Glycinol (pterocarpan)

Glycinol

Names
IUPAC name 6H-[1]benzofuro[3,2-c]chromene-3,6a(11aH),9-triol
Identifiers
3D model (Jmol)	Interactive image
ChemSpider	114790 N
PubChem CID	129648
InChI InChI=1S/C15H12O5/c16-8-1-3-10-12(5-8)19-7-15(18)11-4-2-9(17)6-13(11)20-14(10)15/h1-6,14,16-18H,7H2/t14-,15+/m0/s1 N Key: QMXOFBXZEKTJIK-LSDHHAIUSA-N N InChI=1/C15H12O5/c16-8-1-3-10-12(5-8)19-7-15(18)11-4-2-9(17)6-13(11)20-14(10)15/h1-6,14,16-18H,7H2/t14-,15+/m0/s1 Key: QMXOFBXZEKTJIK-LSDHHAIUBH
SMILES O3c1c(ccc(O)c1)[C@@H]4Oc2cc(O)ccc2[C@]4(O)C3
Properties
Chemical formula	C15H12O5
Molar mass	272.25 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Glycinol is a pterocarpan, a type of natural phenol. It is a phytoalexin found in the soybean (Glycine max). It is formed by the cyclisation of daidzein. It has antiestrogenic activities.

It can be synthethised chemically and possesses two chiral centers.

Glycinol is the direct precursor of glyceollins through the action of a prenyltransferase.

Experiments show that the 6a oxygen of glycinol is derived from molecular oxygen.