3528-22-1

Basic information

• Product Name: 1H-Naphtho[2,1-b]pyran-1-one
• Synonyms: 1H-Naphtho[2,1-b]pyran-1-one
• CAS NO: 3528-22-1
• Molecular Formula: C₁₃H₈O₂
• Molecular Weight: 196.20142
• Mol File: 3528-22-1.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1H-Naphtho[2,1-b]pyran-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Naphtho[2,1-b]pyran-1-one(3528-22-1)
• EPA Substance Registry System: 1H-Naphtho[2,1-b]pyran-1-one(3528-22-1)

Safety Data

• Hazardous Substances Data: 3528-22-1(Hazardous Substances Data)

Usage

Appearance

Sweet odor and vanilla-like flavor

Occurrence

Commonly found in plants such as tonka beans, woodruff, and cinnamon

Uses

Perfumes, flavoring agent in food and beverages, precursor for the synthesis of pharmaceuticals

Medicinal properties

Anticancer, anti-inflammatory, and anticoagulant effects have been investigated

Safety concerns

High doses have been associated with liver toxicity, and its use in food has been restricted in some countries.

Upstream product

• 574-19-6 1-(2-hydroxy-1-naphthyl)ethan-1-one 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 135-19-3 β-naphthol 
• 14233-72-8 3-(naphthalen-2-yloxy)propanenitrile 
• 4707-36-2 2,3-dihydronaphtho[2,1-b]pyran-1-one 
• 109-94-4 formic acid ethyl ester 
• 99515-49-8 2-bromo-2,3-dihydro-1H-naphtho[2,1-b]pyran-1-one 

Downstream Products

• 133527-73-8 2-phenyl-benzo[f]chromen-1-one 

Relevant articles and documents

Acylation and palladium-mediated couplings of maltol, a biobased γ-pyrone

Maltol triflate 3 undergoes palladium-mediated carbon-carbon bond formation with styrene, boronic acids and alkynes. Benzyl ether 2 can be acylated. The acylation products can be readily converted into furo[3,2-b]pyranones.

Thallium(III) p-tosylate mediated oxidative rearrangement in substituted chromanones: A novel approach to the synthesis of substituted chromones and tetrahydroxanthones

On treatment with thallium(III) p-tosylate, subtituted chromanones undergo smooth dehydrogenation to afford substituted chromones while 2,2-dialkylchromanones undergo oxidative 2,3-alkyl migration to yield 2,3-dialkylchromones in high yields.The migratory aptitude of different alkyl groups with respect to methyl group has also been studied. 2-Spirochromanones undergo oxidative 2,3-alkyl migration to afford tetrahydroxanthones which on dehydrogenation with DDQ afford xanthones in good yields.

Dehydrogenation of Chromanones and Flavanones by 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ): A Facile Method for the Synthesis of Chromones and Flavones

-