Synthesis of the racemate and both enantiomers of massoilactone

Biosci Biotechnol Biochem. 2003 Oct;67(10):2210-4. doi: 10.1271/bbb.67.2210.

Abstract

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).

MeSH terms

  • Aldehydes / chemistry
  • Animals
  • Butter
  • Flavoring Agents / chemical synthesis*
  • Lactones / chemical synthesis*
  • Milk
  • Stereoisomerism

Substances

  • Aldehydes
  • Flavoring Agents
  • Lactones
  • Butter
  • n-hexanal