232
Views
17
CrossRef citations to date
0
Altmetric
Miscellany

METHYL DIHYDROJASMONATE AND ITS STEREOISOMERS: SENSORY PROPERTIES AND ENANTIOSELECTIVE ANALYSIS

, , , &
Pages 103-122 | Published online: 02 Nov 2011

REFERENCES

  • Fráter , G. , Bajgrowicz , J.A. and Kraft , Ph. 1998 . Fragrance Chemistry . Tetrahedron , 54 : 7633 – 7703 .
  • Demole , E.P. 1982 . “ The Fragrance of Jasmine ” . In Fragrance Chemistry Edited by: Theimer , E.T. 349 – 396 . New York : Academic Press .
  • Dobbs , D.A. , Vanhessche , K.P.M. , Brazi , E. , Rautenstrauch , V. , Lenoir , J.-Y. , Genêt , J.-P. , Wiles , J. and Bergens , S.H. 2000 . Industrial Synthesis of (+)-cis-Methyl Dihydrojasmonate by Enantioselective Catalytic Hydrogenation; Identification of the Precatalyst [Ru((−)-Me-Du PHOS)(H)-(η6-1,3,5-cyclooctatriene)] (BF4) . Angew. Chem. Int. Ed. , 39 ( 11 ) : 1992 – 1995 .
  • Acree , T.E. , Barnard , J. and Cunningham , D.G. 1984 . “ The Analysis of Odor-Active Volatiles in Gas Chromatographic Effluents ” . In Analysis of Volatiles Edited by: Schreier , P. 251 – 267 . Berlin : Walter de Gruyter .
  • Acree , T.E. , Nishida , R. and Fukami , H. 1985 . Odor Thresholds of the Stereoisomers of Methyl Jasmonate . J. Agric. Food Chem. , 33 : 425 – 427 .
  • Nishida , R. , Acree , T.E. and Fukami , H. 1985 . Optical Resolution of Methyl Jasmonate and Methyl Epijasmonate . Agric. Biol. Chem. , 49 ( 3 ) : 769 – 772 .
  • Acree , T.E. and Nishida , R. 1985 . “ The Odor of Methyl Jasmonate Stereoisomers ” . In Semiochemistry: Flavors and Pheromones Edited by: Acree , T.E. and Soderlund , D.M. 33 – 45 . Berlin : Walter de Gruyter .
  • Acree , T.E. , Barnard , J. and Cunningham , D.G. 1984 . A Procedure for the Sensory Analysis of Gas Chromatographic Effluents . Food Chem. , 14 : 273 – 286 .
  • Weinges , K. , Gethöffer , H. , Huber-Patz , U. , Rodewald , H. and Irngartinger , H. 1987 . EPC-Synthese von (1R,2R,2″Z)-(−)-Methyljasmonat aus Catalpol-Kristall-und Molekularstruktur von Methyl-Dehydrojasmonatsemicarbazon . Liebigs Ann. Chem. , : 361 – 366 .
  • Weinges , K. and Lernhardt , U. 1990 . Synthese von Enantiomerenreinem (1R,2S,2″Z)-(+)-Methyljasmonat aus Catalpol . Liebigs Ann. Chem. , 2 : 751 – 754 .
  • Montforts , F.P. , Gesing-Zibulak , I. , Grammenos , W. , Schneider , M. and Laumen , K. 1989 . Methyljasmonat: Ein kurzer Weg zum Naturstoff und Seinem Unnatürlichen Enantiomer Via Palladium(O)-induzierte, Enantiodivergente Alkylierung von Cyclopent-2-en-1,3-diol-Derivaten . Helv. Chim. Acta , 72 : 1852 – 1859 .
  • Sarkar , T.K. and Ghorai , B.K. 1999 . Methyl Epijasmonate: Historical Perspective and Total Synthesis . J. Ind. Chem. Soc. , 76 : 693 – 706 .
  • Ebata , T. , Matsumoto , K. and Matsushita , H. 1994 . Synthesis of (+)-Methyl Dihydroepijasmonate . Heterocycles , 38 ( 10 ) : 2231 – 2241 .
  • Perrard , Th. , Plaquevent , J.-Ch. , Desmurs , J.-R. and Hébrault , D. 2000 . Enantioselective Synthesis of Both Enantiomers of Methyl Dihydrojasmonate Using Solid–Liquid Asymmetric Phase-Transfer Catalysis . Org. Lett. , 2 ( 19 ) : 2959 – 2962 .
  • Fehr , Ch. and Galindo , J. 2000 . A New Variant of the Claisen Rearrangement from Malonate-Derived Allylic Trimethylsilyl Ketene Acetals: Efficient, Highly Enantio- and Diastereoselective Syntheses of (+)-Methyl Dihydroepijasmonate and (+)-Methyl Epijasmonate . Angew. Chem. Int. Ed. , 39 ( 3 ) : 569 – 573 .
  • Renold , W. , Näf-Müller , R. , Keller , U. , Willhalm , B. and Ohloff , G. 1974 . An Investigation of the Tea Aroma. Part I. New Volatile Black Tea Constituents . Helv. Chim. Acta , 57 ( 5 ) : 1301 – 1308 .
  • Kharebava , L.G. and Tsirgvava , A.G. 1979 . Study of the Effect of the Method of Cultivation of Tea Plants on the Composition of the Volatile Complex of Black Tea . Chai. Kul'tura i Pr-vo, Tbilisi , 2 ( 38 ) : 26 – 33 .
  • Sardzhveladze , A.G. , Chernavina , I.A. and Kharebava , L.G. 1985 . Effect of Fertilization Patterns of Tea Plants on the Composition of Volatile Complexes of Black Tea . Subtrop. Kul't. , 6 : 78 – 85 .
  • Buchbauer , G. , Jirovetz , L. and Kaul , V.K. 1995 . Volatiles of the Absolute of Cestrum nocturnumL. . J. Essent. Oil Res. , 7 : 5 – 9 .
  • Cano , M.C.S. , Plaza , E.G. , Muñoz , R.G. and Benavente , A.G. 1998 . Volatile Compounds of Three LimoniumSpecies: L. latifolia, L. x altaicaand L. perezii . J. Essent. Oil Res. , 10 : 67 – 69 .
  • Gogiya , V.T. , Kharebava , L.G. , Gogiya , R.V. and Gvatua , E.B. 1986 . Composition of Volatile Compounds in Flowers of Osmanthus fragrans(Thund.) . Lour. Rastit. Resur. , 22 ( 2 ) : 243 – 248 .
  • Cheng , Y.-Sh. 1979 . Chemical Composition of Jasminum grandiflorumL. and Siu-eng Flowers . K'o Hsueh Fa Chan Yueh K'an , 7 ( 2 ) : 140 – 146 .
  • Sing , A.Sh.Ch. , Barbier , J. and Smadja , J. 1997 . Some Volatile Compounds of Sugars . J. Nature , 9 ( 1 ) : 8 – 16 .
  • Mosciano , G. , Fasano , M. , Cassidy , J. , Connelly , K. , Mazeiko , P. , Montenegro , A. , Michalski , J. and Sadural , S. 1995 . Organoleptic Characteristics of Flavor Materials . Perfum. Flavor. , 20 ( 3 ) : 63 – 65 .
  • König , W.A. and Gehrcke , B. 1993 . Gas Chromatographic Enantiomer Separation with Modified Cyclodextrins: Carboxylic Acid Esters and Epoxides . HRC , 16 : 175 – 181 .
  • Okamota , M. and Nakazawa , H. 1992 . Direct Chromatographic Separation of the Enantiomers of Methyl Jasmonate and Its Derivatives . Biosci. Biotechnol. Biochem. , 56 ( 7 ) : 1172 – 1173 .
  • Kobayashi , A. , Kawamura , M. , Yamamoto , Y. , Shimizu , K. , Kubota , K. and Yamanishi , T. 1988 . Methyl Epijasmonate in the Essential Oil of Tea . Agric. Biol. Chem. , 52 ( 9 ) : 2299 – 2303 .
  • Hamberg , M. and Gardner , H.W. 1992 . Oxylipin Pathway to Jasmonates: Biochemistry and Biological Significance . Biochim. Biophys. Acta , 1165 : 1 – 18 .
  • Sembdner , G. and Parthier , B. 1993 . The Biochemistry and the Physiological and Molecular Actions of Jasmonates . Annu. Rev. Plant. Physiol. Plant Mol. Biol. , 44 : 569 – 589 .
  • Mueller , M.J. 1997 . Enzymes Involved in Jasmonic Acid Biosynthesis . Physiol. Plant. , 100 : 653 – 663 .
  • Miersch , O. , Kramell , R. , Parthier , B. and Wasternack , C. 1999 . Structure–Activity Relations of Substituted, Deleted or Stereospecifically Altered Jasmonic Acid in Gene Expression of Barley Leaves . Phytochemistry , 50 : 353 – 361 .
  • Werkhoff , P. , Güntert , M. , Krammer , G. , Sommer , H. and Kaulen , J. 1998 . Vacuum Headspace Method in Aroma Research: Flavor Chemistry of Yellow Passion Fruits . J. Agric. Food Chem. , 46 ( 3 ) : 1076 – 1093 .
  • Engel , W. , Bahr , W. and Schieberle , P. 1999 . Solvent Assisted Flavour Evaporation—A New and Versatile Technique for the Careful and Direct Isolation of Aroma Compounds from Complex Food Matrices . Eur. Food Res. Technol. , 209 : 237 – 241 .
  • Beale , M.H. and Ward , J.L. 1998 . Jasmonates: Key Players in the Plant Defence . Nat. Prod. Rep. , : 533 – 548 .
  • Gundlach , H. and Zenk , M.H. 1998 . Biological Activity and Biosynthesis of Pentacyclic Oxylipins: The Linoleic Acid Pathway . Phytochemistry , 47 ( 4 ) : 527 – 537 .
  • Wang , D. , Kubota , K. and Kobayashi , A. 1996 . Optical Isomers of Methyl Jasmonate in Tea Aroma . Biosci. Biotechnol. Biochem. , 60 ( 3 ) : 508 – 510 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.