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Isorhamnetin information


Isorhamnetin
Isorhamnetin structure
Isorhamnetin 3D structure
Names
IUPAC name
3,4′,5,7-Tetrahydroxy-3′-methoxyflavone
Systematic IUPAC name
3,5,7-Trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-one
Other names
3-methylquercetin
3-Methylquercetin
Isorhamnetol
isorhamentin
isorhamnetine
iso-rhamnetin
3'-Methoxyquercetin
Identifiers
CAS Number
  • 480-19-3 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:6052 ☒N
ChEMBL
  • ChEMBL379064 ☒N
ChemSpider
  • 4444973 ☒N
ECHA InfoCard 100.006.860 Edit this at Wikidata
KEGG
  • C10084 ☒N
PubChem CID
  • 5281654
UNII
  • 07X3IB4R4Z ☒N
CompTox Dashboard (EPA)
  • DTXSID10197379 Edit this at Wikidata
InChI
  • InChI=1S/C16H12O7/c1-22-11-4-7(2-3-9(11)18)16-15(21)14(20)13-10(19)5-8(17)6-12(13)23-16/h2-6,17-19,21H,1H3 ☒N
    Key: IZQSVPBOUDKVDZ-UHFFFAOYSA-N ☒N
  • InChI=1/C16H12O7/c1-22-11-4-7(2-3-9(11)18)16-15(21)14(20)13-10(19)5-8(17)6-12(13)23-16/h2-6,17-19,21H,1H3
    Key: IZQSVPBOUDKVDZ-UHFFFAOYAD
SMILES
  • COC1=C(C=CC(=C1)C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O)O
Properties
Chemical formula
C16H12O7
Molar mass 316.26 g/mol
Melting point 307 °C (585 °F; 580 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Isorhamnetin is an O-methylated flavon-ol from the class of flavonoids. A common food source of this 3'-methoxylated derivative of quercetin and its glucoside conjugates are pungent yellow or red onions, in which it is a minor pigment, quercetin-3,4'-diglucoside and quercetin-4'-glucoside and the aglycone quercetin being the major pigments.[1] Pears, olive oil, wine and tomato sauce are rich in isorhamnetin.[2] Almond skin is a rich source of isorhamnetin-3-O-rutinoside and isorhamnetin-3-O-glucoside, in some cultivars they comprise 75% of the polyphenol content, the total of which can exceed 10 mg/100 gram almond.[3] Others sources include the spice, herbal medicinal[4] and psychoactive Mexican tarragon (Tagetes lucida), which is described as accumulating isorhamnetin and its 7-O-glucoside derivate.[5] Nopal (Opuntia ficus-indica (L.)) is also a good source of isorhamnetin, which can be extracted by supercritical fluid extraction assisted by enzymes.[6]

  1. ^ Slimestad, R; Fossen, T; Vågen, IM (December 2007). "Onions: a source of unique dietary flavonoids". J. Agric. Food Chem. 55 (25): 10067–80. doi:10.1021/jf0712503. PMID 17997520.
  2. ^ Holland, Thomas M.; Agarwal, Puja; Wang, Yamin; Leurgans, Sue E.; Bennett, David A.; Booth, Sarah L.; Morris, Martha Clare (2020-01-29). "Dietary flavonols and risk of Alzheimer dementia". Neurology. 94 (16): e1749–e1756. doi:10.1212/WNL.0000000000008981. ISSN 0028-3878. PMC 7282875. PMID 31996451.
  3. ^ PMID 25544797 PMC4276397
  4. ^ Céspedes, Carlos L. (2006). "Antifungal and Antibacterial Activities of Mexican Tarragon (Tagetes lucida)". Journal of Agricultural and Food Chemistry. 54 (10): 3521–3527. doi:10.1021/jf053071w. PMID 19127719.
  5. ^ Abdala, 1999
  6. ^ Antunes-Ricardo M, Garcia-Cayuela T, Mendiola JA, Ibañez E, Gutierrez-Uribe JA, Cano MP, Guajardo-Flores D (November 2018). "Supercritical CO2 enzyme hydrolysis as a pretreatment for the release of isorhamnetin conjugates from Opuntia ficus-indica (L.) Mill". The Journal of Supercritical Fluids. 141: 21–28. doi:10.1016/j.supflu.2017.11.030. S2CID 103893093.

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Isorhamnetin

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Isorhamnetin is an O-methylated flavon-ol from the class of flavonoids. A common food source of this 3'-methoxylated derivative of quercetin and its glucoside...

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Oenanthe javanica

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Minari-ganghoe (water dropwort rolls) The plant contains persicarin and isorhamnetin. Nanakusa-no-sekku Zhuang, X.; Lansdown, R.V. (2011). "Oenanthe javanica"...

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Parietaria officinalis

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quercetin, kaempferol and isorhamnetin, 3-sophorosides of quercetin and kaempferol and 3-neohesperosides of kaempferol and isorhamnetin. They also contain caffeoylmalic...

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Tamarind

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often be fatal. Lupanone, lupeol, catechins, epicatechin, quercetin, and isorhamnetin are present in the leaf extract. Ultra-high performance liquid chromatography...

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Gomphrena globosa

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phenolic content. Other flavanols include quercetin, kaempferol, and isorhamnetin derivatives. The major betacyanins identified in globe amaranth are gomphrenin...

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Eucalyptus globulus

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quercetin-hexoside, methylellagic acid (EA)-pentose conjugate, myricetin-rhamnoside, isorhamnetin-rhamnoside, mearnsetin, phloridzin, mearnsetin-hexoside, luteolin and...

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Onion

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Olsson, M.E.; Gustavsson, K.E. & Vågen, I.M. (2010). "Quercetin and isorhamnetin in sweet and red cultivars of onion (Allium cepa L.) at harvest, after...

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Fisetin

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Rutin

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Ginkgo biloba

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proanthocyanidins, flavonoid glycosides, such as myricetin, kaempferol, isorhamnetin, and quercetin, and the terpene trilactones ginkgolides and bilobalides...

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Flavonols

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Kaempferol 3,4′,5,7-tetrahydroxy-2-phenylchromen-4-one OH H OH H H H OH H H Isorhamnetin 3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)chromen-4-one OH H OH H...

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Quercetin

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Tagetes lucida

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contains the following compounds: Anethole Chavicol Coumarin Estragole Isorhamnetin Methyleugenol Quercetin "Tagetes lucida". Germplasm Resources Information...

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Dandelion coffee

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Esculin Scopoletin Flavonoids Apigenin-7-glucoside Luteolin-7-glucoside Isorhamnetin 3-glucoside Luteolin-7-diglucoside Quercetin-7-glucoside Quercetin Luteolin...

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Ardisia elliptica

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terpenoids bauerenol and amyrin, and the phenolic compounds syringic acid, isorhamnetin, quercetin, bergenin, 5-(Z-heptadec-4'-enyl)resorcinol and 5-pentadecylresorcinol...

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Icariin

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Mercurialis annua

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recorded. Isorhamnetin-3-rutinoside-4′-glucoside, rutin, narcissin (Isorhamnetin 3-rutinoside), quercetin-3-(2G-glucosyl)-rutinoside and isorhamnetin...

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Flavonoid

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3-hydroxy-2-phenylchromen-4-one ✓ ✗ Quercetin, Kaempferol, Myricetin, Fisetin, Galangin, Isorhamnetin, Pachypodol, Rhamnazin, Pyranoflavonols, Furanoflavonols,...

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Isoquercetin

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Quercitrin

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Redheaded pine sawfly

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caterpillars contain chemical compounds including (+)-Catechin 7-O-β-glucoside, isorhamnetin 3,7,4′-tri-O-β-glucoside, kaempferol 3,7,4′-tri-O-β-glucoside and quercetin...

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Viola tricolor

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plants contain aglycones[clarification needed] apigenin, chrysoeriol, isorhamnetin, kaempferol. V. tricolor is one of many viola plant species containing...

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Prosopis

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Prosopis species have been found to contain 5-hydroxytryptamine, apigenin, isorhamnetin-3-diglucoside, l-arabinose, quercetin, tannin, and tryptamine. The tannins...

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Troxerutin

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Hyperforin

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hypericin, pseudohypericin, hyperforin and the flavonoids quercetin and isorhamnetin following single and multiple oral dosing of a hypericum extract containing...

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List of phytochemicals in food

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fruits, asparagus, buckwheat, parsley, tomatoes, apricots, rhubarb, tea. Isorhamnetin red turnip, goldenrod, mustard leaf, ginkgo biloba, onion. Flavanones...

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Phenolic content in wine

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kaempferol, laricitrin, isorhamnetin, and syringetin. In white grapes, the main flavonol is quercetin, followed by kaempferol and isorhamnetin. The delphinidin-like...

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