2,3-Dihydro-3,5-dihydroxy-6-methyl-4(H)-pyran-4-one

• CAT Number: M006945
• CAS Number: 28564-83-2
• Molecular Formula: C6H8O4
• Molecular Weight: 144.126
• Purity: ≥95%
• Synonyms: 2,3-Dihydro-3,5-dihydroxy-6-methyl-4(H)-pyran-4-one;2-Methyl-3,5-dihydroxy-5,6-dihydro-4H-pyran-4-one;3,5-Dihydroxy-2-methyl-5,6-dihydro-4H-pyran-4-one;4H-Pyran-4-one, 2,3-dihydro-3,5-dihydroxy-6-methyl-;Ccris 8144;Dnd-omi 70 nmol/l;3,5-dihydroxy-6-m
• Storage: -20°C
• Related CAS: 88140-27-6
• IUPAC Name: 3,5-dihydroxy-6-methyl-2,3-dihydropyran-4-one
• InChI: InChI=1S/C6H8O4/c1-3-5(8)6(9)4(7)2-10-3/h4,7-8H,2H2,1H3
• InChIKey: VOLMSPGWNYJHQQ-UHFFFAOYSA-N
• SMILES: CC1=C(C(=O)C(CO1)O)O

2,3-Dihydro-3,5-dihydroxy-6-methyl-4(H)-pyran-4-one (CAS 28564-83-2) is one of the Mallard reaction product with intense bitter and strong antioxidant activity. A study shows that it generated active oxygen species to cause DNA strand breaking and mutagenesis.

Reference

1.Li, He, et al. "Formation of 2, 3-dihydro-3, 5-Dihydroxy-6-Methyl-4 (H)-Pyran-4-One (DDMP) in glucose-amino acids Maillard reaction by dry-heating in comparison to wet-heating." LWT 105 (2019): 156-163.
2.Kim, Myong-Ock, and Werner Baltes. "On the role of 2, 3-dihydro-3, 5-dihydroxy-6-methyl-4 (H)-pyran-4-one in the Maillard reaction." Journal of Agricultural and Food Chemistry 44.1 (1996): 282-289.
3.Hiramoto, Kazuyuki, et al. "DNA strand-breaking activity and mutagenicity of 2, 3-dihydro-3, 5-dihydroxy-6-methyl-4H-pyran-4-one (DDMP), a Maillard reaction product of glucose and glycine." Mutation Research/Genetic Toxicology and Environmental Mutagenesis 395.1 (1997): 47-56.