Tangeretin

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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)

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

methyl iodide
5,8-dihydroxy-6,7-dimethoxy-2-(4-methoxyphenyl)chromen-4-one
Dimethyl sulfate
1-(2-hydroxy-3,4,5,6-tetramethoxyphenyl)ethanone
4-(Benzyloxy)benzaldehyde
1-(2-hydroxy-3,4,5,6-tetramethoxy-phenyl)-3-(4-phenylmethoxyphenyl)prop-2-en-1-one
4'-benzyloxy-5,6,7,8-tetramethoxyflavanone
Salvigenin

DownStream

Gardenin B
Salvigenin
5-Demethylsinensetin
Artemetin
5-O-Demethylnobiletin
5-OH-HxMF
4H-1-Benzopyran-4-one,2-[4-(acetyloxy)phenyl]-5,6,7,8-tetramethoxy-
5,6,7,8-tetrahydroxy-2-(4-hydroxyphenyl)chromen-4-one

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...