Quinic acid

천연물약품화학연구실석 사 2 기 장 성 완

contents

♠ Quinic acid

♠ Journal

1. Molecule2. Helvetica Chimica Acta3. Chemistry & Biodiversity4. Bioorganic & Medicinal Chemistry5. Food Chemistry6. Journal of Natural Products

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 Nico-las 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

Quinic acid

♠ Journal

1. Molecule2. Helvetica Chimica Acta3. Chemistry & Biodiversity4. Bioorganic & Medicinal Chemistry5. Food Chemistry6. Journal of Natural Products

왜히어리 ( 조록나무과 )

아토피와일광화상 치료

항암 / 항산화 활성 유용물질 연구활발

HO COOH

OH

HO O

O

OH

OH

H3CO COOH

OH

HO O

O

OH

OH

HO COOH

HO

O

OH

O

OH

HO

Helvetica Chimica Acta 황금퉁퉁마디 ( 국화과 )

Bathochromic shift 를 통해 ortho 치환 잔기 , Caffeoyl 치환체 확인

MS 로 caffeoyl moiety, free caffeic acid 확인2 쌍의 이중선 - two (E)-olefinic protonAromatic region – ABX spin sys-tem

Quinic acid 특징 peak 확인

MeO peak 확인

치환체는 free quinic acid, chloro-genic acid 의 NMR data 로 비교

Chemistry & Biodiversity 국화과

참나물

Food Chemistry

국화과

2-4, 3-4 약한 NOE, 2-6, 3-6 강한 NOEH4,H5,H6 – ax. H-2,3,6 – equi.

물질의 항산화능은 벤젠링에 붙은 OH 의 수만이 아닌 벤젠 어느 위치에 치환되어있는 지도 중요한 요소가 된다