21554-71-2

Basic information

• Product Name: 4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-3-(4-hydroxyphenyl)-
• Synonyms: 4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-3-(4-hydroxyphenyl)-
• CAS NO: 21554-71-2
• Molecular Formula: C₁₅H₁₂O₅
• Molecular Weight: 272.25278
• Mol File: 21554-71-2.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 577.9±50.0 °C(Predicted)
• Appearance: /
• Density: 1.485±0.06 g/cm3(Predicted)
• PKA: 7.52±0.40(Predicted)
• CAS DataBase Reference: 4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-3-(4-hydroxyphenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-3-(4-hydroxyphenyl)-(21554-71-2)
• EPA Substance Registry System: 4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-3-(4-hydroxyphenyl)-(21554-71-2)

Safety Data

• Hazardous Substances Data: 21554-71-2(Hazardous Substances Data)

Usage

Description

4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-3-(4-hydroxyphenyl)-, also known as Dihydrogenistein, is a hydroxyisoflavanone derivative of Genistein (G350000). It is characterized by its chemical structure, which includes three hydroxy substituents at positions 5, 7, and 4'. 4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-3-(4-hydroxyphenyl)has been found to exhibit specific inhibitory activity against tyrosine kinases, including the autophosphorylation of epidermal growth factor receptor kinase.

Uses

Used in Pharmaceutical Industry:
Dihydrogenistein is used as a pharmaceutical agent for its specific inhibitory activity against tyrosine kinases. This property makes it a potential candidate for the development of treatments targeting various diseases and conditions related to the dysregulation of these enzymes.
Used in Cancer Research:
In cancer research, Dihydrogenistein is used as a compound with potential therapeutic applications. Its ability to inhibit tyrosine kinases, particularly the autophosphorylation of epidermal growth factor receptor kinase, suggests that it may play a role in the development of targeted cancer therapies.
Used in Drug Development:
Dihydrogenistein is utilized in drug development as a starting point for the creation of new compounds with improved pharmacological properties. Its unique chemical structure and biological activity make it a valuable tool for researchers working on the design and synthesis of novel therapeutic agents.

Upstream product

• 446-72-0 5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on 

Relevant articles and documents

Dietary phytoestrogens and their synthetic structural analogues as calcium channel blockers in human platelets.

Phytoestrogens have been shown to inhibit platelet activation by blocking platelet calcium channels. This study examined the effect of several synthetic derivatives of trans-resveratrol, genistein, and daidzein on platelet free intracellular calcium ([Ca2+]i) elevation in thrombin-activated platelets and the possible mechanisms of this inhibitory effect. Studies were conducted on fresh human platelets from healthy volunteers. The fluorescent dye fura-2 was used to monitor [Ca2+]i in platelets. At 10 microM-resveratrol, triacetyl-trans-resveratrol, and trimethoxy-trans-resveratrol produced, respectively, 57 +/- 4%, 40 +/- 4%, and 21 +/- 1% inhibition; genistein, acetylgenistein, and dihydrogenistein produced 51 +/- 10%, 26 +/- 7%, and 16 +/- 2% inhibition, respectively; daidzein and diacetyldaidzein produced 56 +/- 5% and 45 +/- 10% inhibition of thrombin-induced [Ca2+]i elevation. The inhibitory effect was immediate and appeared to directly affect the calcium influx channels. Phytoestrogen action on [Ca2+]i did not cause alteration in nitric oxide signaling. Tyrosine phosphorylation was not involved in the inhibition of [Ca2+]i elevation by phytoestrogens, because the percent inhibition produced by the tyrosine kinase inhibitor genistein and its inactive analogue daidzein on thrombin-induced and thapsigargin-induced [Ca2+]i elevation was not significantly different for either compound at any concentration tested. Structure-activity relationship studies on this limited set of compounds reveal the requirements for the stilbene pharmacophore for the calcium-blocking activity.

Isoflavanones from the heartwood of Swartzia polyphylla and their antibacterial activity against cariogenic bacteria

The methanolic extract of Swartzia polyphylla DC. heartwood had antibacterial activity against cariogenic bacteria, the mutans Streptococci. The chromatographic purification of the extract afforded seven flavonoids. Among them, three known isoflavanones, dihydrobiochanin A, ferreirin and darbergioidin, and one new isoflavanone, 5,2',4'-trihydroxy-7-methoxyisoflavanone (dihydrocajanin) had potent antibacterial activity against cariogenic bacteria. This effect was not detected on isoflavone derivatives. A comparative antibacterial study of various flavonoids was further performed, and their structure-activity relationship was discussed.

NADPH: BIOCHANIN A OXIDOREDUCTASE FROM THE FUNGUS FUSARIUM JAVANICUM

A soluble enzyme which catalyses the NADPH-dependent reduction of the heterocyclic double bond of the isoflavone biochanin A (5,7-dihydroxy-4'-methoxy-isoflavone) yielding the corresponding isoflavanone was isolated from the fungus Fusarium javanicum.The NADPH: biochanin A oxidoreductase was constitutively present in the mycelium with an extractable average activity of 4 pkat/g fresh weight.The enzyme was purified ca 4500 fold to apparent homogeneity.The native enzyme had Mr of ca 87000 and consisted of two identical subunits of Mr 43000.The enzyme reaction showed a pH-optimum at pH 7.5 and a temperature optimum between 30 and 35 deg.The apparent Km values were 43 μM for biochanin A and 190 μM for NADPH with a maximum velocity of 4 mkat/kg protein.The enzyme exhibited a remarkable substrate specificity for biochanin A. - Key Word Index: Fusarium javanicum; Hyphomycetes; NADPH: biochanin A oxidoreductase; isoflvone metabolism; biochanin A.