Métrica de Usabilidad de Atributos del Modelo

7. Buck L, Axel R, A novel multigene family may encode odorant receptors – a molecular basis for odor recognition, Cell 65:175–187, 1991.

8. Bernreuther A, Epperlein U, Koppenhoefer B, Enantiomers: Why they are important and how to resolve them, in Marsili, R (ed.) Techniques for Analyzing Food Aroma. Marcel Dekker, New York, USA, pp. 143–207, 1997.

9. Brenna E, Fuganti C, Serra S, Enantioselective perception of chiral odorants, Tetrahedron: Assymetry 14:1–42, 2003.

10. Leffingwell JC, Chirality and Odour Perception, www.leffingwell.com/chirality, 2003.

11. Abate A, Brenna E, Fuganti C, Gatti FG, Serra S, Odor and (bio)diversity: Single enantiomers of chiral fragrant substances, Chemistry and Biodiversity 1:1888– 1898, 2004.

12. Sell CS, Scent through the looking glass, Chemistry & Biodiversity 1:1899–1920, 2004.

13. Stinson SC, Chiral Chemistry C&EN, 79(20):45–57, 2001.

14. Challener CA (ed.), Chiral Intermediates. Ashgate: Brookfield, Vermont, USA, 2001.

15. Fluka Chemika, Chiral Compounds Chemistry, Fluka Chemie AG, Switzerland, 1994.

16. Merck-Schuchardt, Chiralica — Reagents, catalysts and building blocks for enantioselective synthesis; Resolving Agents, E Merck Co., Germany, 1985. 17. Silverstein RM, Chiral semiochemicals, in Acree TE, Soderlund DM (eds.),

Semiochemistry: Flavors and Pheromones, Walter de Gruyter, Berlin, Germany, pp. 121–140, 1985.

18. Ho TL, Enantioselective synthesis: Natural products from chiral terpenes, Wiley- Interscience, New York, USA, 1992.

19. Mori K, Semiochemicals – Synthesis, stereochemistry and bioactivity. Eur J Org Chem 1479–1489, 1998.

20. Werkhoff P, Brennecke S, Bretschneider W, Güntert M, Hopp R, Surburg H, Chirospecific analysis in essential oil, fragrance and flavor research, Z Lebensm Unters Forsch 196:307–328, 1993.

21. Formáˆcek V, Kubeczka KH, Essential Oils Analysis by Capillary Gas Chromatog- raphy and Carbon-13 NMR Spectroscopy, John Wiley & Sons, Chichester, Great Britain, 1982.

22. König WA, Fricke C, Saritas Y, Momeni B, Hohenfeld G, Adulteration or natural variability? Enantioselective gas chromatography in purity control of essential oils, J High Resolut Chromatogr 20:55–61, 1997.

23. König WA, Hochmuth DH, Enantioselective gas chromatography in flavor and fragrance analysis: Strategies for the identification of known and unknown plant volatiles J Chromatogr Sci. 42:423–439, 2004.

24. Marchelli R, Dossena A, Pala G, The potential of enantioselective analysis as a quality control tool, Trends Food Sci Technol 7:113–119, 1996.

25. Mosandl A, Juchelka D, Advances in the authenticity assessment of citrus oils. J Essent Oil Res 9:5–12, 1997.

26. Larkov O, Dunkelblum E, Zada A, Lewinsohn E, Freiman L, Dudai N, Ravid U, Enantiomeric composition of trans- and cis- sabinene hydrate and their acetates in five Origanum spp., Flavour Fragr J 22:109–114, 2005.

27. Boelens M, Boelens H, van Gemert LJ, Sensory properties of optical isomers, Perfum Flavor 18(6), 1–16, 1993.

28. Friedman L, Miller JG, Odor incongruity and chirality, Science 172:1044–1046, 1971.

29. Jones FN, Elliot D, Individual and substance differences in the discriminability of optical isomers, Chem Senses and Flavor 1:317–321, 1975.

30. Koppenhoefer B, Behnisch R, Epperlein U, Holzschuh H, Bernreuther A, Piras P, Roussel C, Enantiomeric odor differences and gas chromatographic properties of flavors and fragrances, Perfum Flavorist 19(5):1–14, 1994.

31. Laska M, Teubner P, Olfactory discrimination ability of human subjects for ten pairs of enantiomers, Chem. Senses 24:161–170, 1999.

32. Ohloff G, in Schneider D (ed.), Odorous properties of enantiomeric compounds: Olfaction and Taste IV, Wissenschaft Verlagsgesellschaft, Stuttgart, Germany, pp. 156–160, 1972.

33. Theimer ET, McDaniel MR, Odor and optical activity, J Soc Cosmet Chem 22:15– 26, 1970.

34. Zawirska-Wojtasiak R, Chirality and the nature of food authenticity of aroma, Acta Sci Pol Technol Aliment, 5:21–36, 2006.

35. Theimer ET, Yoshida T, Klaiber EM, Olfaction and molecular shape. Chirality as a requisite for odor, J Agric Food Chem 25:1168–1177, 1977.

36. Pelosi P, Viti R, Specific anosmia to l-carvone: The minty primary odour, Chem Senses 3:331–337, 1978.

37. Emberger R, Hopp R, Synthesis and sensory characterization of menthol enan- tiomers and their derivatives for the use in nature identical peppermint oils, in Berger RG, Nitz N, Schreier P, (eds.), Topics in Flavour Research, H. Eichhorn, Marzling-Hangenham, Germany, pp. 201–218, 1985.

38. Werkhoff P, Hopp R, Isolation and gas chromatographic separation of menthol and menthone enantiomers from natural peppermint oils, in Brunke EJ (ed.), Progress in Essential Oil Research, Walter de Gruyter, Berlin, Germany, pp. 529– 549, 1986.

39. Skorianetz W, Giger H, Ohloff G, Darstellung von (+) und (−)-7-hydroxy- dihydrocitronellal aus (+)-pulegon. Ein Beitrag zur kenntnis olfactorischer eigenschaften von enantiomern, Helv Chim Acta 54:1797–1801, 1971. 40. Grob K, Neukom HP, Etter R, Romann E, Food control by government lab-

oratories: Innovation, flexibility and no restriction by reglementation, Chimia

46:420–424, 1992.

41. Gübitz G, Schmid G, Chiral separation by choromatographic and electromigra- tion techniques, A review, Biopharm. Drug Dispos 22:291–336, 2001.

42. Siegwart Y, Some critical comments on the legislative control of flavouring in food, Flavour Fragr J 8:87–90, 1993.

43. Schurig V, Separation of enantiomers by gas chromatograpy, J Chromatogr

906:275–299, 2001.

44. Schurig V. Enantiomer separation by complexation gas chromatography — Applications in chiral analysis of pheromones and flavours, in Schreier P (ed.), Bioflavour’87, Walter de Gruyter, Berlin, Germany, pp. 35–54, 1988.

45. Weber R, Schurig V, Complexation gas chromatography — a valuable tool for the stereochemical analysis of pheromones, Naturwissenschaften, 71:408–413, 1984. 46. König WA, The Practice of Enantiomer Separation by Capillary Gas Chromatogra-

47. König WA, Gas Chromatographic Enantiomer Separation with Modified Cyclodex- trins, Hüthig, Heidelberg, Germany, 1992.

48. Schurig V, Nowotny HP, Gas chromatographic separation of enantiomers on cyclodextrin derivatives, Angew Chem 29, 939–957, 1990.

49. Bicchi C, Manzin V, D’Amato A, Rubiolo P, Cyclodextrin derivatives in GC separation of enantiomers of essential oil, aroma and flavour compounds, Flavour Fragr J 10:127–137, 1995.

50. Bicchi C, D’Amato A, Rubiolo P, Cyclodextrin derivatives as chiral selectors for direct gas chromatographic separation of enantiomers in the essential oil, aroma and flavor fields, J Chromatogr A 843:99–121, 1999.

51. König WA, Enantioselective capillary gas chromatography in the investigation of stereochemical correlations of terpenoids, Chirality 10:499–504, 1998. 52. Marriott PJ, Shellie R, Cornwell C, Gas chromatographic technologies for the

analysis of essential oils, J Chromatogr A 936:1–22, 2001.

53. Mosandl A, Capillary gas chromatography in quality assessment of flavours and fragrances J Chromatogr 624:267–292, 1992.

54. Mosandl A, Enantioselective capillary gas chromatography and stable isotope ratio mass spectrometry in the authenticity control of flavors and essential oils, Food Rev Int 11:597–664, 1995.

55. Mosandl A, Authenticity assessment: A permanent challenge in food flavor and essential oil analysis, J Chromatogr Sci 42:440–449, 2004.

56. Ravid U, Enantiomeric distribution of oxygenated monoterpenes in some Men- tha essential oils, Perfum Flavor 23(4):25–30, 1998.

57. Werkhoff P, Brennecke S, Bretschneider W, Progress in the chirospecific analysis of naturally occurring flavour and fragrance compounds, Chem Mikrobiol Technol Lebebsm 13:129–152, 1991.

58. Chirbase/Flavor; http://www.uni-tubingen.de/AK_Koppenhoefer/chirgc1. html (accessed on Nov. 28, 2006)

59. Koppenhoefer B, Epperlin U, Schlunk R, Information technology for enan- tiomer separation of flavors and fragrances, Chimica OGGI/ Chemistry Today, Jan–Feb, 1996.

60. Schmalzing D, Jung M, Mayer S, Rickert J, Schurig V, Extending the scope of enantiomer separation on Chirasil-Dex by GLC: Comparison with permethy- latedβ-cyclodextrin dissolved in 0V-1701, J High Resolut Chromatogr 15:723– 729, 1992.

61. Bicchi C, Artuffo G, D’Amato A, Nano GM, Galli A, Galli M, Permethylated cyclodextrins in the GC separation of racemic mixtures of volatiles: Part 1, J High Resolut Chromatogr 14:301–305, 1991.

62. Bicchi C, Artuffo G, D’Amato A, Manzin V, Galli A, Galli M, Cyclodextrin derivatives for the GC separation of racemic mixtures of volatile compounds, Part VI: The influence of the diluting phase on the enantioselectivity of 2,6-di- O-methyl-3-O-pentyl-β-cyclodextrin, J High Resolut Chromatogr 16:209–214, 1993.

63. Spilkin A, GC analysis using Cyclodex-BTM, The J & W Separation Times, 5(2): 6–7, 1991.

64. König WA, Krebber R, Mischnick P, Cyclodextrins as chiral stationary phases in capillary gas chromatography; Part V: Octakis(3-O-butyryl-2,6-di-O-pentyl)- γ-cyclodextrin, HRC 12:732–738, 1989.

65. Bicchi C, Artuffo G, D’Amato A, Manzin V, Galli A, Galli M, Cyclodextrin derivatives in the GC separation of racemic mixtures of volatile compounds, Part V: Heptakis 2,6-dimethyl-3-pentyl-β-cyclodextrins, J High Resolut Chromatogr

15:710–714, 1992.

66. Askari C, Hener U, Schmarr HG, Rapp A, Mosandl A, Stereodifferentiation of some chiral monoterpenes using multidimensional gas chromatography, Frese- nius J Anal Chem, 340:768–772, 1991.

67. Lawrence BM, Essential oils as sources of natural aroma chemicals, Perfum. Flavor

17(5):15–28, 1992.

68. Furia TE, Bellanca N (eds.), Fenaroli’s Handbook of Flavor Ingredients, CRC Press, Press, Boca Raton, Florida, USA, 1975.

69. Guenther E, The Essential Oils, Van Nostrand, New York, USA, 1949.

70. O’Neil MJ (ed.), The Merck Index, 13thed., Merck & Co., Whitehouse Station, New Jersey, USA, 2001.

71. Dev S (ed.), Handbook of Terpenoids, CRC Press, Boca Raton, Florida, USA, 1982.

72. Dewick PM, The biosynthesis of C5-C25terpenoid compounds, Nat Prod Rep

14:111–114, 1997.

73. Ravid U, Putievsky E, Katzir I, Enantiomeric distribution of piperitone in essen- tial oils of some Mentha spp., Calamintha incãna (Sm.) Heldr. and Artemisia judaica L, Flavour Fragr J, 9:85–87, 1994.

74. König WA, Krebber R, Evers P, Bruhn G, Stereochemical analysis of constituents of essential oils and flavor compounds by enantioselective capillary gas chro- matography HRC 13:328–332, 1990.

75. Larkov O, Matasyoh JC, Dudai N, Lewinsohn E, Mayer AA, Ravid U, Distri- bution of piperitone oxide stereoisomers in Mentha and Micromeria species and their chemical syntheses, Flavour Fragr J 22:328–333, 2007.

77. Croteau R, Venkatachalam KV, Metabolism of monoterpenes: Demonstra- tion that (+)-cis-isopulegone, not piperitenone, is the key intermediate in the conversion of (−)- isopiperitenone to (+)-pulegone in peppermint (Mentha piperita), Arch Biochem Biophys 249:306–315, 1986.

78. Ravid U, Putievsky E, Katzir I, Chiral GC analysis of (1R)(+)- pulegone with high enantiomeric purity in essential oils of some Lamiaceae aromatic plants, Flavour Fragr J 9:205–207, 1994.

79. Bauer K, Garbe D, Surburg H, Common Fragrance and Flavor Materials, VCH, Weinheim, Germany, 1990.

80. Köpke T, Mosandl A, Stereoisomeric flavor compounds. Part LIV: 8-Mercapto- p-menthane-3-one -optically pure stereoisomers and chirospecific analysis, Z Lebensm Unters Forsch 194:372–376, 1992.

81. Köpke T, Schmarr HG, Mosandl A, Stereoisomeric flavour compounds. Part LVII: The stereoisomers of 3-oxo-p-menthane-8-thiol acetate, simultaneously stereoanalyzed with their corresponding thiols, Flavour Fragr J 7:205–211, 1992. 82. Köpke T, Dietrich A, Mosandl A, Chiral compounds in essential oils XIV: Simul-

taneous stereoanalysis of buchu leaf oil, Phytochem Anal 5(19):61–67, 1994. 83. Grundy DL, Still CC, Inhibition of acetylcholinesterases by pulegone — 1,2-

epoxide, Pest Biochem Physiol 23:383–388, 1985.

84. Riddle JM, Estes JW, Oral contraceptives in ancient and medieval times, Am Sci

80:226–233, 1992.

85. Madyastha KM, Thulasiram HV, Transformation of a monoterpene ketone, (R)- (+) pulegone, a potent hepatotoxin, in Mucor piriformis, J Agric Food Chem,

47:1203–1207, 1999.

86. Nelson SD, McClanahan RH, Knebel N, Thomassen D, Gordon WP, Doshi S, The metabolism of (R)-(+)-pulegone, a toxic monoterpene, in Petrosky RJ, McCormick SP (eds.), Secondary-Metabolite Biosynthesis and Metabolism, Plenum Press, New York, USA, 1992.

87. Kreis P, Mosandl A, Chiral compounds of essential oils, Part XIII, Simultaneous chirality evaluation of geranium oil constituents, Flavour Fragr J 8:161–168, 1993.

88. Clark GS, An aroma chemical profile: Menthone, Perfum Flavor 19(3):41–45, 1994.

89. Askari C, Kreis P, Mosandl A, Schmarr HG, Chiral compounds of essential oils VII: Quality evaluation of Mentha oils, using enantioselective CGC-analysis of monoterpenoid constituents, Arch Pharm (Weinheim) 325:35–39, 1992. 90. Ravid U, Putievsky E, Katzir I, Chiral GC analysis of menthone and isomenthone

with high enantiomeric purities in laboratory-made and commercial essential oils, Flavour Fragr J 9:139–142, 1994.