The Identification of Methylcyclopentenolone and Other Compounds in Maple Sirup Flavor Extract

Abstract

SUMMARY A number of compounds in the flavor‐containing chloroform extract of maple sirup have been isolated and identified. A major constituent not previously isolated by gas chromatography was acetol. Other constituents present in lesser concentrations which have not previously been reported were acetoin, ethyl vanillate, syringoyl methyl ketone, and methyleyclopentenolone.

Some compounds formed during nonenzymic browning of orange powder

“…Diacetone alcohol, valencene, and methylcyclopentenolone were the remaining identified compounds. Methylcyclopentenolone had been reported previously as a flavor component of maple sirup (7) and also was found in coffee oil (8) but not in orange juice.…”

Flavor properties of compounds related to maltol and isomaltol

“…When 2-hydroxy-3-methyl-2-cyclopenten-l-one (Cyclotene, VII) was panel tested (Table II) at 1000 ppm, most people described the odor and taste as sweet, caramel-like with nuances of maple, nut, chocolate, and celery. This compound is the character impact note of maple syrup (Filipic et al, 1965) and is a well-known ingredient in walnut, maple, and IV.…”

Bio-based building blocks from 5-hydroxymethylfurfural via 1-hydroxyhexane-2,5-dione as intermediate

“…In contrast to acidic systems, intramolecular aldol condensation of HHD under basic conditions led to another cyclopentanone derivative: 2-hydroxy-3-methylcyclopent-2-enone (MCP, 15 ) 38,43,45. MCP is a known naturally occurring flavour ingredient in roasted coffee54 and maple syrup 55. On the basis of these properties it has found commercial use in the food industry as a flavouring agent.…”