7H-Furo(3,2-g)(1)benzopyran-7-one, 2-(1-(beta-D-glucopyranosyloxy)-1-m ethylethyl)-2,3-dihydro-, (S)- Chemical Properties

Melting point:

259-260 °C (decomp)(Solv: water (7732-18-5))

Boiling point:

657.1±55.0 °C(Predicted)

Density 

1.51±0.1 g/cm3(Predicted)

pka

12.90±0.70(Predicted)

form 

Solid

color 

White to off-white

InChIKey

HXCGUCZXPFBNRD-YTLMEVRINA-N

SMILES

C1(=O)OC2=CC3O[C@H](C(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)(C)C)CC=3C=C2C=C1 |&1:7,10,12,15,17,19,r|

7H-Furo(3,2-g)(1)benzopyran-7-one, 2-(1-(beta-D-glucopyranosyloxy)-1-m ethylethyl)-2,3-dihydro-, (S)- Usage And Synthesis

Uses

Marmesinin ((-)-Marmesinin), a natural coumarin, is a biosynthetic precursor of psoralen and linear furanocoumarins. Marmesinin exhibits significant neuroprotective activities against glutamate-induced toxicity[1][2].

Definition

ChEBI: Marmesinin is a member of the class of psoralens that is (-)-marmesin in which the hydroxy hydrogen is replaced by a beta-D-glucosyl residue. It has a role as a plant metabolite, a P450 inhibitor and an antioxidant. It is a beta-D-glucoside, a member of psoralens and a monosaccharide derivative. It is functionally related to a nodakenetin.

References

[1] ABU-MUSTAFA EA, et, al. Natural Coumarins. I. Marmesin and Marmesinin, Further Products from the Fruits of Ammi majus L. J. Org. Chem. 1961 Jan; 26 (1): 161-166.
[2] Kang SY, et, al. Neuroprotective coumarins from the root of Angelica gigas: structure-activity relationships. Arch Pharm Res. 2007 Nov;30(11):1368-73. DOI:10.1007/BF02977358