The Constituents of Natural Butter Flavor and Synthesis of δ-Alkylvalerolactone

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  • KAMEOKA Hiromu
    Department of Applied Chemistry, Faculty of Science and Engineering, Kinki University
  • MASEKI Masayoshi
    Department of Applied Chemistry, Faculty of Science and Engineering, Kinki University
  • HIRAO Nenokichi
    Department of Applied Chemistry, Faculty of Science and Engineering, Kinki University

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Other Title
  • バターの香気成分とδ-アルキルバレロラクトンの合成
  • バター ノ コウキ セイブン ト デルタ-アルキルバレロラクトン ノ ゴウセイ

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The characteristic flavor of natural butter from Hokkaido was studied by means of standard methods. The natural butter was treated with 5% KOH-C2H5OH solution obtaining saponifiable matter. Authors found δ-n-propyl- (VIIIa), δ-n-butyl- (VIII), δ-n-amylvalerolactone (VIIIc) as its new flavor.<BR>δ-Alkylvalerolactone (VIII) was prepared from resorcin (I) as follows : ethyl-, allyl-, and crotylcyclohexane-2, 6-dione (IIIa, b, c) were prepared by reduction of I into dihydroresorcin (II) followed by ethylation, allylation and crotylation. The resulting IIIa, b, c were hydrolyzed by Ba (OH) 2 solution, to give 5-ketocaprylic, 5-keto-8-nonenoic and 5-keto-8-decenoic acid (IVa, b, c), thus IVa, b, c were esterified with ethanol, the resulting ethylester (Va, b, c) were reduced into oxy acid ester (VIIa, b, c) by Meerwein-Ponndorfs' method or catalytic reduction on palladium. VIIa, b, c were saponified with 5% KOH-C2H5OH solution then acidified with 10% H2SO4 solution thus obtaining WIIIa, b, c respectively.

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