Applied Biological Chemistry

The Korean Society for Applied Biological Chemistry (한국응용생명화학회)
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Synthesis of Methyl 3-methyloctanoate, the Key Perfume Component of African Orchid Aerangis confusa

아프리카 난 Aerangis confusa의 향기성분 methyl 3-methyloctanoate의 합성

  • Kim, Hyun-Ok (Department of Microbiology, Kyungpook National University) ;
  • Kim, Young-Ju (Department of Microbiology, Kyungpook National University) ;
  • Kim, Bieong-Kil (Department of Microbiology, Kyungpook National University) ;
  • Seu, Young-Bae (Department of Microbiology, Kyungpook National University)
  • 김현옥 (경북대학교 생명공학부 미생물학과) ;
  • 김영주 (경북대학교 생명공학부 미생물학과) ;
  • 김병길 (경북대학교 생명공학부 미생물학과) ;
  • 서영배 (경북대학교 생명공학부 미생물학과)
  • Published : 2005.09.30
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Abstract

Synthesis of methyl 3-methyloctanoate, a perfume component isolated from African orchid Aerangis confusa (or Aerangis kirkii) was achieved starting from itaconic acid in 9 steps. Itaconic acid is one of the cheapest organic compounds which is the fermentation product of microorganism Asp. terreus. As the key intermediate, 2-methyl-1,4-butanediol 4-acetate was obtained through the enzymatic regioselective hydrolysis of 2-methyl-1,4-butanediol diacetate with lipase. After Grignard reaction and oxidation, 3-methyloctanoic acid was obtained and converted to the various corresponding scented esters with a variety of alkyl alcohols, and the resulting fragrancy esters are expected to be utilized as the aroma additive materials in cosmetics, drinks and foods.

Branched methyl group을 가지는 아프리카산 난(Aerangis confusa, Aerangis kirkii) 꽃의 천연향기성분인 methyl 3-methyloctanoate를 값싼 미생물 발효산물인 itaconic acid를 출발 물질로 하여 제조한 branched metyl group을 부분구조로 가지는 2-methyl-1,4-butandiol를 중간체로 하여 전 공정 9단계로 합성하였다. 최종 향기성분 metyl 3-methyloctanoate의 methyl ester대신 다양한 알킬 ester 화합물을 합성하여 그 향을 비교한 결과 서로 상이한 향 특성을 나타내므로 화장품이나 식품산업에 있어서 유용한 향료조성물의 첨가소재로 개발 가능하리라 사료된다.

Keywords

References

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