56070-89-4

Basic information

• Product Name: 6-(3,4-DIHYDROXYSTYRL)-4-HYDROXY-2-PYRONE
• Synonyms: 6-(3,4-DIHYDROXYSTYRL)-4-HYDROXY-2-PYRONE;HISPIDIN;6-[(1E)-2-(3,4-Dimethoxyphenyl)ethenyl]-4-methoxy-2H-pyran-2-one
• CAS NO: 56070-89-4
• Molecular Formula: C₁₆H₁₆O₅
• Molecular Weight: 288.29524
• Mol File: 56070-89-4.mol
• Article Data: 7

Chemical Properties

• Appearance: yellow to brown/solid
• Storage Temp.: −20°C
• Solubility: DMSO: >10 mg/mL
• CAS DataBase Reference: 6-(3,4-DIHYDROXYSTYRL)-4-HYDROXY-2-PYRONE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-(3,4-DIHYDROXYSTYRL)-4-HYDROXY-2-PYRONE(56070-89-4)
• EPA Substance Registry System: 6-(3,4-DIHYDROXYSTYRL)-4-HYDROXY-2-PYRONE(56070-89-4)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 56070-89-4(Hazardous Substances Data)

Upstream product

• 186581-53-3 diazomethane 
• 87888-40-2 hispidin 
• 1334928-11-8 4-methoxy-6-vinyl-2H-pyran-2-one 
• 771-03-9 3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one 
• 56070-85-0 4-methoxy-2-oxo-2H-pyran-6-carboxaldehyde 
• 672-89-9 4-methoxy-6-methyl-2H-pyran-2-one 
• 675-10-5 4-hydroxy-6-methyl-2-pyron 
• 120-14-9 3,4-dimethoxy-benzaldehyde 

Downstream Products

• 93006-94-1 6-[2-(3,4-dimethoxyphenyl)ethyl]-4-methoxy-2H-pyran-2-one 
• 194160-43-5 6,6'-(2,4-bis(3,4-dimethoxyphenyl)cyclobutane-1,3-diyl)bis(4-methoxy-2H-pyran-2-one) 
• 87888-40-2 6-[2-(3,4-dihydroxyphenyl)ethenyl]-4-hydroxy-2H-pyran-2-one 

Relevant articles and documents

P21-ACTIVATED KINASE INHIBITOR

The present invention addresses the problem of providing an inhibitor which has an excellent inhibitory activity on a p21-activated kinase. The present invention, by which has been solved the above-mentioned problem, is a p21-activated kinase 1 inhibitor containing, as an active ingredient, one or more compounds selected from the group consisting of dehydrokawain compounds, derivatives of dehydrokawain compounds, mimosine, derivatives of mimosine, and cucurbitacin compounds.

Potassium fluoride-barium oxide catalysis in an easy and efficient synthesis of methysticin from piperonal under microwave irradiation

Condensation of compounds containing active methylene group with aromatic aldehyde (piperonal) in the presence of BaO on KF without a solvent under microwave irradiation is an efficient synthetic approach to methysticin and derivatives of kavalactones (4-methoxy-6-styryl-pyran-2-ones).

Synthesis and antimalarial and antituberculosis activities of a series of natural and unnatural 4-methoxy-6-styryl-pyran-2-ones, dihydro analogues and photo-dimers

Previous studies have identified the 3,6-dialkyl-4-hydroxy-pyran-2-one marine microbial metabolites pseudopyronines A and B to be modest growth inhibitors of Mycobacterium tuberculosis and a range of tropical diseases including Plasmodium falciparum and Leishmania donovani. In an effort to expand the structure-activity relationship of this compound class towards infectious diseases, a library of natural product and natural product-like 4-methoxy-6-styryl-pyran-2-ones and a subset of catalytically reduced examples were synthesized. In addition, the photochemical reactivity of several of the 4-methoxy-6-styryl-pyran-2-ones were investigated yielding head-to-head and head-to-tail cyclobutane dimers as well as examples of asymmetric aniba-dimer A-type dimers. All compounds were evaluated for cytotoxicity and activity against M. tuberculosis, P. falciparum, L. donovani, Trypanosoma brucei rhodesiense and Trypanosoma cruzi. Of the styryl-pyranones, natural product 3 and non-natural styrene and naphthalene substituted examples 13, 18, 21, 22 and 23 exhibited antimalarial activity (IC50 10. Δ7 Dihydro analogues were typically less active or lacked selectivity. Head-to-head and head-to-tail photodimers 5 and 34 exhibited moderate IC50s of 2.3 to 17 μM towards several of the parasitic organisms, while the aniba-dimer-type asymmetric dimers 31 and 33 were identified as being moderately active towards P. falciparum (IC50 1.5 and 1.7 μM) with good selectivity (SI ～80). The 4-tert-butyl aniba-dimer A analogue 33 also exhibited activity towards L. donovani (IC50 4.5 μM), suggesting further elaboration of this latter scaffold could lead to the identification of new leads for the dual treatment of malaria and leishmaniasis.