Tangeretin

Modify Date: 2024-01-02 18:07:58

Tangeretin Structure
Tangeretin structure
Common Name Tangeretin
CAS Number 481-53-8 Molecular Weight 372.369
Density 1.2±0.1 g/cm3 Boiling Point 565.3±50.0 °C at 760 mmHg
Molecular Formula C20H20O7 Melting Point 155 °C
MSDS Chinese USA Flash Point 248.4±30.2 °C
Symbol GHS06
GHS06
Signal Word Danger

 Use of Tangeretin


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].

 Names

Name tangeretin
Synonym More Synonyms

 Tangeretin 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
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.

 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

 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
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

 Articles27

More 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...

 Synonyms

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)
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  • Purity: 98.0%
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