Glucovanillin

Glucovanillin is a glucoside of vanillin. It is the compound responsible for the primary flavor and aroma of vanilla, a widely used ingredient in food, beverages, and pharmaceutical products. Glucovanillin is found in the vanilla bean, and is converted to vanillin when the bean is fermented and cured.

Chemical Structure and Properties

Glucovanillin has a molecular formula of C14H18O8. It is a white to off-white crystalline powder with a characteristic aroma of vanilla. The compound is soluble in water and alcohol, but insoluble in ether and chloroform. Its melting point is 81-83°C.

Biosynthesis

Glucovanillin is biosynthesized in the vanilla bean through a process that involves several enzymes. The process begins with the conversion of phenylalanine to cinnamic acid by the enzyme phenylalanine ammonia-lyase. Cinnamic acid is then converted to p-coumaric acid by the enzyme cinnamate 4-hydroxylase. The next step involves the conversion of p-coumaric acid to ferulic acid by the enzyme 4-coumarate-CoA ligase. Finally, ferulic acid is converted to glucovanillin by the enzyme feruloyl-CoA 6'-hydroxylase.

Uses

Glucovanillin is used primarily as a flavoring agent in food and beverages. It is also used in the pharmaceutical industry as a flavoring agent in medicines. In addition, glucovanillin has been studied for its potential health benefits, including antioxidant, anti-inflammatory, and anticancer properties.

See Also

• Vanillin
• Vanilla
• Phenylalanine
• Cinnamic acid
• p-Coumaric acid
• Ferulic acid