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Tangeretin

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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
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.006.883 Edit this at Wikidata
EC Number
  • 207-570-1
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
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,1-5H3Key: ULSUXBXHSYSGDT-UHFFFAOYSA-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,1-5H3Key: ULSUXBXHSYSGDT-UHFFFAOYAG
SMILES
  • O=C2C1=C(OC)C(OC)=C(OC)C(OC)=C1OC(C3=CC=C(OC)C=C3)=C2
Properties
Chemical formula C20H20O7
Molar mass 372.37 g/mol
Density 1.244 ± 0.06 g/cm
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)
Solubility in water 0.037 g/L
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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.

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

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

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. 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.

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

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

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 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.
Flavones and their conjugates
Aglycones
Monohydroxyflavone
Dihydroxyflavones
Trihydroxyflavones
Tetrahydroxyflavones
Pentahydroxyflavones
O-methylated flavones
Glycosides
of apigenin
of baicalein
of hypolaetin
of luteolin
Acetylated
  • Artocarpetin A
  • Artoindonesianin P
    • Sulfated glycosidesTheograndin I and II
    Polymers
    Drugs
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