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.
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.
