Tangeritin

Tangeritin (Tangeretin)

Names
IUPAC names 5,6,7,8-tetramethoxy-2- (4-methoxyphenyl)-4H- 1-benzopyran-4-one
Identifiers
CAS Number	481-53-8 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:9400 N
ChemSpider	61389 N
ECHA InfoCard	100.006.883
EC Number	207-570-1
KEGG	C10190 N
PubChem	68077
UNII	I4TLA1DLX6 Y
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
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)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Tangeritin is an O-polymethoxylated flavone that is found in tangerine and other citrus peels. Tangeritin 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.

Although few randomized, double-blind human studies have been done, animal research shows the potential of tangeritin as a cholesterol lowering agent. A study on rats demonstrated potential protective effects against Parkinson's disease.

Tangeritin also shows enormous potential as an anti cancer agent. In in vitro studies, tangeritin appears to counteract some of the adaptations of cancer cells. Tangeritin induced apoptosis in leukemia cells while sparing normal cells. In a study on two human breast cancer cell lines and one colon cancer cell line, tangeritin blocked cell cycle progression at the G1 (growth) phase in all three cell lines, without inducing apoptosis in the tumor cell lines. Once tangeritin was removed from the tumor cells, their cell cycle progression returned to normal. Tangeritin also counteracts tumor suppression of gap junction intercellular signaling. In summary, in vitro studies show antimutagenic, antiinvasive and antiproliferative effects. One caveat is that tangeritin appears to counteract the anticancer drug tamoxifen and to suppress the activity of natural killer cells. H

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

However, methods for tangeritin 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.

Tangeritin is commercially available as a dietary supplement.