sichaem, J., and Tip-pyang, S.Chemical constituents and antioxidant activity from the stems of Alyxia reinwardtiiRec. Nat. Prod.6(3)288-291(2012) 3.de Araujo Leite, J.C., de Castro, T.M.X., Barbosa-Filho, J.M., et al.Photoprotective effect of coumarin and 3-hydroxycoumarin in sea urchin gametes and embryonic cellsJ. Photochem. Photobiol. B Biol.14644-51(2015)
| Cas No. | 939-19-5 | SDF | |
| 别名 | 3-羟基香豆素 | ||
| Canonical SMILES | O=C1OC2=C(C=C1O)C=CC=C2 | ||
| 分子式 | C9H6O3 | 分子量 | 162.1 |
| 溶解度 | DMF: 15 mg/ml,DMF:PBS (pH 7.2) (1:4): 0.20 mg/ml,DMSO: 10 mg/ml,Ethanol: 1 mg/ml | 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 | 6.169 mL | 30.8452 mL | 61.6903 mL |
| 5 mM | 1.2338 mL | 6.169 mL | 12.3381 mL |
| 10 mM | 0.6169 mL | 3.0845 mL | 6.169 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。
3-Hydroxycoumarin loaded vesicles for recombinant human tyrosinase inhibition in topical applications
Colloids Surf B Biointerfaces 2018 Nov 1;171:675-681.PMID:30107341DOI:10.1016/j.colsurfb.2018.08.008.
Tyrosinase is one of the key enzymes in mammalian melanin biosynthesis. Decreasing tyrosinase activity has been targeted for the prevention of conditions related to the hyperpigmentation of the skin, such as melasma and age spots. This paper is devoted to the engineering of vesicle formulations loaded with 3-Hydroxycoumarin for topical pharmaceutical applications. At first, it was demonstrated the strong inhibiting ability of 3-Hydroxycoumarin against recombinant human tyrosinase. Then, such a drug was effectively encapsulated within liquid or gel-like vesicle formulations, both based on monoolein and lauroylcholine chloride. In vitro skin penetration and permeation studies proved these formulations efficiently overcome the barrier represented by the stratum corneum, delivering 3-Hydroxycoumarin to the deeper skin layers. The effect of applying for different times the liquid and the gel formulation was also evaluated. Results revealed that application of the gel formulation for 2 h favored the drug accumulation into the skin with low transdermal delivery, thus indicating this combination of administration time and formulation as ideal to locally inhibit tyrosinase activity with minimal systemic absorption. Moreover, when incubated with B16F10 melanoma cells, the liquid vesicle formulations did not show cytotoxic activity.
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.
3-Hydroxycoumarin as a new matrix for matrix-assisted laser desorption/ionization time-of-flight mass spectrometry of DNA
J Am Soc Mass Spectrom 2006 Dec;17(12):1665-8.PMID:16908181DOI:10.1016/j.jasms.2006.07.010.
3-Hydroxycoumarin (3-HC) was designed, synthesized, and tested as a matrix for matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS) analyses of a variety of synthetic oligodeoxynucleotides ranging long from three to 70 bases. Using the matrix solution of 3-HC dissolved in a mixed solvent of acetone and diammonium hydrogen citrate, DNA segments over the mass range 800 Da to 6900 Da were isotopically resolved with high signal-to-noise (S/N) ratio. The individual isotopic molecular ion peaks of a group of 23-mer mixed-base oligomers differing by one or two bases with mass differences of 9 or 7 Da were recorded. Larger oligodeoxynucleotide segments of 34-mer, 50-mer, and 70-mer have also been analyzed effectively. Less than 250 attomol of a 10-mer DNA segment was clearly detected without any fragmentation. The new matrix can be used for the analysis of DNA segments in both positive- and negative-ion modes, and the quality of all negative-ion mode spectra are as good as that obtained in positive-ion mode shown in this paper. Compared with conventional matrices of 3-hydroxypicolinic acid (3-HPA) and 6-aza-2-thiothymine (ATT), 3-HC had noticeable improvement in resolution, S/N ratio, spot-to-spot-, and sample-to-sample reproducibility for analyzed DNA segments.
3-Hydroxycoumarin glycosides from Alyxia reinwardti var. Lucida
Phytochemistry 1993 Oct;34(3):825-30.PMID:7764154DOI:10.1016/0031-9422(93)85366-y.
Investigation of the inner bark of Alyxia reinwardti var. lucida led to the isolation of two new coumarin glycosides, 1 and 2, whose structures were determined by interpretation of their spectroscopic data, particularly NMR spectroscopy.
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.