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 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:9400 N
ChemSpider	61389 N
ECHA InfoCard	100.006.883
EC Number	207-570-1
KEGG	C10190 N
PubChem CID	68077
UNII	I4TLA1DLX6 Y
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 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
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[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]
Solubility in water	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). N verify (what is YN ?) 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]