《有机化学》课程教学资源（参考书籍）Organic Acids and Food Preservation 2011, Maria M. Theron J. F. Rykers Lues.pdf_P36-P40

Chapter one: Introduction 17 Galvez, A., Abriouel, H., Lopez, R.L., and Ben, O.N. 2007. Bacteriocin-based strategies for food biopreservation. International Journal of Food Microbiology 120:51–70. Gauthier, R. 2005. Organic acids and essential oils, a realistic alternative to antibiotic growth promoters in poultry. I Forum Internacional de avicultura 17–19 August 2005, pp. 148–157. Geornaras, I., Belk, K.E., Scanga, J.A., Kendall, P.A., Smith, G.C., and Sofos, J.N. 2005. Post-processing antimicrobial treatments to control Listeria monocytogenes in commercial vacuum-packaged bologna and ham stored at 10 degrees C. Journal of Food Protection 68:991–998. Harty, D.W.S., Oakey, H.J., Patrikakis, M., et al. 1994. Pathogenic potential of lactobacilli. International Journal of Food Microbiology 24:179–189. Hazan, R., Levine, A., and Abeliovich, H. 2004. Benzoic acid, a weak organic acid food preservative, exerts specific effects on intracellular membrane trafficking pathways in Saccharomyces cerevisiae. Applied and Environmental Microbiology 70:4449–4457. Hsiao, C.P. and Siebert, K.J. 1999. Modeling the inhibitory effects of organic acids on bacteria. International Journal of Food Microbiology 47:189–201. Jordan, K.N., Oxford, L., and O’Byrne, C.P. 1999. Survival of low-pH stress by Escherichia coli O157:H7: Correlation between alterations in the cell envelope and increased acid tolerance. Applied and Environmental Microbiology 65:3048–3055. Juneja, V.K. and Thippareddi, H. 2004. Inhibitory effects of organic acid salts on growth of Clostridium perfringens from spore inocula during chilling of marinated ground turkey breast. International Journal of Food Microbiology 93:155–163. Kamm, B. and Kamm, M. 2004. Principles of biorefineries. Applied Microbiology and Biotechnology 64:137–145. Kroll, D. 2001. The growing food testing business: Highlighting pathogens, pesticides and GMOs. Food and Beverage. Report Code FOD011C, Published October 2001. http://www.bccresearch.com. (Accessed November 15, 2006). Leguerinel, I. and Mafart, P. 2001. Modeling the influence of pH and organic acid types on thermal inactivation of Bacillus cereus spores. International Journal of Food Microbiology 63:29–34. Leuenberger, S., Widdowson, M.A., Feilchenfeldt, J., Egger, R., and Streuli, R.A. 2007. Norovirus outbreak in a district general hospital—New strain identified. Swiss Medical Weekly 137:57–61. Macfarlane, R. 2002. Integrating the consumer interest in food safety: The role of science and other factors. Food Policy 27:65–80. Marín, S., Abellana, M., Rubinat, M., Sanchis, V., and Ramos, A.J. 2003. Efficacy of sorbates on the control of the growth of Eurotium species in bakery products with near neutral pH. International Journal of Food Microbiology 87:251–258. Martinez, G.M. and Bañados, F. 2004. Impact of EU organic product certification legislation on Chile organic exports. Food Policy 29:1–14. Marz, U. 2000. World markets for fermentation ingredients. Food and Beverage Publications. Report Code FOD020A, Published February 2000. http://www. bccresearch.com. (Accessed July 29, 2006)

8 Organic Acids and Food Preservation Marz U 2002 World markets for citric.ascorbic.isoascorbic acids Highlight age.Report Code FOD017B,Published June 2002.http://www.bccresearch.com.(Accessed July 29,2006). Mbandi,E.and Sh ef,LA.2002.Enhanced antimicrobial ffects of combination of lactate and diacetate on Listeria monocytogenes and sammonela spp.in beet Medeiro 3y76 rfood-banin Mascola.S.2001 safety education.Journal of the American Dietetic Association 101:1326-1339 Molins,R.A.,Motarjemi,Y.,and Kaferstein,F.K.2001.Irradiation:A critical con- in ensuring the microbiological safety of raw toods.Fd Coutro in spoilage yeast Mollaour,M and Piper,P.W.2001.The ZbyMom the foo no nd he maior weak organic acid nre vatives.Molecular Microbiolo 42:919-930 Motarjemi,Y.,Kaferstein,F,Moy,G.,et al.1996.Importance of HACCP for public health and development.The role of the World Health Organization.Food Moy,G nd Kafe World Healh s ,E1997. mprov the safety of street-vended Nakai.S.A rt.K.I.2003.Validat based on molecular Microbiology 86:249-255. Olsen,S.J.,Bis op,R.Brenner,F.W.,Roels,T.H,et al.2001.The changing epidemi- Piper,P,Calde M.2001.Weak acid a acid food pr servatives.Microbiologv 147:2635-2642 ce to organ Piper,P.W.1999.Yeast superoxide dismutase mutants reveal a pro-oxidant action of weak organic acid food preservatives.Free Radical Biology and Medicine 27:11-12. of different noulds grown on h m16723272 ellurite/tellurate X-ray ab sorption spectroscopy. Rekha,B.,Naik,S.N.,and Prasad,R.2006.Pesticide residue in anic and con ventional food-risk analysis.Journal of Chemical Heathand sae hw1312-19 Ricke,S.C.2003.Perspectives on the use of organic acids and short chain fatty acids as antimicrobi 1ce82:6 639 Ricke,S. nger er, and K 08工20s Alterna R4667675 nterventions an Rico.D.Martin-Diana.A.B.Barat.I.M.and Barry -Rva C 2007 Extending and measuring the quality of fresh-cut fruit and vegetables:A review.Trends in Food Science Technology 18:373-386. Rico,D.Martin-Diana,A.B.,Barry-Ryan,C.Frias,J.M.Henehan,G.T.M.and Barat,J.M.200 0m0937-48 ally processed

18 Organic Acids and Food Preservation Marz, U. 2002. World markets for citric, ascorbic, isoascorbic acids: Highlighting antioxidants in food. Food and Beverage. Report Code FOD017B, Published June 2002. http://www.bccresearch.com. (Accessed July 29, 2006). Mbandi, E. and Shelef, L.A. 2002. Enhanced antimicrobial effects of combination of lactate and diacetate on Listeria monocytogenes and Salmonella spp. in beef bologna. International Journal of Food Microbiology 76:191–198. Medeiros, L.C., Kendall, P., Hillers, V., Chen, G., and DiMascola, S. 2001. Identification and classification of consumer food-handling behaviors for food safety education. Journal of the American Dietetic Association 101:1326–1339. Molins, R.A., Motarjemi, Y., and Käferstein, F.K. 2001. Irradiation: A critical control point in ensuring the microbiological safety of raw foods. Food Control 12:347–356. Mollapour, M. and Piper, P.W. 2001. The ZbYME2 gene from the food spoilage yeast Zygosaccharomyces bailii confers not only YME2 functions in Saccharomyces cerevisiae, but also the capacity for catabolism of sorbate and benzoate, two major weak organic acid preservatives. Molecular Microbiology 42:919–930. Motarjemi, Y., Käferstein, F., Moy, G., et al. 1996. Importance of HACCP for public health and development. The role of the World Health Organization. Food Control 7:77–85. Moy, G., Hazzard, A., and Käferstein, F. 1997. Improving the safety of street-vended food. World Health Statistics Quarterley 50:124–131. Nakai, S.A. and Siebert, K.J. 2003. Validation of bacterial growth inhibition models based on molecular properties of organic acids. International Journal of Food Microbiology 86:249–255. Olsen, S.J., Bishop, R., Brenner, F.W., Roels, T.H., et al. 2001. The changing epidemiology of Salmonella: Trends in serotypes isolated from humans in the United States, 1987–1997. Journal of Infectious Diseases 183:753–761. Piper, P., Calderon, C.O., Hatzixanthis, K., and Mollapour, M. 2001. Weak acid adaptation: The stress response that confers yeasts with resistance to organic acid food preservatives. Microbiology 147:2635–2642. Piper, P.W. 1999. Yeast superoxide dismutase mutants reveal a pro-oxidant action of weak organic acid food preservatives. Free Radical Biology and Medicine 27:11–12. Prange, A., Birzele, B., Hormes, J., and Modrow, H. 2005. Investigation of different human pathogenic and food contaminating bacteria and moulds grown on selenite/selenate and tellurite/tellurate by X-ray absorption spectroscopy. Food Control 16:723–728. Rekha, B., Naik, S.N., and Prasad, R. 2006. Pesticide residue in organic and conventional food-risk analysis. Journal of Chemical Health and Safety 13:12–19. Ricke, S.C. 2003. Perspectives on the use of organic acids and short chain fatty acids as antimicrobials. Poultry Science 82:632–639. Ricke, S.C., Kundinger, M.M., Miller, D.R., and Keeton, J.T. 2005. Alternatives to antibiotics: Chemical and physical antimicrobial interventions and foodborne pathogen response. Poultry Science 84:667–675. Rico, D., Martin-Diana, A.B., Barat, J.M., and Barry-Ryan, C. 2007. Extending and measuring the quality of fresh-cut fruit and vegetables: A review. Trends in Food Science & Technology 18:373–386. Rico, D., Martin-Diana, A.B., Barry-Ryan, C., Frias, J.M., Henehan, G.T.M., and Barat, J.M. 2008. Use of neutral electrolysed water (EW) for quality maintenance and shelf life extension of minimally processed lettuce. Innovative Food Science & Emerging Technologies 9:37–48

Chapter one: Introduction 19 Rodrigues, G. and Pais, C. 2000. The influence of acetic and other weak carboxylic acids on growth and cellular death of the yeast Yarrowia lipolytica. Food Technology and Biotechnology 38:27–32. Rohr, A., Luddecke, K., Drusch, S., Muller, M.J., and Alvensleben, R. 2005. Food quality and safety—Consumer perception and public health concern. Food Control 16:649–655. Ryu, J.-H. and Beuchat, L.R. 1999. Changes in heat tolerance of Escherichia coli O157:H7 after exposure to acidic environments. Food Microbiology 16:317–324. Saint Xavier University. 2000. Food Preservation. Samelis, J., Sofos, J.N., Kendall, P.A., and Smith, G.C. 2002. Effect of acid adaptation on survival of Escherichia coli O157:H7 in meat decontamination washing fluids and potential effects of organic acid interventions on the microbial ecology of the meat plant environment. Journal of Food Protection 65:33–40. Schnürer, J. and Magnusson, J. 2005. Antifungal lactic acid bacteria as bio-preservatives. Trends in Food Science and Technology 16:70–78. Shtenberg, A.J. and Ignat’ev, A.D. 1970. Toxicological evaluation of some combination of food preservatives. Food and Cosmetics Toxicology 8:369–380. Sidhu, M.S., Langsrud, S., and Holck, A. 2001. Disinfectant and antibiotic resistance of lactic acid bacteria isolated from the food industry. Microbial Drug Resistance 7:73–83. Sims, W. 1964. A pathogenic Lactobacillus. Journal of Pathologic Bacteriology 87:99–105. Smith DeWaal, C. 2003. Safe food from a consumer perspective. Food Control 14:75–79. Smulders, F.J. and Greer, G.G. 1998. Integrating microbial decontamination with organic acids in HACCP programmes for muscle foods: Prospects and controversies. International Journal of Food Microbiology 44:149–169. Soomro, A.H., Masud, T., and Anwaar, K. 2002. Role of lactic acid bacteria (LAB) in food preservation and human health – A review. Pakistan Journal of Nutrition 1:20–24. Steels, H., James, S.A., Roberts, I.N., and Stratford, M. 1999. Zygosaccharomyces lentus: A significant new osmophilic, preservative-resistant spoilage yeast, capable of growth at low temperature. Journal of Applied Microbiology 87:520–527. Steels, H., James, S.A., Roberts, I.N., and Stratford, M. 2000. Sorbic acid resistance: The inoculum effect. Yeast 16:1173–1183. Struijk, C.B., Mossel, D.A.A., and Moreno Garcia, B. 2003. Improved protection of the consumer community against food-transmitted diseases with a microbial aetiology: A pivotal food safety issue calling for a precautionary approach. Food Control 14:501–506. Suhr, K.I. and Nielsen, P.V. 2004. Effect of weak acid preservatives on growth of bakery product spoilage fungi at different water activities and pH values. International Journal of Food Microbiology 95:67–78. Tamblyn, K.C. and Conner, D.E. 1997. Bactericidal activity of organic acids in combination with transdermal compounds against Salmonella typhimurium attached to broiler skin. Food Microbiology 14:477–484. Tang, Y. and Wu, M. 2007. The simultaneous separation and determination of five organic acids in food by capillary electrophoresis. Food Chemistry 103:243–248

chapter two Nature and composition of organic acids 2.1 General characterization Organic acids are typical products of microbial metabolism.All organic na variety of vegetable andanimal and can,therefore, esent as constit ituents of foods as reof obhemical metabolic proe turally pre ulants,hydrolysis,or bacterial growth,or can later be added directly or indirectly to the products(Gomis,1992). An organic acid is an organic compound with acidic properties and containing carbon,as do all organic compounds.The most common organic acids are the carboxylic acids whose acidity is associated with their carboxyl group-COOH.These are nerally weak acids,whereas ng the group are re str The acidity an ac id i determined by the relativ gate base of the acid,although other groups can as stability of ger acids confer acidity.Thi acidity is,however,usually weak and is the result of the-OH,-SH,enol group,and the phenol group(Figure 2.1)(Theron and Lues,2007). Organic acids do not dissociate completely in water as opposed to the strong mineral acids.Although the lower molecular weight acids such as formic and acetic acids are water soluble,the higher molecular weight rganic acids such as benzoic acid,are insoluble in the molecular (neutral) orm.Most】 acids are,however,ve er soluble in organic olvents Exceptions to this s solubility may be preval ent in the presence or sub stituents that may have an effect on the polarity of the compound(Theron and Lues,2007). Organic acids have the common denominator of having carbon in their structure,and although less reactive than inorganic acids,they are able to dissolve minerals in the mineral reserve in the soil.Organic acids that have 10 or fewer carbons in their structure,are distinguished from fatty acids that,on the ther hand have stra ght carbon cha 0f12t0240 rgan acids exist i sic forms:pur e acids 0 buffered acid s.Included in the pure acids s are lactic acid,propionic acid acetic acid,citric acid,and benzoic acid,whereas the calcium and sodium salts of propionic,acetic,citric,and benzoic acids are buffered organic 21

21 chapter two Nature and composition of organic acids 2.1 General characterization Organic acids are typical products of microbial metabolism. All organic acids occur naturally in a variety of vegetable and animal substrates and can, therefore, be either naturally present as constituents of foods as a result of normal biochemical metabolic processes, direct addition as acidulants, hydrolysis, or bacterial growth, or can later be added directly or indirectly to the products (Gomis, 1992). An organic acid is an organic compound with acidic properties and containing carbon, as do all organic compounds. The most common organic acids are the carboxylic acids whose acidity is associated with their carboxyl group –COOH. These are generally weak acids, whereas sulfonic acids, containing the group OSO3H, are relatively stronger acids. The acidity of an acid is determined by the relative stability of the conjugate base of the acid, although other groups can also confer acidity. This acidity is, however, usually weak and is the result of the –OH, –SH, enol group, and the phenol group (Figure 2.1) (Theron and Lues, 2007). Organic acids do not dissociate completely in water as opposed to the strong mineral acids. Although the lower molecular weight acids such as formic and acetic acids are water soluble, the higher molecular weight organic acids such as benzoic acid, are insoluble in the molecular (neutral) form. Most organic acids are, however, very soluble in organic solvents. Exceptions to this solubility may be prevalent in the presence of other substituents that may have an effect on the polarity of the compound (Theron and Lues, 2007). Organic acids have the common denominator of having carbon in their structure, and although less reactive than inorganic acids, they are able to dissolve minerals in the mineral reserve in the soil. Organic acids that have 10 or fewer carbons in their structure, are distinguished from fatty acids that, on the other hand, have straight carbon even-number chains of 12 to 24. Organic acids exist in two basic forms: pure acids or buffered acids. Included in the pure acids are lactic acid, propionic acid, acetic acid, citric acid, and benzoic acid, whereas the calcium and sodium salts of propionic, acetic, citric, and benzoic acids are buffered organic