489-53-2

Basic information

• Product Name: 7-Methoxy-8-(3,3-dimethylglycidyl)-2H-1-benzopyran-2-one
• Synonyms: 7-Methoxy-8-(3,3-dimethylglycidyl)-2H-1-benzopyran-2-one;8-[(3,3-Dimethyloxiranyl)methyl]-7-methoxy-2H-1-benzopyran-2-one;Aurapten【C15H16O4】;Merangin
• CAS NO: 489-53-2
• Molecular Formula: C15H16 O4
• Molecular Weight: 260.29
• Mol File: 489-53-2.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 7-Methoxy-8-(3,3-dimethylglycidyl)-2H-1-benzopyran-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 7-Methoxy-8-(3,3-dimethylglycidyl)-2H-1-benzopyran-2-one(489-53-2)
• EPA Substance Registry System: 7-Methoxy-8-(3,3-dimethylglycidyl)-2H-1-benzopyran-2-one(489-53-2)

Safety Data

• Hazardous Substances Data: 489-53-2(Hazardous Substances Data)

Upstream product

• 484-12-8 osthole 
• 124555-69-7 8-(2-bromo-3-hydroxy-3-methylbutyl)-7-methoxycoumarin 

Downstream Products

• 5980-07-4 7-Methoxy-8-(2'-formyl-2'-methylpropyl)coumarin 
• 1088-17-1 isomeranzin 
• 5673-37-0 7-methoxy-8-(2',3'-dihydroxy-3'-methylbutyl)coumarin 
• 93525-01-0 7-Methoxy-8-(2'-trifluoracetoxy-3'-hydroxy-3'-methylbutyl)coumarin 
• 51559-35-4 2'-hydroxylisoosthole 
• 93525-00-9 Auraptenol acetate 
• 93524-99-3 7-Methoxy-8-(2'-chloro-3'-hydroxy-3'-methylbutyl)coumarin 

Relevant articles and documents

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TASTE MODIFYING COMPOUND

The present invention relates to the use of Formula (I) where Y represents * denoting the point at which the moiety bonds to the bicyclic ring, in any one of its stereoisomenc forms or mixtures thereof to confer, enhance, impart and/or modify the tingling sensation.

Side-chain bromination of osthol using N-bromosuccinimide and some related reactions

Osthol when treated with N-bromosuccinimide under free radical conditions gives 8-(3-bromomethyl-2-butenyl)-7-methoxycoumarin (2), whereas under ionic conditions the product obtained is 8-(2-bromo-3-hydroxy-3-methylbutyl)-7-methoxycoumarin (5) which on reaction with sodium borohydride affords osthol epoxide (7) (meranzin).The epoxide 7 is converted back into the bromohydrin 5 by the action of HBr in dioxane and to 8-(2-amino-3-hydroxy-3-methylbutyl)-7-methoxycoumarin (8) by the action of ammonia.