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Volumn 57, Issue 21, 2009, Pages 9909-9915

Stereochemical studies of odorous 2-substituted-3(2H)-furanones by vibrational circular dichroism

Author keywords

Absolute configuration; Chiral; Furanone; Supercritical fluid chromatography (sfc); Vibrational circular dichrolsm (vcd)

Indexed keywords

FURAN DERIVATIVE;

EID: 70449120804     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf901439v     Document Type: Article
Times cited : (22)

References (42)
  • 1
    • 0032984654 scopus 로고    scopus 로고
    • 2,5-dimethyl-4hydroxy-2H-furan-3-one and its derivatives: Analysis, synthesis and biosynthesis-a review
    • Zabetakis, I.; Gramshaw, J. W.; Robinson, D. S. 2,5-Dimethyl-4hydroxy-2H- furan-3-one and its derivatives: analysis, synthesis and biosynthesis-a review. Food Chem. 1999, 65, 139-151.
    • (1999) Food Chem. , vol.65 , pp. 139-151
    • Zabetakis, I.1    Gramshaw, J.W.2    Robinson, D.S.3
  • 2
    • 0032812787 scopus 로고    scopus 로고
    • The naturally occurring furanones: Formation and function from pheromone to food
    • Slaughter, J. C. The naturally occurring furanones: formation and function from pheromone to food. Biol. Rev. 1999, 74, 259-276.
    • (1999) Biol. Rev. , vol.74 , pp. 259-276
    • Slaughter, J.C.1
  • 5
    • 0002500566 scopus 로고
    • Dicarbonyls, reductones, and heterocyclic produced by reaction of reducing sugars with sencondary amine salts
    • Hodge, J. E.; Fisher, B. E.; Nelson, H. A. Dicarbonyls, reductones, and heterocyclic produced by reaction of reducing sugars with sencondary amine salts. Am. Soc. Brew. Chem. Proc. 1963, 83, 84-92.
    • (1963) Am. Soc. Brew. Chem. Proc. , vol.83 , pp. 84-92
    • Hodge, J.E.1    Fisher, B.E.2    Nelson, H.A.3
  • 6
    • 0010537768 scopus 로고
    • 2,5-Dimethyl-4-hydroxy-2,3dihydrofuran-3-one
    • Willhalm, B.; Stoll, M.; Thomas, A. F. 2,5-Dimethyl-4-hydroxy-2, 3dihydrofuran-3-one. Chem. Ind. London 1965, 38, 1629-1630.
    • (1965) Chem. Ind. London , vol.38 , pp. 1629-1630
    • Willhalm, B.1    Stoll, M.2    Thomas, A.F.3
  • 7
    • 84981853856 scopus 로고
    • Volatile flavor and aroma components of pineapple. I. Isolation and tentative identification of 2,5-dimethyl-4-hydroxy3(2H)-furanone
    • Rodin, J. O.; Himel, C. M.; Silverstein, R. M.; Leeper, R. W.; Gortner, W. A. Volatile flavor and aroma components of pineapple. I. Isolation and tentative identification of 2,5-dimethyl-4-hydroxy3(2H)-furanone. J. food Sci. 1965, 30, 280-285.
    • (1965) J. Food Sci. , vol.30 , pp. 280-285
    • Rodin, J.O.1    Himel, C.M.2    Silverstein, R.M.3    Leeper, R.W.4    Gortner, W.A.5
  • 9
    • 84988077140 scopus 로고    scopus 로고
    • Supercritical fluid extraction as a preparative tool for strawberry aroma analysis
    • Polesello, S.; Lovati, F.; Rizzolo, A.; Rovida, C. Supercritical fluid extraction as a preparative tool for strawberry aroma analysis. HRC & CC 993, 16, 555-559.
    • HRC & CC , vol.993 , Issue.16 , pp. 555-559
    • Polesello, S.1    Lovati, F.2    Rizzolo, A.3    Rovida, C.4
  • 10
    • 0012803781 scopus 로고    scopus 로고
    • Flavor chemistry and odor thresholds
    • Kluwer Academic/ Plenum Publishers: New York
    • Buttery, R. G.; Huber, U. A. Flavor chemistry and odor thresholds. In Flavor Chemistry: Thirty Years of Progress; Kluwer Academic/ Plenum Publishers: New York, 1999; pp 353-365.
    • (1999) Flavor Chemistry: Thirty Years of Progress , pp. 353-365
    • Buttery, R.G.1    Huber, U.A.2
  • 11
    • 0002848686 scopus 로고
    • Non-enzymatic browning reactions
    • H. W., Day, E. A., Libbey, L. M., Eds.; AVI Publising: Westport, CT
    • Hodge, J. E. Non-enzymatic browning reactions. In Symposium on Foods. Chemistry and Physiology of Flavors; Schultz, H. W., Day, E. A., Libbey, L. M., Eds.; AVI Publising: Westport, CT, 1967; pp 465-491
    • (1967) Symposium on Foods. Chemistry and Physiology of Flavors; Schultz , pp. 465-491
    • Hodge, J.E.1
  • 12
    • 2142770299 scopus 로고    scopus 로고
    • Characterization of 3,4dihydroxy-3-hexen-2,5-dione as the first open-chain caramel-like smelling flavor compound
    • Engel, W.; Hofmann, T.; Schieberle, P. Characterization of 3,4dihydroxy-3-hexen-2,5-dione as the first open-chain caramel-like smelling flavor compound. Eur. Food Res. Technol. 2001, 213, 104-106.
    • (2001) Eur. Food Res. Technol. , vol.213 , pp. 104-106
    • Engel, W.1    Hofmann, T.2    Schieberle, P.3
  • 13
    • 70449107407 scopus 로고    scopus 로고
    • IPCS-International programme on chemical safety
    • WHO Food Additives Series 2006 World Health Organization: Geneva, Switzerland
    • IPCS-International Programme on Chemical Safety. Safety Evaluation of Certain Food Additives; WHO Food Additives Series 2006; World Health Organization: Geneva, Switzerland, 2006; Vol. 54, pp 494-495.
    • (2006) Safety Evaluation of Certain Food Additives , vol.54 , pp. 494-495
  • 15
    • 33749863296 scopus 로고    scopus 로고
    • The nose as a stereochemist. Emantiomers and Odor
    • Bentley, R. The nose as a stereochemist. Emantiomers and Odor. Chem Rev. 2006, 106, 4099-4112.
    • (2006) Chem Rev. , vol.106 , pp. 4099-4112
    • Bentley, R.1
  • 16
    • 0001524485 scopus 로고
    • Sensory properties of optical isomers
    • Boelens, M. H.; Gemert, L. J. Sensory properties of optical isomers. Perfum. Flavor. 1993, 18 (6), 3-16.
    • (1993) Perfum. Flavor. , vol.18 , Issue.6 , pp. 3-16
    • Boelens, M.H.1    Gemert, L.J.2
  • 17
    • 0034841687 scopus 로고    scopus 로고
    • Metabolic fate of isotopes during the biological transformation of carbohydrates to 2,5-dimethyl-4-hydroxy-3(2H)-furanone in strawberry fruits
    • Wein, M.; Lewinsohn, E.; Schwab, W. Metabolic fate of isotopes during the biological transformation of carbohydrates to 2,5-dimethyl-4-hydroxy-3(2H)- furanone in strawberry fruits. J. Agric. Food Chem. 2001, 49, 2427-2432.
    • (2001) J. Agric. Food Chem. , vol.49 , pp. 2427-2432
    • Wein, M.1    Lewinsohn, E.2    Schwab, W.3
  • 18
    • 0035057405 scopus 로고    scopus 로고
    • The role of β-glucosidase in the biosynthesis of 2,5-dimethyl-4-hydroxy-3(2H)-furanone in strawberry (Fragaria x ananassa cv. Elsanta)
    • Orruno, E.; Apenten, R. O.; Zabetakis, I. The role of β-glucosidase in the biosynthesis of 2,5-dimethyl-4-hydroxy-3(2H)-furanone in strawberry (Fragaria x ananassa cv. Elsanta). flavour Fragrance J. 2001, 16, 81-84.
    • (2001) Flavour Fragrance J. , vol.16 , pp. 81-84
    • Orruno, E.1    Apenten, R.O.2    Zabetakis, I.3
  • 19
    • 33745453677 scopus 로고    scopus 로고
    • FaQR, required for the biosynthesis of the strawberry flavor compound 4-hydroxy-2,5-dimethyl-3(2H)furanone, encodes an enone oxidoreductase
    • Raab, T.; López-Ráez, J. A.; Klein, D.; Caballero, J. L.; Moyano, E.; Schwab, W.; Muñoz-Blanco, J. FaQR, required for the biosynthesis of the strawberry flavor compound 4-hydroxy-2,5-dimethyl-3(2H) furanone, encodes an enone oxidoreductase. Plant Cell 2006, 18, 1023-1037.
    • (2006) Plant Cell , vol.18 , pp. 1023-1037
    • Raab, T.1    López-Ráez, J.A.2    Klein, D.3    Caballero, J.L.4    Moyano, E.5    Schwab, W.6    Muñoz-Blanco, J.7
  • 20
    • 0000066439 scopus 로고    scopus 로고
    • Formation of 4-hydroxy-2,5-dimethyl-3(2H)-furanone and 4-hydroxy-2(or 5)-ethyl-5(or 2)-methyl-3(2H)-furanone through maillard reaction based on pentose sugars
    • Blank,I.;Fay,L.Formationof4-hydroxy-2,5-dimethyl-3(2H) furanoneand4-hydroxy-2(or5)-ethyl-5(or2)-methyl-3-(2H)- furanonethroughMaillardreactionbasedonpentosesugars.J.Agric.FoodChem.1996,44, 531-536.(Pubitemid126469463)
    • (1996) Journal of Agricultural and Food Chemistry , vol.44 , Issue.2 , pp. 531-536
    • Blank, I.1    Fay, L.B.2
  • 21
    • 84985261034 scopus 로고
    • Stereoisomeric flavor compounds XLIV: Enantioselective analysis of some important flavor molecules
    • Mosandl, A.; Bruche, G.; Askari, C.; Schmarr, H. G. Stereoisomeric flavor compounds XLIV: enantioselective analysis of some important flavor molecules. J. Hieh Resolut. Chromatogr. 1990, 13, 660-662.
    • (1990) J. Hieh Resolut. Chromatogr. , vol.13 , pp. 660-662
    • Mosandl, A.1    Bruche, G.2    Askari, C.3    Schmarr, H.G.4
  • 22
    • 84985233025 scopus 로고
    • Stereoisomeric flavor compounds, part LVIII; the use of heptakis(2,3-di-O-methyl-6-O-tert-butyldimethylsilyl)-βcyclodextrin 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)-βcyclodextrin 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
  • 23
    • 0000371170 scopus 로고
    • Stereoisomeric flavour compounds LXXI: Determination of the origin of aroma-active dihydrofuranones
    • Bruche, G.; Dietrich, A.; Mosandl, A. Stereoisomeric flavour compounds LXXI: determination of the origin of aroma-active dihydrofuranones. J. Lebensm. Unters. Forsch. 1995, 201, 249-252.
    • (1995) J. Lebensm. Unters. Forsch. , vol.201 , pp. 249-252
    • Bruche, G.1    Dietrich, A.2    Mosandl, A.3
  • 25
    • 0242600808 scopus 로고    scopus 로고
    • Capillary electrophoretic resolution of the enantiomers of 2,5-dimethyl-4-hydroxy-3(2H)-furanone, the key flavor compounds in strawberry fruit
    • DOI 10.1007/BF02492548
    • Raab, T.; Schmitt, U.; Hauck, T.; Knecht, A.; Holzgrabe, U.; Schwab, W. Capillary electrophoretic resolution of the enantiomers of 2,5-dimethyl-4- hydroxy-3(2H)-furanone, the key flavor compounds in strawberry fruit. Chromatoeraohia 2003, 57, 501-504. (Pubitemid 36470153)
    • (2003) Chromatographia , vol.57 , Issue.7-8 , pp. 501-504
    • Raab, T.1    Schmitt, U.2    Hauck, T.3    Knecht, A.4    Holzgrabe, U.5    Schwab, W.6
  • 26
    • 0043166662 scopus 로고    scopus 로고
    • Tautomerism of 4-hydroxy-2,5-dimethyl-3(2H)-furanone: Evidence for its enantioselective biosynthesis
    • DOI 10.1002/chir.10247
    • Raab, T.; Hauck, T.; Knecht, A.; Schmitt, U.; Holzgrabe, U.; Schwab, W. Tautomerism of 4-hydroxy-2,5-dimethyl-3(2H)-furanone: evidence for its enantioselective biosynthesis. Charality 2003, 15, 573-578. (Pubitemid 36935511)
    • (2003) Chirality , vol.15 , Issue.7 , pp. 573-578
    • Raab, T.1    Hauck, T.2    Knecht, A.3    Schmiti, U.4    Holzgrabe, U.5    Schwab, W.6
  • 27
    • 84988087924 scopus 로고
    • Stereoisomeric flavor compounds part LXV. Preparative resolution of the enantiomers of chiral dihydrofuranones by recycling chromatography
    • Bruche, G.; Mosandl, A.; Kinkel, J. N. Stereoisomeric flavor compounds part LXV. Preparative resolution of the enantiomers of chiral dihydrofuranones by recycling chromatography. J. High Resolut. Chromatogr. 1993, 16, 254-257.
    • (1993) J. High Resolut. Chromatogr. , vol.16 , pp. 254-257
    • Bruche, G.1    Mosandl, A.2    Kinkel, J.N.3
  • 28
    • 70449119176 scopus 로고    scopus 로고
    • Lipase catalyzed preparation of optically active flavouring substances
    • P., Engel, K.-.H., Eds.; Deutsche Forschungsanstalt für Lebensmittelchemie: Garching, Germany;
    • Nozaki, M.; Suzuki, N.; Tsuruta, H. Lipase catalyzed preparation of optically active flavouring substances. In Frontuers of Flavour Science; Schieberle, P., Engel, K.-.H., Eds.; Deutsche Forschungsanstalt für Lebensmittelchemie: Garching, Germany; 2000; pp 426-430
    • (2000) Frontuers of Flavour Science; Schieberle , pp. 426-430
    • Nozaki, M.1    Suzuki, N.2    Tsuruta, H.3
  • 30
    • 0035847289 scopus 로고    scopus 로고
    • Enantioseparations in super- And subcritical fluid chromatography
    • DOI 10.1016/S0021-9673(00)00952-3, PII S0021967300009523
    • Terfloth, G. Enantioseparations in super- and subcritical fluid Chromatograph. J. Chromatogr., A 2001, 906, 301-307. (Pubitemid 32056209)
    • (2001) Journal of Chromatography A , vol.906 , Issue.1-2 , pp. 301-307
    • Terfloth, G.1
  • 31
    • 18144400098 scopus 로고    scopus 로고
    • Enantioselective separations by packed column subcritical and supercritical fluid chromatography
    • DOI 10.1007/s00216-005-3074-y
    • Phinney, K. W. Enantioselective separations by packed column subcritical and supercritical fluid chromatography. Anal. Bioanal. Chem. 2005, 382, 639-645. (Pubitemid 40890992)
    • (2005) Analytical and Bioanalytical Chemistry , vol.382 , Issue.3 , pp. 639-645
    • Phinney, K.W.1
  • 32
    • 70449115929 scopus 로고    scopus 로고
    • Preparation of chiral flavor chemicals using enantioselective supercritical fluid carbon dioxide chromatography
    • Hofmann, T., Meyerhof, W., Schieberle, P., Eds.; Deutsche Forschungsanstalt für Lebensmittelchemie: Garching, Germany
    • Sugimoto, D.; Yaguchi, Y.; Kasuga, H.; Okajima, S.; Emura, M. Preparation of chiral flavor chemicals using enantioselective supercritical fluid carbon dioxide chromatography. In Recent Highlights in Flavor Chemistry and Biology; Hofmann, T., Meyerhof, W., Schieberle, P., Eds.; Deutsche Forschungsanstalt für Lebensmittelchemie: Garching, Germany, 2008; pp 340-344.
    • (2008) Recent Highlights in Flavor Chemistry and Biology , pp. 340-344
    • Sugimoto, D.1    Yaguchi, Y.2    Kasuga, H.3    Okajima, S.4    Emura, M.5
  • 33
    • 0000042757 scopus 로고    scopus 로고
    • Peptide and protein conformational studies with vibrational circular dichroism and related spectroscopies
    • Berova, N., Nakanishi, K., Woody, R. W., Eds.; Wiley-VCH: New York
    • Keiderling, T. A. Peptide and protein conformational studies with vibrational circular dichroism and related spectroscopies. In Circular Dichroism: Principles and Applications; Berova, N., Nakanishi, K., Woody, R. W., Eds.; Wiley-VCH: New York, 2000; pp 621 -666.
    • (2000) Circular Dichroism: Principles and Applications , pp. 621-666
    • Keiderling, T.A.1
  • 34
    • 0242322522 scopus 로고    scopus 로고
    • Absolute Configuration Determination of Chiral Molecules in the Solution State Using Vibrational Circular Dichroism
    • DOI 10.1002/chir.10287
    • Freedman, T. B.; Cao, X.; Dukor, R. K.; Nafie, L. A. Absolute configuration determination of chiral molecules in the solution state using vibrational circular dichroism. Chirality 2003, 15, 743-758. (Pubitemid 37356644)
    • (2003) Chirality , vol.15 , Issue.9 , pp. 743-758
    • Freedman, T.B.1    Cao, X.2    Dukor, R.3    Nafie, L.A.4
  • 35
    • 0842283949 scopus 로고    scopus 로고
    • Chiral analysis using mid-IR vibrational CD spectrospcopy
    • Polavarapu, P. L.; He, J. Chiral analysis using mid-IR vibrational CD spectrospcopy. Anal. Chem. 2004, 76, 61A-67A.
    • (2004) Anal. Chem. , vol.76
    • Polavarapu, P.L.1    He, J.2
  • 36
  • 37
    • 84884429318 scopus 로고    scopus 로고
    • Vibrational optical activity in chiral analysis
    • K. W., Busch, M. A., Eds.; Elsevier: Amsterdam, The Netherlands
    • Ñafie, L. A.; Dukor, R. K. Vibrational optical activity in chiral analysis. In Chiral Analysis: Busch, K. W., Busch, M. A., Eds.; Elsevier: Amsterdam, The Netherlands, 2006; pp 505-544.
    • (2006) Chiral Analysis: Busch , pp. 505-544
    • Ñafie, L.A.1    Dukor, R.K.2
  • 38
    • 34548186124 scopus 로고    scopus 로고
    • Chiroptical analysis of glycoconjugates by vibrational circular dichroism (VCD)
    • Taniguchi, T.; Monde, K. Chiroptical analysis of glycoconjugates by vibrational circular dichroism (VCD). Trends Glycosci. Glvcotechnol. 2007, 19, 149-166.
    • (2007) Trends Glycosci. Glvcotechnol. , vol.19 , pp. 149-166
    • Taniguchi, T.1    Monde, K.2
  • 39
    • 49549084167 scopus 로고    scopus 로고
    • Absolute configuration determication of chiral molecules without crystallisation by vibrational circular dichroism (VCD)
    • Kellenbach, E. R.; Dukor, R. K.; Nafie, L. A. Absolute configuration determication of chiral molecules without crystallisation by vibrational circular dichroism (VCD). Spectrosc. Eur. 2007, 19, 15-17.
    • (2007) Spectrosc. Eur. , vol.19 , pp. 15-17
    • Kellenbach, E.R.1    Dukor, R.K.2    Nafie, L.A.3
  • 40
    • 34247242120 scopus 로고    scopus 로고
    • Renaissance in chiroptical spectroscopic methods for molecular structure determination
    • Polavarapu, P. L. Renaissance in chiroptical spectroscopic methods for molecular structure determination. Chemm. Rec. 2007, 7, 125-136.
    • (2007) Chemm. Rec. , vol.7 , pp. 125-136
    • Polavarapu, P.L.1
  • 41
    • 43249097508 scopus 로고    scopus 로고
    • The determination of the absolute configurations of chiral molecules using vibrational circular dichroism (VCD) spectroscopy
    • Stephens, P. J.; Devlin, F. J.; Pan, J.-J. The determination of the absolute configurations of chiral molecules using vibrational circular dichroism (VCD) spectroscopy. Chirality 2008, 20, 643-663.
    • (2008) Chirality , vol.20 , pp. 643-663
    • Stephens, P.J.1    Devlin, F.J.2    Pan, J.-J.3
  • 42
    • 58149161580 scopus 로고    scopus 로고
    • Stereochemical study of chiral tautomeric flavorous furanones by vibrational circular dichroism
    • Yaguchi, Y.; Nakahashi, A.; Miura, N.; Sugimoto, D.; Monde, K.; Emura, M. Stereochemical study of chiral tautomeric flavorous furanones by vibrational circular dichroism. Org. Lett. 2008, 10, 4883-4885.
    • (2008) Org. Lett. , vol.10 , pp. 4883-4885
    • Yaguchi, Y.1    Nakahashi, A.2    Miura, N.3    Sugimoto, D.4    Monde, K.5    Emura, M.6


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