132971-59-6

Basic information

• Product Name: cytogenin
• Synonyms: cytogenin
• CAS NO: 132971-59-6
• Molecular Formula: C11H10O5
• Molecular Weight: 222.195
• Mol File: 132971-59-6.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 482.1°Cat760mmHg
• Flash Point: 196°C
• Appearance: /
• Density: 1.423g/cm³
• Vapor Pressure: 4.17E-10mmHg at 25°C
• Refractive Index: 1.616
• CAS DataBase Reference: cytogenin(CAS DataBase Reference)
• NIST Chemistry Reference: cytogenin(132971-59-6)
• EPA Substance Registry System: cytogenin(132971-59-6)

Safety Data

• Hazardous Substances Data: 132971-59-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H10O5/c1-15-7-2-6-3-8(5-12)16-11(14)10(6)9(13)4-7/h2-4,12-13H,5H2,1H3

Upstream product

• 532394-23-3 5-hydroxy-7-methoxy-2,2-dimethyl-benzo[1,3]dioxin-4-one 
• 137571-73-4 5,7-dihydroxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one 
• 532394-17-5 7-methoxy-2,2-dimethyl-5-(trifluoromethylsulfonyloxy)benzo[1,3]dioxin-4-one 
• 83-30-7 acide 2,4,6-trihydroxybenzoique 
• 4778-99-8 2-carboxymethyl-4,6-dimethoxy-benzoic acid 
• 846003-78-9 3-chloromethyl-6,8-dimethoxyisocoumarin 
• 846003-80-3 6,8-dimethoxy-3-hydroxymethylisocoumarin 

Downstream Products

• 342906-16-5 8-t-butyldimethylsilyloxy-3-(1-benzyl-1-cyano-2-phenyl)ethyl-6-methoxy-1-oxo-1H-2-benzopyran 
• 342906-14-3 8-t-butyldimethylsilyloxy-3-(1-cyano-2-phenyl)ethyl-6-methoxy-1-oxo-1H-2-benzopyran 
• 181427-78-1 NM-3 
• 39051-96-2 6-Methoxy-8-hydroxy-isocumarin-3-carbonsaeure 

Relevant articles and documents

A facile synthesis of cytogenin (8-hydroxy-3-hydroxymethyl-6- methoxyisocoumarin)

A facile and straightforward synthesis of cytogenin 1 (8-hydroxy-3- hydroxymethyl-6-methoxyisocoumarin) metabolite of Streptoverticillium eurocidicum and Certocystis fimbriata has been achieved. Condensation of chloroacetyl chloride with 3,5-dimethoxyhomophthalic acid 2 directly furnished 3-chloromethyl-6,8-dimethoxyisocoumarin 3 which was hydrolyzed to 6,8-dimethoxy-3-hydroxymethylisocoumarin 4 using 0.05% aqueous sodium hydroxide in THE Regioselective demethylation of 4 yielded cytogenin 1. In model experiments, 3-chloromethylisocoumarin was prepared and converted into 3-hydroxymethyl isocoumarin.

Gold(I)-Catalyzed Cyclization for the Synthesis of 8-Hydroxy-3- substituted Isocoumarins: Total Synthesis of Exserolide F

A highly regioselective gold(I)-catalyzed 6-endo-dig cyclization of 2,2-dimethyl-5-(alkynyl)-4H-benzo[d][1,3]dioxin-4-ones for the synthesis of 8-hydroxy-3-substituted isocoumarins is described. Key features of the reaction include the broad substrate scope, scalability, and tolerance for protecting groups. The synthetic utility of this novel method is demonstrated by the first total synthesis of exserolide F, an isocoumarin-containing polyol natural product.