103654-49-5

Basic information

• Product Name: 2-[(E)-2-(3,5-Dihydroxyphenyl)ethenyl]-5-hydroxy-6,7,8-trimethoxy-3-methyl-4H-1-benzopyran-4-one
• Synonyms: 2-[(E)-2-(3,5-Dihydroxyphenyl)ethenyl]-5-hydroxy-6,7,8-trimethoxy-3-methyl-4H-1-benzopyran-4-one;3-Methyl-5-hydroxy-2-[(E)-3,5-dihydroxystyryl]-6,7,8-trimethoxychromone;Hormothamnione
• CAS NO: 103654-49-5
• Molecular Formula: C₂₁H₂₀O₈
• Molecular Weight: 0
• Mol File: 103654-49-5.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-[(E)-2-(3,5-Dihydroxyphenyl)ethenyl]-5-hydroxy-6,7,8-trimethoxy-3-methyl-4H-1-benzopyran-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[(E)-2-(3,5-Dihydroxyphenyl)ethenyl]-5-hydroxy-6,7,8-trimethoxy-3-methyl-4H-1-benzopyran-4-one(103654-49-5)
• EPA Substance Registry System: 2-[(E)-2-(3,5-Dihydroxyphenyl)ethenyl]-5-hydroxy-6,7,8-trimethoxy-3-methyl-4H-1-benzopyran-4-one(103654-49-5)

Safety Data

• Hazardous Substances Data: 103654-49-5(Hazardous Substances Data)

Upstream product

• 117970-68-0 5,6,7,8-Tetramethoxy-2-<2-<3,5-bis(benzyloxy)phenyl>ethenyl>-3-methylchromone 
• 58605-10-0 methyl 3,5-bis(benzyloxy)benzoate 
• 117970-66-8 2-hydroxy-3,4,5,6-tetramethoxy propiophenone 
• 21450-56-6 1,2,3,4-tetramethoxybenzene 
• 13909-75-6 1,2,3,4,5-pentamethoxybenzene 
• 128191-00-4 1-(2-Hydroxy-3,4,5,6-tetramethoxyphenyl)but-2-yn-1-one 
• 128191-04-8 5,6,7,8-Tetramethoxy-2-<2-<3,5-bis(benzyloxy)phenyl>ethenyl>chromone 
• 67231-47-4 5,6,7,8-Tetramethoxy-2-methylchromone 
• 65884-12-0 2,3,4,5-tetramethoxybenzaldehyde 
• 30225-99-1 2,3,4,5-Tetramethoxyphenol 
• 119232-80-3 2,5-dihydroxy-3,4,6-trimethoxypropiophenone 
• 117970-67-9 2,3-dimethyl-5,6,7,8-tetramethoxy chromone 
• 24131-31-5 3,5-dibenzyloxybenzyl alcohol 
• 14615-72-6 3,5-dibenzyloxybenzaldehyde 

Downstream Products

• 119232-82-5 Acetic acid 3-acetoxy-5-[(E)-2-(5-hydroxy-6,7,8-trimethoxy-3-methyl-4-oxo-4H-chromen-2-yl)-vinyl]-phenyl ester 
• 103654-51-9 hormothamnione triacetate 

Relevant articles and documents

Synthesis of hormothamnione and 6-desmethoxyhormothamnione

The antineoplastic styrylchromones hormothamnione 1 and 6-desmethoxyhormothamnione 2 are readily prepared by selective and simultaneous demethylation and debenzylation of chromones 3 and 4 using excess AlCl3-Nal in CH3CN.

Synthesis of Highly Functionalized Flavones and Chromones Using Cycloacylation Reactions and C-3 Functionalization. A Total Synthesis of Hormothamnione

The cycloacylations of hydroxy- and methoxy-substituted phenols with aryl- and alkylpropiolic acids using Eaton's reagent (10percent phosphorus pentoxide in methanesulfonic acid) gives highly substituted flavones and chromones in up to 63 percent yield.Styrylchromones were prepared from 2-methylchromones by condensation reactions of the 2-methyl group with various substituted benzaldehydes in sodium ethoxide and ethanol in almost quantitative yield.Methylation or hydroxylation at C-3 of these highly substituted flavones and styrylchromones was accomplished in a highly regioselective manner employing lithium diisopropylamide followed by quenching with an electrophile.Quenching of the initial anion with methyl triflate gave 3-methyl products while quenching of the initial anion with trimethylborate followed by oxidation gave 3-hydroxy products.A total synthesis of the naturally occurring styrylchromone hormothamnione, containing a 3-methyl substituent, is reported by use of these synthetic techniques.

SYNTHESIS OF HORMOTHAMNIONE

Hormothamnione 1 has been obtained from 2,3-dimethyl-5,6,7,8-tetramethoxy-chromone 18 in 63percent yield.Synthesis of the required chromone 18 as well as of the 2 and 3-styryl analogs 5 and 9 are described.

Hormothamnione, a novel cytotoxic styrylchromone from the marine cyanophyte Hormothamnion enteromorphoides Grunow

The first naturally occurring styrylchromone, hormothamnione, was isolated from the marine cyanophyte Hormothamnion enteromorphoides and its structure determined by an x-ray experiment on its triacetate derivative. Hormothamnione is an exceptionally potent cytotoxin to cancer cells in vitro and appears to be a selective inhibitor of RNA synthesis.