3155-51-9

Basic information

• Product Name: 7,8-dihydro-5,6-dehydrokawain
• Synonyms: 7,8-dihydro-5,6-dehydrokawain;4-Methoxy-6-(2-phenylethyl)-2H-pyran-2-one
• CAS NO: 3155-51-9
• Molecular Formula: C₁₄H₁₄O₃
• Molecular Weight: 230.25916
• Product Categories: Aromatics, Heterocycles, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 3155-51-9.mol
• Article Data: 2

Chemical Properties

• Melting Point: 98.5 °C
• Boiling Point: 415.2 °C at 760 mmHg
• Flash Point: 176.315 °C
• Appearance: /
• Density: 1.159 g/cm³
• Vapor Pressure: 4.2E-07mmHg at 25°C
• Refractive Index: 1.565
• Storage Temp.: Amber Vial, Refrigerator, Under inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly)
• Stability: Light Sensitive
• CAS DataBase Reference: 7,8-dihydro-5,6-dehydrokawain(CAS DataBase Reference)
• NIST Chemistry Reference: 7,8-dihydro-5,6-dehydrokawain(3155-51-9)
• EPA Substance Registry System: 7,8-dihydro-5,6-dehydrokawain(3155-51-9)

Safety Data

• Hazardous Substances Data: 3155-51-9(Hazardous Substances Data)

Usage

Uses

4-Methoxy-6-(2-phenylethyl)-2H-pyran-2-one is a Kawain (K145490) derivative that is known to exhibit antimalarial and antituberculosis activities. 4-Methoxy-6-(2-phenylethyl)-2H-pyran-2-one has been identified as a lead compound for the dual treatment of malaria and leishmaniasis.

InChI:InChI=1/C14H14O3/c1-16-13-9-12(17-14(15)10-13)8-7-11-5-3-2-4-6-11/h2-6,9-10H,7-8H2,1H3

Upstream product

• 100-52-7 benzaldehyde 
• 1952-41-6 4-methoxy-6-(2-phenylethenyl)-2H-pyran-2-one 
• 672-89-9 4-methoxy-6-methyl-2H-pyran-2-one 
• 100374-50-3 6-trans-styryl-pyran-2,4-dione 
• 186581-53-3 diazomethane 
• 100397-04-4 6-phenethyl-pyran-2,4-dione 

Downstream Products

• 33253-32-6 4-Hydroxy-6-phenethyl-2-pyrone 

Relevant articles and documents

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.