Glycinol (pterocarpan)

Glycinol
Names
	Preferred IUPAC name (6aS,11aS)-6H-[1]Benzofuro[3,2-c][1]benzopyran-3,6a,9(11aH)-triol
Identifiers
CAS Number	69393-95-9 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:15649;
ChemSpider	114790 ;
KEGG	C01263;
PubChem CID	129648;
UNII	Q0O9HGR94O;
CompTox Dashboard (EPA)	DTXSID20989207 ;
	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 Key: QMXOFBXZEKTJIK-LSDHHAIUSA-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). verify (what is ?) 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.

More recent literature supports that glycinol has potent phytoestrogenic activity.

The so-called osteogenesis that is causes is postulated to be a preventative factor for osteoporosis.

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.