Tangeretin

Tangeretin is an O-polymethoxylated flavone that is found in tangerine and other citrus peels. Tangeretin strengthens the cell wall and acts as a plant's defensive mechanism against disease-causing pathogens.[2]

Tangeretin (Tangeritin)
Skeletal formula
Ball-and-stick model
Names
IUPAC name
4′,5,6,7,8-Pentamethoxyflavone
Systematic IUPAC name
5,6,7,8-Tetramethoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.006.883
EC Number
  • 207-570-1
KEGG
UNII
  • 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 ☒N
    Key: ULSUXBXHSYSGDT-UHFFFAOYSA-N ☒N
  • InChI=1/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
    Key: ULSUXBXHSYSGDT-UHFFFAOYAG
  • O=C2C1=C(OC)C(OC)=C(OC)C(OC)=C1OC(C3=CC=C(OC)C=C3)=C2
Properties
C20H20O7
Molar mass 372.37 g/mol
Density 1.244 ± 0.06 g/cm3[1]
Melting point 155 to 156 °C (311 to 313 °F; 428 to 429 K)
Boiling point 565.3 ± 50.0 °C (1,049.5 ± 90.0 °F; 838.4 ± 50.0 K)[1]
0.037 g/L[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

It has also been used as a marker compound to detect contamination in citrus juices.[2]

The following is a list of methods used to extract tangeretin from citrus peels:

  • column chromatography
  • preparative-high performance liquid chromatography
  • super critical fluid chromatography
  • high speed counter current chromatography
  • a combination of vacuum flash silica gel chromatography and flash C8 column chromatography
  • flash chromatography
  • isolation using ionic liquids and a cycle of centrifugation and decantation[3]

The low solubility of Tangeretin is one of the main reasons for the low bioavailability of Tangeretin (and other flavonoids in general), and has been reported as a major challenge when using the compound in laboratory procedures.[4] However, methods for tangeretin extraction are currently being tested to maximize efficiency and percent yields as its uses in treatment of cancer and other diseases are becoming better understood.[2]

Tangeretin is commercially available as a dietary supplement. Tangeretin has also demonstrated beneficial applications in other pharmaceutical, nutraceutical, and cosmetic processes.[4]

Tangeretin can be found as various synonyms throughout literature and research, including Tangeritin and 5,6,7,8,4’-pentamethoxyflavone (VIII).[3]

References
  1. SciFinder.com (accessed Nov. 6, 2012). Tangeretin (481-53-8).
  2. Uckoo, RM; et al. Sep. Purif. Technol. 2011.
  3. Mizuno, H.; Yoshikawa, H.; Usuki, T. Extraction of Nobiletin and Tangeretin From Peels of Shekwasha and Ponkan Using [C2mim][(MeO)(H)PO2] and Centrifugation. Natural Product Communications 2019, 14, 1-6.
  4. Panche, A. N.; Diwan, A. D.; Chandra, S. R. Flavonoids: an overview. Journal of Nutritional Science. 2016, 5, 47.
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