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Volumn 61, Issue 9, 2013, Pages 2062-2069

Influence of the stereochemistry on the sensory properties of 4-mercapto-2-heptanol and its acetyl-derivatives

Author keywords

4 acetylthio 2 heptanol; 4 acetylthio 2 heptyl acetate; 4 mercapto 2 heptanol; 4 mercapto 2 heptyl acetate; absolute configuration; GC O; lipase; NMR; odor thresholds; polyfunctional thiols; sensory properties; tropical olfactophore

Indexed keywords

4-ACETYLTHIO-2-HEPTANOL; 4-ACETYLTHIO-2-HEPTYL ACETATE; 4-MERCAPTO-2-HEPTANOL; 4-MERCAPTO-2-HEPTYL ACETATE; ABSOLUTE CONFIGURATION; GC/O; ODOR THRESHOLDS; POLYFUNCTIONAL THIOLS; SENSORY PROPERTIES; TROPICAL OLFACTOPHORE;

EID: 84874926659     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf305447e     Document Type: Article
Times cited : (16)

References (32)
  • 1
    • 0001780918 scopus 로고
    • Volatile character-impact sulfur compounds and their sensory properties
    • Boelens, M. H.; van Gemert, L. J. Volatile character-impact sulfur compounds and their sensory properties Perfum. Flavor. 1993, 18, 29-39
    • (1993) Perfum. Flavor. , vol.18 , pp. 29-39
    • Boelens, M.H.1    Van Gemert, L.J.2
  • 2
    • 0041808908 scopus 로고    scopus 로고
    • Sensory relevance of volatile organic sulfur compounds in food
    • Reineccius, G. A. Reineccius, T. A., Eds.; ACS Symposium Series 826; American Chemical Society: Washington, D.C.
    • Blank, I. Sensory relevance of volatile organic sulfur compounds in food. In Heteroatomic Aroma Compounds; Reineccius, G. A.; Reineccius, T. A., Eds.; ACS Symposium Series 826; American Chemical Society: Washington, D.C., 2002; pp 25-53.
    • (2002) Heteroatomic Aroma Compounds , pp. 25-53
    • Blank, I.1
  • 3
    • 0002282471 scopus 로고
    • Sulfur compounds in foods
    • Mussinan, C. J. Keelan, M. E. ACS Symposium Series 564; American Chemical Society: Washington, D.C.
    • Mussinan, C. J.; Keelan, M. E. Sulfur compounds in foods. In Sulfur Compounds in Foods; Mussinan, C. J.; Keelan, M. E., Eds.; ACS Symposium Series 564; American Chemical Society: Washington, D.C., 1994; pp 1-6.
    • (1994) Sulfur Compounds in Foods , pp. 1-6
    • Mussinan, C.J.1    Keelan, M.E.2
  • 4
    • 33748250842 scopus 로고    scopus 로고
    • Combinatorial synthesis and screening of novel odorants such as polyfunctional thiols
    • Vermeulen, C.; Collin, S. Combinatorial synthesis and screening of novel odorants such as polyfunctional thiols Comb. Chem. High Throughput Screening 2006, 9, 583-590
    • (2006) Comb. Chem. High Throughput Screening , vol.9 , pp. 583-590
    • Vermeulen, C.1    Collin, S.2
  • 5
    • 0038689283 scopus 로고    scopus 로고
    • Combinatorial synthesis and sensorial properties of 21 mercapto esters
    • Vermeulen, C.; Collin, S. Combinatorial synthesis and sensorial properties of 21 mercapto esters J. Agric. Food Chem. 2003, 51, 3618-3622
    • (2003) J. Agric. Food Chem. , vol.51 , pp. 3618-3622
    • Vermeulen, C.1    Collin, S.2
  • 6
    • 0038146831 scopus 로고    scopus 로고
    • Combinatorial synthesis and sensorial properties of mercapto primary alcohols and analogues
    • Vermeulen, C.; Guyot-Declerck, C.; Collin, S. Combinatorial synthesis and sensorial properties of mercapto primary alcohols and analogues J. Agric. Food Chem. 2003, 51, 3623-3628
    • (2003) J. Agric. Food Chem. , vol.51 , pp. 3623-3628
    • Vermeulen, C.1    Guyot-Declerck, C.2    Collin, S.3
  • 7
    • 0037174461 scopus 로고    scopus 로고
    • Synthesis and sensorial properties of mercaptoaldehydes
    • Vermeulen, C.; Collin, S. Synthesis and sensorial properties of mercaptoaldehydes J. Agric. Food Chem. 2002, 50, 5654-5659
    • (2002) J. Agric. Food Chem. , vol.50 , pp. 5654-5659
    • Vermeulen, C.1    Collin, S.2
  • 8
    • 11844272619 scopus 로고    scopus 로고
    • Sensorial contribution and formation pathways of thiols in foods: A review
    • Vermeulen, C.; Gijs, L.; Collin, S. Sensorial contribution and formation pathways of thiols in foods: A review Food Rev. Int. 2005, 21, 69-137
    • (2005) Food Rev. Int. , vol.21 , pp. 69-137
    • Vermeulen, C.1    Gijs, L.2    Collin, S.3
  • 9
    • 84874818857 scopus 로고    scopus 로고
    • Structure/odor relationships in homologous series of primary, secondary and tertiary thiols
    • Hofmann, T. Meyerhof, W. Schieberle, P. Proceedings of the 9th Wartburg Symposium; Deutsche Forschungsanstalt für Lebensmittelchemie: Eisenach, Germany
    • Polster, J.; Schieberle, P. Structure/odor relationships in homologous series of primary, secondary and tertiary thiols. In Advances and Challenges in Flavor Chemistry and Biology; Hofmann, T.; Meyerhof, W.; Schieberle, P., Eds.; Proceedings of the 9th Wartburg Symposium; Deutsche Forschungsanstalt für Lebensmittelchemie: Eisenach, Germany, 2011; pp 69-74.
    • (2011) Advances and Challenges in Flavor Chemistry and Biology , pp. 69-74
    • Polster, J.1    Schieberle, P.2
  • 11
    • 2142725147 scopus 로고    scopus 로고
    • Aroma chemicals for the sweet field
    • Rowe, D.; Tangel, B. Aroma chemicals for the sweet field Perfum. Flavor. 1999, 24, 36-44
    • (1999) Perfum. Flavor. , vol.24 , pp. 36-44
    • Rowe, D.1    Tangel, B.2
  • 12
    • 0542441666 scopus 로고
    • Identification of new sulfur-containing volatiles in yellow passion fruits (Passiflora edulis f. flavicarpa)
    • Engel, K.-H.; Tressl, R. Identification of new sulfur-containing volatiles in yellow passion fruits (Passiflora edulis f. flavicarpa) J. Agric. Food Chem. 1991, 39, 2249-2252
    • (1991) J. Agric. Food Chem. , vol.39 , pp. 2249-2252
    • Engel, K.-H.1    Tressl, R.2
  • 13
    • 0031825535 scopus 로고    scopus 로고
    • Identification of new volatile thiols in the aroma of Vitis vinifera L. var. Sauvignon blanc wines
    • Tominaga, T.; Furrer, A.; Henry, R.; Dubourdieu, D. Identification of new volatile thiols in the aroma of Vitis vinifera L. var. Sauvignon blanc wines Flavour Fragrance J. 1998, 13, 159-162
    • (1998) Flavour Fragrance J. , vol.13 , pp. 159-162
    • Tominaga, T.1    Furrer, A.2    Henry, R.3    Dubourdieu, D.4
  • 15
    • 0000625345 scopus 로고
    • Chirale, schwefelhaltige Aromastoffe der gelben Passionsfrucht (Passiflora edulis f. flavicarpa). Darstellung der Enantiomeren und absolute Konfiguration
    • Heusinger, G.; Mosandl, A. Chirale, schwefelhaltige Aromastoffe der gelben Passionsfrucht (Passiflora edulis f. flavicarpa). Darstellung der Enantiomeren und absolute Konfiguration Tetrahedron Lett. 1984, 25, 507-510
    • (1984) Tetrahedron Lett. , vol.25 , pp. 507-510
    • Heusinger, G.1    Mosandl, A.2
  • 16
    • 33749674486 scopus 로고    scopus 로고
    • Stereoisomeric distribution of 3-mercaptohexan-1-ol and 3-mercaptohexyl acetate in dry and sweet white wines made from Vitis vinifera (Var. Sauvignon Blanc and Semillon)
    • Tominaga, T.; Niclass, Y.; Frérot, E.; Dubordieu, D. Stereoisomeric distribution of 3-mercaptohexan-1-ol and 3-mercaptohexyl acetate in dry and sweet white wines made from Vitis vinifera (Var. Sauvignon Blanc and Semillon) J. Agric. Food Chem. 2006, 54, 7251-7255
    • (2006) J. Agric. Food Chem. , vol.54 , pp. 7251-7255
    • Tominaga, T.1    Niclass, Y.2    Frérot, E.3    Dubordieu, D.4
  • 17
    • 47049106817 scopus 로고    scopus 로고
    • Characterization of the aroma-active compounds in pink guava (Psidium guajava, L.) by application of the aroma extract dilution analysis
    • Steinhaus, M.; Sinuco, D.; Polster, J.; Osorio, C.; Schieberle, P. Characterization of the aroma-active compounds in pink guava (Psidium guajava, L.) by application of the aroma extract dilution analysis J. Agric. Food Chem. 2008, 56, 4120-4127
    • (2008) J. Agric. Food Chem. , vol.56 , pp. 4120-4127
    • Steinhaus, M.1    Sinuco, D.2    Polster, J.3    Osorio, C.4    Schieberle, P.5
  • 18
    • 0009400827 scopus 로고    scopus 로고
    • Enantioselective syntheses and sensory properties of the 3-mercapto-2-methylpentanols
    • Sabater Lüntzel, C.; Widder, S.; Vössing, T.; Pickenhagen, W. Enantioselective syntheses and sensory properties of the 3-mercapto-2- methylpentanols J. Agric. Food Chem. 2000, 48, 424-427
    • (2000) J. Agric. Food Chem. , vol.48 , pp. 424-427
    • Sabater Lüntzel, C.1    Widder, S.2    Vössing, T.3    Pickenhagen, W.4
  • 19
    • 38949170571 scopus 로고    scopus 로고
    • New volatile sulfur-containing constituents in a simultaneous distillation-extraction extract of red bell peppers (Capsicum annuum)
    • Naef, R.; Velluz, A.; Jaquier, A. New volatile sulfur-containing constituents in a simultaneous distillation-extraction extract of red bell peppers (Capsicum annuum) J. Agric. Food Chem. 2008, 56, 517-527
    • (2008) J. Agric. Food Chem. , vol.56 , pp. 517-527
    • Naef, R.1    Velluz, A.2    Jaquier, A.3
  • 20
    • 84905574863 scopus 로고    scopus 로고
    • Analytical and sensory characterization of chiral 4-mercapto-2-alkanones, 4-acetylthio-2-alkanones and the corresponding alcohols
    • Toth, S. Mussinan, C. ACS Symposium Series 1098; American Chemical Society: Denver, CO
    • Wakabayashi, M.; Wakabayashi, H.; Nörenberg, S.; Reichardt, B.; Kubota, K.; Engel, K.-H. Analytical and sensory characterization of chiral 4-mercapto-2-alkanones, 4-acetylthio-2-alkanones and the corresponding alcohols. In Recent Advances in the Analysis of Food and Flavors; Toth, S.; Mussinan, C., Eds.; ACS Symposium Series 1098; American Chemical Society: Denver, CO, 2012; pp 27-39.
    • (2012) Recent Advances in the Analysis of Food and Flavors , pp. 27-39
    • Wakabayashi, M.1    Wakabayashi, H.2    Nörenberg, S.3    Reichardt, B.4    Kubota, K.5    Engel, K.-H.6
  • 21
    • 2542458777 scopus 로고    scopus 로고
    • Synthesis and sensorial properties of 2-alkylalk-2-enals and 3-(acetylthio)-2-alkyl alkanals
    • Robert, F.; Héritier, J.; Quiquerez, J.; Simian, H.; Blank, I. Synthesis and sensorial properties of 2-alkylalk-2-enals and 3-(acetylthio)-2-alkyl alkanals J. Agric. Food Chem. 2004, 52, 3525-3529
    • (2004) J. Agric. Food Chem. , vol.52 , pp. 3525-3529
    • Robert, F.1    Héritier, J.2    Quiquerez, J.3    Simian, H.4    Blank, I.5
  • 23
    • 34047272388 scopus 로고
    • A generalization of the retention index system including linear temperature programmed gas-liquid partition chromatography
    • Van den Dool, H.; Kratz, P. D. A generalization of the retention index system including linear temperature programmed gas-liquid partition chromatography J. Chromatogr. 1963, 11, 463-471
    • (1963) J. Chromatogr. , vol.11 , pp. 463-471
    • Van Den Dool, H.1    Kratz, P.D.2
  • 24
    • 84985201303 scopus 로고
    • Stereoisomeric flavor compounds. Part LV: Stereodifferentiation of some chiral volatiles on heptakis(2,3-di- O -acetyl-6- O - Tert -butyldimethylsilyl)- β-cyclodextrin
    • Dietrich, A.; Maas, B.; Karl, V.; Kreis, P.; Lehmann, D.; Weber, B.; Mosandl, A. Stereoisomeric flavor compounds. Part LV: Stereodifferentiation of some chiral volatiles on heptakis(2,3-di- O -acetyl-6- O-tert -butyldimethylsilyl)-β-cyclodextrin J. High Resolut. Chromatogr. 1992, 15, 176-179
    • (1992) J. High Resolut. Chromatogr. , vol.15 , pp. 176-179
    • Dietrich, A.1    Maas, B.2    Karl, V.3    Kreis, P.4    Lehmann, D.5    Weber, B.6    Mosandl, A.7
  • 26
    • 84985233025 scopus 로고
    • Stereoisomeric flavor compounds. Part LVIII: The use of heptakis(2,3-di- O -methyl-6- O - Tert -butyldimethylsilyl)-β-cyclodextrin as a chiral stationary phase in flavor analysis
    • Dietrich, A.; Maas, B.; Messer, W.; Bruche, G.; Karl, V.; Kaunzinger, A.; Mosandl, A. Stereoisomeric flavor compounds. Part LVIII: The use of heptakis(2,3-di- O -methyl-6- O-tert -butyldimethylsilyl)-β-cyclodextrin as a chiral stationary phase in flavor analysis J. High Resolut. Chromatogr. 1992, 15, 590-593
    • (1992) J. High Resolut. Chromatogr. , vol.15 , pp. 590-593
    • Dietrich, A.1    Maas, B.2    Messer, W.3    Bruche, G.4    Karl, V.5    Kaunzinger, A.6    Mosandl, A.7
  • 27
    • 34250103394 scopus 로고
    • Identification of the most intense volatile flavour compounds formed during autoxidation of linoleic acid
    • Ullrich, F.; Grosch, W. Identification of the most intense volatile flavour compounds formed during autoxidation of linoleic acid Z. Lebensm. Unters. Forsch. 1987, 184, 277-282
    • (1987) Z. Lebensm. Unters. Forsch. , vol.184 , pp. 277-282
    • Ullrich, F.1    Grosch, W.2
  • 28
    • 0342439009 scopus 로고
    • Detection of potent odorants in foods by aroma extract dilution analysis
    • Grosch, W. Detection of potent odorants in foods by aroma extract dilution analysis Trends Food Sci. Technol. 1993, 4, 68-73
    • (1993) Trends Food Sci. Technol. , vol.4 , pp. 68-73
    • Grosch, W.1
  • 29
    • 33751392170 scopus 로고
    • Stereocontrol in the Mukaiyama aldol addition to chiral α- And β-thio-substituted aldehydes
    • Annunziata, R.; Cinquini, M.; Cozzi, F.; Cozzi, P. G.; Consolandi, E. Stereocontrol in the Mukaiyama aldol addition to chiral α- and β-thio-substituted aldehydes J. Org. Chem. 1992, 57, 456-461
    • (1992) J. Org. Chem. , vol.57 , pp. 456-461
    • Annunziata, R.1    Cinquini, M.2    Cozzi, F.3    Cozzi, P.G.4    Consolandi, E.5
  • 30
    • 1442301826 scopus 로고    scopus 로고
    • Diastereo- and enantioselective synthesis of anti -1,3-mercapto alcohols from α,β-unsaturated ketones via tandem Michael addition-MPV reduction
    • Ozeki, M.; Nishide, K.; Teraoka, F.; Node, M. Diastereo- and enantioselective synthesis of anti -1,3-mercapto alcohols from α,β-unsaturated ketones via tandem Michael addition-MPV reduction Tetrahedron: Asymmetry 2004, 15, 895-907
    • (2004) Tetrahedron: Asymmetry , vol.15 , pp. 895-907
    • Ozeki, M.1    Nishide, K.2    Teraoka, F.3    Node, M.4
  • 31
    • 0001571874 scopus 로고
    • Stereochemistry of desulfurization of thietane derivatives
    • Trost, B. M.; Schinski, W. L.; Chen, F.; Mantz, I. B. Stereochemistry of desulfurization of thietane derivatives J. Am. Chem. Soc. 1971, 93, 676-684
    • (1971) J. Am. Chem. Soc. , vol.93 , pp. 676-684
    • Trost, B.M.1    Schinski, W.L.2    Chen, F.3    Mantz, I.B.4
  • 32
    • 33644626515 scopus 로고    scopus 로고
    • Chiral multidimensional gas chromatography (MDGC) and chiral GC-olfactometry with a double-cool-strand interface: Application to malodors
    • Begnaud, F.; Starkenmann, C.; Van de Waal, M.; Chaintreau, A. Chiral multidimensional gas chromatography (MDGC) and chiral GC-olfactometry with a double-cool-strand interface: Application to malodors Chem. Biodiversity 2006, 3, 150-160
    • (2006) Chem. Biodiversity , vol.3 , pp. 150-160
    • Begnaud, F.1    Starkenmann, C.2    Van De Waal, M.3    Chaintreau, A.4


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