| Identification | More | [Name]
Tangeretin | [CAS]
481-53-8 | [Synonyms]
4',5,6,7,8-PENTAMETHOXYFLAVONE
5,6,7,8,4'-PENTAMETHOXYFLAVONE
5,6,7,8-Tetramethoxy-2-(4-methoxyphenyl)-4-benzopyrone
TANGERETIN
TANGERITIN
2-(4-methoxyphenyl)-5,6,7,8-tetramethoxy-4h-1-benzopyran-4-on
2-(4-methoxyphenyl)-5,6,7,8-tetramethoxy-4h-1-benzopyran-4-one
4’,5,6,7,8-pentamethoxy-flavon
Flavone, 5,6,7,8,4'-pentamethoxy
ponkanetin
TANGERETIN(P)
TANGERETIN(RG)
TANGARETIN
TANGERETIN, NATURAL
2-(4-methoxyphenyl)-
4H-1-Benzopyran-4-one,5,6,7,8-tetramethoxy-
5,6,7,8-Tetramethoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one
Tangeritine | [EINECS(EC#)]
207-570-1 | [Molecular Formula]
C20H20O7 | [MDL Number]
MFCD00017438 | [Molecular Weight]
372.37 | [MOL File]
481-53-8.mol |
| Chemical Properties | Back Directory | [Melting point ]
153.0 to 157.0 °C | [Boiling point ]
565.3±50.0 °C(Predicted) | [density ]
1.244±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
DMSO : 25 mg/mL (67.14 mM; Need ultrasonic) | [form ]
neat | [color ]
White to Almost white | [BRN ]
351695 | [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 | [InChIKey]
ULSUXBXHSYSGDT-UHFFFAOYSA-N | [SMILES]
C1(C2=CC=C(OC)C=C2)OC2=C(OC)C(OC)=C(OC)C(OC)=C2C(=O)C=1 | [LogP]
1.788 (est) | [CAS DataBase Reference]
481-53-8(CAS DataBase Reference) | [NIST Chemistry Reference]
Tangeretin(481-53-8) |
| Safety Data | Back Directory | [Hazard Codes ]
T,Xi | [Risk Statements ]
R25:Toxic if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [RIDADR ]
UN 2811 | [WGK Germany ]
3 | [RTECS ]
DJ3102725 | [HS Code ]
29329990 | [Toxicity]
rat,LD50,intraperitoneal,> 1gm/kg (1000mg/kg),Advances in Teratology. Vol. 3, Pg. 181, 1968. |
| Hazard Information | Back Directory | [Chemical Properties]
Yellow powder | [Uses]
Tangeretin[481-53-8] has been used as an antioxidant and antifungal agent to test its effects on ferroptosis inhibition, conidial development, and appressorium formation against Magnaporthe oryzae. It has also been used as a co-chemotherapeutics agent to study its cytotoxic effects in combination with 5-Fluorouracil (5-Fu) on WiDr colon cancer cells. | [Definition]
ChEBI: Tangeretin is a pentamethoxyflavone flavone with methoxy groups at positions 4', 5, 6 , 7 and 8. It has a role as an antineoplastic agent and a plant metabolite. | [General Description]
Tangeretin is a polymethoxyflavone extracted primarily from the peels of citrus fruits like Citrus sinensis and Citrus reticulata. | [Biological Activity]
Tangeretin is a flavonoid found in the peel of citrus fruits where it most likely provides natural resistance to fungi. Tangeretin has been shown to counteract tumor promoter-induced inhibition of intercellular communication and to inhibit cell proliferation in several cancer lines. | [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]. | [References]
[1] K. AGRAWAL Y. M. Tangeretin: A Biologically Potential Citrus Flavone[J]. Current Traditional Medicine, 2022. DOI:10.2174/2215083808666220304100702.
[2] JUHEE SEO . Tangeretin, a citrus flavonoid, inhibits PGDF-BB-induced proliferation and migration of aortic smooth muscle cells by blocking AKT activation[J]. European journal of pharmacology, 2011, 673 1: Pages 56-64. DOI:10.1016/j.ejphar.2011.10.011.
[3] Z CHENG. Tangeretin and its metabolite 4′-hydroxytetramethoxyflavone attenuate EGF-stimulated cell cycle progression in hepatocytes; role of inhibition at the level of mTOR/p70S6K[J]. British Journal of Pharmacology, 2010, 162 8: 1781-1791. DOI:10.1111/j.1476-5381.2010.01185.x.
[4] GUY LEWIN*. Semisynthesis of Natural Flavones Inhibiting Tubulin Polymerization, from Hesperidin[J]. Journal of Natural Products , 2010, 73 4: 702-706. DOI:10.1021/np100065v.
[5] WASEEM RAZA Abha M Suaib Luqman. Prospects of tangeretin as a modulator of cancer targets/pathways[J]. Pharmacological research, 2020, 161: Article 105202. DOI:10.1016/j.phrs.2020.105202. |
|
|