34170-18-8

Basic information

• Product Name: 4H-1-Benzopyran-4-one, 3,5,6,7,8-pentamethoxy-2-(4-methoxyphenyl)-
• CAS NO: 34170-18-8
• Molecular Formula: C21H22O8
• Molecular Weight: 402.401
• Mol File: 34170-18-8.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 4H-1-Benzopyran-4-one, 3,5,6,7,8-pentamethoxy-2-(4-methoxyphenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 4H-1-Benzopyran-4-one, 3,5,6,7,8-pentamethoxy-2-(4-methoxyphenyl)-(34170-18-8)
• EPA Substance Registry System: 4H-1-Benzopyran-4-one, 3,5,6,7,8-pentamethoxy-2-(4-methoxyphenyl)-(34170-18-8)

Safety Data

• Hazardous Substances Data: 34170-18-8(Hazardous Substances Data)

Upstream product

• 5071-47-6 2-hydroxy-3,4,5,6,ο-pentamethoxyacetophenone 
• 794-94-5 p-Methoxybenzoic anhydride 
• 73213-66-8 7-hydroxy-5,6,8,4′-tetramethoxyflavone 
• 17306-46-6 rhoifolin 
• 13698-23-2 apigenin 4',5-dimethyl ether 
• 481-53-8 tangeritin 
• 50461-91-1 3-hydroxy-5,6,7,8,4′-pentamethoxyflavone 
• 77-78-1 dimethyl sulfate 
• 14787-34-9 5-hydroxy-3,4',6,7-tetramethoxyflavone 
• 855937-65-4 1-(2,5-dihydroxy-3,4,6-trimethoxy-phenyl)-2-methoxy-ethanone 
• 1027152-43-7 4-Methoxy-benzoic acid 2-acetyl-3,5,6-trimethoxy-4-methoxymethoxy-phenyl ester 
• 173217-35-1 5,7,8-Trimethoxy-6-methoxymethoxy-2-(4-methoxy-phenyl)-chromen-4-one 
• 169130-15-8 6-hydroxy-4',5,7,8-tetramethoxyflavone 
• 55742-65-9 2',5'-dihydroxy-3',4',6'-trimethoxyacetophenone 

Downstream Products

• 5071-47-6 2-hydroxy-3,4,5,6,ο-pentamethoxyacetophenone 
• 4431-48-5 5-hydroxyauranetin 
• 50461-92-2 5,8-dihydroxy-3,4',6,7-tetramethoxyflavone 
• 50439-46-8 5-hydroxy-3,6,7,8,4′-pentamethoxyflavone 

Relevant articles and documents

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.

Cytotoxic and anti-HIV-1 constituents of Gardenia obtusifolia and their modified compounds

5α-Cycloart-24-ene-3,23-dione (1), 5α-cycloart-24-ene-3,16,23-trione (2) and methyl 3,4-seco-cycloart-4(28),24-diene-29-hydroxy-23-oxo-3-oate (3), together with five known flavones 5,7,4′-trihydroxy-3,8-dimethoxyflavone (4), 5,7,4′-trihydroxy-3,8,3′-tri-methoxyflavone (5), 5,7,4′-trihydroxy-3,6,8-trimethoxyflavone (6), 5,4′-dihydroxy-3,6,7,8-tetramethoxyflavone (7) and 5,3′-dihydroxy-3,6,7,8,4′-pentamethoxyflavone (8) have been isolated from the leaves and twigs of Gardenia obtusifolia. The structures were assigned on the basis of spectroscopic methods. Compounds 3-8 and some of the modified compounds showed significant cytotoxic activities in several mammalian cell lines, especially 8 and its diacetate 21 which exhibited potent cytotoxicities (compound 8: P-388 0.05μg/mL, KB 0.09μg/mL, BCA-1 0.63μg/mL, Lu-1 0.09μg/mL, ASK 0.70μg/mL; its diacetate: P-388 0.27μg/mL, KB 0.06μg/mL, BCA-1 0.53μg/mL, Lu-1 0.49μg/mL). It was also found that 5, 8 and 21 showed antimitotic acitivity in the ASK assay. Compounds 2, 4, 6, 7 and some of the modified compounds displayed interesting anti-HIV activity in the syncytium assay, but were inactive or exhibited weak activity in the HIV-1 RT assay; while compound 3 was found to be active in the HIV-1 RT assay (99.9 % inhibition at 200μg/mL), but cytotoxic in the syncytium assay.