7-Methylcoumarin
(Synonyms: 7-甲基香豆素) 目录号 : GC65409
7-Methylcoumarin can inhibit the growth of S. aureus and the growth of Gram-positive bacteria within a concentration of 0.8–3.6 μg/ml, and also has a strong hepatoprotective activity.
Cas No.:2445-83-2
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
7-Methylcoumarin can inhibit the growth of S. aureus and the growth of Gram-positive bacteria within a concentration of 0.8–3.6 μg/ml, and also has a strong hepatoprotective activity.
7-methylcoumarin is equipotent in inhibiting the growth of S. aureus and the growth of Gram-positive bacteria within a concentration of 0.8-3.6 μg/ml, displaying no effects against Gram-negative bacteria and fungi.[1]
Pretreatment with MC significantly decreases alanine aminotransferase (ALT), aspartate aminotransferase (AST) and serum bilirubin (TB) in the serum of CCl(4)-induced liver damaged rats in a dose-dependent manner, also prevents oxidative stress induced by CCl(4), thereby, increasing superoxide dismutase (SOD) and catalase (CAT) levels and decreasing thiobarbituric-acid-related substances (TBARS) levels in liver homogenates.[2]
[1] El-Gendy MM, et al. Appl Biochem Biotechnol. 2008 Jul;150(1):85-96. [2] Sancheti S, et al. Drug Chem Toxicol. 2013 Jan;36(1):42-7.
| Cas No. | 2445-83-2 | SDF | Download SDF |
| 别名 | 7-甲基香豆素 | ||
| 分子式 | C10H8O2 | 分子量 | 160.17 |
| 溶解度 | DMSO : 100 mg/mL (624.34 mM; Need ultrasonic) | 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 | 6.2434 mL | 31.2168 mL | 62.4337 mL |
| 5 mM | 1.2487 mL | 6.2434 mL | 12.4867 mL |
| 10 mM | 0.6243 mL | 3.1217 mL | 6.2434 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。
Inhibitory effects and oxidation of 6-methylcoumarin, 7-Methylcoumarin and 7-formylcoumarin via human CYP2A6 and its mouse and pig orthologous enzymes
Xenobiotica 2016;46(1):14-24.PMID:26068522DOI:10.3109/00498254.2015.1048327.
1. Information about the metabolism of compounds is essential in drug discovery and development, risk assessment of chemicals and further development of predictive methods. 2. In vitro and in silico methods were applied to evaluate the metabolic and inhibitory properties of 6-methylcoumarin, 7-Methylcoumarin and 7-formylcoumarin with human CYP2A6, mouse CYP2A5 and pig CYP2A19. 3. 6-Methylcoumarin was oxidized to fluorescent 7-hydroxy-6-methylcoumarin by CYP2A6 (Km: 0.64-0.91 µM; Vmax: 0.81-0.89 min(-1)) and by CYP2A5 and CYP2A19. The reaction was almost completely inhibited at 10 µM 7-Methylcoumarin in liver microsomes of human and mouse, but in pig only 40% inhibition was obtained with the anti-CYP2A5 antibody or with methoxsalen and pilocarpine. 7-Methylcoumarin was a mechanism-based inhibitor for CYP2A6, but not for the mouse and pig enzymes. 7-Formylcoumarin was a mechanism-based inhibitor for CYP2As of all species. 4. Docking and molecular dynamics simulations of 6-methylcoumarin and 7-Methylcoumarin in the active sites of CYP2A6 and CYP2A5 demonstrated a favorable orientation of the 7-position of 6-methylcoumarin towards the heme moiety. Several orientations of 7-Methylcoumarin were possible in CYP2A6 and CYP2A5. 5. These results indicate that the active site of CYP2A6 has unique interaction properties for ligands and differs in this respect from CYP2A5 and CYP2A19.
Ameliorative effects of 7-Methylcoumarin and 7-methoxycoumarin against CCl4-induced hepatotoxicity in rats
Drug Chem Toxicol 2013 Jan;36(1):42-7.PMID:23126493DOI:10.3109/01480545.2011.648329.
The available conventional remedies for the treatment of drug-induced liver diseases are highly inadequate and possess serious adverse effects; therefore, the development of new, effective drugs is considered necessary. This article explores the hepatoprotective and antioxidant potential of 7-Methylcoumarin (MC) and 7-methoxycoumarin (MOC) in CCl(4)-induced hepatotoxicity in rats. MC and MOC individually, at doses of 50 and 100 mg/kg body weight, were administered orally once-daily for 7 days. The hepatoprotective activity was assessed using various biochemical parameters, such as alanine aminotransferase (ALT), aspartate aminotransferase (AST), serum bilirubin (TB), total protein (TP), and albumin (TA). Serum antioxidant enzyme [e.g., superoxide dismutase (SOD) and catalase (CAT)] levels were determined. Also, thiobarbituric-acid-related substances (TBARS) levels, along with histopathological studies of liver tissue, were scrutinized. Pretreatment with MC and MOC significantly decreased ALT, AST, and TB in the serum of CCl(4)-induced liver damaged rats in a dose-dependent manner. TA and TP levels in the serum were also restored significantly in all presupplemented MC and MOC groups. In addition, oxidative stress induced by CCl(4) was prevented significantly; thereby, increasing SOD and CAT levels and decreasing TBARS levels in liver homogenates. Histopathological studies revealed the ameliorative natures of both the compounds. This study demonstrates the strong hepatoprotective activity of MC and MOC, which could be attributed to their potent antioxidant effects.
The sensitizing capacity of coumarins (II)
Contact Dermatitis 1986 Nov;15(5):289-94.PMID:3816192DOI:10.1111/j.1600-0536.1986.tb01370.x.
5 coumarins used in perfumery, cosmetics, therapeutic ointments or occurring naturally were investigated by Freund's complete adjuvant technique (FCAT) in guinea pigs to determine their contact sensitizing potency. 4-Methylesculetin was also studied. Esculetin, dihydrocoumarin and daphnetin were found to be moderate to strong sensitizers, while fraxetin was nearly and 7-Methylcoumarin completely inactive. The results corroborate the hypothetical view that only those coumarins having a catecholic disubstitution in the benzene ring, e.g., esculetin, 4-methylesculetin, daphnetin, can become sensitizers on the basis that they are capable of forming ortho-quinones under oxidizing conditions.
Electroreductive dimerization of coumarin and coumarin analogues at carbon cathodes
J Org Chem 2015 Jan 2;80(1):274-80.PMID:25427227DOI:10.1021/jo502272g.
Electrochemical reduction of coumarin (1), 6-methylcoumarin (2), 7-Methylcoumarin (3), 7-methoxycoumarin (4), and 5,7-dimethoxycoumarin (5) at carbon cathodes in dimethylformamide containing 0.10 M tetra-n-butylammonium tetrafluoroborate has been investigated by means of cyclic voltammetry and controlled-potential (bulk) electrolysis. Cyclic voltammograms for reduction of 1-5 exhibit two irreversible cathodic peaks: (a) the first peak arises from one-electron reduction of the coumarin to form a radical-anion intermediate, which is protonated by the medium to give a neutral radical; (b) although most of this radical undergoes self-coupling to yield a hydrodimer, reduction of the remaining radical (ultimately to produce a dihydrocoumarin) causes the second cathodic peak. At a potential corresponding to the first voltammetric peak, bulk electrolysis of 1-5 affords the corresponding hydrodimer as a mixture of meso and dl diastereomers. Although the meso form dominates, the dl-to-meso ratio varies, due to steric effects arising from substituents on the aromatic ring. Electroreduction of an equimolar mixture of 1 and 4 gives, along with the anticipated symmetrical hydrodimers, an unsymmetrical product derived from the two coumarins. A mechanistic scheme involving both radical-anion and radical intermediates is proposed to account for the formation of the various products.
Bioactive benzopyrone derivatives from new recombinant fusant of marine Streptomyces
Appl Biochem Biotechnol 2008 Jul;150(1):85-96.PMID:18551256DOI:10.1007/s12010-008-8192-5.
In our searching program for bioactive secondary metabolites from marine Streptomycetes, three microbial benzopyrone derivatives (1-3), 7-Methylcoumarin (1) and two flavonoides, rhamnazin (2) and cirsimaritin (3), were obtained during the working up of the ethyl acetate fraction of a marine Streptomyces fusant obtained from protoplast fusion between Streptomyces strains Merv 1996 and Merv 7409. The structures of the three compounds (1-3) were established by nuclear magnetic resonance, mass, UV spectra, and by comparison with literature data. Marine Streptomyces strains were identified based on their phenotypic and chemotypic characteristics as two different bioactive strains of the genus Streptomyces. We described here the fermentation, isolation, as well as the biological activity of these bioactive compounds. The isolated compounds (1-3) are reported here as microbial products for the first time.