In a 500ml three-necked flask equipped with a stirrer, dropping funnel and thermometer, add 140ml formic acid and 56g urea-peroxide adduct, stir and dissolve. 28 g (0.17 mol) of 2-hexylcyclopentanone was added dropwise at room temperature, and the dropwise addition was completed in about 1 hour. 168 ml of water was added, and the layers were stirred and separated. The aqueous layer was extracted three times with 28 ml of toluene, and the organic Chemicalbook layers were combined. The toluene in the organic layer was distilled off under reduced pressure, and the temperature was controlled not to exceed 70° C. The residue was the crude product of butyl-undecalactone with a purity of 85% and a yield of 96%. The crude product was distilled with a vacuum thin film distillation device, at 128° C/1.4 kPa, and the distilled product was butyl-undecalactone, purity 98% ,yield 84%.
Undecanolactone has a sweet, fruity, milky, creamy, buttery, estery, waxy, coconut aroma and taste. It is the key ingredient for the special flavor of natural cream and can be used for flavoring soft drinks, candy, margarine, ice cream, cold and baked goods, etc.
Δ-Undecalactone has a creamy, peach-like aroma.
Colorless to light-yellow liquid; peachlike
odor. Soluble in 4–5 volumes of 60% alcohol; soluble
in benzyl alcohol, benzyl benzoate, and most fixed
oils. Combustible.
Reported found in coconut flavor, melon, blackberry, blueberry, heated butter, milk, milk powder, cream,
coconut meat and starfruit.
Perfumery, flavoring agent.
Undecanoic δ-lactone has been used as substrate to investigate the activities of stimulated and nonstimulated human serum paraoxonase (PON1) samples.
By intramolecular Cannizzaro-type rearrangement of 2-hexylglutaraldehyde.
ChEBI: 6-Hexyltetrahydro-2H-pyran-2-one is a delta-lactone.
Taste characteristics at 10 ppm: creamy, coconut, milky, creamy, lactonic and butter fat with a waxy, fruity
nuance.
Undecanoic δ-lactone has been found to be best substarte for good substrates for lactonase from Sulfolobus islandicus (SisLac).
