Tangeretin

Names

[ CAS No. ]:
481-53-8

[ Name ]:
Tangeretin

[Synonym ]:
4H-1-Benzopyran-4-one, 2-(4-methoxyphenyl)-5,6,7,8-tetramethoxy-
Ponkanetin
4',5,6,7,8-pentamethoxyflavone
4H-1-Benzopyran-4-one, 5,6,7,8-tetra-methoxy-2-(4-methoxyphenyl)-
Flavone, 5,6,7,8,4'-pentamethoxy
Flavone, 4',5,6,7,8-pentamethoxy-
TANGERETIN,NATURAL
MFCD00017438
4H-1-Benzopyran-4-one, 5,6,7,8-tetramethoxy-2-(p-methoxyphenyl)-
5,6,7,8,4'-Pentamethoxyflavone
4H-1-Benzopyran-4-one, 5,6,7,8-tetramethoxy-2-(4-methoxyphenyl)-
5,6,7,8-Tetramethoxy-2-(4-methoxyphenyl)-4H-chromen-4-one
TANGARETIN
Tangeritin
Tangeritine
EINECS 207-570-1
Tangeretin
5-18-05-00491 (Beilstein Handbook Reference)

Biological Activity

[Description]:

Tangeretin, a flavonoid from citrus fruit peels, has been proven to play an important role in anti-inflammatory responses and neuroprotective effects in several disease models, and was also selected as a Notch-1 inhibitor.IC50 value:Target: Notch-1In vitro: Tangeretin enhanced the radiosensitivity of GC cells as demonstrated by MTT and colony formation assays. Tangeretin also attenuated radiation-induced EMT, invasion and migration in GC cells, accompanied by a decrease in Notch-1, Jagged1/2, Hey-1 and Hes-1 expressions. Tangeretin triggered the upregulation of miR-410, a tumor-suppressive microRNA. Furthermore, re-expression of miR-410 prevented radiation-induced EMT and cell invasion [1]. In vivo: In this study, we investigated the in vivo anti-RSV activity of tangeretin in 3-week-old male BALB/c mice. A plaque reduction assay and fluorescence quantitative polymerase chain reaction (FQ-PCR) showed that tangeretin inhibited RSV replication in the lung of mice [2].

[Related Catalog]:

Signaling Pathways >> Stem Cell/Wnt >> Notch

Research Areas >> Inflammation/Immunology

Natural Products >> Flavonoids

[References]

[1]. Zhang X, et al. Tangeretin enhances radiosensitivity and inhibits the radiation-induced epithelial-mesenchymal transition of gastric cancer cells. Oncol Rep. 2015 Jul;34(1):302-10.

[2]. Xu JJ, et al. Tangeretin from Citrus reticulate Inhibits Respiratory Syncytial Virus Replication and Associated Inflammation in Vivo. J Agric Food Chem. 2015 Nov 4;63(43):9520-7.

[3]. Hagenlocher Y, et al. Citrus peel polymethoxyflavones nobiletin and tangeretin suppress LPS- and IgE-mediated activation of human intestinal mast cells. Eur J Nutr. 2016 Mar 28.

[Related Small Molecules]

RO4929097 | Crenigacestat(LY3039478) | YO-01027 | LY-411575 | FLI-06 | Avagacestat | IMR-1 | BMS-983970 | Semagacestat(LY450139) | Z-Ile-Leu-aldehyde | Psoralidin | tCFA15

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
565.3±50.0 °C at 760 mmHg

[ Melting Point ]:
155 °C

[ Molecular Formula ]:
C₂₀H₂₀O₇

[ Molecular Weight ]:
372.369

[ Flash Point ]:
248.4±30.2 °C

[ Exact Mass ]:
372.120911

[ PSA ]:
76.36000

[ LogP ]:
2.66

[ Vapour Pressure ]:
0.0±1.5 mmHg at 25°C

[ Index of Refraction ]:
1.566

[ Water Solubility ]:
insoluble

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DJ3102725

CHEMICAL NAME :: 4H-1-Benzopyran-4-one, 2-(4-methoxyphenyl)-5,6,7,8-tetramethoxy-

CAS REGISTRY NUMBER :: 481-53-8

BEILSTEIN REFERENCE NO. :: 0351695

LAST UPDATED :: 199612

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C20-H20-O7

MOLECULAR WEIGHT :: 372.40

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >1 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: ADTEAS Advances in Teratology. (New York, NY) V.1-5, 1966-72. Discontinued. Volume(issue)/page/year: 3,181,1968

Safety Information

[ Symbol ]:

GHS06

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H300

[ Precautionary Statements ]:
P264-P301 + P310

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges

[ Hazard Codes ]:
T:Toxic;

[ Risk Phrases ]:
R25

[ Safety Phrases ]:
S45

[ RIDADR ]:
UN 2811

[ RTECS ]:
DJ3102725

[ Hazard Class ]:
6.1

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Phytochemical profile and antioxidant activity of physiological drop of citrus fruits.

J. Food Sci. 78(1) , C37-42, (2013)

The phytochemical content and the antioxidant activity (AA) of physiological drop of the main citrus species grown in China were investigated. Among the flavonoids, hesperidin was found mostly in mand...

Polymethoxylated flavones potentiate the cytolytic activity of NK leukemia cell line KHYG-1 via enhanced expression of granzyme B.

Biochem. Biophys. Res. Commun. 456(3) , 799-803, (2015)

Polymethoxylated flavones (PMFs) are found in the peel tissues of some citrus species. Here, we report that PMFs, such as nobiletin, potentiate the cytolytic activity of KHYG-1 natural killer (NK) leu...

Tangeretin stimulates glucose uptake via regulation of AMPK signaling pathways in C2C12 myotubes and improves glucose tolerance in high-fat diet-induced obese mice.

Mol. Cell. Endocrinol. 358(1) , 127-34, (2012)

Although the flavonoid tangeretin (5, 6, 7, 8, 4'-pentamethoxyflavone) is known to possess beneficial health effects, the anti-diabetic effects and the mechanism of action have not been elucidated. Tr...