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Revision as of 14:18, 17 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 477352029 of page Astilbin for the Chem/Drugbox validation project (updated: 'CASNo').  Latest revision as of 18:56, 31 January 2024 edit Donotforgetmycode (talk | contribs)19 editsm Natural occurrences: Corrected capitalization of "In food" 
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
{{chembox {{chembox
| Verifiedfields = changed | Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 460313836 | verifiedrevid = 477368956
| Name = Astilbin
| ImageFile = Astilbin.svg | Name = Astilbin
| ImageFile = Astilbin.svg
| ImageSize = 250px | ImageSize = 250px
| IUPACName = (2''R'',3''R'')-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-oxy-2,3-dihydrochromen-4-one | IUPACName = (2''R'',3''R'')-3′,4′,5,7-Tetrahydroxy-3-(α-<small>L</small>-rhamnopyranosyloxy)flavan-4-one
| SystematicName = (2''R'',3''R'')-2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-3-{oxy}-2,3-dihydro-4''H''-1-benzopyran-4-one
| OtherNames = Isoastilbin<br>Neoastilbin<br>Neoisoastilbin<br>] 3-O-]<br>Taxifolin 3-rhamnoside<br>(2''R''-trans)-3-((6-Deoxy-alpha-L-mannopyranosyl)oxy)-2-(3,4- dihydroxyphenyl)-2,3-dihydro-5,7-dihydroxy-4H-1-benzopyran-4-one<ref name="anwabio">http://anwabio.com/asti.htm</ref> | OtherNames = Isoastilbin<br>Neoastilbin<br>Neoisoastilbin<br>] 3-O-]<br>Taxifolin 3-rhamnoside<br>(2''R''-trans)-3-((6-Deoxy-alpha-L-mannopyranosyl)oxy)-2-(3,4- dihydroxyphenyl)-2,3-dihydro-5,7-dihydroxy-4H-1-benzopyran-4-one<ref name="anwabio">http://anwabio.com/asti.htm{{dead link|date=October 2016 |bot=InternetArchiveBot |fix-attempted=yes }}</ref>
| Section1= {{Chembox Identifiers |Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}} | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = <!-- blanked - oldvalue: 54141-72-9 --> | CASNo = 54141-72-9
| ChEMBL_Ref = {{ebicite|changed|EBI}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = KA92CW3M68
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 486017 | ChEMBL = 486017
| ChEBI_Ref = {{ebicite|changed|EBI}} | ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 38200 | ChEBI = 38200
| PubChem = 119258 | PubChem = 119258
| KEGG = C17449
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 106533 | ChemSpiderID = 106533
| SMILES = O=C3c4c(O)cc(O)cc4O(c1ccc(O)c(O)c1)3O2O((O)(O)2O)C | SMILES = O=C3c4c(O)cc(O)cc4O(c1ccc(O)c(O)c1)3O2O((O)(O)2O)C
| InChI = 1/C21H22O11/c1-7-15(26)17(28)18(29)21(30-7)32-20-16(27)14-12(25)5-9(22)6-13(14)31-19(20)8-2-3-10(23)11(24)4-8/h2-7,15,17-26,28-29H,1H3/t7-,15-,17+,18+,19+,20-,21-/m0/s1 | InChI = 1/C21H22O11/c1-7-15(26)17(28)18(29)21(30-7)32-20-16(27)14-12(25)5-9(22)6-13(14)31-19(20)8-2-3-10(23)11(24)4-8/h2-7,15,17-26,28-29H,1H3/t7-,15-,17+,18+,19+,20-,21-/m0/s1
| InChIKey = ZROGCCBNZBKLEL-MPRHSVQHBV | InChIKey = ZROGCCBNZBKLEL-MPRHSVQHBV
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C21H22O11/c1-7-15(26)17(28)18(29)21(30-7)32-20-16(27)14-12(25)5-9(22)6-13(14)31-19(20)8-2-3-10(23)11(24)4-8/h2-7,15,17-26,28-29H,1H3/t7-,15-,17+,18+,19+,20-,21-/m0/s1 | StdInChI = 1S/C21H22O11/c1-7-15(26)17(28)18(29)21(30-7)32-20-16(27)14-12(25)5-9(22)6-13(14)31-19(20)8-2-3-10(23)11(24)4-8/h2-7,15,17-26,28-29H,1H3/t7-,15-,17+,18+,19+,20-,21-/m0/s1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = ZROGCCBNZBKLEL-MPRHSVQHSA-N | StdInChIKey = ZROGCCBNZBKLEL-MPRHSVQHSA-N
}} }}
|Section2= {{Chembox Properties |Section2={{Chembox Properties
| Formula = C<sub>21</sub>H<sub>22</sub>O<sub>11</sub> | Formula = C<sub>21</sub>H<sub>22</sub>O<sub>11</sub>
| MolarMass = 450.39 g/mol | MolarMass = 450.39 g/mol
| Appearance = brown powder<ref name="anwabio"/>
| ExactMass = 450.116212 u
| Density=
| Appearance = brown powder<ref name="anwabio"/>
| Density= | MeltingPt=
| MeltingPt= | BoilingPt=
| Solubility =
| BoilingPt=
| Solubility =
}} }}
|Section3= {{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards= | MainHazards=
| FlashPt= | FlashPt=
| AutoignitionPt =
| Autoignition=
}} }}
}} }}
'''Astilbin''' is a ], a type of flavonoid. Astilbin is the (2R-trans)-isomer; neoisoastilbin is the (2S-cis)-isomer and isoastilbin is the (2R-cis)-isomer.<ref name="PubChem"></ref>

== Natural occurrences ==
Astilbin can be found in ] (''Hypericum perforatum'', Clusiaceae, subfamily Hypericoideae, formerly often considered a full family Hypericaceae), in '']''<ref name="Batista"></ref> (Fava d'anta, Fabaceae), in the leaves of '']'' (Hypericaceae),<ref name="Moulari">, </ref> in the rhizome of '']'',<ref name="Yoshiyuki"></ref> in the root of '']''<ref name="Ohmori"></ref>(Saxifragaceae), in the rhizome of '']''<ref name="Jianming">{{Cite web |url=http://www.clinchem.org/cgi/content/abstract/clinchem.2006.077297v1 |title=Identification of a New Metabolite of Astilbin, 3'-O-Methylastilbin, and Its Immunosuppressive Activity against Contact Dermatitis, Jianming Guo, Feng Qian, Jianxin Li, Qiang Xu, Ting Chen, 2006 |access-date=2009-08-30 |archive-url=https://web.archive.org/web/20110607122209/http://www.clinchem.org/cgi/content/abstract/clinchem.2006.077297v1 |archive-date=2011-06-07 |url-status=dead }}</ref> (Chinaroot, Smilacaceae) and in the bark of '']''.<ref></ref>

; In food
It can be isolated from ] processed from '']'' (huang-qui).<ref name="PubChem"/> It is also present in certain wines.<ref>Levels of Stilbene Oligomers and Astilbin in French Varietal Wines and in Grapes during Noble Rot Development, Nicolas Landrault, Fabienne Larronde, Jean-Claude Delaunay, Chantal Castagnino, Joseph Vercauteren, Jean-Michel Merillon, Francis Gasc, Gérard Cros and Pierre-Louis Teissedre, J. Agric. Food Chem., 2002, 50 (7), pages 2046–2052, {{doi|10.1021/jf010794g}}</ref>

== Uses ==
Astilbin can act as an insecticide against '']'' and '']''.<ref name="Batista"/> It shows ''in vitro'' antibacterial activity<ref name="Moulari"/> and activity on burn wound healing.<ref name="Yoshiyuki"/> Astilbin is used in ].<ref name="Ohmori"/>

<!--==Metabolism==
The enzyme [[ -->

== Related compounds ==
] shows an immunosuppressive activity against ].<ref name="Jianming"/>

<!-- ===Glycosides=== -->

== References ==
{{reflist}}

{{Flavanonol}}

]
]