97770-37-1

Basic information

• Product Name: 4H-1-Benzopyran-4-one, 3-(3,4-dimethoxyphenyl)-7,8-dihydroxy-
• CAS NO: 97770-37-1
• Molecular Formula: C17H14O6
• Molecular Weight: 314.295
• Mol File: 97770-37-1.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 4H-1-Benzopyran-4-one, 3-(3,4-dimethoxyphenyl)-7,8-dihydroxy-(CAS DataBase Reference)
• NIST Chemistry Reference: 4H-1-Benzopyran-4-one, 3-(3,4-dimethoxyphenyl)-7,8-dihydroxy-(97770-37-1)
• EPA Substance Registry System: 4H-1-Benzopyran-4-one, 3-(3,4-dimethoxyphenyl)-7,8-dihydroxy-(97770-37-1)

Safety Data

• Hazardous Substances Data: 97770-37-1(Hazardous Substances Data)

Upstream product

• 93435-58-6 1-(2,3,4-trihydroxyphenyl)-2-(3',4'-dimethoxyphenyl)ethanone 
• 68-12-2 N,N-dimethyl-formamide 
• 93-40-3 (3,4-Dimethoxyphenyl)acetic acid 
• 87-66-1 2-hydroxyresorcinol 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 

Downstream Products

• 94413-08-8 3',4'-dimethoxy-7,8-methylenedioxyisoflavone 
• 116718-16-2 3'-O-methylxanthocercin B 
• 116718-15-1 3'-O-methylxanthocercin A 
• 116718-14-0 3',4-di-O-methylxanthocercin B 
• 116718-11-7 3',4-di-O-methylxanthocercin A 
• 116718-17-3 di-O-acetyl-3'-O-methylxanthocercin B 

Relevant articles and documents

The effectiveness of synthetic methoxylated isoflavones in delivering to the skin and alleviating psoriasiform lesions via topical absorption

This study was conducted to appraise the possible potential of synthetic isoflavones (SIFs) on psoriasis treatment. A practical and easy-to-operate approach was employed in synthesizing a series of SIFs, considering that acquiring flavonoids from natural resources is usually expensive, time-consuming, and non-eco-friendly. Seven SIFs derived from daidzein were produced with differences in the location of the hydroxyl groups and degree of methoxylation. The in vitro and in vivo skin absorption of topically applied SIFs was estimated. Further, keratinocytes (HaCaT) were employed as the model to investigate the anti-inflammatory activity of the isoflavones. The lipophilicity was increased from SIF-1 to ?7. Noteworthily, there was a parabolic relationship between lipophilicity and skin absorption, with SIF-5 (4′,7-dihydroxyisoflavone, daidzein) and SIF-6 (7-hydroxy-3′,4′-dimethoxyisoflavone, cladrin) demonstrating the highest retention in pig skin. The methoxylated isoflavone SIF-5 showed the greatest permeation into barrier-deficient skin among the compounds tested, with a 6- and 8-fold increase after lipid and protein removal. The cell-based study exhibited the capability of SIFs to restrain the overexpressed IL-6, IL-8, and CXCL1 in stimulated HaCaT. The therapeutic index (TI) predicted the potential candidates of SIF-5 and SIF-6 for topical application to treat psoriatic inflammation. The imiquimod (IMQ)-driven psoriasiform murine model manifested the inhibition of hyperplasia and immune cell infiltration by topically administered SIF-5 and SIF-6. The epidermal thickness of IMQ-treated skin was decreased from 172 to 40 μm by both isoflavones. This effect was comparable with that of betamethasone, the positive control. The topical treatment of SIF-6 significantly reduced cytokine/chemokine upregulation by IMQ. The methoxylated isoflavone with dramatic anti-inflammatory activity is promising for the development of an antipsoriatic agent.

Oxidative dimerisation of isoflavones: Synthesis of kudzuisoflavone a and related compounds

Kudzuisoflavone-A was successfully synthesised via oxidative dimerisation of daidzein in the presence of cuprous chloride. Appropriately substituted isoflavones also undergo regioselective oxidative dimerisation when treated with thallium trifluoroacetate to give novel 6′,6′″-biisoflavones in good yield. A rationale for the regioselectivity is proposed.