Glycinol (pterocarpan)

Glycinol

Names
IUPAC name 6H-[1]benzofuro[3,2-c]chromene-3,6a(11aH),9-triol
Identifiers
ChemSpider	114790
Jmol interactive 3D	Image
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 and 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 and 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.