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6-Methylcoumarin

$43

  • Brand : BIOFRON

  • Catalogue Number : BF-M2009

  • Specification : 98%

  • CAS number : 92-48-8

  • Formula : C10H8O2

  • Molecular Weight : 160.172

  • PUBCHEM ID : 7092

  • Volume : 20mg

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Catalogue Number

BF-M2009

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

-20℃

Molecular Weight

160.172

Appearance

Powder

Botanical Source

synthesis

Structure Type

Phenylpropanoids

Category

Standards;Natural Pytochemical;API

SMILES

CC1=CC2=C(C=C1)OC(=O)C=C2

Synonyms

6-Methyl-2H-1-benzopyran-2-one/6-Methyl-2H-chromen-2-one/6-methylchromen-2-one/2H-1-Benzopyran-2-one, 6-methyl-/6-Methylcoumarin/T66 BOVJ H1/6 METHYL COUMARIN

IUPAC Name

6-methylchromen-2-one

Density

1.2±0.1 g/cm3

Solubility

Flash Point

124.3±19.5 °C

Boiling Point

304.6±21.0 °C at 760 mmHg

Melting Point

73-76 °C(lit.)

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

2932200000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:92-48-8) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

26068522

Abstract

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.

KEYWORDS

Coumarin derivative; cytochrome P450; enzyme assay; fluorescence; metabolism.

Title

Inhibitory Effects and Oxidation of 6-methylcoumarin, 7-methylcoumarin and 7-formylcoumarin via Human CYP2A6 and Its Mouse and Pig Orthologous Enzymes

Author

Risto O Juvonen 1 , Mira Kuusisto 1 2 , Carolin Fohrgrup 1 , Mari H Pitkanen 1 , Tapio J Nevalainen 1 , Seppo Auriola 1 , Hannu Raunio 1 , Markku Pasanen 1 , Olli T Pentikainen 2

Publish date

2016

PMID

7364969

Abstract

Sporadic cases of a severe photocontact dermatitis have appeared in the last few years following use of fruity-smelling suntan preparations and sunlight exposure. We report five such cases in women who developed severe edema and erythema of sun-exposed areas shortly after application of agents containing 6-methylcoumarin used as fragance. Routine photopatch testing was unproductive in reproducing the reaction, but immediate application of 6-methylcoumarin before ultraviolet A (UVA) radiation elicited significant positive results.

Title

6-Methylcoumarin Photocontact Dermatitis

Author

R T Jackson, L T Nesbitt Jr, V A DeLeo

Publish date

1980 Feb

PMID

24854221

Abstract

A sensitive, specific and reproducible HPLC method has been developed and validated for the quantitative determination of 6-methylcoumarin (6MC) in plasma and other tissues in Wistar rats. A C18 column was used with UV detection at 321 nm and a gradient system consisting of methanol-deionized water was used as mobile phase. The retention time for 6MC was 14.921 min and no interfering peaks were observed for any of the matrices. Linear relationships (r(2) > 0.997) were obtained between the peak height ratios and the corresponding biological sample concentrations over the range 0.4-12.8 µg/mL. Precision and accuracy were evaluated; the coefficient of variation and the relative error for all of the organs were <2 and 7%, respectively. The limit of quantitation was 0.20 µg/mL for the heart and 0.30 µg/mL for the other tissues evaluated. This HPLC method was successfully used in the determination of 6MC in the biodistribution study after administration of 200 mg/kg of both 6MC-free and 6MC-loaded polymeric microparticles. In this study, extensive 6MC was found, in both free and microencapsulated forms, in all the organs tested. The 6MC-free showed a range of between 1.7 and 11.5 µg/g, while the microencapsulated 6MC showed concentrations of between 6.35 and 17.7 µg/g, suggesting that 6MC improved absorption rate.

KEYWORDS

6-methylcoumarin; HPLC; biodistribution; microparticles.

Title

Biodistribution Study of Free and Microencapsulated 6-methylcoumarin in Wistar Rats by HPLC

Author

Aura Rocio Hernandez 1 , Luis Fernando Ospina, Diana Marcela Aragon

Publish date

2015 Feb


Description :

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