5,6-Dihydro-4-methoxy-2H-pyran-2-one
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| Category | Mycotoxins |
| Catalog number | BBF-01841 |
| CAS | 83920-64-3 |
| Molecular Weight | 128.13 |
| Molecular Formula | C6H8O3 |
| Purity | 95% |
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Description
It is produced by the strain of Penicillum italicum MRC 1360.
Specification
| Synonyms | 2H-Pyran-2-one,5,6-dihydro-4-methoxy-(9CI) |
| IUPAC Name | 4-methoxy-2,3-dihydropyran-6-one |
| Canonical SMILES | COC1=CC(=O)OCC1 |
| InChI | InChI=1S/C6H8O3/c1-8-5-2-3-9-6(7)4-5/h4H,2-3H2,1H3 |
| InChI Key | MEZHTUKDGVTUCD-UHFFFAOYSA-N |
Properties
| Appearance | Light Yellow Crystalline |
| Melting Point | 77°C |
Reference Reading
1. Untargeted Metabolomics Approach for the Discovery of Environment-Related Pyran-2-ones Chemodiversity in a Marine-Sourced Penicillium restrictum
Van-Tuyen Le, Samuel Bertrand, Thibaut Robiou du Pont, Fabrice Fleury, Nathalie Caroff, Sandra Bourgeade-Delmas, Emmanuel Gentil, Cedric Logé, Gregory Genta-Jouve, Olivier Grovel Mar Drugs. 2021 Jun 29;19(7):378. doi: 10.3390/md19070378.
Very little is known about chemical interactions between fungi and their mollusc host within marine environments. Here, we investigated the metabolome of a Penicillium restrictum MMS417 strain isolated from the blue mussel Mytilus edulis collected on the Loire estuary, France. Following the OSMAC approach with the use of 14 culture media, the effect of salinity and of a mussel-derived medium on the metabolic expression were analysed using HPLC-UV/DAD-HRMS/MS. An untargeted metabolomics study was performed using principal component analysis (PCA), orthogonal projection to latent structure discriminant analysis (O-PLSDA) and molecular networking (MN). It highlighted some compounds belonging to sterols, macrolides and pyran-2-ones, which were specifically induced in marine conditions. In particular, a high chemical diversity of pyran-2-ones was found to be related to the presence of mussel extract in the culture medium. Mass spectrometry (MS)- and UV-guided purification resulted in the isolation of five new natural fungal pyran-2-one derivatives-5,6-dihydro-6S-hydroxymethyl-4-methoxy-2H-pyran-2-one (1), (6S, 1'R, 2'S)-LL-P880β (3), 5,6-dihydro-4-methoxy-6S-(1'S, 2'S-dihydroxy pent-3'(E)-enyl)-2H-pyran-2-one (4), 4-methoxy-6-(1'R, 2'S-dihydroxy pent-3'(E)-enyl)-2H-pyran-2-one (6) and 4-methoxy-2H-pyran-2-one (7)-together with the known (6S, 1'S, 2'S)-LL-P880β (2), (1'R, 2'S)-LL-P880γ (5), 5,6-dihydro-4-methoxy-2H-pyran-2-one (8), (6S, 1'S, 2'R)-LL-P880β (9), (6S, 1'S)-pestalotin (10), 1'R-dehydropestalotin (11) and 6-pentyl-4-methoxy-2H-pyran-2-one (12) from the mussel-derived culture medium extract. The structures of 1-12 were determined by 1D- and 2D-MMR experiments as well as high-resolution tandem MS, ECD and DP4 calculations. Some of these compounds were evaluated for their cytotoxic, antibacterial, antileishmanial and in-silico PTP1B inhibitory activities. These results illustrate the utility in using host-derived media for the discovery of new natural products.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
