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{{chembox
{{Chembox
| Watchedfields = changed
| verifiedrevid = 443408352
| verifiedrevid = 443408352
| Name = Ayanin
| Name = Ayanin
| ImageFile = Ayanin.PNG
| ImageFile = Ayanin.svg
| ImageSize = 200px
| ImageName = Chemical structure of ayanin
| ImageName = Chemical structure of ayanin
| IUPACName = 5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,7-dimethoxychromen-4-one
| IUPACName = 3′,5-Dihydroxy-3,4′,7-trimethoxyflavone
| SystematicName = 5-Hydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,7-dimethoxy-4''H''-1-benzopyran-4-one
| OtherNames = 3,7,4'-Tri-O-methylquercetin<br>3,7,4'-trimethylquercetin<br>5,3'-dihydroxy-3,7,4'-trimethoxyflavone
| OtherNames = {{ubl|3,7,4'-Tri-''O''-methylquercetin|3,7,4'-Trimethylquercetin}}
|Section1= {{Chembox Identifiers
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4444274
| ChemSpiderID = 4444274
Line 20: Line 21:
| StdInChIKey = KPCRYSMUMBNTCK-UHFFFAOYSA-N
| StdInChIKey = KPCRYSMUMBNTCK-UHFFFAOYSA-N
| CASNo = 572-32-7
| CASNo = 572-32-7
| CASNo_Ref =
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| CASOther =
| UNII = YA465UF3LK
| CASNoOther =
| PubChem = 5280682
| PubChem = 5280682
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 27825
| ChEBI = 27825
| SMILES = COC1=C(C=C(C=C1)C2=C(C(=O)C3=C(C=C(C=C3O2)OC)O)OC)O
| SMILES = COC1=C(C=C(C=C1)C2=C(C(=O)C3=C(C=C(C=C3O2)OC)O)OC)O
| InChI =
| MeSHName =
| MeSHName =
}}
}}
|Section2= {{Chembox Properties
|Section2={{Chembox Properties
| C=18 | H=16 | O=7
| Formula = C<sub>18</sub>H<sub>16</sub>O<sub>7</sub>
| MolarMass = 344.31 g/mol
| ExactMass = 344.089603 u
| Appearance =
| Appearance =
| Density =
| Density = 1.454 g/mL
| MeltingPtC =
| MeltingPt = <!-- °C -->
| BoilingPtC =
| BoilingPt = <!-- °C -->
| Solubility =
| Solubility =
⚫
}}
}}
}}
⚫
}}
⚫
'''Ayanin''' is a [[O-methylated flavonol]], a type of flavonoid. It is the 3,7,4'-tri-O-methylation of [[quercetin]].


⚫
'''Ayanin''' is an [[O-methylated flavonoid|''O''-methylated flavonol]], a type of flavonoid. It is the 3,7,4'-tri-''O''-methylated [[derivative (chemistry)|derivative]] of [[quercetin]].
⚫
It can be found in ''[[Croton schiedeanus]]''. It can also be synthetized<ref>[http://www3.interscience.wiley.com/journal/122301975/abstract?CRETRY=1&SRETRY=0 Partial methylation of quercetin: Direct synthesis of tamarixetin, ombuin and ayanin. Koppaka V. Rao, Jacob A. Owoyale, Journal of Heterocyclic Chemistry, Volume 13 Issue 6, Pages 1293 - 1295]</ref>.

⚫
It can be found in ''[[Croton schiedeanus]]''. It can also be synthesized.<ref>{{cite journal | doi = 10.1002/jhet.5570130629| title = Partial methylation of quercetin: Direct synthesis of tamarixetin, ombuin and ayanin| journal = Journal of Heterocyclic Chemistry| volume = 13| issue = 6| pages = 1293–1295| year = 1976| last1 = Rao| first1 = Koppaka V.| last2 = Owoyale| first2 = Jacob A.| doi-access = free}}</ref>


==Biosynthetis==
== Biosynthesis ==
The enzyme [[3,7-dimethylquercetin 4'-O-methyltransferase]] uses [[S-adenosyl methionine]] and [[5,3',4'-trihydroxy-3,7-dimethoxyflavone]] (rhamnazin) to produce [[S-adenosylhomocysteine]] and 5,3'-dihydroxy-3,7,4'-trimethoxyflavone (ayanin).
The enzyme [[3,7-dimethylquercetin 4'-O-methyltransferase]] uses [[S-Adenosyl methionine|''S''-adenosyl methionine]] and [[rhamnazin]] to produce [[S-Adenosyl-L-homocysteine|''S''-adenosylhomocysteine]] and ayanin.


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


{{flavonol}}
{{flavonol}}


[[Category:Flavonols]]
[[Category:O-methylated flavonols]]
[[Category:Phenol ethers]]


{{Natural-phenol-stub}}


{{aromatic-stub}}
[[pl:Ajanina]]

Latest revision as of 00:08, 9 November 2023

Ayanin
Chemical structure of ayanin
Names
IUPAC name
3′,5-Dihydroxy-3,4′,7-trimethoxyflavone
Systematic IUPAC name
5-Hydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,7-dimethoxy-4H-1-benzopyran-4-one
Other names
  • 3,7,4'-Tri-O-methylquercetin
  • 3,7,4'-Trimethylquercetin
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
UNII
  • InChI=1S/C18H16O7/c1-22-10-7-12(20)15-14(8-10)25-17(18(24-3)16(15)21)9-4-5-13(23-2)11(19)6-9/h4-8,19-20H,1-3H3 checkY
    Key: KPCRYSMUMBNTCK-UHFFFAOYSA-N checkY
  • InChI=1/C18H16O7/c1-22-10-7-12(20)15-14(8-10)25-17(18(24-3)16(15)21)9-4-5-13(23-2)11(19)6-9/h4-8,19-20H,1-3H3
    Key: KPCRYSMUMBNTCK-UHFFFAOYAE
  • COC1=C(C=C(C=C1)C2=C(C(=O)C3=C(C=C(C=C3O2)OC)O)OC)O
  • O=C1c3c(O/C(=C1/OC)c2ccc(OC)c(O)c2)cc(OC)cc3O
Properties
C18H16O7
Molar mass 344.319 g·mol−1
Density 1.454 g/mL
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Ayanin is an O-methylated flavonol, a type of flavonoid. It is the 3,7,4'-tri-O-methylated derivative of quercetin.

It can be found in Croton schiedeanus. It can also be synthesized.[1]

Biosynthesis[edit]

The enzyme 3,7-dimethylquercetin 4'-O-methyltransferase uses S-adenosyl methionine and rhamnazin to produce S-adenosylhomocysteine and ayanin.

References[edit]

  1. ^ Rao, Koppaka V.; Owoyale, Jacob A. (1976). "Partial methylation of quercetin: Direct synthesis of tamarixetin, ombuin and ayanin". Journal of Heterocyclic Chemistry. 13 (6): 1293–1295. doi:10.1002/jhet.5570130629.


source: https://en.wikipedia.org/w/index.php?title=Ayanin&diff=1184204851&oldid=443409641

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