481-53-8

Basic information

• Product Name: Tangeretin
• 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
• CAS NO: 481-53-8
• Molecular Formula: C₂₀H₂₀O₇
• Molecular Weight: 372.37
• EINECS: 207-570-1
• Product Categories: Flavanols;Natural Plant Extract;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Inhibitors
• Mol File: 481-53-8.mol

Chemical Properties

• Melting Point: 153.0 to 157.0 °C
• Boiling Point: 565.3 °C at 760 mmHg
• Flash Point: 248.4 °C
• Appearance: yellow crystalline
• Density: 1.244 g/cm³
• Vapor Pressure: 8.41E-13mmHg at 25°C
• Refractive Index: 1.565
• Storage Temp.: Sealed in dry,Room Temperature
• BRN: 351695
• CAS DataBase Reference: Tangeretin(CAS DataBase Reference)
• NIST Chemistry Reference: Tangeretin(481-53-8)
• EPA Substance Registry System: Tangeretin(481-53-8)

Safety Data

• Hazard Codes: T,Xi
• Statements: 25-36/37/38
• Safety Statements: 45-36-26
• RIDADR: UN 2811
• WGK Germany: 3
• RTECS: DJ3102725
• Hazardous Substances Data: 481-53-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Tangeretin is used as an antineoplastic agent for its ability to inhibit the growth and progression of cancer cells. It is particularly effective against various types of cancer, including liver, breast, lung, pancreatic, colorectal, and ovarian cancers.
Used in Drug Delivery Systems:
Tangeretin is also utilized in the development of novel drug delivery systems to enhance its applications and efficacy against cancer cells. Various organic and metallic nanoparticles have been employed as carriers for Tangeretin delivery, aiming to improve its delivery, bioavailability, and therapeutic outcomes.

InChI: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

Upstream product

• 2798-20-1 gardenin B 
• 77-78-1 dimethyl sulfate 
• 10176-66-6 nevadensin 
• 36950-98-8 4'-hydroxy-5,6,7,8-tetramethoxy flavone 
• 74-88-4 methyl iodide 
• 40110-95-0 4-benzyloxy-2'-hydroxy-3',4',5',6'-tetramethoxychalcone 
• 55742-65-9 2',5'-dihydroxy-3',4',6'-trimethoxyacetophenone 
• 13698-23-2 apigenin 4',5-dimethyl ether 
• 17306-46-6 rhoifolin 
• 73213-66-8 7-hydroxy-5,6,8,4′-tetramethoxyflavone 
• 66074-96-2 5,6,7,8,4'-penta methoxyl-flavanone 
• 4323-80-2 5,7-dihydroxy-2-(4-hydroxyphenyl)-6,8-dimethoxy-4H-chromen-4-one 
• 1486-50-6 4-(benzyloxy)benzoic acid chloride 
• 85374-52-3 1-(4-benzyloxyphenyl)-3-(2-hydroxy-3,4,5,6-tetramethoxyphenyl)propane-1,3-dione 

Downstream Products

• 1370734-44-3 ethyl 2-(5,6,7,8-tetramethoxy-2-(4-methoxyphenyl)-4-oxo-4H-chromen-3-yl)acetate 
• 1382191-86-7 4',5,6,7,8-pentamethoxy-4-flavanol 
• 1443134-14-2 4',5,6,7,8-pentamethoxy-3-flavene 
• 1443134-15-3 4',5,6,7,8-pentamethoxy-2-flavene 
• 50461-91-1 3-hydroxy-5,6,7,8,4′-pentamethoxyflavone 
• 34170-18-8 3,5,6,7,8,4′-hexamethoxyflavone 
• 50439-46-8 5-hydroxy-3,6,7,8,4′-pentamethoxyflavone 
• 1370734-49-8 ethyl 2-(5,6,7,8-tetramethoxy-2-(4-methoxyphenyl)-4-oxo-4H-chromen-3-yl)propanoate 
• 1370734-48-7 3-(2-(4-chlorophenyl)-2-oxoethyl)-5,6,7,8-tetramethoxy-2-(4-methoxyphenyl)-4H-chromen-4-one 
• 2798-20-1 gardenin B 
• 19103-54-9 5-hydroxy-4',6,7-trimethoxyflavone 
• 21763-80-4 5-desmethylsinensetin 
• 479-90-3 artemetin 
• 2174-59-6 5-hydroxy-6,7,8,3',4'-pentamethoxyflavone 

Relevant articles and documents

Synthesis of Citrus polymethoxyflavonoids and their antiproliferative activities on Hela cells

Abstract: A series of polymethoxyflavonoids (3–16) were synthesized through dehydrogenation, O-methylation, glycoside hydrolysis, bromination, microwave-assisted aromatic nucleophilic substitution, dimethyldioxirane oxidation and regioselective demethylation, starting from abundant and inexpensive natural sources naringin and hesperidin. All the synthetic compounds were test for antiproliferative activities on human cervical carcinoma Hela cell line by the standard CCK-8 assay, the result showed that most of the target compounds exhibited moderate to potent antiproliferative activities on Hela cells comparable with the positive control cis-Platin. Among them, 5-hydroxypolymethoxy flavonoid 13 showed the strongest activity (IC50 0.791 μM). Graphical Abstract: [InlineMediaObject not available: see fulltext.].

Use of flavone and flavanone derivatives in preparation of sedative and hypnotic drugs

Disclosed is a use of flavones derivatives and flavanone derivatives in preparation of sedative and hypnotic drugs.

Methoxyflavones from Stachys glutinosa with binding affinity to opioid receptors: In silico, in vitro, and in vivo studies

Fractionation of the bioactive dichloromethane extract from the aerial parts of Stachys glutinosa led to the isolation of four flavones, xanthomicrol (1), sideritoflavone (2), 8-methoxycirsilineol (3), and eupatilin (4), along with two neo-clerodane diterpenes, roseostachenone (8) and a new compound, 3α,4α-epoxyroseostachenol (7). In order to study structure-activity relationships, two methoxyflavones [5-demethyltangeretin (5) and tangeretin (6)] were synthesized by the methoxylation of xanthomicrol. The isolated compounds (1-4, 7, and 8) as well as the xanthomicrol semisynthetic derivatives (5 and 6) were evaluated for their binding affinity to the μ and δ opioid receptors. Xanthomicrol was the most potent binder to both μ and δ receptors, with a Ki value of 0.83 and 3.6 μM, respectively. Xanthomicrol administered intraperitoneally in mice at a dose of 80 mg/kg significantly reduced morphine-induced antinociception in the tail flick test. Our results suggested that xanthomicrol is a μ opioid receptor antagonist. Docking experiments were carried out to acquire a deeper understanding about important structural aspects of binding of xanthomicrol. In summary, these data suggest that xanthomicrol is a valuable structure for further development into a potential μ opioid receptor antagonist.

USE OF FLAVONE AND FLAVANONE DERIVATIVES IN PREPARATION OF SEDATIVE AND HYPNOTIC DRUGS

Disclosed is a use of flavones derivatives and flavanone derivatives in preparation of sedative and hypnotic drugs.

Semisynthesis of polymethoxyflavonoids from naringin and hesperidin

Polymethoxyflavonoids (PMFs) possess important biological activities, notably as anticancer agents. Semisynthesis of a series of PMFs were performed by glycoside hydrolysis, dehydrogenation, bromination, aromatic nucleophilic substitution, O-methylation, dimethyldioxirane oxidation and regioselective demethylation, starting from abundant and inexpensive natural sources naringin and hesperidin. A new synthetic method for selective methylation using CuBr catalysed and microwave-assisted reaction was developed, and the dimethyl dioxirane oxidation of flavones to flavonols was much improved. The new semisynthetic route has the advantages of easy availability of starting materials, simple operation and good yields.

B-Ring-modified and/or 5-demethylated nobiletin congeners: Inhibitory activity against pro-MMP-9 production

Three metabolites and 12 analogues of nobiletin (1) were synthesized. Whereas nobiletin derivatives 2-4 inhibited pro-MMP-9 production similarly in both PMA- and TNF-α-stimulated human lens epithelial cells, the 2′-hydroxylated analogue 5a exerted marked inhibitory effects (IC 50: 0.4 μM) on PMA-treated cells, which were 170-fold more potent than those on TNF-α-treated cells. This activity may be closely related to PKC-mediated transcriptional regulation of pro-MMP-9.

Chemical constituents of Limnophila indica

Two flavonoids, 5,6-dihydroxy-7,8,4′-trimethoxy flavone 1 and 5,2′-dihydroxy-8,3prime;,4′-trimethoxyflavone 2 together with three known compounds, 5-hydroxy-7,2′-dimethoxyflavone 3, 5,2′-dihydroxy- 7,8-dimethoxyflavone 4 and β-sitosterol 5, have been isolated from the aerial parts and roots of Limnophila indica (Scrophulariaceae). The structures of compounds 1-5 have been elucidated on the basis of spectral and chemical studies.

Regioselective hydroxylation of 2-hydroxychalcones by dimethyldioxirane towards polymethoxylated flavonoids

The flavone nucleus is part of a large number of natural products and medicinal compounds. In this presentation the novel regioselective hydroxylation of hydroxyarenes with DMD is described. The results showed further that flavonoids with 5-hydroxy group were selectively oxyfunctionalized at the para-position C8 carbon atom by DMD. Finally, according to this methodology, the naturally occurring isosinensetin, tangeretin, sinensetin, nobiletin, natsudaidain, gardenin B, 3,3′,4′,5,6,7,8- heptamethoxyflavone, quercetin and its derivatives were synthesized.

5,8-Dihydroxy-6,7,4′-trimethoxyflavone, a novel flavonoid constituent of Limnophila indica

The petrol extract of the aerial parts and roots of Limnophila indica (Scrophulariaceae) has yielded a new flavone, 5,8-dihydroxy-6,7,4′- trimethoxyflavone 1 characterized by chemical as well as spectral studies.

Compositions and methods of treating, reducing and preventing cardiovascular diseases and disorders with polymethoxyflavones

Compositions and methods for the treatment, reduction and/or prevention of cardiovascular diseases and disorders are described. Individuals at high risk for developing or having cardiovascular disease or disorder may be treated with an effective dose of a polymethoxyflavone including limocitrin derivatives, quercetin derivatives, naturally occurring polymethoxyflavones, tocotrienols, and mixtures of these compounds.