Chemical Properties
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clear colorless to light yellow oily liquid
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Chemical Properties
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5-Decanolide is a flavor constituent of many types of fruit, cheese, and other dairy products. It is a colorless, viscous liquid with a creamy-coconut, peach-like aroma.
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Chemical Properties
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δ-Decalactone has an oily, peach odor and taste.
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Occurrence
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Reported found in rum, coconut, raspberry, apricot, bilberry, peach, strawberry, Swiss cheese, other cheeses, butter, milk, milk powder, mutton fat, mango and nectarine.
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Uses
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Used in pharmaceutical preparations, feed additive, flavorings agent. Also used by food and flavor industries for its coconut fragrance and taste. It is also used as a reagent in the synthesis of (±)-Massoilactone (M197600); a chemical component with antibacterial activity found in volatile oils.
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Preparation
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δ-Decalactone can be prepared by peracid oxidation of 2-pentylcyclopentanone. (R)-δ-decalactone is obtained in high optical purity by starting from (R)-2- pentylcyclopentanone . Hydrogenation or fermentation of massoia lactone is also a practicable method to produce this enantiomer.
A newer development for the preparation ofδ-decalactone describes a carboxylation of 1-nonen-4-ol with carbon mon oxide in the presence of a homogenous palladium catalyst in an aqueous system.
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Definition
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ChEBI: A delta-lactone that is 5-valerolactone substituted by a pentyl group at position 6.
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Aroma threshold values
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Detection: 100 ppb
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Taste threshold values
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Taste characteristics at 2 ppm: waxy, coconut, lactonic, fatty, creamy, nutty and fruity.
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Synthesis Reference(s)
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The Journal of Organic Chemistry, 55, p. 462, 1990
DOI:
10.1021/jo00289a016
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General Description
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Measurement of optical rotatory dispersion and circular dichroism of (+) 5-decanolide (tetrahydro-6-pentyl-2
H
-pyran-2-one) has been reported.
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Chemical Synthesis
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From hexylethylene oxide and sodium malonic ester; also from decanoic acid.
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