93012-86-3

Basic information

• Product Name: 4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-2,3-dihydro-5-hydroxy-7-methoxy-
• CAS NO: 93012-86-3
• Molecular Formula: C16H14O6
• Molecular Weight: 302.284
• Mol File: 93012-86-3.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-2,3-dihydro-5-hydroxy-7-methoxy-(CAS DataBase Reference)
• NIST Chemistry Reference: 4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-2,3-dihydro-5-hydroxy-7-methoxy-(93012-86-3)
• EPA Substance Registry System: 4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-2,3-dihydro-5-hydroxy-7-methoxy-(93012-86-3)

Safety Data

• Hazardous Substances Data: 93012-86-3(Hazardous Substances Data)

Upstream product

• 7507-89-3 2,6-dihydroxy-4-methoxy-acetophenone 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 90-24-4 2-hydroxy-4,6-dimethoxyacetophenone 
• 10496-67-0 3-(3,4-dimethoxyphenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)prop-2-en-1-one 
• 520-29-6 (-)-(S)-sakuranetin 
• 6515-06-6 3,4-bis-methoxymethoxy-benzaldehyde 
• 129750-75-0 2,6-di(methoxymethoxy)-4-methoxyacetophenone 
• 2174-64-3 5-methoxyresorcinol 
• 108-73-6 3,5-dihydroxyphenol 
• 111285-98-4 3,4-Dibenzyloxy-2'-hydroxy-4',6'-dimethoxychalkone 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 17060-20-7 2,3-dihydro-5,7-dimethoxy-2-(4'-dimethoxyphenyl)-4H-1-benzopyran-4-one 
• 5447-02-9 3,4-dibenzyloxybenzaldehyde 
• 111285-99-5 3',4'-Dibenzyloxy-5,7-dimethoxyflavanone 

Downstream Products

• 51857-11-5 (-)-(2S)-5,3’,4’-trihydroxy-7-methoxyflavanone 
• 102599-74-6 5-acetoxy-2-(3,4-diacetoxy-phenyl)-7-methoxy-chroman-4-one 

Relevant articles and documents

Sterubin: Enantioresolution and Configurational Stability, Enantiomeric Purity in Nature, and Neuroprotective Activity in Vitro and in Vivo

Alzheimer′s disease (AD) is a neurological disorder with still no preventive or curative treatment. Flavonoids are phytochemicals with potential therapeutic value. Previous studies described the flavanone sterubin isolated from the Californian plant Eriodictyon californicum as a potent neuroprotectant in several in vitro assays. Herein, the resolution of synthetic racemic sterubin (1) into its two enantiomers, (R)-1 and (S)-1, is described, which has been performed on a chiral chromatographic phase, and their stereochemical assignment online by HPLC-ECD coupling. (R)-1 and (S)-1 showed comparable neuroprotection in vitro with no significant differences. While the pure stereoisomers were configurationally stable in methanol, fast racemization was observed in the presence of culture medium. We also established the occurrence of extracted sterubin as its pure (S)-enantiomer. Moreover, the activity of sterubin (1) was investigated for the first time in vivo, in an AD mouse model. Sterubin (1) showed a significant positive impact on short- and long-term memory at low dosages.

Synthesis of hydroxyflavanones from substituted acetophenones and benzaldehydes in the presence of silica gel, boric acid and piperidine

Direct synthesis of hydroxyflavanones from appropriately substituted acetophenones and benzaldehydes was achieved in the presence of boric acid, silica gel and piperidine. The formation of flavanones presumably involved the reaction between the acetopheno

Synthesis of a Typical Chalkone and a Flavanone of Wyethia glabra

The constitution of a new chalkone as 2',4',6'-trihydroxy-4-methoxychalkone (1), isolated from Wyethia glabra has now been confirmed by its synthesis using 2'-hydroxy-4',6'-dibenzoyloxy-4-methoxychalkone (1a) as an essential intermediate.The structure of another compound as 5,3',4'-trihydroxy-7-methoxyflavanone (2) (eriodictyol-7-methyl ether) isolated from the same source, has also been confirmed by its synthesis using vanillin as the starting material.