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{{chembox {{chembox
| Watchedfields = changed
| verifiedrevid = 401004005 | verifiedrevid = 424693354
| name = Fustin
| ImageFile = Fustin.svg | Name = Fustin
| ImageFile = Fustin.svg
| ImageSize = 250px | ImageSize = 200px
| IUPACName = 2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-2,3-dihydrochromen-4-one | IUPACName = (2''R'',3''R'')-3,3′,4′,7-Tetrahydroxyflavan-4-one
| SystematicName = (2''R'',3''R'')-2-(3,4-Dihydroxyphenyl)-3,7-dihydroxy-2,3-dihydro-4''H''-1-benzopyran-4-one
| OtherNames = Dihydrofisetin<br>Tetrahydroxyflavanone<br>3,7,3',4'-Tetrahydroxyflavanone<br>2,3-Dihydrofisetin<br>3′,4′,7-trihydroxyflavanol | OtherNames = 2,3-Dihydrofisetin<br>3,7,3',4'-Tetrahydroxyflavanone<br>2,3-Dihydrofisetin<br>3′,4′,7-Trihydroxyflavanol
| Section1= {{Chembox Identifiers |Section1={{Chembox Identifiers
⚫ | CASNo = 20725-03-5
| CASNo_Ref = {{cascite|correct|??}}
⚫ | PubChem = 5317435
⚫ | CASNo = 20725-03-5
⚫ | SMILES = C1=CC(=C(C=C1C2C(C(=O)C3=C(O2)C=C(C=C3)O)O)O)O
| ChEBI = 5202
| ChEMBL = 470267
| ChemSpiderID = 4476304
| EINECS = 243-989-6
| KEGG = C01378
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 4994C1X19A
⚫ | PubChem = 5317435
| StdInChI=1S/C15H12O6/c16-8-2-3-9-12(6-8)21-15(14(20)13(9)19)7-1-4-10(17)11(18)5-7/h1-6,14-18,20H/t14-,15+/m0/s1
| StdInChIKey = FNUPUYFWZXZMIE-LSDHHAIUSA-N
⚫ | SMILES = C1=CC(=C(C=C12(C(=O)C3=C(O2)C=C(C=C3)O)O)O)O
}} }}
| Section2= {{Chembox Properties |Section2={{Chembox Properties
| C=15|H=12|O=6
| Formula=C<sub>15</sub>H<sub>12</sub>O<sub>6</sub>
| Appearance =
| MolarMass = 288.25 g/mol
| Density =
| ExactMass = 288.063388
| Appearance = | MeltingPt =
| Density = | BoilingPt =
| MeltingPt = | Solubility =
| BoilingPt =
| Solubility =
}} }}
| Section3= {{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards = | MainHazards =
| FlashPt = | FlashPt =
| Autoignition = | AutoignitionPt =
}} }}
}} }}
'''Fustin''' is a ], a type of flavonoid. It can be found in ] (''Cotinus coggygria'')<ref></ref> and in the lacquer tree<ref name="Park"></ref> ('']'', aka ''Rhus verniciflua'').


'''Fustin''', sometimes called "dihydrofisetin", is a ], a type of flavonoid. It can be found in ] (''Cotinus coggygria'')<ref>{{cite journal | doi = 10.1007/s00216-009-2767-z| pmid = 19352635| title = Phytochemical analysis of young fustic (Cotinus coggygria heartwood) and identification of isolated colourants in historical textiles| journal = Analytical and Bioanalytical Chemistry| volume = 394| issue = 3| pages = 871| year = 2009| last1 = Valianou| first1 = Lemonia| last2 = Stathopoulou| first2 = Konstantina| last3 = Karapanagiotis| first3 = Ioannis| last4 = Magiatis| first4 = Prokopios| last5 = Pavlidou| first5 = Eleni| last6 = Skaltsounis| first6 = Alexios-Leandros| last7 = Chryssoulakis| first7 = Yannis| s2cid = 22188491}}</ref> and in the lacquer tree ('']'').<ref name="Park">{{cite journal | doi = 10.1038/emm.2007.35| title = Protective effects of fustin, a flavonoid from Rhus verniciflua Stokes, on 6-hydroxydopamine-induced neuronal cell death| journal = Experimental & Molecular Medicine| volume = 39| issue = 3| pages = 316| year = 2007| last1 = Park| first1 = Byung Chul| last2 = Lee| first2 = Yong Soo| last3 = Park| first3 = Hee-Juhn| last4 = Kwak| first4 = Mi-Kyoung| last5 = Yoo| first5 = Bong Kyu| last6 = Kim| first6 = Joo Young| last7 = Kim| first7 = Jung-Ae| pmid = 17603285| doi-access = free}}</ref>
⚫ Fustin shows protective effects on 6-hydroxydopamine-induced neuronal cell death<ref name="Park"/>.


⚫ Fustin shows protective effects on 6-hydroxydopamine-induced neuronal cell death.<ref name="Park"/>
Fustin is also known as "dihydrofisetin"; see ].


Unlike ], fustin has no double bond in the C-ring. This makes fustin a ], with two ]s and four ]s.
Fustin possesses stereoisomers : (-)-Fustin and (+)-Fustin.


==References== ==References==

Latest revision as of 23:32, 1 May 2023

Fustin
Names
IUPAC name (2R,3R)-3,3′,4′,7-Tetrahydroxyflavan-4-one
Systematic IUPAC name (2R,3R)-2-(3,4-Dihydroxyphenyl)-3,7-dihydroxy-2,3-dihydro-4H-1-benzopyran-4-one
Other names 2,3-Dihydrofisetin
3,7,3',4'-Tetrahydroxyflavanone
2,3-Dihydrofisetin
3′,4′,7-Trihydroxyflavanol
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.039.975 Edit this at Wikidata
EC Number
  • 243-989-6
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C15H12O6/c16-8-2-3-9-12(6-8)21-15(14(20)13(9)19)7-1-4-10(17)11(18)5-7/h1-6,14-18,20H/t14-,15+/m0/s1Key: FNUPUYFWZXZMIE-LSDHHAIUSA-N
SMILES
  • C1=CC(=C(C=C12(C(=O)C3=C(O2)C=C(C=C3)O)O)O)O
Properties
Chemical formula C15H12O6
Molar mass 288.255 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Fustin, sometimes called "dihydrofisetin", is a flavanonol, a type of flavonoid. It can be found in young fustic (Cotinus coggygria) and in the lacquer tree (Toxicodendron vernicifluum).

Fustin shows protective effects on 6-hydroxydopamine-induced neuronal cell death.

Unlike fisetin, fustin has no double bond in the C-ring. This makes fustin a flavan, with two stereocenters and four stereoisomers.

References

  1. Valianou, Lemonia; Stathopoulou, Konstantina; Karapanagiotis, Ioannis; Magiatis, Prokopios; Pavlidou, Eleni; Skaltsounis, Alexios-Leandros; Chryssoulakis, Yannis (2009). "Phytochemical analysis of young fustic (Cotinus coggygria heartwood) and identification of isolated colourants in historical textiles". Analytical and Bioanalytical Chemistry. 394 (3): 871. doi:10.1007/s00216-009-2767-z. PMID 19352635. S2CID 22188491.
  2. ^ Park, Byung Chul; Lee, Yong Soo; Park, Hee-Juhn; Kwak, Mi-Kyoung; Yoo, Bong Kyu; Kim, Joo Young; Kim, Jung-Ae (2007). "Protective effects of fustin, a flavonoid from Rhus verniciflua Stokes, on 6-hydroxydopamine-induced neuronal cell death". Experimental & Molecular Medicine. 39 (3): 316. doi:10.1038/emm.2007.35. PMID 17603285.
Flavanonols and their glycosides
3-Hydroxyflavanones:
O-methylated flavanonols
dihydroflavonol 3-O-glycosides
Glycosides
Acetylated glycosides
Categories: