Tangeretin

Tangeretin (Tangeritin)
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	481-53-8 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:9400 ;
ChemSpider	61389 ;
ECHA InfoCard	100.006.883
EC Number	207-570-1;
KEGG	C10190 ;
PubChem CID	68077;
UNII	I4TLA1DLX6 ;
CompTox Dashboard (EPA)	DTXSID30197417 ;
	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 Key: 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,1-5H3 Key: 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/cm3
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 [77 °F], 100 kPa). verify (what is ?) Infobox references

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]

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

^ ^a ^b ^c SciFinder.com (accessed Nov. 6, 2012). Tangeretin (481-53-8).
^ ^a ^b ^c Uckoo, RM; et al. Sep. Purif. Technol. 2011.
^ ^a ^b 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.
^ ^a ^b Panche, A. N.; Diwan, A. D.; Chandra, S. R. Flavonoids: an overview. Journal of Nutritional Science. 2016, 5, 47.

[SciFinder-1] SciFinder.com (accessed Nov. 6, 2012). Tangeretin (481-53-8).

[Uckoo-2] Uckoo, RM; et al. Sep. Purif. Technol. 2011.

[Mizuno,_H._et_al.-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.

[Panche,_A._N._et_al.-4] Panche, A. N.; Diwan, A. D.; Chandra, S. R. Flavonoids: an overview. Journal of Nutritional Science. 2016, 5, 47.

[1]