Volatile organosulfur compounds (VOSCs) in flavour chemistry;Les composés volatils soufrés en chimie des arômes

Sciences des Aliments

Volumn 27, Issue 1, 2007, Pages 23-46

  Filippi, J J ^a   Fernandez, X ^a   Dunach E ^a  

^a CNRS   (France)

Author keywords

Biosynthetic pathways; Flavour; Flavouring compositions; Specific detectors; Syntheses; Volatile sulfur compounds

Indexed keywords

EID: 34249672268     PISSN: 02408813     EISSN: None     Source Type: Journal    
DOI: 10.3166/sda.27.23-46     Document Type: Article

References (65)

1. ACUNA G., GAUTSCHI M., KUMLI F., SCHMID J., ZSINDELY J., 2000. Mercapto alcohols as flavouring compounds. European Patent no 1 055 667, du 20 mai 2000.
2. th Ed. Wiley-VCH Verlag, Weinheim, p. 162.
3. BENNER R., STEDMAN D., 1989. Universal sulfur detection by chemiluminescence, Anal. Chem., 61, 1268-1271.
4. BERGER R., DRAWERT F., KOLLMANNS-BERGER H., NITZ S., SCHRAUFSETTER B., 1985. Novel volatiles in pineapple fruit and their sensory properties, J. Agric. Food Chem., 33, 232-235.
5. BLOCK E., 1992. The organosulfur chemistry of the genus Allium - Implications for the organic chemistry of sulfur, Angew. Chem. Int. Ed., 31, 1135-1178.
6. BOELENS M., VAN GEMERT L., 1993. Volatile character-impact sulfur compounds and their sensory properties. Perfum. Flavor., 18, 29-39.
7. BOUCHONNET S., LIBONG D., 2004. Le couplage Chromatographie en phase gazeuse - spectrométrie de masse. L'Actualité Chimique, 275, 7-14.
8. BRODY S.S., CHANEY J.E., 1966. Flame photometric detector. Application of a specific detector for phosphorus and for sulfur compounds sensitive to subnanogram quantities, J. Gas Chromatogr., 4, 42-46.
9. BUTTERY R.G., GUADAGNI D.G., LING L.C., SEIFERT R.M., LIPTON W., 1976. Additional volatile components of cabbage, broccoli, and cauliflower, J. Agric. Food Chem., 24, 829-832.
10. BUTTERY R.G., MADDEN W.F., SEIFENT R.M., TURNBAUGH J.G., 1984. Thiamin odor and bis(2-methyl-3-furyl)disulfide, J. Agric. Food Chem., 32, 674-676.
11. BUTTERY R.G., TERANISHI R., LING L.C., 1987. Fresh tomato aroma volatiles: a quantitative study, J. Agric. Food Chem., 35, 540-544.
12. CEE, 2002. The register of flavouring substances used in or on foodstuff, Official Journal of the European Communities, L49, 1-160.
13. CHESKIS S., ATAR E., AMIRAV A., 1993, Pulsed-flame photometer: a novel gas chromatography detector, Anal. Chem., 65, 539-555.
14. DEMOLE E., ENGGIST P., OHLOFF G., 1982. 1-p-menthene-8-thiol: a powerful flavor impact constituent of grapefruit juice (Citrus paradisi). Helv. Chim. Acta, 65, 1785-1794.
15. EICHER T., HAUPTMANN S., 2003. The chemistry of heterocycles, Wiley-VCH: 71-75.
16. EVENHUIS B., 1986. General, legal and safety aspects of the use of flavoring. Perfum. Flavorist, 11, 17-28.
17. FERNANDEZ X., KERVERDO S., DUNACH E., LIZZANI-CUVELIER L., 2002. Les hétérocycles dans la chimie des arômes. L'Actualité Chimique, 275, 4-14.
18. th 2001.
19. GRIESBAUM K., 1970. Problems and possibilities of the free-radical addition of thiols to unsaturated compounds. Angew. Chem. Int. Ed., 9, 273-287.
20. GRUNDSCHOBER F., 1999. In : SWIFT K.A.D. (ed.), Current Topics in Flavours and Fragrances, 215, Kluwer Academic Publishers, Dordrecht.
21. GUICHARD, E., 1992. L'analyse sensorielle par "sniffing", In : RICHARD H., MULTON J.-L. (ed), Les Arômes Alimentaires, 404-421, Tec. & Doc. Lavoisier, Paris.
22. GÜNTERT M., BERTRAM H.-J., HOPP R., SILBERZHAN W., SOMMER H., WERK-HOFF P. 1993. In: HOPP R., MORI K. (ed.), Recent Developments in Flavor and Fragrance Chemistry, 215-230, VCH, Weinheim.
23. HUYNH-BA T., MATTHEY-DORET W., FAY L., BEL RHLID R., 2003. Generation of thiols by biotransformation of cysteine-aldehyde conjugates with baker's yeast. J. Agric. Food Chem., 53, 3629-3635.
24. JAMESON S., 2001. Organosulphur chemistry: Aroma chemicals and beyond - Parts 1&2. Speciality Chemicals Magazine, 21, 17-26.
25. nd 1972.
26. KICE J.L., 1963. A Kinetic Study of the Acid Hydrolysis of a Bunte Salt. J. Org. Chem., 28, 957-961.
27. th 2003.
28. KOVATS E., 1958. Gas Chromatographic characterization of organic compounds. I. Retention indexes of aliphatic halides, alcohols, aldehydes, and ketones. Helv. Chim. Acta, 41, 1915-1932.
29. KUBOTA K., NAKAMOTO A., MORIGUCHI M., KOBAYASHI A., ISHII H., 1991. Formation of pyrrolidino[1,2-e]-4H-2,4-dimethyl-1,3,5-dithiazine in the volatiles of boiled short-necked clam, clam, and corbicula, J. Agric. Food Chem., 39, 1127-1130.
30. KUO M.-C., CHIEN M., HO C.-T., 1990, Novel polysulfides identified in the volatile components from welsh onions (Allium fistulosum L. var. maichuon) and scallions (Allium fistulosum L. var. caepitosum), J. Agric. Food Chem., 38, 1378-1381.
31. LEDL F., SCHLEICHER E., 1990. The Maillard reaction in food and in the human body -new results in chemistry, biochemistry and medicine. New aspects of the Maillard reaction in foods and the human body, Angew. Chem. Int. Ed., 29, 565-626.
32. LEINO R., LÖNNQVIST J.-E., 2004. A very simple method for the preparation of symmetrical disulfides. Tetrahedron Lett., 45, 8489-8491.
33. th 2002.
34. MACLEOD A. J., MACLEOD G., 1968. Volatiles of cooked cabbage, J. Sci. Food Agric., 19, 273-277.
35. MAGA U.A., 1975. Role of sulfur compounds in food flavour. I. Thiazoles, Crit. Rev. Food Sci. Nutr., 6, 153-176.
36. MAGA J.A., 1975. Role of sulfur compounds in food flavour. II. Thiophenes, Crit. Rev. Food Sci. Nutr., 6, 241-270.
37. MAILLARD L.-C. 1912. Action des acides amines sur les sucres : formation des mélanoïdines par voies méthodiques. Comptes Rend. Acad. Sci., 154, 66-68.
38. MOTTRAM D.S., MOTTRAM H.R., 2002. An overview of the contribution of sulfur-containing compounds to the aroma in heated foods, ACS Symp. Ser., 826, 73-92.
39. MUKAIYAMA T., TAKAHASHI K., 1968. A convenient method for the preparation of unsymmetrical disulfides by the use of diethyl azodicarboxylate. Tetrahedron Lett., 9, 5907-5908.
40. NIJSSEN L.M., VISSCHER C.A., MAARSE H., WILLEMSENS L.C., BOELENS M.H., 1996. Volatile Compounds in Food. Qualitative and Quantitative Data, 7th ed.; TNO Nutrition and Food Research Institute: Ziest, The Netherlands.
41. NISHIMURA O., YAMAGUCHI K.S.M., SHIBAMOTO T., 1989. Volatile constituents of guava fruits (Psidium guajava L.) and canned puree, J. Agric. Food Chem., 37, 139-142.
42. NISHIO T., 1989. A novel transformation of alcohols to thiols, J. Chem. Soc., Chem. Commun, 4, 205-206.
43. NISHIO T., 1993. Direct conversion of alcohols into thiols, J. Chem. Soc., Perkin Trans., 1, 1113-1117.
44. PELLEGRIN F., 2003. Contribution des techniques de détection spécifique àl'identifica tion de substances aromatisantes issues de matrices naturelles. These de Doctorat de Chimie, Université de Nice-Sophia Antipolis, France.
45. PICKENHAGEN W., BRONNER-SCHINDLER H., 1984. Enantioselective synthesis of (+)- and (-)-cis-2-methyl-4-propyl-1,3-oxathiane and their olfactive properties, Helv. Chim. Acta, 67, 947-952.
46. RIGAUD J., ETIEVANT P., HENRY R., LATRASSE A., 1986. 4-Methoxy-2-methyl- 2-butanethiol, a major constituent of the aroma of the black currant bud (Ribes nigrum L). Sci. Aliments, 6, 213-20.
47. SAHIDI F., 1998. Flavor of meat, meat products and seafood, Blacki Academic & Professional, London.
48. STAUDINGER H., REICHSTEIN, T., 1925. Coffee aroma. GE Patent no 489613.
49. Sulfure d'hydrogène, 1997. Fiche toxicologique no 32, INRS.
50. SULLIVAN J., QUIMBY J., 1989. Detection of carbon, hydrogen, nitrogen, and oxygen in capillary gas chromatography by atomic emission. J. High Resol. Chromatogr., 12, 282-286.
51. TAKEOKA G., 1999. Flavor Chemistry of vegetable. In: TERANISHI R. (ed.), Flavor Chemistry: 30 years of progress, 287-304. Kluwer Academic/Plenum publishers, New York.
52. TRANCHANT J., 1996, Chromatographie en phase gazeuse, Techniques de l'ingé nieur, P 1485, 1-27 et document associé.
53. TRESSL R., SILWAR R., 1981. Investigation of sulfur-containing compounds in roasted coffee. J. Agric. Food Chem., 29, 1078-1081.
54. VAN DEN DOOL H., KRATZ P.A., 1963. Gene-ralization of the retention index system including linear temperature programmed gas-liquid partition chromatography. J. Chromatogr., 11, 463-471.
55. VAN DEN OUWELAND G.A.M., PEER H.G., 1975. Components contributing to beef flavor. Volatile compounds produced by the reaction of 4-hydroxy-5-methyl-3(2H) -furanone and its thio analog with hydrogen sulfide. J. Agric. Food Chem., 23, 501-505.
56. VERNIN G., METZGER J., FRAISSE D., SCHARFF C., 1986. GC-MS (EI, PCI, NCI) computer analysis of volatile sulfur compounds in garlic essential oils. Application of the mass fragmentometry SIM technique. Planta Med., 2, 96-101.
57. VOLANTE R.P., 1981. A new, highly efficient method for the conversion of alcohols to thioesters and thiols. Tetrahedron Lett., 22, 3119-3122.
58. WEENEN H., KOOLHAAS W., APRIYANTONO A., 1996. Sulfur-containing volatiles of durian fruits (Durio zibethinus Murr.). J. Agric. Food Chem., 44, 3291-3293.
59. WEIWER M., COULOMBEL L., DUNACH E., 2006. Regioselective indium (III) trifluoromethanesulfonate-catalyzed hydrothiolation of non-activated olefins. Chem. Commun., 332-334.
60. WEIWER M., DUNACH E., 2006. Indium(III)-catalysed highly regioselective addition of thiolacetic acid to non-activated olefins. Tetrahedron Lett., 47, 287-289.
61. WERKHOFF P., GÜNTERT M., KRAMMER G., SOMMER H., KAULEN J., 1998. Vacuum Headspace Method in Aroma Research: Flavor Chemistry of Yellow Passion Fruits. J. Agric. Food Chem., 46, 1076-1093.
62. th 1998.
63. th 1981.
64. WINTER M., FURRER A., WILLHALM B., THEMMEN W., 1976. Identification and synthesis of two new organic sulphur compounds from the yellow passion fruit (Passiflora edulis f. flavicarpa). Helv. Chim. Acta, 59, 1613-1620.
65. th 1980.