Synthesis of the racemate and both enantiomers of massoilactone.
A simple and efficient synthesis of (+/-)-massoilactone (1) as a key substance for the butter and milk flavor was accomplished from n-hexanal in only a few steps. Application of its racemic synthesis enabled natural (R)-(-)- and unnatural (S)-(+)-massoilactone (1a, 1b) to be synthesized by starting from commercially available (R)-(+)-1,2-epoxyheptane (5).
Ishikawa
Masashi
M
Technical Research Center, T. Hasegawa Co., Ltd., Kariyado, Kawasaki, Japan.
Amaike
Masayasu
M
Itoh
Masamichi
M
Warita
Yasuhiro
Y
Kitahara
Takeshi
T
D000447:Aldehydes / Q000737:chemistry; D000818:Animals; D002079:Butter; D005421:Flavoring Agents / Q000138:chemical synthesis*; D007783:Lactones / Q000138:chemical synthesis*; D008892:Milk; D013237:Stereoisomerism
D000447:Aldehydes; D005421:Flavoring Agents; D007783:Lactones; D002079:Butter; C010463:n-hexanal