Glycinol (pterocarpan)

{{Other uses|Glycinol (disambiguation){{!}}Glycinol}}

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 423639149

| Name = Glycinol

| ImageFile = Glycinol.svg

| ImageSize = 240px

| ImageName = Chemical structure of glycinol

| ImageAlt = Chemical structure of glycinol

| ImageFile1 = Glycinol-3D-balls.png

| ImageSize1 = 240

| ImageAlt1 = Glycinol molecule

| PIN = (6aS,11aS)-6H-[1]Benzofuro[3,2-c][1]benzopyran-3,6a,9(11aH)-triol

| OtherNames =

|Section1={{Chembox Identifiers

| CASNo = 69393-95-9

| CASNo_Ref = {{cascite|changed|CAS}}

| ChEBI = 15649

| PubChem = 129648

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 114790

| KEGG = C01263

| UNII = Q0O9HGR94O

| SMILES = O3c1c(ccc(O)c1)[C@@H]4Oc2cc(O)ccc2[C@]4(O)C3

| 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

| InChIKey = QMXOFBXZEKTJIK-LSDHHAIUBH

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = QMXOFBXZEKTJIK-LSDHHAIUSA-N

| MeSHName =

}}

|Section2={{Chembox Properties

| Formula = C₁₅H₁₂O₅

| MolarMass = 272.25 g/mol

| Appearance =

| Density =

| MeltingPt =

| BoilingPt =

| Solubility =

}}

|Section3={{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt =

| GHS_ref =

}}

}}

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.{{cn|date=March 2023}}

More recent literature supports that glycinol has potent phytoestrogenic activity.{{cite journal|last1=Boué|first1=Stephen M.|last2=Tilghman|first2=Syreeta L.|last3=Elliott|first3=Steven|last4=Zimmerman|first4=M. Carla|last5=Williams|first5=K. Y.|last6=Payton-Stewart|first6=Florastina|last7=Miraflor|first7=Allen P.|last8=Howell|first8=Melanie H.|last9=Shih|first9=Betty Y.|last10=Carter-Wientjes|first10=Carol H.|last11=Segar|first11=Chris|last12=Beckman|first12=Barbara S.|last13=Wiese|first13=Thomas E.|last14=Cleveland|first14=Thomas E.|last15=McLachlan|first15=John A.|last16=Burow|first16=Matthew E.|title=Identification of the Potent Phytoestrogen Glycinol in Elicited Soybean (Glycine max)|journal=Endocrinology|volume=150|issue=5|year=2009|pages=2446–2453|issn=0013-7227|doi=10.1210/en.2008-1235|pmid=19116342|pmc=2671905|doi-access=free}}{{cite journal|last1=Strong|first1=Amy L|last2=Jones|first2=Robert B|last3=Glowacki|first3=Julie|last4=Boue|first4=Stephen M|last5=Burow|first5=Matthew E|last6=Bunnell|first6=Bruce A|title=Glycinol enhances osteogenic differentiation and attenuates the effects of age on mesenchymal stem cells|journal=Regenerative Medicine|volume=12|issue=5|year=2017|pages=513–524|issn=1746-0751|doi=10.2217/rme-2016-0148|pmid=28718749}}

The so-called osteogenesis that is causes is postulated to be a preventative factor for osteoporosis.{{cn|date=March 2023}}

It can be synthethised chemically and possesses two chiral centers.{{cite journal | url = http://cat.inist.fr/?aModele=afficheN&cpsidt=22189893 | title = Total Syntheses of Racemic and Natural Glycinol |author1=Luniwal Amarjit |author2=Khupse Rahul S |author3=Reese Michael |author4=Lei Fang |author5=Erhardt Paul W | year = 2009 | volume = 72 | issue = 11 | pages = 2072–2075 | journal = Journal of Natural Products | doi = 10.1021/np900509f | pmid = 19943626| url-access = subscription }}

Glycinol is the direct precursor of glyceollins through the action of a prenyltransferase.{{cn|date=March 2023}}

Experiments show that the 6a oxygen of glycinol is derived from molecular oxygen.{{cite journal | doi = 10.1016/0031-9422(89)85020-4 | title = The 6a oxygen of the pterocarpan glycinol is derived from molecular oxygen | year = 1989 | last1 = Matthews | first1 = David E. | last2 = Plattner | first2 = Ronald D. | last3 = Vanetten | first3 = Hans D. | journal = Phytochemistry | volume = 28 | issue = 1 | pages = 113–115| bibcode = 1989PChem..28..113M | url = https://zenodo.org/record/1258250 | doi-access = free }}