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
PubChem	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 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).
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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.^[1][2]

It can be synthethised chemically and possesses two chiral centers.^[3]

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.^[4]

References

1. Zimmermann, M. C.; Tilghman, S. L.; Boue, S. M.; Salvo, V. A.; Elliott, S.; Williams, K. Y.; Skripnikova, E. V.; Ashe, H.; et al. (2009). "Glyceollin I, a Novel Antiestrogenic Phytoalexin Isolated from Activated Soy". Journal of Pharmacology and Experimental Therapeutics. 332 (1): 35–45. doi:10.1124/jpet.109.160382. PMC 2802480. PMID 19797619.
2. Qi Y.; Moco S.I.A.; Boeren S.; Vos C.H. de; Bovy A.G. (2005). "Isolation and identification of glycinol from Glycine max L. Merri". Chinese Journal of Chromatography. 23 (4): 353–357. PMID 16250441.
3. Luniwal Amarjit; Khupse Rahul S; Reese Michael; Lei Fang; Erhardt Paul W (2009). "Total Syntheses of Racemic and Natural Glycinol". Journal of Natural Products. 72 (11): 2072–2075. doi:10.1021/np900509f. PMID 19943626.
4. Matthews, David E.; Plattner, Ronald D.; Vanetten, Hans D. (1989). "The 6a oxygen of the pterocarpan glycinol is derived from molecular oxygen". Phytochemistry. 28: 113. doi:10.1016/0031-9422(89)85020-4.