Tangeretin is a citrus flavonoid with a very bitter taste. It has the typical flavonoid structure and contains 5 methoxy groups making it highly lipid soluble.
Tangeretin is an inhibitor of the P450 enzyme CYP1A2 [1].
Natural Sources
Commercial tangeretin is extracted from citrus peels. Tangeretin is found in the peel (albedo) of most citrus fruits.
Tangeretin content of Florida citrus peel [2] | |||
---|---|---|---|
Tangeretin concentration (ppm) | |||
Variety | Flavedo | Albedo | Total peel |
Duncan grapefruit | 15 | 0.4 | 5.8 |
Mott grapefruit | 29.2 | 1.6 | 6.8 |
Thompson grapefruit | 19 | 4 | 7.9 |
Valencia orange | 46.8 | 3.2 | 27.4 |
Pineapple orange | 25.8 | 2.5 | 12.8 |
Parson Brown orange | 21.2 | 1.2 | 8.2 |
Temple orange | 13.1 | 1.6 | 8.8 |
King mandarin | 75.1 | 10 | 40.6 |
Dancy tangerine | — | — | 182.8 |
Eureka lemon | T | 0.06 | 0.06 |
Sweet lime | 0.89 | 0.07 | 0.51 |
Chemical Properties
Synonyms: Tangeritin
PubChem Compound ID: 68077
Molecular Weight: 372.3686 [g/mol]
Molecular Formula: C20H20O7
XLogP3-AA: 3
IUPAC Name: 5,6,7,8-tetramethoxy-2-(4-methoxyphenyl)chromen-4-one
InChI: InChI=1S/C20H20O7/c1-22-12-8-6-11(7-9-12)14-10-13(21)15-16(23-2)18(24-3)20(26-5)19(25-4)17(15)27-14/h6-10H,1-5H3
InChIKey: ULSUXBXHSYSGDT-UHFFFAOYSA-N
Canonical SMILES: COC1=CC=C(C=C1)C2=CC(=O)C3=C(O2)C(=C(C(=C3OC)OC)OC)OC