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Volumn 47, Issue 8, 1999, Pages 3145-3150

Structure elucidation, enantioselective analysis, and biogenesis of nerol oxide in Pelargonium species

Author keywords

Biogenesis; Geraniaceae; Geranium oil; Nerol oxide; Pelargonium graveolens; Stable isotope labeling

Indexed keywords

NEROL; NEROL OXIDE; NONANOIC ACID; PYRAN DERIVATIVE; VEGETABLE OIL;

EID: 0032864733     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf981245m     Document Type: Article
Times cited : (7)

References (26)
  • 1
    • 0004238805 scopus 로고
    • Barth Verlagsgesellschaft mbH: Leipzig
    • Becker, H. G. O.; et al. Organikum, 19th ed.; Barth Verlagsgesellschaft mbH: Leipzig, 1993; pp 440-441, 511-12.
    • (1993) Organikum, 19th Ed. , pp. 440-441
    • Becker, H.G.O.1
  • 2
    • 19644397969 scopus 로고
    • New Methods for the Oxidation of Aldehydes to Carboxylic Acids and Esters
    • Corey, E. J.; Gilman, N. W.; Ganem, B. E. New Methods for the Oxidation of Aldehydes to Carboxylic Acids and Esters. J. Am. Chem. Soc. 1968, 90, 5616-5617.
    • (1968) J. Am. Chem. Soc. , vol.90 , pp. 5616-5617
    • Corey, E.J.1    Gilman, N.W.2    Ganem, B.E.3
  • 3
    • 33845282240 scopus 로고
    • Biosynthesis and Catabolism of Monoterpenes
    • Croteau, R. Biosynthesis and Catabolism of Monoterpenes. Chem. Rev. 1987, 87, 929-954.
    • (1987) Chem. Rev. , vol.87 , pp. 929-954
    • Croteau, R.1
  • 4
    • 84988099160 scopus 로고
    • Diluted modified cyclodextrins as chiral stationary phases - Influence of the polysiloxane solvent: Heptakis(2,3-di-O-acetyl-6-O-tert-butyldimethylsilyl)-β-cyclodextrin
    • Dietrich, A.; Maas, B.; Mosandl, A. Diluted modified cyclodextrins as chiral stationary phases - Influence of the polysiloxane solvent: Heptakis(2,3-di-O-acetyl-6-O-tert-butyldimethylsilyl)-β-cyclodextrin. J. High Resolut. Chromatogr. 1995, 18, 152-156.
    • (1995) J. High Resolut. Chromatogr. , vol.18 , pp. 152-156
    • Dietrich, A.1    Maas, B.2    Mosandl, A.3
  • 6
    • 84937193430 scopus 로고
    • Gezielte präparative Trennung enantiomerer Carbonsäuren und Lactone via Flüssigkeitschromatographie und nachbargruppenunterstützte Hydrolyze diastereomerer Amide
    • Helmchen, G.; Nill, G.; Flockerzi, D.; Yousef, M. S. Gezielte präparative Trennung enantiomerer Carbonsäuren und Lactone via Flüssigkeitschromatographie und nachbargruppenunterstützte Hydrolyze diastereomerer Amide (Separation of enantiomeric carboxylic acids and lactones by liquid chromatography and hydrolysis of diastereomeric amides). Angew. Chem. 1979, 91, 65-66.
    • (1979) Angew. Chem. , vol.91 , pp. 65-66
    • Helmchen, G.1    Nill, G.2    Flockerzi, D.3    Yousef, M.S.4
  • 7
    • 6844256515 scopus 로고
    • 134. (5R*,9S*)- and (5R*,9R*)-2,2,9-Trimethyl-1,6-dioxaspiro[4.4]non-3-ene and their dihydro derivatives as new constituents of geranium oil
    • Kaiser, R. 134. (5R*,9S*)- and (5R*,9R*)-2,2,9-Trimethyl-1,6-dioxaspiro[4.4]non-3-ene and their dihydro derivatives as new constituents of geranium oil. Helv. Chim. Acta 1984, 67, 1198-1203.
    • (1984) Helv. Chim. Acta , vol.67 , pp. 1198-1203
    • Kaiser, R.1
  • 8
    • 0038572414 scopus 로고    scopus 로고
    • (S)-3,7-Dimethyl-5-octene-1,7-diol and related oxygenated monoterpenoids from petals of Rosa damascene Mill
    • Knapp, H.; Straubinger, M.; Fornari, S.; Oka, N.; Watanabe, N.; Winterhalter, P. (S)-3,7-Dimethyl-5-octene-1,7-diol and related oxygenated monoterpenoids from petals of Rosa damascene Mill. J. Agric. Food Chem. 1998, 46, 1966-1970.
    • (1998) J. Agric. Food Chem. , vol.46 , pp. 1966-1970
    • Knapp, H.1    Straubinger, M.2    Fornari, S.3    Oka, N.4    Watanabe, N.5    Winterhalter, P.6
  • 9
    • 0001648370 scopus 로고
    • Composition of essential oils. Part 7. Bulgarian oil of Rose (Rosa damascena Mill)
    • Kováts, E. sz. Composition of essential oils. Part 7. Bulgarian oil of Rose (Rosa damascena Mill). J. Chromatogr. 1987, 406, 185-222.
    • (1987) J. Chromatogr. , vol.406 , pp. 185-222
    • Kováts, E.Sz.1
  • 10
    • 11844298082 scopus 로고
    • A gas chromatographic study of the enantiomeric composition of volatile compounds in Bulgarian rose oil (Rosa damascena Mill). Part 1
    • Lindström, M.; Jaquier, A. A gas chromatographic study of the enantiomeric composition of volatile compounds in Bulgarian rose oil (Rosa damascena Mill). Part 1. Riv. Ital. EPPOS 1993, 130-139.
    • (1993) Riv. Ital. EPPOS , pp. 130-139
    • Lindström, M.1    Jaquier, A.2
  • 11
    • 0027968150 scopus 로고
    • Aqueous hetero Diels-Alder reactions: The carbonyl case
    • Lubineau, A.; Augé, J.; Lubin, N. Aqueous hetero Diels-Alder reactions: The carbonyl case. Tetrahedron 1994, 50, 10265-10265.
    • (1994) Tetrahedron , vol.50 , pp. 10265-10265
    • Lubineau, A.1    Augé, J.2    Lubin, N.3
  • 12
    • 0026345966 scopus 로고
    • Isotope effect in gas-liquid chromatography of labelled compounds
    • Matucha, M.; Jockisch, W.; Verner, P.; Anders, G. Isotope effect in gas-liquid chromatography of labelled compounds. J. Chromatogr. 1991, 588, 251-258.
    • (1991) J. Chromatogr. , vol.588 , pp. 251-258
    • Matucha, M.1    Jockisch, W.2    Verner, P.3    Anders, G.4
  • 13
    • 4243844619 scopus 로고
    • Synthesis of (-)-cis-rose oxide from D-glucose
    • Ogawa, T.; Takasaka, N.; Matsui, M. Synthesis of (-)-cis-rose oxide from D-glucose. Carbohydr. Res. 1978, 60, C4-C6.
    • (1978) Carbohydr. Res. , vol.60
    • Ogawa, T.1    Takasaka, N.2    Matsui, M.3
  • 14
    • 84984082292 scopus 로고
    • Zur Darstellung von Tetrahydropyran und Tetrahydrofuranderivaten aus 1,7-bzw. 1,6-Allyldiolen durch Dehydratation in der Allylstellung
    • Ohloff, G.; Schulte-Elte, K.-H.; Willhalm, B. Zur Darstellung von Tetrahydropyran und Tetrahydrofuranderivaten aus 1,7-bzw. 1,6-Allyldiolen durch Dehydratation in der Allylstellung (Preparation of tetrahydropyran and tetrahydrofuran derivatives by dehydratation in allylic position using 1,7- and 1,6 allylic diols). Helv. Chim. Acta 1964, 47, 602-626.
    • (1964) Helv. Chim. Acta , vol.47 , pp. 602-626
    • Ohloff, G.1    Schulte-Elte, K.-H.2    Willhalm, B.3
  • 15
    • 0001451842 scopus 로고
    • Synthesis of (R)- and (S)-4-Methyl-6-2′-methyl-prop-1′-enyl-5,6-dihydro-2H-pyran (Nerol oxide) and natural occurrence of its racemate
    • Ohloff, G.; Giersch, W.; Schulte-Elte, K.-H.; Enggist, P.; Demole, E. Synthesis of (R)- and (S)-4-Methyl-6-2′-methyl-prop-1′-enyl-5,6-dihydro-2H-pyran (Nerol oxide) and natural occurrence of its racemate. Helv. Chim. Acta 1980, 63, 1582-1588.
    • (1980) Helv. Chim. Acta , vol.63 , pp. 1582-1588
    • Ohloff, G.1    Giersch, W.2    Schulte-Elte, K.-H.3    Enggist, P.4    Demole, E.5
  • 16
    • 84985288136 scopus 로고
    • Synthese von Glycosiden von Mono-, Sesqui-und Diterpenalkoholen
    • Paulsen, H.; Lê-Nguyên, B.; Sinnwell, V.; Heemann, V.; Seehofer, F. Synthese von Glycosiden von Mono-, Sesqui-und Diterpenalkoholen (Preparation of glycosides of mono-, sesqui- and diterpene alcohols). Liebigs Ann. Chem. 1985, 1513-1536.
    • (1985) Liebigs Ann. Chem. , pp. 1513-1536
    • Paulsen, H.1    Lê-Nguyên, B.2    Sinnwell, V.3    Heemann, V.4    Seehofer, F.5
  • 18
    • 0000291538 scopus 로고
    • Gaschromatographisch-massenspektrometrische Untersuchung flüchtiger Inhaltsstoffe des Weines
    • Schreier, P.; Drawert, F. Gaschromatographisch-massenspektrometrische Untersuchung flüchtiger Inhaltsstoffe des Weines (Investigations on volatiles in wine using GC-MS). Z. Lebensm.-Unters.-Forsch. 1974, 154, 273-278.
    • (1974) Z. Lebensm.-Unters.-Forsch. , vol.154 , pp. 273-278
    • Schreier, P.1    Drawert, F.2
  • 19
    • 0010652616 scopus 로고
    • Enantiomer Separation by Complexation Gas Chromatography-Applications in Chiral Analysis of Pheromones and Flavours
    • Proceedings of the International Conference, Würzburg, Federal Republic of Germany, September 29-30, 1987; Schreier, P., Ed.; de Gruyter: Berlin, Germany
    • Schurig, V. Enantiomer Separation by Complexation Gas Chromatography-Applications in Chiral Analysis of Pheromones and Flavours. In Bioflavour '87: Analysis, Biochemistry, Biotechnology; Proceedings of the International Conference, Würzburg, Federal Republic of Germany, September 29-30, 1987; Schreier, P., Ed.; de Gruyter: Berlin, Germany, 1987; pp 35-54.
    • (1987) Bioflavour '87: Analysis, Biochemistry, Biotechnology , pp. 35-54
    • Schurig, V.1
  • 20
    • 0005123648 scopus 로고
    • Beta-Cleavage of bis (homoallylic) potassium alkoxides. Preparation of 3-hydroxypropyl and 4-hydroxybutyl propenyl ketones from gamma- and delta-lactones. Synthesis of (±)-rose oxide
    • Snowden, R. L.; Linder, S. M.; Muller, B. L.; Schulte-Elte, K. H. Beta-Cleavage of bis (homoallylic) potassium alkoxides. Preparation of 3-hydroxypropyl and 4-hydroxybutyl propenyl ketones from gamma- and delta-lactones. Synthesis of (±)-rose oxide. Helv. Chim. Acta 1987, 70, 1879-1885.
    • (1987) Helv. Chim. Acta , vol.70 , pp. 1879-1885
    • Snowden, R.L.1    Linder, S.M.2    Muller, B.L.3    Schulte-Elte, K.H.4
  • 21
    • 0542414716 scopus 로고
    • N-Iodosuccinimide for the synthesis of rose oxide
    • Taneja, S. C.; Dhar, K. L.; Atal, C. K. N-Iodosuccinimide for the synthesis of rose oxide. J. Org. Chem. 1978, 43, 997-998.
    • (1978) J. Org. Chem. , vol.43 , pp. 997-998
    • Taneja, S.C.1    Dhar, K.L.2    Atal, C.K.3
  • 22
    • 13044304690 scopus 로고    scopus 로고
    • Enantioselektive GC-Analyse chiraler Riech- und Aromastoffe. Teil 3
    • Werkhoff, P.; Brennecke, S.; Bretschneider, W.; Schreiber, K. Enantioselektive GC-Analyse chiraler Riech- und Aromastoffe. Teil 3 (Enantioselective analysis of chiral flavor compounds. Part 3). Contact 65, 4-7.
    • Contact , vol.65 , pp. 4-7
    • Werkhoff, P.1    Brennecke, S.2    Bretschneider, W.3    Schreiber, K.4
  • 23
    • 0043059899 scopus 로고    scopus 로고
    • On the biogenesis of Rose oxide in Pelargonium graveolens L'Héritier and Pelargonium radens H.E. Moore
    • Wüst, M.; Beck, T.; Dietrich, A.; Mosandl, A. On the biogenesis of Rose oxide in Pelargonium graveolens L'Héritier and Pelargonium radens H.E. Moore. Enantiomer 1996, 1, 167-176.
    • (1996) Enantiomer , vol.1 , pp. 167-176
    • Wüst, M.1    Beck, T.2    Dietrich, A.3    Mosandl, A.4
  • 24
    • 2642612837 scopus 로고    scopus 로고
    • Mechanistic aspects of the biogenesis of Rose oxide in Pelargonium graveolens L'Héritier
    • Wüst, M.; Rexroth, A.; Beck, T.; Mosandl, A. Mechanistic aspects of the biogenesis of Rose oxide in Pelargonium graveolens L'Héritier. Chirality 1998a, 9, 229-238.
    • (1998) Chirality , vol.9 , pp. 229-238
    • Wüst, M.1    Rexroth, A.2    Beck, T.3    Mosandl, A.4
  • 25
    • 0041556963 scopus 로고    scopus 로고
    • Biogenesis of geranium oil compounds: On the origin of oxygen in cis-/trans-rose oxide
    • Wüst, M.; Beck, T.; Mosandl, A. Biogenesis of geranium oil compounds: On the origin of oxygen in cis-/trans-rose oxide. J. Agric. Food Chem. 1998b, 46, 3225-3229.
    • (1998) J. Agric. Food Chem. , vol.46 , pp. 3225-3229
    • Wüst, M.1    Beck, T.2    Mosandl, A.3
  • 26
    • 0001913850 scopus 로고
    • Reduction of esters of carboxylic acids into aldehydes with diisobutylaluminium hydride
    • Zakharkin, L. I.; Khorlina, I. M. Reduction of esters of carboxylic acids into aldehydes with diisobutylaluminium hydride. Tetrahedron Lett. 1962, 619-620.
    • (1962) Tetrahedron Lett. , pp. 619-620
    • Zakharkin, L.I.1    Khorlina, I.M.2


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