1290638-51-5

Basic information

• Product Name: 1-(2-hydroxy-4,6-bis(methoxymethoxy)phenyl)-3-(3-methoxy-4-(methoxymethoxy)phenyl)prop-2-en-1-one
• Synonyms: 1-(2-hydroxy-4,6-bis(methoxymethoxy)phenyl)-3-(3-methoxy-4-(methoxymethoxy)phenyl)prop-2-en-1-one
• CAS NO: 1290638-51-5
• Molecular Weight: 434.443
• Mol File: 1290638-51-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1-(2-hydroxy-4,6-bis(methoxymethoxy)phenyl)-3-(3-methoxy-4-(methoxymethoxy)phenyl)prop-2-en-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-hydroxy-4,6-bis(methoxymethoxy)phenyl)-3-(3-methoxy-4-(methoxymethoxy)phenyl)prop-2-en-1-one(1290638-51-5)
• EPA Substance Registry System: 1-(2-hydroxy-4,6-bis(methoxymethoxy)phenyl)-3-(3-methoxy-4-(methoxymethoxy)phenyl)prop-2-en-1-one(1290638-51-5)

Safety Data

• Hazardous Substances Data: 1290638-51-5(Hazardous Substances Data)

Upstream product

• 480-66-0 2,4,6-trihydroxyacetophenone 
• 5533-00-6 3-methoxy-4-methoxymethoxy-benzaldehyde 
• 65490-09-7 2'-hydroxy-4',6'-bis(methoxymethoxy)acetophenone 

Downstream Products

• 491-71-4 chrysoeriol 
• 446-71-9 (+/-)-homoeriodictyol 
• 25515-47-3 3-methoxy-4,2',4',6'-tetrahydroxychalcone 

Relevant articles and documents

Biological Properties and Absolute Configuration of Flavanones From Calceolaria thyrsiflora Graham

Flavanones (–)-(2S)-5,4’-dihydroxy-7-methoxyflavanone (1) and (–)-(2S)-5,3’,4’-trihydroxy-7-methoxyflavanone (2) were isolated from the extracts of Calceolaria thyrsiflora Graham, an endemic perennial small shrub growing in the central zone of Chile. The absolute configuration of these compounds was resolved by optical rotation experiments and in silico calculations. Three analogs (3, 4, and 5) were synthesized to do structure-activity relationships with the biological assays studied. Biological tests revealed that only flavanone 2 exhibited a moderate inhibitory activity against the methicillin-resistant strain S. aureus MRSA 97-77 (MIC value of 50 μg/ml). In addition, flavanone 2 showed a potent, selective, and competitive inhibition of 5-hLOX, which supports the traditional use of this plant as an anti-inflammatory in diseases of the respiratory tract. Also, 2 exhibited cytotoxic and selective effects against B16-F10 (8.07 ± 1.61 μM) but 4.6- and 17-fold lesser activity than etoposide and taxol.

Synthesis and antidiabetic activity of 5,7-dihydroxyflavonoids and analogs

In a study to evaluate the structural elements essential for the antidiabetic activity of flavonoids, we synthesized two series of flavonoids, 5,7-dihydroxyflavanones and 5,7-dihydroxyflavones. In a screening for potential antidiabetic activity, most of the flavonoids showed a remarkable in vitro activity, and compounds 1f, 2d, and 3c were significantly more effective than the positive control, metformin. The biological activity was mainly affected by structural modification at the ring B moiety of the flavonoid skeleton. The results suggest that 5,7-dihydroxyflavonoids can be considered as promising candidates in the development of new antidiabetic lead compounds. Copyright