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6-Methylcoumarin

CAS# 92-48-8

6-Methylcoumarin

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Quality Control of 6-Methylcoumarin

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Chemical structure

6-Methylcoumarin

3D structure

Chemical Properties of 6-Methylcoumarin

Cas No. 92-48-8 SDF Download SDF
PubChem ID 7092 Appearance Powder
Formula C10H8O2 M.Wt 160.17
Type of Compound Coumarins Storage Desiccate at -20°C
Solubility DMSO : ≥ 125 mg/mL (780.42 mM)
*"≥" means soluble, but saturation unknown.
Chemical Name 6-methylchromen-2-one
SMILES CC1=CC2=C(C=C1)OC(=O)C=C2
Standard InChIKey FXFYOPQLGGEACP-UHFFFAOYSA-N
Standard InChI InChI=1S/C10H8O2/c1-7-2-4-9-8(6-7)3-5-10(11)12-9/h2-6H,1H3
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of 6-Methylcoumarin

The barks of Fraxinus chinensis

Biological Activity of 6-Methylcoumarin

Description6-Methylcoumarin, widely used in cosmetics, is capable of inducing contact photoallergy in human volunteers.It has hepatotoxicity.
In vitro

Photocontact allergy to 6-methylcoumarin.[Pubmed: 743874]

Contact Dermatitis, 2010, 4(5):277-282.


METHODS AND RESULTS:
A proprietary sunscreen-induced photosensitivity reactions in a small number of users. Laboratory study revealed that the reactions were of the photoallergic type and were due to the presence of a synthetic fragrance, 6-Methylcoumarin.
CONCLUSIONS:
By photomaximization testing 6-Methylcoumarin was found to be a potent photocontact allergen.

Protocol of 6-Methylcoumarin

Animal Research

Comparison of the hepatic effects of coumarin, 3,4-Dimethylcoumarin, dihydrocoumarin and 6-methylcoumarin in the rat.[Reference: WebLink]

Food and Chemical Toxicology, 1994, 32(8):743-751.

The mechanism of coumarin-induced hepatotoxicity in the rat has been investigated by comparing the effects of coumarin with those of three coumarin derivatives, namely 3,4-dihydrocoumarin (DHC), 3,4-dimethylcoumarin (3,4-DMC) and 6-Methylcoumarin (6-MC).
METHODS AND RESULTS:
Male Sprague-Dawley rats were fed either control diet or diets containing 0.5 or 0.75% coumarin, 0.76% DHC, 0.6 or 0.9% 3,4-DMC or 0.82% 6-MC for 13 wk. The dietary levels of 0.5% coumarin and 0.6% 3,4-DMC, were equimolar (3.43mmol/100g diet), as were the dietary levels of 0.75% coumarin, 0.76% DHC, 0.9% 3,4-DMC and 0.82% 6-MC (5.14mmol/100g diet). All treatments resulted in an increase in relative liver weight, but only coumarin increased plasma alanine aminotransferase and aspartate aminotransferase activities. Morphological examination of liver sections from coumarin treated rats revealed vacuolation of centrilobular hepatocytes and bile duct hyperplasia. Cholangiofibrosis was also observed, particularly in rats given 0.75% coumarin. Treatment with DHC produced no abnormalities, whereas a slight hypertrophy of centrilobular hepatocytes was observed in some 3,4-DMC treated animals and a slight vacuolation of individual hepatocytes was noted in some 6-MC treated rats. DHC, 6-MC and particularly 3,4-DMC treatment resulted in an induction of cytochrome P-450 dependent mixed function oxidase enzyme activities. All treatments induced hepatic GSHS-transferase and γ-glutamyltransferase activities, induction being most marked in rats given coumarin and 6-MC.
CONCLUSIONS:
These results provide further evidence that coumarin-induced hepatotoxicity in the rat is due to the formation of a 3,4-epoxide intermediate.

6-Methylcoumarin Dilution Calculator

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6-Methylcoumarin Molarity Calculator

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Preparing Stock Solutions of 6-Methylcoumarin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 6.2434 mL 31.2168 mL 62.4337 mL 124.8673 mL 156.0842 mL
5 mM 1.2487 mL 6.2434 mL 12.4867 mL 24.9735 mL 31.2168 mL
10 mM 0.6243 mL 3.1217 mL 6.2434 mL 12.4867 mL 15.6084 mL
50 mM 0.1249 mL 0.6243 mL 1.2487 mL 2.4973 mL 3.1217 mL
100 mM 0.0624 mL 0.3122 mL 0.6243 mL 1.2487 mL 1.5608 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on 6-Methylcoumarin

Development of novel in vitro photosafety assays focused on the Keap1-Nrf2-ARE pathway.[Pubmed:26511905]

J Appl Toxicol. 2016 Jul;36(7):956-68.

Although photoallergens require UV energy for antigen formation, the subsequent immune response is considered to be the same as in ordinary skin sensitization. Therefore, in vitro tests for skin sensitization should also be applicable for photoallergy testing. In this study, we examined whether activation of the Keap1 (Kelch-like ECH-associated protein 1)-Nrf2 (nuclear factor-erythroid 2-related factor 2)-ARE (antioxidant response element) pathway could be used to assess the photoallergenic potential of chemicals, using the reporter cell line AREc32 or KeratinoSens(TM) . First, we identified an appropriate UVA irradiation dose [5 J cm(-2) irradiation in phosphate-buffered saline (PBS)] by investigating the effect of UV irradiation on ARE-dependent gene induction using untreated or 6-Methylcoumarin (6-MC)-treated cells. Irradiation of well-known photoallergens under this condition increased ARE-dependent gene expression by more than 50% compared with both vehicle and non-irradiated controls. When the cut-off value for detecting photoallergens was set at 50% induction, the accuracy of predicting photoallergenic/phototoxic chemicals was 70% in AREc32 cells and 67% in KeratinoSens(TM) cells, and the specificity was 100% in each case. We designate these assays as a photo-ARE assay and photo-KeratinoSens(TM) , respectively. Our results suggest that activation of the Keap1-Nrf2-ARE pathway is an effective biomarker for evaluating both photoallergenic and phototoxic potentials. Either of the above tests might be a useful component of a battery of in vitro tests/in silico methods for predicting the photoallergenicity and phototoxicity of chemicals. Copyright (c) 2015 John Wiley & Sons, Ltd.

Simultaneous Analysis of Simple Coumarins and Furocoumarines in Cigarettes by Solid-Phase Extraction with Gas Chromatography-Mass Spectrometry.[Pubmed:28425389]

J AOAC Int. 2017 Sep 1;100(5):1559-1564.

A sensitive, high-throughput analytical method based on a GC-MS method was established for the simultaneous quantitative determination of two categories of harmful coumarins: simple coumarins (coumarin, 6-Methylcoumarin, 7-methoxycoumarin, 3,4-dihydrocoumarin, and 7-ethoxy-4-methylcoumarin) and furocoumarines (psoralen, 8-methoxypsoralen, 5-methoxypsoralen, and trioxysalen). The nine analytes were extracted with ethyl acetate, purified with Oasis HLB solid-phase extraction (SPE) cartridges, and identified and quantitatively determined by GC-MS in selected-ion monitoring mode. The LODs and LOQs of these compounds were in the ranges of 12.5-21.2 and 41.6-70.0 mug/kg, respectively. Average recoveries for the nine analytes ranged from 72.7 to 86.6% at LOQ, 1.5x LOQ, and 2x LOQ spike levels, with RSDs that were typically lower than 5.1%. The SPE-GC-MS method developed in this study was initially applied to research coumarins in cigarette samples; it proved to be accurate, sensitive, convenient, and practical.

Tetramic Acids and Pyridone Alkaloids from the Endolichenic Fungus Tolypocladium cylindrosporum.[Pubmed:26356746]

J Nat Prod. 2015 Sep 25;78(9):2155-60.

Three new tetramic acid derivatives, tolypocladenols A1, A2, and B (1-3), a new pyridone alkaloid, tolypyridone A (4), and a new coumarin derivative, 3,8-dihydroxy-4-(4-hydroxyphenyl)-6-Methylcoumarin (5), together with four known compounds (6-9) were isolated from the endolichenic fungus Tolypocladium cylindrosporum, which inhabits the lichen Lethariella zahlbruckneri. Structures of these compounds were determined by comprehensive analysis of spectroscopic data and single-crystal X-ray diffraction determination. Bioassay of the isolated compounds found that pyridoxatin (7) was cytotoxic to human cancer cells by induction of G0/G1 cell cycle arrest and apoptosis.

Inhibitory effects and oxidation of 6-methylcoumarin, 7-methylcoumarin and 7-formylcoumarin via human CYP2A6 and its mouse and pig orthologous enzymes.[Pubmed:26068522]

Xenobiotica. 2016;46(1):14-24.

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 microM; Vmax: 0.81-0.89 min(-1)) and by CYP2A5 and CYP2A19. The reaction was almost completely inhibited at 10 microM 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.

Electroreductive dimerization of coumarin and coumarin analogues at carbon cathodes.[Pubmed:25427227]

J Org Chem. 2015 Jan 2;80(1):274-80.

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.

Synthesis of new chlorin e6 trimethyl and protoporphyrin IX dimethyl ester derivatives and their photophysical and electrochemical characterizations.[Pubmed:25171181]

Chemistry. 2014 Oct 13;20(42):13644-55.

In view of increasing demands for efficient photosensitizers for photodynamic therapy (PDT), we herein report the synthesis and photophysical characterizations of new chlorin e6 trimethyl ester and protoporphyrin IX dimethyl ester dyads as free bases and Zn(II) complexes. The synthesis of these molecules linked at the beta-pyrrolic positions to pyrano[3,2-c]coumarin, pyrano[3,2-c]quinolinone, and pyrano[3,2-c]naphthoquinone moieties was performed by using the domino Knoevenagel hetero Diels-Alder reaction. The alpha-methylenechromanes, alpha-methylenequinoline, and ortho-quinone methides were generated in situ from a Knoevenagel reaction of 4-hydroxycoumarin, 4-hydroxy-6-Methylcoumarin, 4-hydroxy-N-methylquinolinone, and 2-hydroxy-1,4-naphthoquinone, respectively, with paraformaldehyde in dioxane. All the dyads as free bases and as Zn(II) complexes were obtained in high yields. All new compounds were fully characterized by 1D and 2D NMR techniques, UV/Vis spectroscopy, and HRMS. Their photophysical properties were evaluated by measuring the fluorescence quantum yield, the singlet oxygen quantum yield by luminescence detection, and also the triplet lifetimes were correlated by flash photolysis and intersystem crossing (ISC) rates. The fluorescence lifetimes were measured by a time-correlated single photon count (TCSPC) method, fluorescence decay associated spectra (FDAS), and anisotropy measurements. Magnetic circular dichroism (MCD) and circular dichroism (CD) spectra were recorded for one Zn(II) complex in order to obtain information, respectively, on the electronic and conformational states, and interpretation of these spectra was enhanced by molecular orbital (MO) calculations. Electrochemical studies of the Zn(II) complexes were also carried out to gain insights into their behavior for such applications.

Description

6-Methylcoumarin is a synthetic fragrance widely used in cosmetics.

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