5181. Isomaltol

Nomenclature

CAS number: 3420-59-5
1-(3-Hydroxy-2-furanyl)ethanone; 3-hydroxy-2-furyl methyl ketone.
C6H6O3; mol wt 126.11.
C 57.14%, H 4.80%, O 38.06%.

Description and references

Trace constituent of bread. Obtained by the action of enzymes on starch: Backe, Compt. Rend. 151, 78 (1910). Synthesis from α-lactose and a secondary amine: Hodge, Nelson, US 3054805 (1962 to USDA). Structure: Hodge, Nelson, Cereal Chem. 38, 207 (1961); Fischer, Hodge, J. Org. Chem. 29, 776 (1964).

Chemical structure

Properties

Crystals from water or ether, mp 98-103°. uv max (abs methanol): 280 nm (E1%1cm 1270). Sol in alcohols, acetone, chloroform, benzene, ethyl acetate, hot water. Practically insol in cold water and petr ether.

Derivative

Benzoate.
C13H10O4; mol wt 230.22.
C 67.82%, H 4.38%, O 27.80%.

Properties

Crystals from benzene-toluene, mp 100-101°.

Derivative

p-Nitrophenylhydrazone.
C12H11N3O4; mol wt 261.23.
C 55.17%, H 4.24%, N 16.09%, O 24.50%.

Properties

Deep red crystals from nitrobenzene, mp 100-101°.