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 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:15649
ChemSpider	114790 Y
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 Y Key: QMXOFBXZEKTJIK-LSDHHAIUSA-N Y
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). Infobox references

Glycinol is a pterocarpan, a type of natural phenol. It is a phytoalexin found in the soybean (Glycine max) and is biosynthesised from daidzein.

Glycinol has potent phytoestrogenic activity. The so-called osteogenesis that this causes is postulated to be a preventative factor for osteoporosis.^[1][2]

Glycinol can be synthethised chemically and possesses two chiral centers.^[3] It is a precursor to glyceollins through the action of prenyltransferase enzymes such as trihydroxypterocarpan dimethylallyltransferase.^[4]