Glycinol (pterocarpan)

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.

Glycinol

Names
IUPAC name 6H-[1]benzofuro[3,2-c]chromene-3,6a(11aH),9-triol
Identifiers
3D model (JSmol)	Interactive image
ChemSpider	114790
PubChem CID	129648
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).
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Infobox references

More recent literature supports that glycinol has potent phytoestrogenic activity.[1][2]

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.[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. Boué, Stephen M.; Tilghman, Syreeta L.; Elliott, Steven; Zimmerman, M. Carla; Williams, K. Y.; Payton-Stewart, Florastina; Miraflor, Allen P.; Howell, Melanie H.; Shih, Betty Y.; Carter-Wientjes, Carol H.; Segar, Chris; Beckman, Barbara S.; Wiese, Thomas E.; Cleveland, Thomas E.; McLachlan, John A.; Burow, Matthew E. (2009). "Identification of the Potent Phytoestrogen Glycinol in Elicited Soybean (Glycine max)". Endocrinology. 150 (5): 2446–2453. doi:10.1210/en.2008-1235. ISSN 0013-7227. PMC 2671905. PMID 19116342.
2. Strong, Amy L; Jones, Robert B; Glowacki, Julie; Boue, Stephen M; Burow, Matthew E; Bunnell, Bruce A (2017). "Glycinol enhances osteogenic differentiation and attenuates the effects of age on mesenchymal stem cells". Regenerative Medicine. 12 (5): 513–524. doi:10.2217/rme-2016-0148. ISSN 1746-0751. PMID 28718749.
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: 113–115. doi:10.1016/0031-9422(89)85020-4.