Glycinol
Names
Preferred IUPAC name
(6aS ,11aS )-6H -[1]Benzofuro[3,2-c ][1]benzopyran-3,6a,9(11aH )-triol
Identifiers
ChEBI
ChemSpider
KEGG
UNII
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
N Key: QMXOFBXZEKTJIK-LSDHHAIUSA-N
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
O3c1c(ccc(O)c1)[C@@H]4Oc2cc(O)ccc2[C@]4(O)C3
Properties
C15 H12 O5
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).
Chemical compound
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 .[citation needed
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.[citation needed
It can be synthethised chemically and possesses two chiral centers.[ 3]
Glycinol is the direct precursor of glyceollins through the action of a prenyltransferase .[citation needed
Experiments show that the 6a oxygen of glycinol is derived from molecular oxygen .[ 4]
References
^ 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 . ^ 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 . ^ 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 . ^ Matthews, David E.; Plattner, Ronald D.; Vanetten, Hans D. (1989). "The 6a oxygen of the pterocarpan glycinol is derived from molecular oxygen" . Phytochemistry . 28 (1): 113– 115. Bibcode :1989PChem..28..113M . doi :10.1016/0031-9422(89)85020-4
