21763-80-4

Basic information

• Product Name: 5-hydroxy-3',4',6,7-tetramethoxyflavone
• Synonyms: 2-(3,4-Dimethoxyphenyl)-5-hydroxy-6,7-dimethoxy-4H-1-benzopyran-4-one;3',4',6,7-Tetramethoxyluteolin;Belamcanidin;Eupatilin 7-methyl ether;Santoflovone;5-hydroxy-3',4',6,7-tetramethoxyflavone;2-(4-Methoxyphenyl)-3,6,7-trimethoxy-5-hydroxy-4H-1-benzopyran-4-one;3,4',6,7-Tetramethoxy-5-hydroxyflavone
• CAS NO: 21763-80-4
• Molecular Formula: C₁₉H₁₈O₇
• Molecular Weight: 358.34
• Mol File: 21763-80-4.mol

Chemical Properties

• Boiling Point: 556.8°Cat760mmHg
• Flash Point: 200.7°C
• Appearance: /
• Density: 1.309g/cm³
• Vapor Pressure: 5.27E-13mmHg at 25°C
• Refractive Index: 1.593
• CAS DataBase Reference: 5-hydroxy-3',4',6,7-tetramethoxyflavone(CAS DataBase Reference)
• NIST Chemistry Reference: 5-hydroxy-3',4',6,7-tetramethoxyflavone(21763-80-4)
• EPA Substance Registry System: 5-hydroxy-3',4',6,7-tetramethoxyflavone(21763-80-4)

Safety Data

• Hazardous Substances Data: 21763-80-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Applications:
5-hydroxy-3',4',6,7-tetramethoxyflavone is used as a therapeutic agent for its potential anticancer properties, as it has been studied for its ability to inhibit the growth of cancer cells. It may also be used for its anti-inflammatory and antinociceptive properties, which could be beneficial in treating various inflammatory and pain-related conditions.
Used in Nutraceutical Applications:
5-hydroxy-3',4',6,7-tetramethoxyflavone is used as a dietary supplement for its antioxidant properties, which can help protect the body from oxidative stress and support overall health. Its potential benefits in treating neurological disorders, such as Alzheimer's disease and Parkinson's disease, may also contribute to its use in nutraceutical products aimed at promoting brain health and cognitive function.
Used in Neurological Disorder Treatment:
5-hydroxy-3',4',6,7-tetramethoxyflavone is used as a potential treatment for various neurological disorders, including Alzheimer's disease and Parkinson's disease, due to its demonstrated promise in research studies. Its potential neuroprotective effects and ability to target specific pathways involved in these disorders make it a promising candidate for further investigation and development in this area.

InChI:InChI=1/C19H18O7/c1-22-12-6-5-10(7-14(12)23-2)13-8-11(20)17-15(26-13)9-16(24-3)19(25-4)18(17)21/h5-9,21H,1-4H3

Upstream product

• 18003-33-3 3',4',5,6,7-pentahydroxyflavone 
• 77-78-1 dimethyl sulfate 
• 71372-29-7 5-acetoxy-2-(3,4-dimethoxy-phenyl)-6,7-dimethoxy-chromen-4-one 
• 186581-53-3 diazomethane 
• 25782-23-4 2-(3,4-dimethoxyphenyl)-5,6-dihydroxy-7-methoxy-4H-chromen-4-one 
• 2306-27-6 sinensetin 
• 114021-60-2 2'-hydroxy-3,4,4',6'-tetramethoxychalcone 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 832-58-6 1-(2,4,6-trimethoxyphenyl)ethanone 
• 6962-57-8 3,6-dihydroxy-2,4-dimethoxyacetophenone 
• 24824-54-2 3,4-dimethoxybenzoic anhydride 
• 1168-42-9 5,6,7,4'-tetramethoxyflavone 
• 481-53-8 tangeritin 
• 1251-84-9 3,5,6,7,3',4'-Hexamethoxyflavon 

Downstream Products

• 683278-67-3 5,8-dihydroxy-6,7-dimethoxy-2-(3,4-dimethoxyphenyl)-4-benzopyrone 
• 71306-34-8 2-(3,4-dimethoxy-phenyl)-5-hydroxy-6,7-dimethoxy-8-morpholin-4-ylmethyl-chromen-4-one 
• 478-01-3 nobiletin 
• 35154-55-3 3-hydroxy-5,6,7,8,3′,4′-hexamethoxyflavone 
• 1178-24-1 3,3',4',5,6,7,8-heptamethoxyflavone 
• 2192-25-8 5-hydroxy-3',4',6,7,8-pentamethoxyflavone 

Relevant articles and documents

Antitumor activity of flavones isolated from Artemisia argyi

The flavones 5,6-dihydroxy-7,3′,4′-trimethoxyflavone (1), 5,6,4′-trihydroxy-7,3′-dimethoxyflavone (2), 5-hydroxy-3′,4′,6,7-tetramethoxyflavone, 5,7,3′-trihydroxy-6,4′,5′-trimethoxyflavone, ladanein, and hispidulin were isolated from the methanolic extracts of the aerial parts of Artemisia argyi and structures of the compounds were elucidated on the basis of their spectral data. These flavones inhibited farnesyl protein transferase with IC50 values of 25-200/ μg/mL. Compound 2 inhibited proliferation of a couple of tumor cell lines and also inhibited neovascularization in a chick chorioallantoic membrane assay. Without loss of body weight of nude mice, compounds I and 2 inhibited growth of a colon tumor (SW620) by 44.6% and 14.6%, respectively.

Synthesis and anti-proliferative activities of 5,6,7-trimethoxyflavones and their derivatives

A series of 5,6,7-trimethoxyflavones 1a-1g and their derivatives 2a-2g, 3a-3d, 4 and 5, including the natural products 5,6,7-trimethoxy-4’-hydroxyflavone (1a), 5,6,7,3’,4’ -pentamethoxyflavone (sinensetin, 1 b), 5,6,7-trimethoxy-3’,4’-methyl enedioxy flavone (1c), 5,6,7,3’-tetramethoxy-4,5’-methylenedioxyflavone (1e), 5,6,7, 3’,4’,5’-hextamethoxyflavone (1 g), 5-hydroxy-3,4,2’,3’,4’-pentamethoxy chal-cone (2 b), 5,4’-dihydroxy-6,7-dimethoxy flavone (cirsimaritin, 3a) and 5-hydroxy-6,7,3’, 4’-tetramethoxyflavone (5-demethylsinensetin, 3 b), 3,5,6,7,3’,4’-hexamethoxyflavone (3-methoxysinensetin, 4) and 5’-hydroxy-3,6,7,3’,4’-pentamethoxyflavone (5) were synthesized. Their anti-proliferative activity in?vitro was evaluated against a panel of four human cancer cell lines (Aspc-1, HCT-116, HepG-2 and SUN-5) by the CTG assay. The results showed that most of the synthetic compounds exhibited moderate to high anti-proliferative activities. In particular, compound 3c possess IC50 (5.30 μM) values below 10 μM against Aspc-1 cells and are worthy of further investigation.

PROCESS TO PREPARE FLAVONES

The present invention relates to the field of flavor ingredients. More particularly it provides, a process for making 5- hydroxy -polyitιethoxy-f lavones (5-OH-PMF) (I) or improving the organoleptic properties of natural polymethoxy-f lavones (PMF) . The invention's process comprises treating flavones (II) in the presence of a HCl solution in a non-acidic and non -aqueous solvent. (I) (II).

Isolation and syntheses of polymethoxyflavones and hydroxylated polymethoxyflavones as inhibitors of HL-60 cell lines

Fifteen polymethoxyflavones (PMFs) and hydroxylated PMFs were isolated from sweet orange (Citrus sinensis) peel extract and synthesized to investigate their biological activity. All obtained compounds were tested in HL-60 cancer cell proliferation and apoptosis induction assays. While some PMFs and hydroxylated PMFs had moderate anti-carcinogenic activities, 5-hydroxy-6,7,8,3′,4′-pentamethoxyflavone and 5-hydroxy-3,6,7,8,3′,4′-hexamethoxyflavone showed strong inhibitory activities against the proliferation and induced apoptosis of HL-60 cell lines.

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.

Gastroprotective flavone/flavanone compounds with therapeutic effect on inflammatory bowel disease

PCT No. PCT/KR97/00144 Sec. 371 Date Jan. 14, 1999 Sec. 102(e) Date Jan. 14, 1999 PCT Filed Jul. 25, 1997 PCT Pub. No. WO98/04541 PCT Pub. Date Feb. 5, 1998The present invention relates to novel flavone/flavanone compounds or their pharmaceutically acceptable salts and process for preparation thereof for protecting gastrointestinal tracts against gastritis, ulcers and inflammatory bowel disease.

DEACYLATION OF AROMATIC ACETATES. A NEW METHOD OF SELECTIVE PROTECTION OF THE HYDROXYL FUNCTION.

Acetoxyaromatic compounds are selectively deacylated, via a catalytic-type reaction, to the corresponding phenolic derivatives, by treatment with activated zinc in methanol.