Marmesin

Marmesin (nodakenetin) is a chemical compound precursor in psoralen and linear furanocoumarins biosynthesis.^[1]

Marmesin

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
CAS Number	13849-08-6 Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL442813
ChemSpider	296611
PubChem CID	334704
UNII	H5D33D6K5D Y
CompTox Dashboard (EPA)	DTXSID001030448
InChI InChI=1S/C14H14O4/c1-14(2, 16)12-6-9-5-8-3-4-13(15)18-10(8)7-11(9)17-12/h3-5,7,12,16H,6H2, 1-2H3/t12-/m0/s1 Key: FWYSBEAFFPBAQU-LBPRGKRZSA-N
SMILES CC(C)([C@@H]1CC2=C(O1)C=C3C(=C2)C=CC(=O)O3)O
Properties
Chemical formula	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). Infobox references

Marmesin plays a central role in the biosynthesis of furocoumarins in the plant ruta graveolens, more commonly known as rue. It acts as the natural intermediate in the formation of the furan ring that leads to a 4’,5’-dihydro furocoumarin-derivative. This substance can then be transformed into psoralen and other furocoumarins present in rue. Upon feeding the herb a dose of marmesin, radioactivity became strongly incorporated into psoralen and thus the plant itself.^[2] It is constituent of Aegle marmelos, Ammi majus, Poncirus trifoliata and Prangos bucharica and others ^[3]

Spectra

IR Spectra

IR (ATR): νmax 3480, 2971, 1699, 1631, 1488 cm-1.^[4]

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.^[5]

UV-Vis

UV: [neutral]λmax  217 (ε7420); 338 (ε17700)( MeOH)   [neutral]λmax  332( EtOH).^[6]

Production

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.^[7]