식품과학과산업특집 식품산업에서향미의역할 청국장과된장의휘발성향기성분데이터베이스 Compilation of volatile flavor compounds in Cheonggukjang and Doenjang 백형희 Hyung Hee Baek 단국대학교식품공학과 Depart

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1 식품과학과산업특집 식품산업에서향미의역할 청국장과된장의휘발성향기성분데이터베이스 Compilation of volatile flavor compounds in Cheonggukjang and Doenjang 백형희 Hyung Hee Baek 단국대학교식품공학과 Department of Food Engineering, Dankook University Abstract Volatile flavor compounds of cheonggukjang and doenjang, which are the most representative Korean soybean fermented foods, were compiled throughout literature review. Total of 225 and 404 volatile flavor compounds were found in cheonggukjang and doenjang, respectively. The most characteristic volatile flavor compounds in cheonggukjang are thought to be pyrazine compounds. In addition, acids, such as 2-methyl propanoic acid, butanoic acid, 2-methyl butanoic acid, and 3-methyl butanoic acid, contribute to aroma characteristics of cheonggukjang. On the other hand, ester compounds are the most predominant volatile flavor compounds in doenjang. Ninety six ester compounds were detected in doenjang while 22 ester compounds were identified in cheonggukjang. Pyrazine compounds and acids also play an important role in the flavor of doenjang. Compilation of volatile flavor compounds from cheonggukjang and doenjang will provide basic information to food industry to understand and improve aroma characteristics of cheonggukjang and doenjang. Keywords: volatile compounds, flavor, aroma, cheonggukjang, doenjang * Corresponding Author: Hyung Hee Baek Department of Food Engineering, Dankook University 119 Dandae-ro, Dongnam-gu, Cheonan, Chungnam 31116, Korea Tel: Fax: baek@dankook.ac.kr Received December 24, 2017; revised December 27, 2017; accepted December 27, 식품과학과산업 12 월호 (2017)

2 서론향미 (flavor) 란향 (aroma) 과맛 (taste) 으로이루어진매우복잡한감각이다. 또한시각, 청각, 텍스쳐 (texture) 나온도에의해서도영향을받는복합적인감각을말한다 (1). 멘톨 (menthol) 에의한청량감, 고추에의한매운맛과떪은맛 (astringent taste) 까지도넓은의미에서향미에포함된다. 하지만향미에가장큰영향을주는것은향기성분으로향미의 80% 는향에의해서, 20% 는맛에의해서좌우된다. 이처럼향미에있어서향의중요성으로인해향미연구는식품의휘발성향기성분 (volatile flavor compound) 에초점을맞추어왔다. 네덜란드의 TNO (Netherlands Organization for Applied Scientific Research) 는식품중에존재하는휘발성성분데이터베이스를제작하여책으로발간하였다. 1963년에 Volatile Compounds in Food- Qualitative Data 를시작으로 1982년에는 IOFI (International Organization of Flavor Industry) 후원으로 Volatile Compounds in Food-Quantitative Data 를간행했으며, 1996년 7차개정판이발간되었다. 식품중휘발성성분데이터는식품종류별, 조리형태별로세세히분류되어있으며, 휘발성성분은작용기별로정성및정량데이터가정리되어있다. 다양한식품에서 7,100개이상의휘발성성분이동정되어데이터베이스화되었으며 (1-4), 현재는 Triskelion에서 online으로서비스하고있다 (5). 한국전통식품의향미특성에대한연구는활발히이루어지고있으나한국전통식품의휘발성향기성분데이터베이스를작성하려는시도는아직이루어지지않고있다. 한국전통식품의향미특성을개선하기위한기초자료로서휘발성향기성분의데이터베이스작성은중요하다. 따라서본논문에서는한국전통식품의휘발성향기성분데이터베이스를작성하려는첫시도로써한국전통식품중특유 의향을가지고있는청국장과된장의휘발성향기성분데이터베이스를작성하고이를비교분석하여청국장과된장의독특한향미특성의차이를알아보고자하였다. 청국장과된장의휘발성향기성분데이터베이스작성을위해국내외에게재된청국장과된장의휘발성향기성분관련논문을 NDSL과 Scopus를통해검색하였다. 본결과는한국전통식품의향미특성을연구하는연구자들에게도움이될것으로생각한다. 본론 1. 청국장의휘발성향기성분청국장은단기발효방법으로제조되는대두발효식품으로전통적제조방법은삶은콩을볏짚으로발효시켜서제조하고있으며개량식은 Bacillus subtilis를이용하여발효하고있다. 청국장은 에서 2-4일동안발효를시키는데 (6,7), 발효기간동안단백질이 Bacillus subtilis가분비하는효소에의해분해된다. 청국장은건강기능성은우수하나특유의불쾌취로인해소비량이감소추세이며젊은세대가기피하고있는실정이다. 따라서청국장의불쾌취를저감화하려는연구가계속진행되고있다 (8). 청국장의휘발성향기성분에관해서 15편의논문을검토하였으며 (9-23), 그논문들을검토하여 Table 1에지금까지청국장에서동정된휘발성향기성분들을정리하였다. 청국장의휘발성향기성분은청국장발효방법에따라차이가있으며전통적인방식으로발효를한것과종균을접종시켜발효한것을구분하여 Table 1에나타내었다. 또한향기성분추출방법에따라서도동정된향기성분이차이가날수있기때문에향기성분추출방법도 Table 1에 25 Food Science and Industry (Vol.50 No.4)

3 특집 : 청국장과된장의휘발성향기성분데이터베이스 Table 1. Volatile flavor compounds of cheonggukjang Hydrocarbon Compound Aroma description method 2) Sample 3) Reference chloroform - - A a 9 1-ethoxy-1-methoxy ethane - - B f 21 ethoxy ethene - - C e 20 2-ethoxy propane - - C e 20 3-ethoxy-1-propene - - C e 20 2-methoxy pentane - - A d 18 5-methyl-3-hexane(?) 4) - - C c 16 4-methyl-3-hexane(?) - - C c 16 1H-indene - - A b 9, 13 3-methyl heptane - - C c 16 3,3,5-trimethyl heptane - - C c 16 2,2,6,6-tetramethyl heptane - - C c 16 octane - - C c 16 2,2-dimethyl octane - - C c 16 2,3,6-trimethyl octane - - C c 16 2,2,7,7-tetramethyl octane - - C c 16 2-octene - - C c 16 nonane - - A b 10 4-methyl nonane - - C c 16 decane - - A, C b, c 10, 16 2,2,6-trimethyl decane - - C c 16 dodecane - - A, D b 10, 23 tridecane - - D b 23 tetradecane - - C, D b, c 16, 23 pentadecane - - A, D b 10, 23 nonadecane - - A a 12 eicosane - - A a 12 tricosane - - A d 18 tetracosane - - A d 18 pentacosane(?) - - A a, b 10, 12 hexacosane(?) - - A b 10 heptacosane(?) - - A a, b 10, 12 octacosane(?) - - A a, b 10, 12 methyl benzene (toluene) - - A, C, D a, b, c 9, 13, 16, 23 ethyl benzene - - A a, b 9, 13 1,2-dimethylbenzene (o-xylene) - - A a, b 9, 13 styrene - 730* C, D b, e 20, 23 1-propenyl benzene - - A b 9 26 식품과학과산업 12 월호 (2017)

4 Alcohol Compound Aroma description method 2) Sample 3) Reference 2-ethenyloxy ethanol - - C e 20 1-propanol pungent 6,640-9,000 C e 20 2-propanol - - C e 20 ethanol ethanol-like 24, ,000 A, B, C, D a, b, d, e 10, 12, 14, 17, 19, 20, 23 2-propoxy ethanol - - C e 20 2-butanol - - C e 20 2-methyl-1-propanol (isobutanol) solvent-like 1,000 C c 16 2-methyl-1-butanol malty 320 A, C, D b, c 10, 16, 23 3-methyl-1-butanol (isoamyl alcohol) malty 250 1,810 A, C, D b, d, e 9, 11, 18, 20, 23 2-methyl-2-buten-1-ol - - A a, d 13, 18 3-methyl-2-buten-1-ol - - A b 9 1,2-butanediol - - A a 11 2,3-butanediol - - A a 12 2-methyl-3-pentanol - - A a 12 3-methyl-3-pentanol - - C e 20 1-pentanol - - A, C a, b, c 10, 11, 16 2-pentenol - - A a 11 1-hexanol green, flowery 50-2,500 A, B, C a, b, d, e 9, 13, 14, 17, 18, 20 3-hexanol - - A d 18 (Z)-3-hexen-1-ol leaf-like A, B a 11, 15 1-hexen-3-ol - - C e 20 cyclohexanol - - C e 20 2-methyl-2-hexanol - - A d 18 5-methyl-3-hexanol - - A d 18 1-heptanol - 3* A b 10 1-octanol * D d 23 3-octanol - - A d 18 1-octen-3-ol mushroom-like 1 A, C, D a, b, c, d 9, 11-13, 16, 18, 23 7-octen-4-ol - - A d 18 2-nonanol - - D b 23 2-furanmethanol (furfuryl alcohol) - - A a, b, d 9-13, 18 benzyl alcohol (benzenemethanol) - - A a, b 10, 11 2-phenylethanol (β-phenylethyl alcohol, benzeneethanol) honey-like, spicy 1,000 A, D a, b, d 9, 10, 13, 18, Food Science and Industry (Vol.50 No.4)

5 특집 : 청국장과된장의휘발성향기성분데이터베이스 Aldehyde Ketone Compound Aroma description method 2) Sample 3) Reference acetaldehyde pungent, fruit C c 16 2-methyl propanal (isobutanal) green, pungent C c 16 3-(methylthio) propanal (methional) potato-like D b 23 2-methyl butanal green, almond-like C, D b, c 16, 23 3-methyl butanal malty C, D b, c, e 16, 20, 23 pentanal pungent, almond-like C, D b, c, e 16, 20, 23 hexanal tallowy, leaf-like A, C, D b, c 10, 16, 23 heptanal fatty C, D b, e 20, 23 2-hexenal apple-like C e 20 2-heptenal fatty, almond-like C, D b, c 16, 23 (E)-2-octenal fatty, nutty 4 D b 23 nonanal tallowy, fruity 1-5 D b 23 decanal (E)-2-decenal orange skin-like, flowery tallowy, orange-like D b D b 23 (E,E)-2,4-heptadienal fatty - A d 18 2,4-decadienal deep-fried A, D b, d 10, 18, 23 benzaldehyde almond-like 350-3,500* A, C, D a, b, c, d, e 9-13, 16, 18, 20, 23 2-hydroxy-6-methyl benzaldehyde - - A a 9 2-furancarboxaldehyde (furfural) sweet 3,000 A, D a, b, d 9, 10, 12, 13, 18, 23 5-methyl-2-furancarboxaldehyde - - C e 20 2-phenylethanal (benzeneacetaldehyde) honey-like, flowery 4 A, D a, b, d 9, 13, 18, 23 tetradecanal - - D b 23 heliotropine (piperonal) - - A b 10 2-propanone (acetone) - - B, C, D a, b, c, d 2-butanone etheric 23,200-50,000 12, 14, 16, 17, 19, 23 C c, e 16, 20 3-hydroxy-2-butanone (acetoin) buttery 800-5,000 A, C, D a, b, e 12, 20, 23 3-methyl-2-butanone - - C e 20 3-hydroxy-3-methyl-2-butanone - - C e 20 2,3-butanedione (diacetyl) buttery 4-15 A, C a, b, c, e 10, 12, 16, 19, 20 2-pentanone - 70,000* A, C a, b, e 9, 13, 20 3-methyl-2-pentanone - - C e 식품과학과산업 12 월호 (2017)

6 Ketone Acid Ester Compound Aroma description method 2) Sample 3) Reference 2-hydroxy-3-pentanone - - A a 12 2-heptanone soapy, fruity A, C, D a, b, c 9, 16, 23 2-octanone 50* C e 20 3-octanone - 28* A, D b, d 9, 18, 23 2-nonanone fruity, soapy C e 20 decanone - - A d 18 2-tridecanone - - A d 18 5-tridecanone - - A d 18 2-tetradecanone - - A d 18 2-pentadecanone - - A d 18 6,10,14-trimethyl-2-pentadecanone - - A d 18 2-dodecanone - - A d 18 dihydro-2(3h)-furanone (γ-butyrolactone) - - C e 20 3-hydroxy-2-methyl-4H-pyran- 4-one (maltol) 2,3-dihydro-3,5-dihydroxy- 6-methyl-4H-pyran-4-one caramel-like 9,000-35,000 B, D b, f 21, B f 21 1-(2-hydroxy-5-methylphenyl) ethanone - - A d 18 1-(2,6,6)-trimethyl-2-buten- 1-one - - A a 12 4-hydroxy-3-methylacetophenone - - A d 18 acetic acid vinegar-like, pungent 22,000-50,000 C, D a, b, e 12, 19, 20, 22, 23 cyano acetic acid - - C e 20 ethanedioic acid - - C e 20 propanoic acid fruity, pungent 2,190-20,000 C e 20 2-methyl propanoic acid sweaty 50-8,100 A, D a 11, 12, 22 butanoic acid sweaty, rancid 50-2,150 A a, b 9, 10 2-methyl butanoic acid sweaty, sweet 50-6,600 B, D a, b, f 12, 21, 22, 23 3-methyl butanoic acid (isovaleric acid) sweaty 132-1,600 A, B, D b, f 9, 21, 23 pentanoic acid (valeric acid) sweaty 2,100 A a, b 10, 11 hexanoic acid (caproic acid) goat-like, sweaty 290-5,000 A b 10 heptanoic acid - - A b 10 octanoic acid (caprylic acid) sweaty 3,000 A b 9 hexadecanoic acid - - A b, d 10, 18 benzoic acid - - A b 10 methyl acetate - - C c 16 ethyl acetate solvent-like, fruity 5-19,900 A, D a, b 9, 13, 23 ethenyl acetate - - C e Food Science and Industry (Vol.50 No.4)

7 특집 : 청국장과된장의휘발성향기성분데이터베이스 Ester Pyrazine Pyrazine Compound Aroma description method 2) Sample 3) Reference ethyl propanoate fruity C e 20 ethyl 2-methylpropanoate fruity, sweet D b 23 ethyl 2-methylbutanoate fruity C e 20 ethyl 3-methylbutanoate fruity 0.20 C e 20 ethyl 2-methylbutenoate - - C e 20 hexyl formate - - C e 20 hexyl acetate fruity 2-5 A b 9 methyl benzeneacetate - - A b 9, 18 ethyl benzeneacetate (ethyl phenylacetate) fruity, sweet 650* A d 18 ethyl 4-heptenoate - - A d 18 ethyl tetradecanoate - - A d 18 methyl pentadecanoate - - A d 18 methyl hexadecanoate - - A d 18 ethyl hexadecanoate - >2000* A d 18 methyl heptadecanoate - - A d 18 methyl benzoate - - D b 23 ethyl heptadecanoate - - A d 18 2-phenylethyl acetate flowery, fruity 20 # A b 9 ethenyl acetate (vinyl acetate) - - B f 21 2-methyl pyrazine ,000* A, B, D a, b, d 2,3-dimethyl pyrazine - 2,500-35,000* A, B, D a, b, d 2,5-dimethyl pyrazine ,800* A, B, C, D a, b, d, e 2,6-dimethyl pyrazine ,000* A, B, C, D a, b, d 10, 13, 14, 15, 17, 23 10, 13, 14, 17, 18, , 17, 18, , 14, 15, 17, 19 methyl ethyl pyrazine - - A b 10 2-ethyl-5-methyl pyrazine - 100* A a, b 10, 13 2-ethyl-6-methyl pyrazine - - D b 23 2-ethyl-3,5-dimethylpyrazine potato-like A, D a, b, d 10, 11, 13, 18, 22 2-ethyl-3,6-dimethylpyrazine potato-like A a, b, d 10, 11, 18 5-ethyl-2,3-dimethyl pyrazine - - A a 9 3,5-diethyl-2-methyl pyrazine - - A a, b 9, 13 2,6-diethylpyrazine - - A d 18 trimethyl pyrazine potato-like, musty A, B, C, D a, b, d, e, f 9-11, 13-15, 17, 18, ethyl-3,5,6-trimethylpyrazine - - A, D a, b, d 11, 18, 22, 식품과학과산업 12 월호 (2017)

8 Pyrazine Nitrogen- containing compound Sulfur compound Phenol Furan Compound Aroma description method 2) Sample 3) Reference tetramethyl pyrazine - 1,000-10,000* A, B, C, D a, b, c, d, e 9-13, 15, 16, 18, 20, 22, 23 2-methyl-3-propylpyrazine - - A d 18 2-isoamyl-6-methylpyrazine - - A d 18 2-acetyl pyrazine roasty 62 A b 10 2-methylpyridine (2-picoline) - - A a, d 9, 13, 18 3-methylpyridine (3-picoline) - - A a 9 4-methylpyridine (4-picoline) - - A a 13 5-ethyl-2-methylpyridine - - A a 9, 13 4-methyl pyrimidine - - B a, d 14, 17 1H-pyrrole - 49,600* C e 20 2-acetyl pyrrole - 170,000* A b 10 2-formylpyrrole - - D b 23 Indole sweet, burnt 90 D b 23 1,2,6-trimethyl piperidine - - A a, d 9, 18 dimethyl disulfide cabbage-like A, C, D a, b, c, e 13, 16, 20, 23 dimethyl trisulfide sulfury 0.01 A, D b, d 18, 23 2-acetyl thiazole roasty, sulfury 10 D b 23 2,4,5-trimethyl thiazole earthy 50 A a, d 9, 13, 18 4,5-dimethyl-2-butyl thiazole - - A d 18 4,5-dimethyl-2-(2-methylpropyl) thiazole - - A d 18 3,5-dimethyl-1,2,4-trithiolane - - A d 18 2-methyl benzothiazole - - A d 18 phenol phenolic 5,900 A, D a, b, d 9-11, 13, 18, 23 4-vinylphenol - 10* A a 12 2-tert-butyl-4,5-dimethylphenol - - A a 13 2-(1,1-dimethylethyl)-4-methyl phenol - - A a, b 9, 13 2,4-bis(1,1-dimethylethyl) phenol - - A d 18 2-methoxyphenol (guaiacol) smoky, sweet A, D a, b, d 2-methoxy-4-(2-propenyl) phenol (eugenol) 4-ethyl-2-methoxy phenol (4-ethyl guaiacol) 2-methoxy-4-vinylphenol (4-vinyl guaiacol) 2-pentyl furan 9, 10, 12, 13, 18, 23 spicy, honey-like 6-30 A b 10 clove-like 50 A a, b, d 9, 18 clove-like A, D a, b, d 10, 12, 29 buttery, green beanlike 6 A, C, D a, b, c, d 9, 10, 12, 13, 16, 18, 23 2-heptyl furan - - D b 23 2-octyl furan - - D b Food Science and Industry (Vol.50 No.4)

9 특집 : 청국장과된장의휘발성향기성분데이터베이스 Furan Miscellaneous Compound Aroma description method 2) Sample 3) Reference 2-acetyl furan - 10,000* A b 10 2,3-dihydrobenzofuran - - A, D b, d 18, 23 2-furfuryl pyrrole - - A b 10 dibutyl phthalate - - A a, d 12, 18 limonene citrus-like B a, d 14, 17 α-pinene terpeny 6* C c 16 β-pinene terpeny 140* C c 16 ethylene carbonate - - B f 21 trimethyl oxazole - - A, C a, c, d, e 9, 13, 16, 18, 20 butylated hydroxytoluene - - A, B d, f 18, 21 2-methyl benzo quinoline - - C e 20 pentadecylamine - - C e 20 1-octanamine - - C e 20 pentamethyldisilane - - C e 20 (1-phenylethyl) trimethylsilane - - C e 20 N-(1-methylheptyl)-2-octanamine - - C e 20 ammonium oxalate - - C e 20 dimethylamine - - C e 20 butanamide - - C e 20 1-(trimethyl)-1H-indole-3- acetonitrile - - C e 20 2,4,5-trimethyl-3-oxazoline - - A a 13 1) Reference 24. * Orthonasal threshold in water (μg/l). # Retronasal threshold in water (μg/l). 2) A: SDE, B: solvent extraction, C: headspace method, D: solid phase microextraction (SPME). 3) a: cheonggukjang fermented with Bacillus sp., b: traditional cheonggukjang, c: commercial cheonggukjang powder, d: commercial cheonggukjang, e: cheonggukjang fermented with mixed culture of Bacillus natto and Bacillus licheniformis, f: not specified. 4) The identification is questionable. 명시하였다. 냄새특성과역치 (threshold) 는 Rychlik 등 (24) 의자료를참조하여함께정리하였다. 청국장의휘발성향기성분은총 225개가동정되었으며어떤휘발성향기성분은한편의논문에서만동정되고어떤휘발성향기성분은여러편의논문에서일관되게동정되고있는데여러편의논문에서동정된휘발성향기성분은동정의신뢰도와특징적향기성분으로서중요성이큰휘발성향기성 분으로생각된다. 작용기별로분류하여볼때탄화수소 (hydrocarbon) 가 38개동정되어가장많은갯수가동정되었다. 탄화수소는청국장제조방법과향기성분추출방법에상관없이동정되었지만톨루엔 (toluene) 을제외한대부분의탄화수소는특정논문에서만동정되어정확한동정이의문시된다. 많은경우에용매나기타요인에의한인공물 (artifact) 일가능성이높다고생각된 32 식품과학과산업 12 월호 (2017)

10 다. 탄화수소는역치가높기때문에대부분은청국장향에중요한역할을하지못할것으로생각된다. 알코올 (alcohol) 은에탄올 (ethanol), 2-메틸-1- 뷰탄올 (2-methyl-1-butanol), 3-메틸-1- 뷰탄올 [3-methyl-1-butanol, 아이소아밀알코올 (isoamyl alcohol), 1-펜탄올 (1-pentanol), 1-헥산올 (1-hexanol), 1-옥텐-3- 올 (1-octen-3-ol), 2- 퓨란메탄올 (2-furanmethanol) 및 2- 페닐에탄올 (2-phenyl ethanol) 등이여러편의논문에서동정되었다. 알데하이드 (aldehyde) 는 3-메틸뷰탄알 (3-methyl butanal), 펜탄알 (pentanal), 헥산알 (hexanal), 2,4- 데카다이엔알 (2,4-decadienal), 벤즈알데하이드 (benzaldehyde), 2- 퓨란카복스알데하이드 (2-furancarboxaldehyde) 및 2-페닐에탄알 (2-phenylethanal) 등이발효방법및향기성분추출방법에상관없이여러편의논문에서보고되고있다. 케톤 (ketone) 은 2-프로판온 (2-propanone), 3- 하이드록시-2-뷰탄온 [3-hydroxy-2-butanone, 아세토인 (acetoin)], 2,3- 뷰테인다이온 [2,3-butanedione, 다이아세틸 (diacetyl)], 2-헵탄온 (2-heptanone) 및 3- 옥탄온 (3-octanone) 등이청국장에서보고되고있다. 산 (acid) 중에는아세트산 (acetic acid), 2-메틸프로판산 (2-methyl propanoic acid), 뷰탄산 (butanoic acid), 2-메틸뷰탄산 (2-methyl butanoic acid), 펜탄산 (pentanoic acid) 등이여러편의논문에서일관되게보고되고있다. 특히, 2-메틸프로판산, 뷰탄산, 2-메틸뷰탄산및 3-메틸뷰탄산은다른산에비해낮은역치를가지고있으며불쾌한냄새특성을가지고있다. Park 등 (25) 은이러한산이청국장의특징적인냄새에중요한역할을한다고생각하고청국장에서발효기간에따른산의함량을 stable isotope dilution assay (SIDA) 법을이용하여정량하였다. 산의함량은발효후반으로갈수록증가하였으며, 분지산 (branched-chain acid) 의함량이직쇄산 (straight chain) 보다더높았다. 에스터 (ester) 화합물중에는아세트산에틸 (ethyl acetate) 만이여러편의논문에서동정된에스터화합물이었다. 청국장에서가장특징적인것은피라진 (pyrazine) 화합물이많이들어있는점이었다. 총 18개의피라진화합물이동정되었으며, 특히 2,5-다이메틸피라진 (2,5-dimethyl pyrazine), 트라이메틸피라진 (trimethyl pyrazine) 과테트라메틸피라진 (tetramethyl pyrazine) 은거의모든청국장논문에서보고되고있는휘발성향기성분이다. 피라진화합물의함량은청국장이된장보다 4.3배더많았다 (23). 질소함유화합물중에는 2-메틸피리딘 (2-methyl pyridine) 이여러편의논문에서동정된휘발성향기성분이었고, 황함유화합물중에는다이메틸다이설파이드 (dimethyl disulfide) 와 2,4,5-트라이메틸싸이아졸 (2,4,5-trimethyl thiazole) 이, 페놀 (phenol) 화합물중에는페놀, 2-메톡시페놀 (2-methoxyphenol, 구아이아콜, guaiacol), 2-메톡시-4-바이닐페놀 [2-methoxy-4-vinylphenol, 4-바이닐구아이아콜 (4-vinyl guaiacol)] 및 4-바이닐페놀 (4-vinylphenol) 이청국장의휘발성향기성분으로동정되었다. 퓨란 (furan) 은 2-펜틸퓨란 (2-pentyl furan) 이, 기타화합물로는트라이메틸옥사졸 (trimethyl oxazole) 이여러편의논문에서동정되었다. 2. 된장의휘발성향기성분된장은메주를사용해서만드는재래식된장과 Aspergillus oryzae 등의국균을사용하여만드는개량식된장으로나눌수있으며풍미증진을위해 Bacillus subtilis 균주를사용하기도한다 (6,7). 재래식된장은삶은콩을 1-2개월발효시켜메주를제조한후소금물을붓고숙성시킨후간장을걸러내서제조하며, 개량식된장은삶은쌀, 보리, 콩등에 Aspergillus oryzae를인위적으로접종하여 30 에서 3일간배양하여된장고지 (koji) 를만든후메주대신사용한다 (26). 재래식된장의고유풍미는 Bacillus subtilis에의해생성되는데개량식된장은 33 Food Science and Industry (Vol.50 No.4)

11 특집 : 청국장과된장의휘발성향기성분데이터베이스 Aspergillus oryzae만을사용하므로재래식된장의고유풍미가생성되지않는다 (27,30,33). 된장의휘발성향기성분에관해서는 15편의논문을검토하였으며 (23,26-39), Table 2에지금까지된장에서동정된휘발성향기성분들을정리하였다. 된장의휘발성향기성분은총 404개가동정되었는데, Ba 등 (23) 은된장과청국장의휘발성향기성분을비교한논문에서된장에서더많은개수의휘발성향기성분이동정되었으나휘발성향기성분의함량은청국장이더높았다고보고하였다. 알코올은에탄올, 2-메틸-1-프로판올 (2-methyl-1-propanol), 1-뷰탄올 (1-butanol), 2-메틸-1- 뷰탄올, 3-메틸-1-뷰탄올, 2,3-뷰테인다이올 (2,3 -butanediol), 1-헥산올, 3-옥탄올 (3-octanol), 1- 옥텐-3-올, 2-퓨란메탄올, 2-페닐에탄올및벤질알코올 (benzyl alcohol) 등이여러편의논문에서동정되었다. 된장에서동정된대부분의알코올은청국장에서도동정된화합물로알코올은된장과청국장에서큰차이를보이지않았다. 알코올은 1-옥텐-3-올을제외하고는대부분냄새역치가높아청국장과된장의향에크게기여하지못할것으로생각된다. 알데하이드는 2-메틸뷰탄알, 3-메틸뷰탄알, 헥산알, (E)-2-헵텐알[(E)-2-heptenal], 노난알 (nonanal), 벤즈알데하이드, 2-페닐-2-뷰텐알 (2-phenyl-2-butenal), 5-메틸-2-페닐-2-헥센알 (5-methyl-2-phenyl-2-hexenal), 알파-에틸리덴벤젠아세트알데하이드 (α-ethylidene benzeneacetaldehyde), 2-퓨란카복스알데하이드및 2-페닐에탄알 (2-phenylethanal) 등이여러편의논문에서보고되고있다. 케톤은 3-하이드록시-2-뷰탄온, 2-헵탄온, 3-옥탄온, 감마-노나락톤 (γ-nonalactone) 및말톨 (maltol) 등이보고되었다. 산은아세트산, 프로판산 (propanoic acid), 2-메틸프로판산, 뷰탄산, 2-메틸뷰탄산, 3-메틸뷰탄산, 펜탄산, 4-메틸펜탄산 (4-methyl pentanoic acid), 헥산산 (hexanoic acid), 헵탄산 (heptanoic acid), 옥탄산 (octanoic acid) 및페닐아세트산 (phenylacetic acid) 등이동정되었다. 청국장에서는 14개의산이동정되었으나된장에서는 29개의산이동정되었다. 된장에는청국장보다더많은종류의산이들어있어된장과청국장의향미차이에영향을줄것으로생각된다. Shukla 등 (40) 은전통된장의냄새에중요한역할을하는아세트산, 프로판산, 뷰탄산과 3-메틸뷰탄산을정량하였는데, 그양은각각 91.7, 70.1, 29.5 및 19.8 mg% 라하였다. 된장의휘발성향기성분에서가장특징적인것은에스터화합물이많다는것이었다. 청국장에서는 22개의에스터화합물이동정된반면, 된장에서는 96개의에스터화합물이동정되었다. 아세트산에틸, 뷰탄산에틸 (ethyl butanoate), 2-메틸뷰탄산에틸 (ethyl 2-methylbutanoate), 3-메틸뷰탄산에틸 (ethyl 3-methylbutanoate), 헥산산에틸 (ethyl hexanoate), 헵탄산에틸 (ethyl heptanoate), 옥탄산에틸 (ethyl octanoate) 등많은에스터화합물이된장에서동정되었다. 에스터화합물의종류및함량은된장의제조방법에따라차이가크며이는메주나고지의미생물상 (microflora) 의차이에기인한다 (29,32,33). 청국장에비해서월등히많은에스터화합물이된장에서동정되었으며이러한에스터화합물은향미특성뿐아니라낮은역치로인해청국장과된장의향미특성차이에중요한역할을할것으로생각된다. 총 15개의피라진화합물이된장에서동정되었으며 2-메틸피라진 (2-methyl pyrazine), 2,3-다이메틸피라진 (2,3-dimethylpyrazine), 2,5- 다이메틸피라진, 2,6- 다이메틸피라진 (2,6-dimethylpyrazine), 3-에틸-2,5-다이메틸피라진 (3-ethyl-2,5-dimethylpyrazine), 2,3,5- 트라이메틸-6- 에틸피라진 (2,3,5-trimethyl-6-ethylpyrazine), 트라이메틸피라진및테트라메틸피라진등이된장에서동정된주요휘발성향기성분이다. 된장에서동정된대부분의피라진화합물은 34 식품과학과산업 12 월호 (2017)

12 Table 2. Volatile flavor compounds of doenjang Hydrocarbon Compound name Aroma description method 2) Sample 3) Reference 1,1-diethoxy ethane - - A c 31 3-ethoxy-1-propene - - C b, c 26 2-methyl-3-propoxy-1-propene - - A e 30 1-ethoxybutane - - A c 31 2-methylpentene - - A c 28 5-butoxy-2-pentene - - A c 31 hexane - - D d 38 2,3-dimethylhexane - - A c 28 3-methyl-1-heptene - - A e 30 5-methyl-1-heptene - - A e 30 octane - - D b, d 34, 39 1-octene - - D d 32, 39 2-octene - - D b, d 34, 39 3-methyl-5-propylnonane - - A c 31 undecane - - D d 23 1-undecene - - D d 38 dodecane - - B, D b, d, f 23, 34, 39 1-dodecyne - - A c 27 5-dodecyne - - A e 30 tridecane - - B, D b, d, f 23, 34, 39 tetradecane - - B, D b, d 23, 34, 39 (E)-5-tetradecen-3-yne - - A c 27 pentadecane - - B, D d, f 23, 39 eicosane - - A c 31 3-eicosene - - A c 31 9-eicosene - - A c 31 1,2-diethyl cyclobutane - - B d 39 ethyl cyclopentane - - A c 28 cyclohexadecane - - A c 31 benzene - - D b, d 34, 38, 39 methyl benzene (toluene) - - B, C, D a, b, c, d, f 26, 34, 39 ethenyl benzene (styrene) - 730* B, D b, d, e, f 23, 34, 35, 37, 39 1,2-dimethyl benzene (o-xylene) - - B, C, D a, b, d, f 26, 34, 39 1,3-dimethyl benzene (m-xylene) - - B, D b, d, f 34, 39 1,4-dimethyl benzene (p-xylene) - - A, B, D b, c, d, f 31, 34, 39 ethylbenzene - - A, B, D b, c, d, f 31, 34, 39 1-ethyl-4-methylbenzene - - B, D d 39 1,2,4-trimethylbenzene - - B, D b, d, f 34, Food Science and Industry (Vol.50 No.4)

13 특집 : 청국장과된장의휘발성향기성분데이터베이스 Hydrocarbon Alcohol Compound name Aroma description method 2) Sample 3) Reference 1,3-bis(1,1-dimethylethyl)benzene - - B d, f 39 methoxybenzene (anisole) sweet, phenolic 50 A c 31 1,2-dimethoxybenzene - - A, B, D a, c, d, e 27, 29, 32, 37, 39 1,3-dimethoxybenzene - - A, D c, d, e 29, 32, 38 ethoxybenzene - - A c 31 1-ethyl-4-methoxybenzene - - A c 31 1-ethenyl-4-methoxy benzene - - A c 27 naphthalene - - A c 27, 31 1-methylnaphthalene - - A c 31 1-methylhexyl hydroperoxide - - A c 27 2-ethyl-3-methyl oxetane - - A b, c 27 tetrachloroethane - - A c 28 1,1-bis(2-methylpropyl)hydrazine - - C b 26 3-ethyl-2-methyl-1,3-hexadiene - - D d 23 methanol - - A c 31 ethanol ethanol-like 24, ,000 A, C, D a, b, c, d, e, f 23, 26, 27, 31, 32, (2-ethoxyethoxy) ethanol - - A e 29 1-propanol pungent 6,640-9,000 A, D c, d 23, 31 2-methyl-1-propanol solvent-like 1,000 A, D c, d, e 27, 29, 32, 37 2-methyl-2-propanol - - A c 31 1-methoxy-2-methyl-2-propanol - - A c 31 3-(methylthio)-1-propanol(methionol) potato-like 5# A, D b, c, e 29, 34 1-butanol fruity 500-1,280 A, C, D b, c, d, e 26, 27, 29, 32, butanol - - A c 27, 31 2-methyl-1-butanol malty 320 D a, d 23, 32, 38, 2-methyl-2-butanol A c 31 3-methyl-1-butanol (isoamyl alcohol) malty 250 1,810 A, C, D a, b, c, d, e, f 23, 26-30, 32-35, 37, 38 3-methoxy-2-butanol - - A c 28 2,2-dimethyl-1-butanol - - D d 32 1,3-butanediol - - A c 28 2,3-butanediol - - C, D a, b, c, d 26, 32, 36, 37 1-pentanol - - A b 27 2-pentanol - - A c 31 3-methyl-1-pentanol - - A c 27 4-methyl-1-pentanol - - A c, e 28, 식품과학과산업 12 월호 (2017)

14 Alcohol Aldehyde Compound name Aroma description method 2) Sample 3) Reference 3-penten-2-ol - - A c, e 29 2-methyl-1-penten-3-ol - - A c 31 2,3,4-trimethyl-3-pentanol - - D a 32 1-hexanol green, flowery 50-2,500 A, D a, b, c, d, e 29, 32, 34, 37, 38 (E)-2-hexenol - - D b 34 (E)-3-hexenol - - D b 34 (Z)-3-hexenol leaf-like D b 34 5-methyl-2-hexanol - - A c 27 2-ethyl-1-hexanol - 270,000* A, D b, e 29, 34 1-heptanol - 3* D b 34 4-methyl-3-heptanol - - A b, c 27 1-octanol * D b, d 23, 34 2-octanol - - D a, d 32 3-octanol - - A, D b, c, d, e 1-octen-3-ol mushroomlike 1 A, D a, b, c, d, e, f 29, 30, 32, 34 36, 38 23, 27-30, 32-36, 38 1-nonanol - 50 D b 34 2-nonanol - - A, D d, e 23, 39 1-nonen-3-ol - - A c undecen-1-ol - - A c 31 1-tridecyn-4-ol - A c 27 2-pentadecanol - - D a 32 9,12-octadecadien-1-ol - - A c 31 phenethyl alcohol (2-phenyl ethanol, benzeneethanol) honey-like, spicy 1,000 A, B, D a, b, c, d, e, f benzyl alcohol (benzenemethanol) - 10,000 A, B, D a, b, c, d, e, f 23, 27-30, 32, , 32, 34 37, 39 2-methyl benzenemethanol - - A e 30 α-methyl benzenemethanol - - A c 28 2-furanmethanol (furfuryl alcohol) - - A, C, D B a, b, c, d, e, f 23, 26-30, 32, 34, 39 1-aziridineethanol - - A b 27 8-amino-2-naphthalenol - - A b 27 acetaldehyde pungent, fruit D d, f 39 hydroxyacetaldehyde - - C a 26 3-(methylthio) propanal (methional) potato-like A, D c, d 23, 28 2-methylbutanal green, almond-like D b, d, f 23, 34, Food Science and Industry (Vol.50 No.4)

15 특집 : 청국장과된장의휘발성향기성분데이터베이스 Aldehyde Compound name Aroma description method 2) Sample 3) 3-methylbutanal malty A, C, D a, b, c, d, f Reference 23, 26, 31, 34, 36, 37, 39 2-methyl-2-butenal - - D d, f 23, 39 pentanal hexanal pungent, almond-like tallowy, leaf-like C, D c, d 23, A, D a, b, c, d, e 23, 27-29, 33, 34, 37, 39 heptanal fatty A, D c, d 23, 31 (E)-2-heptenal fatty, almond-like A, D c, b, d 23, 28, 34 octanal fatty D b 34 (E)-2-octenal fatty, nutty 4 D b 34 nonanal tallowy, fruity 1-5 A, D b, c, d (E)-2-nonenal decanal (E)-2-decenal tallowy, cucumber-like orange skinlike, flowery tallowy, orange-like 23, 28, 31, 32, 34, 0.15 A c 27, D d D d 23 (Z)-7-hexadecenal - - D d 32 (E)-11-hexadecenal - - D a 32 (E,E)-2,4-decadienal deep-fried A, D c, e, d 23, 29 tetradecanal - - D d 23 benzaldehyde almond-like 350-3,500* A, B, D a, b, c, d, e f 23, methyl benzaldehyde - - D a, d 32, 37 3-methyl benzaldehyde - - D a 32 4-methyl benzaldehyde - - B d, f 39 2-hydroxy-6-methylbenzaldehyde - - A c 31 2-aminobenzaldehyde - - B d 39 2-phenyl-2-butenal - - A, D b, c, d, e 29, 34, 35 5-methyl-2-phenyl-2-hexenal - - A, D c, d, e 23, 29, 30, 32, 35, 37, α-ethylidene benzeneacetaldehyde - - A c, d, e 27, 30, 31, 37 phenylacetaldehyde (2-phenylethanal, benzeneacetaldehyde) honey-like, flowery 4 A, B, D a, b, c, d, e, f 23, furancarboxaldehyde (furfural) sweet 3,000 A, C, D a, b, c, d, e, f 5-methyl-2-furancarboxaldehdye - - A, C, D a, b, c, d, e 23, 26-30, 32-35, , 26, 27, 29, 30, 35, 38 식품과학과산업 12 월호 (2017)

16 Ketone Compound name Aroma description method 2) Sample 3) Reference 2-propanone (acetone) - - C, D a, b, c 26, 32 2-butanone etheric 23,200-50,000 D b, d 34, 39 (E)-3-penten-2-one - 1.5* A c, e 29, 31 2-hexanone - - A c 31 4-methyl-3-hexanone - - D f 39 2-heptanone soapy, fruity A, D b, c, d, e, f 23, 28, 29, 31, 34, 39 4-methyl-2-heptanone - - D b 34 3-heptanone - - D b 34 2-octanone - 50* A, D b, c, e 29, 34 3-octanone - - A, B, D c, d, e 1-octen-3-one mushroomlike, metallic 23, 29, 32, 35, 37, A, D b, c 28, 34 2,3-butanedione (diacetyl) buttery 4-15 C, D a 26, 32 1-hydroxy-2-propanone - - A, C b, c, e 26, 29 2-nonanone fruity, soapy A c, e 29 2-decanone - - D b 34 2-undecanone fruity 7* D d 38 3-hydroxy-2-butanone buttery 800-5,000 A, C, D a, b, c, e 26, 29, 32 2,3-hexadione - - A b 27 1-phenylethanone (acetophenone) - 65* D a 32 1-(2-hydroxy-5-methylphenyl) ethanone - - A c 27, 31 1-(1H-pyrrol-2-yl) ethanone - - C, D a, b, c, d, f 26, 39 6-methyl-4H-pyran-4-one - - C b, c 26 4-phenyl-2-butanone - - A b 27 1-phenyl-2-propanone - - B, D d 39 dihydro-2-methyl-3(2h)-furanone - - A, C b, c, e 26, 29 dihydro-2(3h)-furanone (γ-butyrolactone) - - B d, f 39 4-methyl-2H-furan-5-one - - D b 34 dihydro-5-methyl-2(3h)-furanone (γ-valerolactone) dihydro-5-ethyl-2(3h)-furanone (γ-hexalactone) dihydro-5-propyl-2(3h)-furanone (γ-heptalactone) dihydro-5-pentyl-2(3h)-furanone (γ-nonalactone) - - B d 39 sweet 1,600 A, B c, d, e, f 29, * A c 28 fruity, peach-like A, D a, b, c, e 29-32, Food Science and Industry (Vol.50 No.4)

17 특집 : 청국장과된장의휘발성향기성분데이터베이스 Ketone Acid Compound name dihydro-5-hexyl-2(3h)-furanone (γ-decalactone) Aroma description fruity, peach-like method 2) Sample 3) Reference 5-11 A, D a, c 31, 32 dihydro-5-(2-octenyl)-2(3h)-furanone - - B d 39 3-hydroxy-2-methyl-4H-pyran-4-one (maltol) caramel-like 9,000-35,000 A, B, D a, b, c, d, e, f 23, 29, 32, 34, 35, 37, 39 methyl maltol - - B d, f 39 dihydro-6-methyl-2h-pyran-3(4h)- one 2,3-dihydro-3,5-dihydroxy-6-methyl- 4H-pyran-4-one β-damascenone - - B d, f B d, f 39 honey-like, fruity, sweet A c, e 29 5-penoxymethyloxol-3-en-2-one (?) 4) - - A e 30 2-pentadecanone - - D d 32 2-hydroxy-3-methyl-2-cyclopenten-1-one (cyclotene) * B d, f 39 cyclohexanone - - A c 31 4-isopropyl-1,3-cyclohexanedione - - B d, f 39 1,2,3-trimethylcyclohexane - - B d, f 39 2-cyclohexen-1-one - - B d 39 3-methyl-2-cyclohexen-1-one - - A c 31 acetic acid propanoic acid vinegar-like, pungent fruity, pungent 22,000-50,000 2,190-20,000 A, B, C, D a, b, c, d, e, f A, B, D c, d, e, f 2-methyl propanoic acid sweaty 50-8,100 A, B, D c, d, e, f 23, 26, 27, 29, 32, , 30, 32, 35, , 30, 32, 35, 37, 39 3-(methylthio)propanoic acid - - B d 39 butanoic acid sweaty, rancid 50-2,150 A, B, C, D b, c, d, e, f 26, 27, 29, 30, 32, 33, 35, methyl butanoic acid sweaty, sweet 50-6,600 A, D c, d, e 23, 29, 35 3-methyl butanoic acid (isovaleric acid) sweaty 132-1,600 A, B, C, D a, b, c, d, e, f 23, 26, 27, 29, 30, 32, 35, 37, 39 2-methyl-2-butenoic acid B d, f 39 3-methyl-2-butenoic acid B d, f 39 pentanoic acid (valeric acid) sweaty 2,100 A, B, D a, b, c, d, e 29, 30, 32, 34, 39 3-methyl pentanoic acid D d 32 4-methyl pentanoic acid A, B, D c, d, e, f 29, 35, 39 hexanoic acid (caproic acid) goat-like, sweaty 290-5,000 A, B, D a, b, c, d, e 27, 29, 30, 32, 34, 37, 39 heptanoic acid - - A, D b, d, e 30, 32, 34, 식품과학과산업 12 월호 (2017)

18 Acid Ester Compound name Aroma description method 2) Sample 3) Reference octanoic acid (caprylic acid) sweaty 3,000 A, B, D a, d, e 30, 32, 37, 39 nonanoic acid - 3,000 D a, d 32 tetradecanoic acid - - D f 38 hexadecanoic acid - - A, D a, c, d, f 28, 31, 33, 38 2,4-hexadienoic acid (sorbic acid) - - A, D d, e, f 30, 38 benzoic acid - - A, B, D b, c, d, e, f 27, 29, 30, 32, 38, 39 2-hydroxy benzoic acid - - D c 36 3-nitropropanoic acid - - D a 32 8,11-octadecadienoic acid - - A c 33 (Z,Z)-9,12-octadecadienoic acid - - A, D c, e 28, 32, pentadecenoic acid* - - D e 32 phenylacetic acid (benzeneacetic acid) sweet, honey-like 1,000-10,000 B, D d, f 32, 38, 39 benzenepropanoic acid - - B f 39 3-hydroxymandelic acid - - D f 38 2-furancarboxylic acid - - A c, e 29 ethyl formate - - A c 31 ethyl acetate solvent-like, fruity 5-19,900 A, C, D a, b, c, d, e, f 23, 26, 30-32, 34, methoxy ethyl acetate - - D e 32 ethyl propanoate fruity D b, d, f 34, 39 ethyl 2-methylpropanoate fruity, sweet D b, d, f 23, 34, 39 ethyl-2-methylpropenoate D b 34 ethyl butanoate fruity A, B, C, D b, c, d, e, f ethyl 2-methylbutanoate fruity A, B, D b, c, d, e, f ethyl 3-methylbutanoate fruity 0.20 A, B, D b, c, d, e, f 26, 29, 31, 32, 34, 35, 37, 39 29, 31, 32, 34, 35, 37, 39 29, 31, 32, 34, 35, 37, 39 ethyl (Z)-2-butenoate - - D b 34 ethyl pentanoate * A, B, D c, d, e, f 39, 37, 39 ethyl 2-methylpentanoate - - D e 32 ethyl 4-methylpentanoate - - B, D d, f 32, 39 ethyl hexanoate fruity A, B, D b, c, d, e, f 23, 29, 31, 32, 34, 35, ethyl heptanoate fruity 2.2 A, D b, c, e 29, 34, 35 ethyl octanoate fruity, fatty 70 A, B, D b, c, d, e, f 29, 32, 34, 35, 37, 39 ethyl 4-methyloctanoate - - D d, e 32, Food Science and Industry (Vol.50 No.4)

19 특집 : 청국장과된장의휘발성향기성분데이터베이스 Ester Compound name Aroma description method 2) Sample 3) Reference ethyl nonanoate - - A, D b, c, d, e 29, 34, 37 ethyl decanoate - - D b 34 ethyl dodecanoate - - A, D b, c, e 29, 34, 35 ethyl tridecanoate - - D e 32 ethyl tetradecanoate - - A, B, C, D a, b, c, d, e, f 26, 29, 31, 32, 34, 35, 39 ethyl pentadecanoate - - A, D b, c, d, e 29, 30, 32, 34, 35 ethyl hexadecanoate - >2,000* A, B, C, D a, b, c, d, e, f 26, 28-32, 34, 35, 37, 39 ethyl heptadecanoate - - D b, e 32, 34, 35 ethyl octadecanoate - - A, B, D b, c, d, e, f 30-32, 34, 39 ethyl (Z)-9-octanoate(?) - - A e 30 ethyl 9-hexadecenoate - - A, C, D a, b, c, d, e 26, 29, 34, 35 ethyl E11-hexadecenoate - - D e 32 ethyl 9-octadecenoate (ethyl oleate) - - A, B, D b, c, d, e, f 30-32, 34, 38, 39 ethyl 9,12-octadecadienoate (ethyl linoleate) - - A, B, D a, b, c, d, e, f 28, 30, 32, 34, 38, 39 ethyl 9,12,15-octadecatrienoate - - A, D b, d, e 30, 32, 34 ethyl benzeneacetate (ethyl phenylacetate) fruity, sweet 650* A, B, D b, c, d, e, f 23, 27, 29-31, 34, 35, 37, 39 ethyl lactate - 14,000* A, D c, e 29, 32, 35 ethyl 3-phenylpropionate (ethyl benzenepropanoate) - - A, B, D b, c, e, f 29, 34, 39 ethyl 3-(methylthio) propionate - 7* D e 35 ethyl benzoate - 60 A, B, D b, c, d, e, f 29, 30, 32, 34, 35, 37, 39 ethyl sorbate - - A, D d, e, f 30, 38 ethyl cinnamate fruity 0.06# B, D f 39 ethyl vanillate - - B f 39 ethyl N-allylcarbamate - - D f 38 ethyl 2-hydroxy-3-phenylpropanoate - - B f 39 ethyl nicotinate - - B, D f 39 ethyl 2-cyclopenten-1-undecanoate - - A e 30 methyl 2-methylpropanoate fruity, sweet A c 31 methyl 2-methylpropenoate - - D b 34 methyl butanoate fruity, sweet 5-60 A, D c, d 31, 39 methyl 2-methylbutanoate apple-like D d 39 methyl 3-methylbutanoate - - D d 39 methyl 3-methyl-2-butenoate - - D b 식품과학과산업 12 월호 (2017)

20 Ester Compound name methyl 4,6,10,14-tetramethyl pentadecanoate Aroma description method 2) Sample 3) Reference - - A c 27 methyl 4-methyl-2-oxo pentanoate - - A c 27 methyl undecanoate - - A c 31 methyl tetradecanoate - A c 31 methyl hexadecanoate - - A, C, D b, c, d, e 26, 28, 31, 32, 34, 35 methyl octadecanoate - - A c 31 methyl 9-octadecenoate - - A, D c, d, e 28, 31, 32 methyl 9,12-Z,Z,-octadecadienoate - - A, C, D a, b, c, d, e 26, 28, 31, 32, 34 methyl 9,12,15-octadecatrienoate - - A, C a, c, e 26, 30 methyl 11,14-eicosadienoate - - A c 27, 28 methyl 2-methyl hexadecanoate - - A b 27 methyl 14-methyl pentadecanoate - - D e 32 methyl benzoate - - A, B, D b, c, d, e, f 23, 31, 34, 35, 39 methyl phenylacetate - - D d 37 methyl 2-hydroxybenzoate - - A c 31 diethyl succinate (diethyl butanedioate) - - A, B, D b, c, e, f 29, 34, 38, 39 triethyl borate(?) - - A e 30 isobutyl acetate - 66* D b 34 isobutyl butanoate D d 39 isoamyl acetate - 2* A, D b, c, d, e, f 29, 34, 37, 39 isoamyl butyrate - - D d 37 isoamyl hexanoate - - D b 34 isoamyl octanoate - - D b 34 isoamyl 2-methylbutanoate - - D d 38 2-phenylethyl acetate flowery, fruity 20# A, B, D b, c, d, e 29, 34, 39 2-acetyl ethylhexanoate - - C c 26 bis(2-ethyl-)1,2-benzenecarboxylic acid - - A e 30 (Z,Z)-2,3-dimethyl 9,12-octadecadienoic acid(?) - - A e 30 dimethyl butanedioate - - A c 31 propyl acetate - - D d 39 propyl butanoate * B, D d 39 propyl 2-methylbutanoate - - D d 39 propyl 3-methylbutanoate - - B, D d 39 butyl butanoate - 100* A c 28, 31 butyl isobutyrate - 80* D d 39 butyl hexadecanoate - - D b 34 butyl benzoate - - D d Food Science and Industry (Vol.50 No.4)

21 특집 : 청국장과된장의휘발성향기성분데이터베이스 Ester Pyrazine Nitrogencontaining compound Compound name Aroma description method 2) Sample 3) Reference pentyl propanoate - - D b 34 2-octyl benzoate - - D a, d 32 dimethyl 1,2-benzenedicarboxylate - - A c 31 dibutyl 1,2-benzenedicarboxylate - - A c 31 dipentyl 1,2-benzenedicarboxylate - - A c 31 2-methylpropyl 2-methylpropanoate - - D a 32 2-methylhexyl propanoate - - D a 32 butyl heptadecyl sulfuroate - - D a 32 hexadecyl trichloroacetate - - D a 32 2-methylpyrazine ,000* A, B, C, D b, c, d, e 2,3-dimethylpyrazine - 2,500-35,000* A, B, D c, d, e 2,5-dimethylpyrazine ,800* A, B, D a, c, d, e, f 23, 26, 29-31, 34, , 29, 31, 35, , 28-30, 32, 33, 35, ,6-dimethylpyrazine ,000* A, B, D c, d, e 29, 31, 35, 37, 39 2-ethyl-5-methylpyrazine - 100* B, D d 39 2-ethyl-6-methylpyrazine - - A, D c, d, e 29, 37 2-ethyl-3,5-dimethylpyrazine potato-like D d, e 35, 38 3-ethyl-2,5-dimethylpyrazine potato-like A, B, D c, d, e 28, 29, 31, 35, 39 2,3,5-trimethyl-6-ethylpyrazine - - A, B, D c, d, e, f 23, 29, 35, ,3,5-trimethyl-6-propylpyrazine - - A, B c, f 28, 39 trimethylpyrazine potato-like, musty tetramethylpyrazine A, B, D a, b, c, d, e, f 1,000-10,000* 23, 27-30, 32, 33, A, B, D b, c, d, e, f 23, 27-32, ,6-diethylpyrazine - - D d 37 acetyl pyrazine roasty 62 D d 23 2,5-dimethyl-3-propylpyrazine - - A c 31 1H-pyrrole - 49,600* A c 27, 28, 39 acetyl pyrrole - 170,000* A, D c, d, e 29, 35, 37 2-formyl pyrrole - - D d 23 1-methyl-2-pyrrolidone - - B d, f 39 1-methyl-2,5-pyrrolidinedione - - B f 39 pyridine - 2,000* A c, e 29, 30, 31 N,N,-dimethylformamide - - C c 26 3-methyl benzonitrile - - A c 31 1-butyl-1H-pyrrole - A c 31 9-octadecanamide - - A c 31 1H-indole sweet, burnt 90 A, B, D b, c, d, f 23, 28, 34, 식품과학과산업 12 월호 (2017)

22 Nitrogencontaining compound Sulfur compound Phenol Compound name Aroma description method 2) Sample 3) Reference 2,3-indole - - D d 38 6-methyl-2-phenylindole - - D a 32 4-phenyl pyridine - - D d 32 N,N'-diethylidene-1,1'-diaminoethane - - A c 28 phenylacetonitrile (benzeneacetonitrile, benzyl nitrile) - - A, B, D b, d, f 27, 37, 39 benzenepropanenitrile - - B, D f 39 dimethyl disulfide cabbage-like D b, d, e, f 23, 32, 34, 39 dimethyl trisulfide sulfury 0.01 A, D b, c, d, e 23, 27, 29, 34, 36, 39 2-acetyl thiazole roasty, sulfury 10 D d 23 trimethyl thiazole earthy 50 A c, e 29, 31 2-methyl thiazole - - A c 31 4-ethyl-2,5-dimethyl thiazole - - A c 31 thiophene - - D b 34 2-methylthiophene - - D b 34 4,5-dimethyl-2-isopropyl thiazole - - A c 31 methanesulfonic anhydride - - D a 32 allyl isothiocyanate - - B, D e, f 32, 39 1,3-dimethylthioindole - - D e 32 dimethyl sulfone - - B d 39 ethyl thioisobutyrate - - D e, f 32, 39 1-docosanethiol - - D a 32 n-ethyl hydrazinecarbothioamide - - D a 32 thialdine - - A e 29 2-methylphenol (o-cresol) phenolic 650 A, D a, c, d 28, 32 3-methylphenol (m-cresol) - 680* A c, e 29 4-methylphenol (p-cresol) smoky, phenolic 55 A c 28 2,6-dimethyl phenol - - A c 28 2-ethylphenol - - A, D c, d, e 27, 30, 32 4-ethylphenol - - A, B, D c, d, e, f 23, 28, 29, 32, 35, ethylphenol - - A e 30 4-vinylphenol - 10* A, B, D a, b, c, d, e, f 23, 29, 32, 34, 35, 39 2-propyl phenol - - A c 28 5-methyl-2-(1-methylethyl) phenol - - A e 30 2-methoxy phenol (guaiacol) smoky, sweet A, B, D a, b, c, d, e, f 23, 27-30, 32, 34, 35, Food Science and Industry (Vol.50 No.4)

23 특집 : 청국장과된장의휘발성향기성분데이터베이스 Phenol Furan Miscellaneous Compound name Aroma description method 2) Sample 3) 2-methoxy-4-vinylphenol (4-vinyl guaiacol) clove-like A, B, D a, b, c, d, e, f 2-methoxy-4-(2-propenyl) phenol (eugenol) 4-ethyl-2-methoxy phenol (4-ethyl guaiacol) spicy, honey-like Reference 23, 29, 32, 34, 35, 38, A, B c, d, e 29, 39 clove-like 50 A, B, D c, d, e, f 27-30, 32, 35, ,6-dimethoxy phenol - 1,850* B, D a, d, f 23, 32, 39 2,6-bis(1,1-dimethylethyl) phenol - - A c 28 3,5-bis(1-methylethyl) phenol - - A c 31 2-methylfuran - - D b, d 34, 38, 39 2,5-dimethylfuran - - D d 39 2-ethylfuran - - D b, d 34, 39 2-ethenylfuran - - D b 34 2-butylfuran - - D d 39 2-pentyl furan buttery, green bean-like 6 A, B, D a, b, c, d, e 23, 28, 29, 32, 33, 34-37, 39 2-heptyl furan - - D d 23 2-octyl furan - - D d 23 2-acetyl furan - 10,000* A c, e 29 1-(2-furanyl) ethanone - - C, D b, c, d 26, 39 furfuryl acrolein - - A e 30 2-methyl-3-β-furyl propanal(?) - - A e 30 furfurylideneacetone - - A e 30 4-methyl-2,3-dihydrofuran - - D d 39 2,3-dihydro benzofuran - - A, D a, c 28, 32 tetrahydro-2-methylfuran - - A c 31 decanoic acid, silver(+) salt(?) - - A e 30 trimethyloxazole - - D d 39 cadinene - - A c 31 3,4-dihydro-2H-pyran - - B f 39 cadina-1,4-diene - - B d 39 (+)-epi-bicyclosesquiphellandrene - - B d 39 1,1-bis(2-methylpropyl) hydrazine - - C b 26 β-caryophyllene - 64* B f 39 N-(2-methyl-2propyl) ethanamide - - B f 39 N-(3-methylbutyl) acetamide - - B f 39 N, N-dimethylformaide - - C b, c 26 3(2H)-pyridazinone - - A c 28 maleic hydrazide - - B d, f 식품과학과산업 12 월호 (2017)

24 Miscellaneous Compound name Aroma description method 2) Sample 3) Reference N,N-bis(1-methylethyl) acetamide - - B f 39 N-methyl-n-propyl-1-butylamine - - B f 39 N-phenethyl acetamide - - B d 39 1) Reference 24. * Orthonasal threshold in water (μg/l). # Retronasal threshold in water (μg/l). 2) A: SDE, B: solvent-assisted flavor evaporation (SAFE), C: headspace method, D: solid phase microextraction (SPME). 3) a: doenjang fermented with Bacillus koji, b: doenjang fermented with Aspergillus koji, c: traditional doenjang fermented with meju, d: commercial traditional doenjang fermented with meju, e: commercial doenjang fermented with Aspergillus koji, f: commercial doenjang fermented with koji. 4) The identification is questionable. 청국장에서도동정되었으며함량에있어서는청국장이된장보다 4.3배더많았다 (23). 질소함유화합물중에는 1H-피롤 (1H-pyrrole), 아세틸피롤 (acetyl pyrrole), 피리딘 (pyridine), 1H-인돌 (1H-indole) 및페닐아세토나이트릴 (phenylacetonitrile) 등이된장에서자주동정되는휘발성향기성분이다. 황함유화합물중에는다이메틸다이설파이드와다이메틸트라이설파이드 (dimethyl trisulfide), 페놀화합물중에는페놀, 4-에틸페놀 (4-ethylphenol), 4-바이닐페놀 (4-vinylphenol), 2-메톡시페놀 (2-methoxyphenol), 2-메톡시-4-바이닐페놀 (2-methoxy-4-vinylphenol) 및 4-에틸-2-메톡시페놀 (4-ethyl-2-methoxy phenol, 4-에틸구아이아콜 (4-ethyl guaiacol)) 등이된장의주요휘발성향기성분으로보고되었다. 퓨란은 2-메틸퓨란 (2-methyl furan) 과 2-펜틸퓨란등이동정되었다. 한국전통식품의휘발성향기성분을데이터베이스화하는일은우리전통식품의향미특성을이해하고개선하는데있어서중요한일이라고생각된다. 외국은자기나라식품의향기성분데이터베이스를잘구축하고있어식품향개발이나이취문제해결에중요한자료로활용하고있으나우리나라는아직미흡한실정이다. 한편관능검사나 GC-MS 를이용한휘발성향기성분분석을통해한국전 통식품의향미특성을이해하려는연구는어느정도이루어지고있으나향활성화합물 (aroma-active compound) 을밝히려는연구는아직구체적으로이루어지지않고있다. 결론한국전통식품의휘발성향기성분을데이터베이스화하는작업의일환으로국내외논문검색을통해청국장과된장의휘발성향기성분데이터베이스를작성하였다. 지금까지청국장과된장에서각각 225 개와 404개의휘발성향기성분이동정되었다. 청국장과된장의휘발성향기성분은제조방법, 발효기간및향기성분추출방법에따라차이가있었으며휘발성향기성분의종류와구성비율에따라청국장과된장의향미특성에차이가있었다. 청국장에서가장특징적인휘발성향기성분은피라진화합물이었으며, 2-메틸프로판산, 뷰탄산, 2-메틸뷰탄산및 3-메틸뷰탄산같은산도청국장의향미특성에크게기여할것으로생각된다. 된장의휘발성향기성분에서가장특징적인것은에스터화합물이많다는것이었다. 청국장에서는 22개의에스터화합물이동정된반면, 된장에서는 96개의에스터화합물이동정되었다. 산과피라진화합물도된장의 47 Food Science and Industry (Vol.50 No.4)

25 특집 : 청국장과된장의휘발성향기성분데이터베이스 향미특성에중요한역할을할것으로생각된다. 청 국장과된장의휘발성향기성분데이터베이스는청국장과된장및이를이용한조미소재의향미특성을이해하는기초자료로활용될수있을것이다. 또한청국장과된장의향미특성을개선하는기초자료로도활용될수있을것이다. 앞으로청국장과된장이외의한국전통식품에대해서도휘발성향기성분데이터베이스를작성하는작업이계속이루어지기를바라며, 아울러가스크로마토그래피-후각측정법 (gas chromatography-olfactometry) 을이용하여한국전통식품의향활성화합물을동정하는연구가활발히이루어져야할것으로생각된다. 참고문헌 1. Reineccius G. Flavor Chemistry and Technology. 2nd ed. Taylor & Francis, Boca Raton, FL, USA (2006) 2. Boelens MH. Volatile Compounds in Food-Database. TNO Nutrition and Food Research Institute, Zeist, The Netherlands (2000) 3. Maarse H. Volatile Compounds in Foods and Beverages. Marcel Dekker, Inc., New York, NY, USA (1991) 4. Leffingwell & Associates. Flavor-Base. Available from: Accessed Dec. 15, Triskelion BV. VCF online: Volatile compounds in Food Available from: Accessed Dec. 15, Shin D, Jeong D. Korean traditional fermented soybean products: jang. J. Ethnic Foods 2: 2-7 (2015) 7. Patra JK, Das G, Paramithiotis S, Shin HS. Kimchi and other widely consumed traditional fermented foods of Korea: A review. Frontiers Microbiol. 7: 1-15 (2016) 8. Hong EJ, Kim YJ, Noh BS. The reduction of off-flavor in cheonggukjang and kimchi. Korean J. Food Culture 25: (2010) 9. Choi UK, Lee SI, Son DH, Ji WD. Changes of flavor during chunggugjang fermentation by Bacillus sp. CS-17. J. Korean Soc. Hyg. Sci. 8: (2002) 10. Choe JS, Yoo SM, Kim HR, Kim JS, Chang CM. Volatile compounds of chonggugjang prepared by different fermentation methods and soybean cultivars. J. Korean Soc. Agric. Chem. Biotechnol. 42: (1999) 11. Choi SH, Ji YA. Changes in flavor of chungkookjang during fermentation. Korean J. Food Sci. Technol. 21: (1989) 12. Yoon HS, Choi HS, Joo SJ, Kim KS, Kim SJ. Aroma characteristic of chungkukjang with Astragalus membranaceus. Korean J. Food Preserv. 13: (2006) 13. Choi UK, Ji WD, Chung YG. Characteristics of chunggugjang produced by Bacillus subtilis DC-2. J. Korean Soc. Food Sci. Nutr. 27: (1998) 14. Park WJ, Park HY, Yoo JH, Rhee MS. Effect of Artmisia asiatica Nakai extract on the flavor of chung-kuk-jang. Food Eng. Prog. 5: (2001) 15. In JP, Lee SK, Ahn BK, Chung IM, Jang CH. Flavor improvement of chungkookjang by addition of yucca (Yucca shidigera) extract. Korean J. Food Sci. Technol. 34: (2002) 16. Kwon JH, Shin JK, Moon KD, Chung HS. Color, volatiles and organoleptic acceptability of mixed powders of red ginseng and cheonggukjang. Korean J. Food Preserv. 13: (2006) 17. Joo HK. Studies on chemical composition of commercial chungkuk-jang and flavor compounds of chung-kuk-jang by mugwort (Artmisia asiatica) or red pepper seed oil. Korea Soybean Digest 13: (1996) 18. Lee EJ, Kim JK. Characteristic flavor compounds of traditional Korean chongkukjang. Food Sci. Biotechnol. 13: (2004) 19. Choi HS, Joo SJ, Yoon HS, Kim KS, Song IG, Min KB. Quality characteristic of Hwangki (Astagalus membranaceus) chungkukjang during fermentation. Korean J. Food Preserv. 14: (2007) 20. Youn KC, Kim DH, Kim JO, Park BJ, Yook HS, Cho JM, Byun MW. Quality characteristics of the chungkookjang fermented by the mixed culture of Bacillus natto and B. licheniformis. J. Korean Soc. Food Sci. Nutr. 31: (2002) 21. Jeong SH, Park SY, Jeong ES, Kim YS, Mun SP. Effect of various additives on reduction of unpleasant odor and inhibition of Bacillus cereus growth in cheonggukjang. Korean J. Food Sci. Technol. 48: (2016) 22. Park JH, Han CK, Choi SH, Lee BH, Lee HJ, Kim SS. Development of odor-reduced Korean traditional cheonggukjang added with Job's tears. J Korean Soc. Food Sci. Nutr. 40: (2011) 23. Ba HV, Ryu KS, Hwang I. Flavor characteristics of hanwoo beef in comparison with other Korean foods. Asian-Aust. J. Anim. Sci. 25: (2012) 24. Rychlik M, Schieberle P, Grosch W. Compilation of Odor Thresholds, Odor Qualities and Retention Indices of Key Food Odorants. Technischen Universitat Munchen, Garching, Germany (1998) 25. Park MK, Choi HK, Kwon DY, Kim YS. Study of volatile organic acids in freeze-dried cheonggukjang formed during fermentation using SPME and stable-isotope dilution assay (SIDA). Food Chem. 105: (2007) 26. Park JS, Lee MY, Kim KS, Lee TS. Volatile flavor components of soybean paste (doenjang) prepared from different types of strains. Korean J. Food Sci. Technol. 26: (1994) 27. Ji WD, Lee EJ, Kim JK. Volatile flavor components of soybean 48 식품과학과산업 12 월호 (2017)

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