1. Quinic acid
천연물약품화학연구실
석 사 2 기 장 성 완

2. contents ♠ Quinic acid ♠ Journal 1. Molecule 2. Helvetica Chimica Acta
3. Chemistry & Biodiversity
4. Bioorganic & Medicinal Chemistry
5. Food Chemistry
6. Journal of Natural Products

3. Quinic acid
Quinic acid is a cyclitol, a cyclic polyol, and a cyclohexane-
carboxylic acid.
a crystalline acid obtained from cinchona bark, coffee beans, and other plant products and made synthetically by hydrolysis of chlorogenic acid. Quinic acid is also implicated in the perceived acidity of coffee.
isolated for the first time in the 1800s by French pharmacist Nicolas Vauquelin and further reactions from this acid to synthesize other compounds were studied by German chemist E. Lautemann in 1863.
A medication for the treatment of influenza A and B strains called Tamiflu has been successfully developed and launched into the market

4. Quinic acid

5. 2. Helvetica Chimica Acta 3. Chemistry & Biodiversity
♠ Journal
1. Molecule
2. Helvetica Chimica Acta
3. Chemistry & Biodiversity
4. Bioorganic & Medicinal Chemistry
5. Food Chemistry
6. Journal of Natural Products

6. 왜히어리(조록나무과)

7. 아토피와
일광화상 치료
항암/항산화 활성 유용물질 연구활발

10. Helvetica Chimica Acta
황금퉁퉁마디(국화과)

13. Bathochromic shift 를 통해 ortho 치환 잔기, Caffeoyl 치환체 확인
MS로 caffeoyl moiety,
free caffeic acid 확인
2쌍의 이중선 - two (E)-olefinic proton
Aromatic region – ABX spin system
Quinic acid 특징 peak 확인
MeO peak 확인
치환체는 free quinic acid, chlorogenic acid의 NMR data로 비교

15. Chemistry & Biodiversity
국화과

18. 참나물

24. Food Chemistry
국화과

28. 2-4, 3-4 약한 NOE, 2-6, 3-6 강한 NOE
H4,H5,H6 – ax. H-2,3,6 – equi.

29. 물질의 항산화능은 벤젠링에
붙은 OH의 수만이 아닌
벤젠 어느 위치에 치환되어있는 지도 중요한 요소가 된다