Structure via PubChem · Public domain (PubChem)
isorhamnetin
Sign in to saveAlso known as 3,5,7,4'-tetrahydroxy-3'-methoxyflavone, 3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-benzopyran-4-one, quercetin 3'-methyl ether, 3-methylquercetin, isorhamnetol, 3,4',5,7-tetrahydroxy-3'-methoxy-Flavone, 3'-methoxyquercetin, 3-methylquercetine
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. Pears, olive oil, wine and tomato sauce are rich in isorhamnetin. 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/
Chemical data
- Formula
- C16H12O7
- Molecular weight
- 316.26 g/mol
- IUPAC name
- 3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)chromen-4-one
- SMILES
- COC1=C(C=CC(=C1)C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O)O
- InChIKey
- IZQSVPBOUDKVDZ-UHFFFAOYSA-N
- XLogP
- 1.9
- Polar surface area
- 116 Ų
- H-bond donors
- 4
- H-bond acceptors
- 7
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Subclass of
- flavone
- Mass
- 316.058303
Show 4 more facts
- chemical formula
- C₁₆H₁₂O₇
- canonical SMILES
- COC1=C(C=CC(=C1)C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O)O
- found in taxon
- Trigonella foenum-graecum
- has characteristic
- bitterness
via Wikidata · CC0
~2 min read
Encyclopedic overview
5 sectionsContents
- Metabolism
- Glycosides
- See also
- References
- External links
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. Pears, olive oil, wine and tomato sauce are rich in isorhamnetin. 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. Others sources include the spice, herbal medicinal and psychoactive Mexican tarragon (Tagetes lucida), which is described as accumulating isorhamnetin and its 7-O-glucoside derivate. Nopal (Opuntia ficus-indica (L.)) is also a good source of isorhamnetin, which can be extracted by supercritical fluid extraction assisted by enzymes.
==Metabolism== The enzyme quercetin 3-O-methyltransferase uses S-adenosyl methionine and quercetin to produce S-adenosylhomocysteine and isorhamnetin.
Excerpted from Wikipedia’s “isorhamnetin” article, available under the CC BY-SA 4.0 licence.