85613-04-3

Basic information

• Product Name: 4H-Pyran-4-one, 2,3-dihydro-2-[(1E)-2-phenylethenyl]-
• CAS NO: 85613-04-3
• Molecular Formula: C13H12O2
• Molecular Weight: 200.237
• Mol File: 85613-04-3.mol

Chemical Properties

• CAS DataBase Reference: 4H-Pyran-4-one, 2,3-dihydro-2-[(1E)-2-phenylethenyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: 4H-Pyran-4-one, 2,3-dihydro-2-[(1E)-2-phenylethenyl]-(85613-04-3)
• EPA Substance Registry System: 4H-Pyran-4-one, 2,3-dihydro-2-[(1E)-2-phenylethenyl]-(85613-04-3)

Safety Data

• Hazardous Substances Data: 85613-04-3(Hazardous Substances Data)

Upstream product

• 100-42-5 styrene 
• 82093-20-7 2-vinyl-2H-pyran-4(3H)-one 
• 54125-02-9 danishefsky's diene 
• 14371-10-9 (E)-3-phenylpropenal 
• 91879-81-1 (1E,6E)-1-Methoxy-7-phenyl-5-trimethylsilanyloxy-hepta-1,6-dien-3-one 
• 91879-80-0 (1E,6E)-5-hydroxy-1-methoxy-7-phenylhepta-1,6-dien-3-one 

Downstream Products

• 1380293-83-3 (E)-2-styryl-4H-pyran-4-one 
• 83095-28-7 (E)-4-Methoxy-1-[6-((E)-styryl)-4-trimethylsilanyloxy-5,6-dihydro-2H-pyran-2-yl]-but-3-en-2-one 

Relevant articles and documents

Synthesis of methoxylated goniothalamin, aza-goniothalamin and γ-pyrones and their in vitro evaluation against human cancer cells

The present work describes the preparation of three novel series of compounds based on the structure of goniothalamin, a natural styryl lactone which has been found to display cytotoxic and antiproliferative activities against a variety of cancer cell lines. A focused library of 29 novel goniothalamin analogues was prepared and evaluated against seven human cancer cell lines. While the γ-pyrones and the aza-goniothalamin analogues were less potent than the lead compound, 2,4-dimethoxy analogue 88 has shown to be more potent in vitro than goniothalamin against all cancer cell lines evaluated. Furthermore, it was more potent than doxorubicin against NCI-ADR/RES, OVCAR-03 and HT-29 while being less toxic to human keratinocytes (HaCat). The 3,5-dimethoxy analogue 90 and 2,4,5-trimethoxy analogue 92 also displayed promising antiproliferative activity when compared to goniothalamin (1). These results provide new elements for the design and synthesis of novel representatives of this family of natural compounds.

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