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词条 Glycinol (pterocarpan)
释义

  1. References

{{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
| IUPACName = 6H-[1]benzofuro[3,2-c]chromene-3,6a(11aH),9-triol
| OtherNames =
|Section1={{Chembox Identifiers
| CASNo =
| CASNo_Ref = {{cascite|correct|??}}=
| CASNoOther =
| PubChem = 129648
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 114790
| 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 =
| RPhrases =
| SPhrases =
}}
}}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. ^{{cite journal | doi = 10.1124/jpet.109.160382 | title = Glyceollin I, a Novel Antiestrogenic Phytoalexin Isolated from Activated Soy | year = 2009 | last1 = Zimmermann | first1 = M. C. | last2 = Tilghman | first2 = S. L. | last3 = Boue | first3 = S. M. | last4 = Salvo | first4 = V. A. | last5 = Elliott | first5 = S. | last6 = Williams | first6 = K. Y. | last7 = Skripnikova | first7 = E. V. | last8 = Ashe | first8 = H. | last9 = Payton-Stewart | first9 = F. | last10 = Vanhoy-Rhodes | first10 = L. | last11 = Fonseca | first11 = J. P. | last12 = Corbitt | first12 = C. | last13 = Collins-Burow | first13 = B. M. | last14 = Howell | first14 = M. H. | last15 = Lacey | first15 = M. | last16 = Shih | first16 = B. Y. | last17 = Carter-Wientjes | first17 = C. | last18 = Cleveland | first18 = T. E. | last19 = McLachlan | first19 = J. A. | last20 = Wiese | first20 = T. E. | last21 = Beckman | first21 = B. S. | last22 = Burow | first22 = M. E. | journal = Journal of Pharmacology and Experimental Therapeutics | volume = 332 | pages = 35–45 | pmid = 19797619 | issue = 1 | pmc = 2802480| display-authors = 8 }}
2. ^{{cite journal | url = http://library.wur.nl/WebQuery/wurpubs/lang/348057 | title = Isolation and identification of glycinol from Glycine max L. Merri |author1=Qi Y. |author2=Moco S.I.A. |author3=Boeren S. |author4=Vos C.H. de |author5=Bovy A.G. | journal = Chinese Journal of Chromatography | volume = 23 | year = 2005 | pages = 353–357 | pmid = 16250441 | issue = 4}}
3. ^{{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}}
4. ^{{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 | pages = 113}}
{{Pterocarpan}}{{natural-phenol-stub}}

2 : Pterocarpans|Phytoalexins

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