87888-40-2

Basic information

• Product Name: 2H-Pyran-2-one, 6-[2-(3,4-dihydroxyphenyl)ethenyl]-4-hydroxy-
• Synonyms: 2H-Pyran-2-one,6-[2-(3,4-dihydroxyphenyl)ethenyl]-4-hydroxy;2-[2-(3,4-dihydroxyphenyl)ethenyl]-6-hydroxy-4h-pyran-4-one;2-[2-(3,4-dihydroxyphenyl)ethenyl]-6-hydroxypyran-4-one
• CAS NO: 87888-40-2
• Molecular Formula: C13H10O5
• Molecular Weight: 246.219
• Mol File: 87888-40-2.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 2H-Pyran-2-one, 6-[2-(3,4-dihydroxyphenyl)ethenyl]-4-hydroxy-(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-Pyran-2-one, 6-[2-(3,4-dihydroxyphenyl)ethenyl]-4-hydroxy-(87888-40-2)
• EPA Substance Registry System: 2H-Pyran-2-one, 6-[2-(3,4-dihydroxyphenyl)ethenyl]-4-hydroxy-(87888-40-2)

Safety Data

• Hazardous Substances Data: 87888-40-2(Hazardous Substances Data)

Upstream product

• 2082-94-2 4-hydroxy-6-<(E)-2-phenylethenyl>-2H-pyran-2-one 
• 13709-20-1 4-methoxy-6-(3',4'-dihydroxystyryl)-2-pyrone 
• 149947-22-8 4-methoxy-6-(3',4'-dihydroxystyryl)-2-pyrone 
• 94385-96-3 6-(3,4-bis-methoxymethoxy-styryl)-4-methoxymethoxy-pyran-2-one 
• 91716-13-1 4-(methoxymethoxy)-6-methyl-2H-pyran-2-one 
• 6515-06-6 3,4-bis-methoxymethoxy-benzaldehyde 
• 675-10-5 4-hydroxy-6-methyl-2-pyron 
• 56070-89-4 6-[2-(3,4-dimethoxyphenyl)ethenyl]-4-methoxy-2H-pyran-2-one 

Downstream Products

• 2743-14-8 4-methoxy-6-(2-(3,4-dimethoxyphenyl)ethenyl)-2H-pyran-2-one 

Relevant articles and documents

Total synthesis and structure activity relationship studies of phelligridins C and D, and phellifuropyranone A

α-Pyrone polyphenols, phelligridins C and D (meshimakobnols B and A), and phellifuropyranone A, isolated from a Japanese mushroom, are growth inhibitors of cancer cells. Herein, we report full details of the total synthesis of phelligridins C and D. The key reactions of the synthetic pathways were Pd catalyzed cross-coupling and aldol-type condensation. This strategy also enabled the total synthesis of phellifuropyranone A and artificial analogs of phelligridins. Subsequent biological evaluation of these compounds clarified that the whole skeleton of phelligridin C and the catechol group of the left hand side are essential for the cytotoxicity.

The Chemical Basis of Fungal Bioluminescence

Many species of fungi naturally produce light, a phenomenon known as bioluminescence, however, the fungal substrates used in the chemical reactions that produce light have not been reported. We identified the fungal compound luciferin 3-hydroxyhispidin, which is biosynthesized by oxidation of the precursor hispidin, a known fungal and plant secondary metabolite. The fungal luciferin does not share structural similarity with the other eight known luciferins. Furthermore, it was shown that 3-hydroxyhispidin leads to bioluminescence in extracts from four diverse genera of luminous fungi, thus suggesting a common biochemical mechanism for fungal bioluminescence.

A β-secretase (BACE1) inhibitor hispidin from the mycelial cultures of Phellinus linteus

In the course of screening for anti-dementia agents from natural products, a β-secretase (BACE1) inhibitor was isolated from the culture broth of Phellinus linteus and identified as hispidin. It showed an IC50 value of 4.9 × 10-6 M and a Ki value of 8.4 × 10 -6 M. The compound was a non-competitive inhibitor. Hispidin also inhibited a prolyl endopeptidase (IC50 = 1.6 × 10-5 M, Ki = 2.4 × 10-5 M), but it was less inhibitory to α-secretase (TACE) and other serine proteases such as chymotrypsin, trypsin, and elastase.