Tangeretin

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

Bibliography
1. Obermeier M.T., White R.E., Yang C.S. Effects of bioflavonoids on hepatic P450 activities. Xenobiotica 1995;25:575-584.
2. R. L. Rouseff and S. V. Tlng. TANGERETIN CONTENT OF FLORIDA CITRUS PEEL AS DETERMINED BY HPLC. Florida Department of Citrus, Agriculture Research and Education Center, Proc. Fla. State Hort. Soc. 92: 1979.
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