향신료 중 주요 향기성분의 거울상이성질체 조성비 분석과 마이크로캡슐 제조에 관한 연구

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This study was performed to provide industrial application data of volatile flavor compounds from spices, the isolation and identification of volatile flavor compounds from spices, screening of chiral flavor compounds from identified volatile flavor compounds exhibited characteristic spice note, confirmation of an enantiomeric composition of chiral flavor compound by MDGC method, and microencapsulation of characteristic spice note, which is green note, by molecular inclusion and coacervation.

I. Analysis of volatile flavor compounds of spices

To extract the volatile flavor components in spice, simultaneous steam distillation & Extraction SDE) and solid phase microextraction SPME) methods were carried out and compared. In these results, the optimal extraction method and analysis condition were established. The volatile compounds of spices (dried garlic, ginger, red pepper and Chinese pepper) were extracted by simultaneous steam distillation and extraction (SDE) method and identified with gas chro- matography/mass spectrometer (GC/MS) analysis.
A total of 48 compounds were identified in dried garlic and sulfur containing compounds were detected as the major compounds, and alcohols, aldehydes and esters were detected as minor compounds. Diallyl disulfide, diallyl trisulfide, 2-butyl-tetrahydrothiophene, allyl methyl disulfide, 2-allylthiopropionic acid, 3-vinyl-1,2-4H-dithiin, methyl propyl trisulfide were detected main components in dried garlic, and diallyl disulfide (38.80%), diallyl trisulfide (29.77%) were the major compounds. A total of 83 compounds were identified in dried ginger. α-Zingiberene (29.82%) and β-sesquiphellandrene (10.77%) were the major compounds and geranial, (Z,E)-α-farnesene, β-phellandene, β-bisabolene and camphene were detected as considerable amounts. A total of 71 compounds were identified in dried red pepper, and the major compounds were 2-methyl propanal, furfural, benzaldehyde, nerolidol, 4-hydroxy-β-ionone up to 4%. α-Cedrol, linalool, 3-methyl butanal were also detected. A total of 60 compounds were identified and quantified in dried Chinese pepper, and the major compounds were identified estragole, nonanoic acid, octanoic acid, octanal, hexanal, (E)-2- undecenal and sabinene. Among them, estragole (47.47%) was found as the predominantly abundant component of dreid Chinese pepper.

II. Analysis of chiral flavor compounds of spices

To evaluate enantiodifferentiation of chiral compounds in the previous analysis of volatile flavor components in spices, selected chiral compounds in volatile flavor constituents of dried garlic, ginger, red pepper and Chinese pepper were characterized by multidimensional gas chromato graphy/mass spectrometry (MDGC/MS).
Selected chiral compound in dried garlic was 2-propanol and that was detected by high enantiomeric purity (>99%) for (R)-enantiomer. α-Pinene and nerolidol in dried ginger were detected by high enantiomeric purity (>96%) for (S)-form, and β-pinene was detected only (R)-form. The enantiomeric composition of α-terpineol in dried ginger revealed 72.0% for (R)-form, and linalool and 4-terpineol showed mixtures of both enantiomers. (S)-Enantiomer was the major enantiomer of limonene in dried ginger having enatiomeric excess of 17.2%. Linalool in dried red pepper were determined mixtures of both enantiomer and nerolidol was detected only (S)-form. α-Pinene and nerolidol, and β-pinene and linalool which are chiral compounds in Chinese pepper were determined to be enantiomerically pure (>99%) for their (S)-form and (R)-form, respectively. The enantiomeric composition of limonene in Chinese pepper revealed 83.9% purity for the (S)-enantiomer, whereas (E)- and (Z)-rose oxides showed mixtures of both enantiomers. The enantiomeric excess (%) for citronellal was 22.6% with the (R)-enantiomer as major enantiomer. The enantiomeric composition of these compounds can be used as parameter for authenticity control of dried garlic, ginger, red pepper, and Chinese pepper.

III. Study on the Microencapsulation of Green note in Spices

Microcapsules of green note such as β-ionone, (Z)-3-hexenol, (E,Z)-2,6- nonadienal in spices were prepared by molecular inclusion and complex coacervation.
β-Ionone was complexed with α-cyclodextrin (αCD) and β-cyclodextrin (βCD) in the mole ratio 1:1 and 1:2 host:guest, and the complexes formed by co-precipitation were analyzed by FT-IR, SEM, DSC and TGA. Percent β-ionone included in the complex was also determined by hexane extraction and GC-MS analysis. The best condition of complex formation was 1:1 mole ratio of β-ionone:βCD. In this condition, flavor/CD complex prepared with (Z)-3-hexenol and (E,Z)-2,6-nonadienal and the release characteristics of flavoring materials in complex were evaluated. The release rate of flavor was considerably faster than those of encapsulated flavor. (Z)-3-Hexenol/CD complex were stable at 60℃ for 14 days.
Flavor microcapsules were prepared by complex coacervation between gelatin and arabic gum. Microcapsules were characterized by FT-IR, particle analyzer, optical microscopy, DSC and TGA according to hardening agent volume, emulsifier, stirring speed and core material amounts. It was found that addition of emulsifier result in threefold smaller microcapsule size. When the stirring speed and amounts of core material increased, the particle mean diameter was increased. Thermal profile of microcapsules by DSC and TGA analysis were stable under 80℃. Consequently, microencapsulation possibility of green note by molecular inculsion and compolex coacervation were confirmed.
Alternative Author(s)
Seo, Hye-Young
조선대학교 식품영양학과
일반대학원 식품영양학과
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Table Of Contents

Part Ⅰ. 향신료의 휘발성 향기성분 분석 1

제 1 장 서 론 2

제 2 장 재료 및 방법 6

제 1 절 실험재료 및 기기 6
1. 시료 6
2. 시약 6
3. 분석기기 6

제 2 절 휘발성 향기성분의 추출 및 분석조건 수립 8
1. 추출방법에 따른 휘발성 향기성분의 수율 및 특성 8
가. 연속수증기증류추출법 8
나. SPME법 9
2. 추출된 휘발성 향기성분의 분리 및 분석을 위한 최적의 기기분석 조건 수립
가. Gas chromatography 분석 10
나. Gas chromatograph-Mass spectrometer 분석 10

제 3 절 향신료의 휘발성 향기성분 분석 12
1. 휘발성 향기성분의 추출 12
2. 휘발성 향기성분의 확인 및 정량 분석 12
가. 머무름 지수의 수립 12
나. 휘발성 향기성분의 확인 13
다. 휘발성 향기성분의 정량 13

제 3 장 결과 및 고찰 15

제 1 절 휘발성 향기성분 분석 조건 수립 15
1. 휘발성 향기성분의 분석기기 조건 15
2. n-Alkane의 머무름 지수 15

제 2 절 향신료의 품종별 휘발성 향기성분 18
1. 건마늘의 휘발성 향기성분 18
2. 건생강의 휘발성 향기성분 26
3. 건고추의 휘발성 향기성분 35
4. 건산초의 휘발성 향기성분 42

제 4 장 요약 50

참고문헌 51

Part Ⅱ. 향신료 중 키랄성 향기성분의 거울상 이성질체
조성비에 관한 연구 58

제 1 장 서 론 59

제 2 장 재료 및 방법 61

제 1 절 실험재료 및 기기 61
1. 시료 61
2. 시약 61
3. 분석기기 61

제 2 절 키랄성 향기성분의 분석을 위한 MDGC/MS의 분석조건 63
1. 키랄성 화합물의 분리를 위한 최적의 column 선택 63
2. MDGC/MS에 의한 키랄화합물의 분석 63

제 3 장 결과 및 고찰 65

제 1 절 키랄성 향기성분의 분석 조건 수립 65
1. 키랄성 향기성분의 분리를 위한 최적의 column 선택 65
2. 키랄성 향기성분의 분리를 위한 cut time 설정 66

제 2 절 향신료에 함유된 키랄성 향기성분의 이성질체 조성비 분석 67
1. 건마늘에 함유된 키랄성 향기성분의 조성비 분석 67
2. 건생강에 함유된 키랄성 향기성분의 조성비 분석 71
3. 건고추에 함유된 키랄성 향기성분의 조성비 분석 77
4. 건산초에 함유된 키랄화합물의 조성비 분석 79

제 4 장 요 약 85

참고문헌 86

Part Ⅲ. 향신료 중 풀내음의 마이크로캡슐 제조에 관한 연구

제 1 장 서 론 92

제 2 장 재료 및 방법 98

제 1 절 실험재료 및 기기 98
1. 재료 및 시약 98
2. 분석기기 99

제 2 절 향기성분의 마이크로캡슐 제조 100
1. 분자포접법에 의한 향기성분의 마이크로캡슐 제조 100
가. Molecular inclusion complex 제조 조건 설정 100
나. 향기성분의 molecular inclusion complex 제조 100
2. 복합상분리법에 의한 향기성분의 마이크로캡슐 제조 102
가. 복합상분리법 조건 설정 102
나. 향기성분의 마이크로캡슐 제조 103

제 3 절 마이크로캡슐의 특성 분석 104
1. 적외선 분광분석 104
2. 마이크로캡슐의 형태 및 입도 분석 104
3. 마이크로캡슐의 열분석 104
4. 향기성분의 마이크로캡슐 효율 104
가. 분자포접법의 효율 104
나. 복합상분리법의 마이크로캡슐 효율 105
5. 마이크로캡슐의 방출특성 분석 106

제 3 장 결과 및 고찰 107

제 1 절 분자포접법에 의한 마이크로캡슐의 특성 107
1. Flavor/CD complex 형성의 확인 107
2. Flavor/CD complex의 표면형태 110
3. Flavor/CD complex의 열적특성 110
4. Flavor/CD complex의 포접효율 116
5. 심물질 종류에 따른 flavor/CD complex의 특성 117
가. FT-IR 분석 117
나. 표면형태 117
다. 포접효율 121
6. Flavor/CD complex의 방출특성 122

제 2 절 복합상분리법에 의한 마이크로캡슐의 제조 특성 124
1. FT-IR 분석 124
2. 마이크로캡슐의 형태 및 입도 분석 124
가. 경화제 첨가량에 따른 캡슐의 형태, 입도분포 및 크기 124
나. 계면활성제 첨가유무에 따른 형태, 입도분포 및 크기 130
다. 교반속도에 따른 형태, 입도분포 및 크기 132
라. 심물질 첨가량에 따른 입도분포 및 크기 134
3. 마이크로캡슐의 열적특성 137
4. 향기성분의 마이크로캡슐 효율 141
5. 심물질의 종류에 따른 마이크로캡슐의 특성 141
가. 입도분포 및 크기 141
가. 캡슐효율 141

제 4 장 요 약 144

참고문헌 145
서혜영. (2007). 향신료 중 주요 향기성분의 거울상이성질체 조성비 분석과 마이크로캡슐 제조에 관한 연구.
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