1952-41-6

Basic information

• Product Name: 5,6-dehydrokawain
• Synonyms: 4-Methoxy-6-(2-phenylethenyl)-2H-pyran-2-one;4-Methoxy-6-(2-phenylvinyl)-2H-pyran-2-one;Desmethoxyangonin;2H-Pyran-2-one, 4-methoxy-6-(2-phenylethenyl)-
• CAS NO: 1952-41-6
• Molecular Formula: C₁₄H₁₂O₃
• Molecular Weight: 0
• Mol File: 1952-41-6.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 440°Cat760mmHg
• Flash Point: 188°C
• Appearance: /
• Density: 1.18g/cm³
• CAS DataBase Reference: 5,6-dehydrokawain(CAS DataBase Reference)
• NIST Chemistry Reference: 5,6-dehydrokawain(1952-41-6)
• EPA Substance Registry System: 5,6-dehydrokawain(1952-41-6)

Safety Data

• Hazardous Substances Data: 1952-41-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C14H12O3/c1-16-13-9-12(17-14(15)10-13)8-7-11-5-3-2-4-6-11/h2-10H,1H3/b8-7+

Upstream product

• 500-64-1 kawain 
• 100-52-7 benzaldehyde 
• 77037-53-7 4-methoxy-6-methyl-3-trimethylsilyl-2H-pyran-2-one 
• 771-03-9 3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one 
• 675-10-5 4-hydroxy-6-methyl-2-pyron 
• 672-89-9 4-methoxy-6-methyl-2H-pyran-2-one 
• 1007476-32-5 sodium ethyl acetylacetate enolate 
• 2082-94-2 4-hydroxy-6-<(E)-2-phenylethenyl>-2H-pyran-2-one 
• 77-78-1 dimethyl sulfate 
• 4192-77-2 ethyl cinnamate 
• 104-55-2 3-phenyl-propenal 
• 35471-25-1 ethyl γ-bromo-β-methoxy-cis-crotonate 
• 100374-50-3 6-trans-styryl-pyran-2,4-dione 
• 186581-53-3 diazomethane 

Downstream Products

• 2082-94-2 4-hydroxy-6-<(E)-2-phenylethenyl>-2H-pyran-2-one 
• 3155-51-9 7,8-dihydro-4-methoxy-6-styryl-2H-pyran-2-one 
• 2082-94-2 4-hydroxy-6-(2-phenylethenyl)-2H-pyran-2-one 
• 587-63-3 7,8-dihydrokawain 
• 138744-79-3 4-acetoxy-6-<(E)-2-phenylethenyl>-2H-pyran-2-one 

Relevant articles and documents

Linderapyrone: A Wnt signal inhibitor isolated from Lindera umbellata

Linderapyrone, a Wnt signal inhibitor was isolated from the methanolic extract of the stems and twigs of Lindera umbellata together with epi-(-)-linderol A. Linderapyrone inhibited TCF/β-catenin transcriptional activity that was evaluated using cell-based TOPFlash luciferase assay system. To evaluate the structure-activity relationship and mechanism, we synthesized linderapyrone and its derivatives from piperitone. As the results of further bioassay for synthesized compounds, we found both of pyrone and monoterpene moieties were necessary for inhibitory effect. cDNA microarray analysis in a linderapyrone derivative treated human colorectal cancer cells showed that this compound downregulates Wnt signaling pathway. Moreover, we successes to synthesize the derivative of linderapyrone that has stronger inhibitory effect than linderapyrone and ICG-001 (positive control).

Regioselective functionalization of pyrones: Facile synthesis of 6-styrylpyrones via KHMDS-mediated aldol condensation

Herein, we disclose our efforts directed toward the synthesis of the kavalactone-based natural product penstyrylpyrone and other related 4-OMe-2-pyrones possessing diverse substituents at the 3-, 5-, and 7-positions. Further, a facile approach to access 6-styrylpyrones via the KHMDS-mediated regioselective aldol condensation of 2-pyrones is described with moderate substrate scope and good to high yields (58–80%). The utility of this methodology was exemplified by the stereoselective construction of desmethoxyyangonin, asnipyrone A, and asnipyrone B.

Hispidine compound and application thereof

The invention relates to the technical field of synthetic medicine, in particular to a hispidine compound and pharmaceutical salt thereof, and application to the aspect of treating and preventing obesity and hyperlipemia. The hispidine compound can obviously inhibit the accumulation of triglyceride and total fat in the 3T3-L1 preadipocyte differentiation process; the inhibition effect is superiorto that of a positive control compound of jamaicin; no obvious cytotoxicity exists. In addition, a beta-lactam hispidine compound can also regulate and control the phosphorylation of transcription factors AMPK and ACC of fat metabolism and the SIRT1 expression quantity, and can regulate and control the expression quantity of transcription factors PPAR-gamma, SREBP-1c and FABP4 of the adipocyte differentiation. Therefore the medicine containing the hispidine compound and/or the pharmaceutical salt has good effects of inhibiting the adipocyte differentiation and reducing oil drops and triglyceride in the adipocyte; good development prospects are realized in the aspects of treating or preventing obesity and reducing the blood fat.