Volatile components of the thermal degradation of 2,5-dimethyl-4-hydroxy-3(2H)-furanone

• Published in: Journal of agricultural and food chemistry 1985-05, Vol.33 (3), p.446-448
• Main Authors: Shu, Chi Kuen, Mookherjee, Braja D, Ho, Chi Tang
• Format: Article
• Language: English
• Subjects: Aroma and flavouring agent industries; Biological and medical sciences; Food industries; Fundamental and applied biological sciences. Psychology
• ISSN: 0021-8561; 1520-5118
• DOI: 10.1021/jf00063a030

2,5-Dimethyl-4-hydroxy-3(2H)-furanone or DMHF has been described as being "burnt pineapple" like and the major "character impact" compound of pineapple flavor concentrate. 2,5-Dimethyl-4-hydroxy-3(2H)-furanone or DMHF was subjected to a roasting temperature of 160 degree C for 30 min in a closed system at various pH values (2.2, 5.1, and 7.1). The yield of the total volatiles generated decreased with increasing pH value, indicating that degradations occurred more readily at a lower pH. Generally, the volatiles identified were acyclic carbonyls and 3(2H)-furanone derivatives, with furanone production favored at the higher pH values. Formation of the described products implies that during thermal degradations in water, DMHF undergoes ring opening and hydrolysis first, then, by a retroaldolization, produces the primary degradations products which react in an intermolecular fashion to form the secondary products. Possible formation mechanisms for the products are postulated.