Retusin (flavonol): Difference between revisions

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	{{distinguish\|retusin (isoflavone)}}		{{distinguish\|retusin (isoflavone)}}
	{{chembox		{{chembox
			\| Verifiedfields = changed
⚫	\| verifiedrevid = ~~407331260~~
			\| Watchedfields = changed
		⚫	\| verifiedrevid = 449638802
	\| Name = Retusin		\| Name = Retusin
	\| ImageFile = Retusin.svg		\| ImageFile = Retusin.svg
	\| ImageSize = 250px		\| ImageSize = 250px
	\| ImageName = Chemical structure of		\| ImageName = Chemical structure of
	\| IUPACName = ~~2-(3,4-dimethoxyphenyl)-~~5-~~hydroxy~~-3,7-~~dimethoxychromen-4-one~~		\| IUPACName = 5-Hydroxy-3,3′,4′,7-tetramethoxyflavone
			\| SystematicName = 2-(3,4-Dimethoxyphenyl)-5-hydroxy-3,7-dimethoxy-4''H''-1-benzopyran-4-one
	\| OtherNames = Quercetin tetramethylether<br>Quercetin-3,7,3',4'-tetramethyl ether<br>Tetramethylquercetin<br>Retusine		\| OtherNames = Quercetin tetramethylether<br>Quercetin-3,7,3',4'-tetramethyl ether<br>Tetramethylquercetin<br>Retusine
	\|Section1= {{Chembox Identifiers		\|Section1={{Chembox Identifiers
			\| CASNo_Ref = {{cascite\|correct\|??}}
	\| CASNo = 1245-15-4		\| CASNo = 1245-15-4
	\| ~~CASNo_Ref~~ =		\| CASNoOther =
			\| UNII_Ref = {{fdacite\|correct\|FDA}}
	\| CASOther =
			\| UNII = M8591903SD
	\| PubChem = 5352005		\| PubChem = 5352005
	\| SMILES = COC1=C(C=C(C=C1)C2=C(C(=O)C3=C(C=C(C=C3O2)OC)O)OC)OC		\| SMILES = COC1=C(C=C(C=C1)C2=C(C(=O)C3=C(C=C(C=C3O2)OC)O)OC)OC
	\| ~~InChI~~ =		\| EINECS = 214-991-4
			\| ChemSpiderID_Ref = {{chemspidercite\|changed\|chemspider}}
	\| MeSHName =
			\| ChemSpiderID = 4508983
			\| InChI = 1/C19H18O7/c1-22-11-8-12(20)16-15(9-11)26-18(19(25-4)17(16)21)10-5-6-13(23-2)14(7-10)24-3/h5-9,20H,1-4H3
			\| InChIKey = HHGPYJLEJGNWJA-UHFFFAOYAJ
			\| StdInChI_Ref = {{stdinchicite\|changed\|chemspider}}
			\| StdInChI = 1S/C19H18O7/c1-22-11-8-12(20)16-15(9-11)26-18(19(25-4)17(16)21)10-5-6-13(23-2)14(7-10)24-3/h5-9,20H,1-4H3
			\| StdInChIKey_Ref = {{stdinchicite\|changed\|chemspider}}
			\| StdInChIKey = HHGPYJLEJGNWJA-UHFFFAOYSA-N
			\| ChEBI = 144861
			\| ChEMBL_Ref = {{ebicite\|changed\|EBI}}
			\| ChEMBL = 77966
	}}		}}
	\|Section2= {{Chembox Properties		\|Section2={{Chembox Properties
	\| Formula = C<sub>19</sub>H<sub>18</sub>O<sub>7</sub>		\| Formula = C<sub>19</sub>H<sub>18</sub>O<sub>7</sub>
	\| MolarMass = 358.34 g/mol		\| MolarMass = 358.34 g/mol
	\| ExactMass = 358.105253 u
	\| Appearance =		\| Appearance =
	\| Density =		\| Density =
	\| MeltingPt = ~~<!-- °C -->~~		\| MeltingPt =
	\| BoilingPt = ~~<!-- °C -->~~		\| BoilingPt =
	\| Solubility =		\| Solubility =
	}}		}}
	}}		}}
	'''Retusin''' is a ], a type of flavonoid. It can be found in '']''<ref></ref> and in '']''.<ref></ref>		'''Retusin''' is an ], a type of flavonoid. It can be found in '']''<ref>{{cite journal \| url=http://www.sciencedirect.com/science/article/pii/S030519780800063X \| doi=10.1016/j.bse.2008.05.003 \| title=Exudate flavones and flavanones in Origanum species and their interspecific variation \| date=2008 \| last1=Skoula \| first1=Melpomene \| last2=Grayer \| first2=Renée J. \| last3=Kite \| first3=Geoffrey C. \| last4=Veitch \| first4=Nigel C. \| journal=Biochemical Systematics and Ecology \| volume=36 \| issue=8 \| pages=646–654 \| bibcode=2008BioSE..36..646S }}</ref> and in '']''.<ref></ref>

	==References==		== References ==
	{{reflist}}		{{reflist}}

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	{{flavonol}}		{{flavonol}}

	]		]
	]

			{{aromatic-stub}}

	{{Natural-phenol-stub}}

Latest revision as of 18:38, 8 September 2024

Not to be confused with retusin (isoflavone).

Retusin
Names

IUPAC name 5-Hydroxy-3,3′,4′,7-tetramethoxyflavone
Systematic IUPAC name 2-(3,4-Dimethoxyphenyl)-5-hydroxy-3,7-dimethoxy-4H-1-benzopyran-4-one
Other names Quercetin tetramethylether Quercetin-3,7,3',4'-tetramethyl ether Tetramethylquercetin Retusine
Identifiers
CAS Number	1245-15-4
3D model (JSmol)	Interactive image
ChEBI	CHEBI:144861
ChEMBL	ChEMBL77966
ChemSpider	4508983
ECHA InfoCard	100.013.629
EC Number	214-991-4
PubChem CID	5352005
UNII	M8591903SD
CompTox Dashboard (EPA)	DTXSID60924839
InChI InChI=1S/C19H18O7/c1-22-11-8-12(20)16-15(9-11)26-18(19(25-4)17(16)21)10-5-6-13(23-2)14(7-10)24-3/h5-9,20H,1-4H3Key: HHGPYJLEJGNWJA-UHFFFAOYSA-N InChI=1/C19H18O7/c1-22-11-8-12(20)16-15(9-11)26-18(19(25-4)17(16)21)10-5-6-13(23-2)14(7-10)24-3/h5-9,20H,1-4H3Key: HHGPYJLEJGNWJA-UHFFFAOYAJ
SMILES COC1=C(C=C(C=C1)C2=C(C(=O)C3=C(C=C(C=C3O2)OC)O)OC)OC
Properties
Chemical formula	C₁₉H₁₈O₇
Molar mass	358.34 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). N verify (what is ?) Infobox references

Chemical compound

Retusin is an O-methylated flavonol, a type of flavonoid. It can be found in Origanum vulgare and in Ariocarpus retusus.

References

Skoula, Melpomene; Grayer, Renée J.; Kite, Geoffrey C.; Veitch, Nigel C. (2008). "Exudate flavones and flavanones in Origanum species and their interspecific variation". Biochemical Systematics and Ecology. 36 (8): 646–654. Bibcode:2008BioSE..36..646S. doi:10.1016/j.bse.2008.05.003.
Retusin (Ariocarpus) on kanaya.naist.jp

Flavonols and their conjugates

Backbone

Aglycones	3-Hydroxyflavone (synthetic) and derivatives

Flavonols

Aglycones

Conjugates

Glycosides of herbacetin

Glycosides of kaempferol

Afzelin (Kaempferol 3-rhamnoside)
Astragalin (kaempferol 3-O-glucoside)
Kaempferitrin (kaempferol 3,7-dirhamnoside)
Juglanin (Kaempferol 3-O-arabinoside)
Kaempferol 3-alpha-L-arabinopyranoside
Kaempferol 3-alpha-D-arabinopyranoside
Kaempferol 7-alpha-L-arabinoside
Kaempferol 7-O-glucoside
Kaempferol 3-lathyroside
Kaempferol 4'-rhamnoside
Kaempferol 5-rhamnoside
Kaempferol 7-rhamnoside
Kaempferol 7-O-alpha-L-rhamnofuranoside
Kaempferol 3-xyloside
Kaempferol 7-xyloside
Robinin (kaempferol-3-O-robinoside-7-O-rhamnoside)
Kaempferol 3-O-rutinoside
Sophoraflavonoloside (Kaempferol 3-O-sophoroside)
Trifolin (Kaempferol 3-O-beta-D-galactoside)

Glycosides of myricetin

Conjugates of quercetin

Sulfates

Glycosides

Avicularin (quercetin-3-O-α-L-arabinofuranoside)
CTN-986
Guaijaverin (quercetin 3-O-arabinoside)
Heliosin (quercetin 3-digalactoside)
Hyperoside (quercetin 3-O-galactoside)
Isoquercetin (quercetin 3-O-glucoside)
Miquelianin (quercetin 3-O-glucuronide)
Quercetin 3,4'-diglucoside
Quercetin-3-sophorodide
Quercitrin (quercetin 3-O-rhamnoside)
Rutin (quercetin rutinoside)
Reinutrin (quercetin-3-D-xyloside)
Spiraeoside (quercetin 4'-O-glucoside)
Taxillusin (galloylated 3-O-glucoside of quercetin°

O-Methylated flavonols

Aglycones

Glycosides

of isorhamnetin	Narcissin (Isorhamnetin 3-O-rutinoside) Isorhamnetin 3-O-glucoside Tamarixetin 7-rutinoside
other	Azalein (Azaleatin 3-O-α-L-rhamnoside) Centaurein (Centaureidin 7-O-glucoside) Eupalin (Eupalitin 3-0-rhamnoside) Eupatolin (Eupatolitin 3-O-rhamnoside) Jacein (Jaceidin 7-O-glucoside) Patulitrin (Patuletin 7-O-glucoside Xanthorhamnin (Rhamnetin glycoside)

Derivative flavonols

Aglycones	Noricaritin Dihydronoricaritin
Glycosides	Amurensin Icariin Phelloside Dihydrophelloside Rutin S

Pyranoflavonols

Aglycones	Karanjachromene

Furanoflavonols

Aglycones	Karanjin
Glycosides	Pongamoside A, B and C

Semisynthetic

Glycosides	Hydroxyethylrutosides Monoxerutin Troxerutin

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