Marmesin
Chemical compound
From Wikipedia, the free encyclopedia
Marmesin (nodakenetin) is a chemical compound precursor in psoralen and linear furanocoumarins biosynthesis.[1]
 | |
| Names | |
|---|---|
| Preferred IUPAC name
(2S)-2-(2-Hydroxypropan-2-yl)-2,3-dihydro-7H-furo[3,2-g][1]benzopyran-7-one | |
| Other names
Nodakenetin | |
| Identifiers | |
3D model (JSmol) |
|
| ChEMBL | |
| ChemSpider | |
PubChem CID |
|
| UNII | |
CompTox Dashboard (EPA) |
|
| |
| |
| Properties | |
| C14H14O4 | |
| Molar mass | 246.262 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |
Marmesin plays a central role in the biosynthesis of furocoumarins in the plant Ruta graveolens, more commonly known as rue. It is the biosynthetic precursor for psoralen and other furocoumarins present in rue. It also a constituent of Aegle marmelos, Ammi majus, Poncirus trifoliata and Prangos bucharica and others [2]
Spectra
IR Spectra
IR (ATR): νmax 3480, 2971, 1699, 1631, 1488 cm-1.[3]
Proton-NMR
1H-NMR (300 MHz, CDCl3): δ 7.59 (d, J = 9.5 Hz, 1H, aromatic), 7.22 (s, 1H, aromatic), 6.75 (d, J = 21.6 Hz, 1H, aromatic), 6.20 (d, J = 9.5 Hz, 1H, aromatic), 4.74 (t, J = 8.8 Hz, 1H, CH), 3.28-3.15 (m, 2H, CH2), 1.87 (s, 1H, OH), 1.37 (s, 3H, CH3), 1.24 (s, 3H, CH3) ppm.[4]
UV-Vis
UV: [neutral]λmax 217 (ε7420); 338 (ε17700)( MeOH) [neutral]λmax 332( EtOH).[5]
Laboratory synthesis
Synthesis of marmesin has been successfully conducted in the laboratory on multiple occasions. One way of doing so is by a strategy based on the palladium-catalyzed intramolecular coupling reaction. This reaction would construct the dihydropyran ring and synthesize the compound from the intermediate (-)-peucedanol. The key step in the overall synthesis uses catalytic asymmetric epoxidation of an enone.[6]
Metabolism in plants
(+)-Marmesin is converted to psoralen by the enzyme psoralen synthase.[7]
This is part of the pathway to a group of natural products called furanocoumarins.[8]