Isorhamnetin
Isorhamnetin
 |
| Names |
| IUPAC name
3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)chromen-4-one |
| Other names
3-methylquercetin
3-Methylquercetin
Isorhamnetol
isorhamentin
isorhamnetine
iso-rhamnetin
3'-Methoxyquercetin |
| Identifiers |
| |
480-19-3  Y |
| ChEBI |
CHEBI:6052  N |
| ChEMBL |
ChEMBL379064 N |
| ChemSpider |
4444973 N |
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 NKey: IZQSVPBOUDKVDZ-UHFFFAOYSA-N NInChI=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
|
| Jmol-3D images |
Image |
| PubChem |
5281654 |
COC1=C(C=CC(=C1)C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O)O
|
| UNII |
73WRA8Z8M8 N |
| Properties |
| |
C16H12O7 |
| Molar mass |
316.26 g/mol |
| Melting point |
307 °C (585 °F; 580 K) |
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa) |
| N verify (what is: Y/N?) |
| Infobox references |
|
|
Isorhamnetin is an O-methylated flavonol, a type of flavonoid. It can be found in Tagetes lucida,[1] a psychedelic plant from Mexico and Central America.
Metabolism
The enzyme quercetin 3-O-methyltransferase uses S-adenosyl methionine and quercetin to produce S-adenosylhomocysteine and isorhamnetin.
The enzyme 3-methylquercetin 7-O-methyltransferase uses S-adenosyl methionine and 5,7,3',4'-tetrahydroxy-3-methoxyflavone (isorhamnetin) to produce S-adenosylhomocysteine and 5,3',4'-trihydroxy-3,7-dimethoxyflavone (rhamnazin).
Glycosides
- Isorhamnetin-3-O-rutinoside-7-O-glucoside
- Isorhamnetin-3-O-rutinoside-4'-O-glucoside
- Narcissin (Isorhamnetin-3-O-rutinoside)
See also
References
- ↑ Bohm, Bruce A.; Tod F. Stuessy (2007). Flavonoids of the sunflower family (Asteraceae). Springer. p. 597. ISBN 978-3-211-83479-4.
External links
See also
Flavonols and their conjugates |
|---|
| | Backbone | |
|---|
| | Flavonols | Aglycones | |
|---|
| Conjugates | | |
|---|
| |
- 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)
|
|---|
| | |
|---|
| | |
|---|
|
|---|
|
|---|
| | 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 | |
|---|
|
|---|
| | Pyranoflavonols | |
|---|
| | Furanoflavonols | |
|---|
| | Semisynthetic | |
|---|
|