Skip to main content
SpringerLink
Log in

The Importance of Sulfur-Containing Compounds to Fruit Flavors

  • Chapter
Flavor Chemistry

Abstract

Sulfur-containing volatiles are of outstanding importance in flavor chemistry (Boelens and van Gemert, 1993; Mussinan and Keelan, 1994). Thermally generated aromas are dominated by a broad spectrum of sulfur compounds ranging from aliphatic thioles (Werkhoff et al., 1996) to heterocycles (Güntert et al., 1990). Sulfur-containing volatiles are not only formed in the course of thermal processing of foods but they also constitute essential components of the biogenetically derived aroma patterns of biological systems such as fruits. Pineapple (Takeoka et al., 1991; Umano et al., 1992), grapefruit (Demole et al., 1982), black currant (Riguad et al., 1986) and durian (Wong and Tie, 1993; Fischer et al.,1995) are representatives of fruits exhibiting sensory properties which are strongly influenced by sulfur compounds.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
eBook
USD 16.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 54.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 54.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  • Boelens, M. H.; van Gemert, L. J. Volatile character-impact sulfur compounds and their sensory properties. Perfum. Flavor. 18, 29–39 (1993)

    CAS  Google Scholar 

  • Demole, E.; Enggist, P.; Ohloff, G. 1-p-Menthene-8-thiol: a powerful impact constituent of grapefruit juice (Citrus paradisi Macfayden). HeIv. Chim. Acta 65, 1785–1794 (1982)

    Article  CAS  Google Scholar 

  • Engel, K.-H.; Heidlas, J.; Albrecht, W; Tressl, R. Biosynthesis of chiral flavor and aroma compounds in plants and microorganisms. In: Teranishi, R.; Buttery, R. G.; Shahidi, E (Eds.) Flavor Chemistry. Trends and Developments. American Chemical Society Symposium Series 388, Washington, D. C., 1989, p. 8–22

    Chapter  Google Scholar 

  • Engel, K.-H.; Tressl, R. Identification of new sulfur-containing volatiles in yellow passion fruits (Passii lora edulis f. flavicarpa). J. Agric. Food Chem. 39, 2249–2252 (1991)

    Article  CAS  Google Scholar 

  • Fischer, N.; Hammerschmidt, F.-J.; Brunke, E.-J. Analytical investigation of the flavor of Cupuaçu (Theobroma grad florum Spreng.). In: Fruit Flavors. Biogenesis, Characterization, and Authentication. Russeff, R., Leahy, M. M. (Eds.); American Chemical Society: Washington, D.C., 1995, pp 8–20

    Chapter  Google Scholar 

  • Friedman, L.; Miller, J. G. Odor incongruity and chirality. Science 172, 1044 (1972)

    Article  Google Scholar 

  • Güntert, M.; Brüning, J.; Emberger, R.; Köpsel, M.; Kuhn, W; Thielmann, T.; Werkhoff, P. Identification and formation of some selected sulfur-containing flavor compounds in various meat model systems. J. Agric. Food Chem. 38, 2027–2041 (1990)

    Article  Google Scholar 

  • Heusinger, G.; Mosandl, A. Chirale, schwefelhaltige Aromastoffe der gelben Passionsfrucht (Pass flora edulis f. flavicarpa). Darstellung der Enantiomeren and absolute Konfiguration. Tetrahedron Lett. 25, 507–510 (1984)

    Article  CAS  Google Scholar 

  • Küntzel, H.; Frater, G. Enantioselective synthesis of (+)- and (–)-cis-and trans-2-methyl-4-propyl-1,3oxathianes. Sulfur Letters 10, 181–186 (1989)

    Google Scholar 

  • Leitereg, T. J.; Guadagni, D. G.; Harris, J.; Mon, T. R.; Teranishi, R. Chemical and sensory data supporting the difference between the odors of the enantiomeric carvones. J. Agric. Food Chem. 19, 785 (1971)

    Article  CAS  Google Scholar 

  • Maga, J. A. Lactones in Foods. CRC Crit. Rev. Food Sci. Nutr. 1–56 (1976)

    Google Scholar 

  • 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)

    Article  CAS  Google Scholar 

  • Mosandl, A.; Heusinger, G. 1,3-Oxathianes, chiral fruit flavor compounds. Liebigs Ann. Chem. 1185–1191 (1985)

    Google Scholar 

  • Mosandl, A.; Heusinger, G.; Wistuba, D.; Schurig, V. Analysis of a chiral aroma compound by complexation gas chromatography. Z Lebensm. Unters. Forsch. 179, 385–386 (1984)

    Article  CAS  Google Scholar 

  • Murray, K. E.; Shipton, J.; Whitfield, F. B. The chemistry of food flavor. I. Volatile constituents of passion fruit, Passii lora edulis. Aust. J. Chem. 25, 1921–1933 (1972)

    Article  CAS  Google Scholar 

  • Mussinan, C. J., Keelan, M. E. (Eds.) Sulfur Compounds in Foods. ACS Symposium Series 564; American Chemical Society, Washington, D.C., 1994

    Book  Google Scholar 

  • Ohlofï, G. Riechstoffe and Geruchssinn. Die molekulare Welt der Düfte. Springer Verlag, Berlin, 1990

    Google Scholar 

  • Pickenhagen, W. Enantioselectivity in odor perception. In: Teranishi, R.; Buttery, R. G.; Shahidi, F. (Eds.) Flavor Chemistry. Trends and Developments. American Chemical Society Symposium Series 388, Washington, D.C., 1989, p. 151–157

    Chapter  Google Scholar 

  • Pickenhagen, W; Brönner-Schindler, H. Enantioselective synthesis of (+)- and (–)-cis-2-methyl-4-propyl-1,3oxathiane and their olfactive properties. Helv. Chim. Acta 67, 947–952 (1984)

    Article  CAS  Google Scholar 

  • Rigaud, J.; Etievant, P.; Henry, R.; Latrasse, A. 4-Methoxy-2-methyl-2-mercaptobutane, a major constituent of the aroma of the black currant bud (Ribes nigrum L.). Sci. Aliments 6, 213–220 (1986)

    CAS  Google Scholar 

  • Roling, I.; Schmarr, H.-G.; Eisenreich, W; Engel, K.-H. Analytical and sensory characterization of γ-and δ-thiolactones. J. Agric. Food Chem. 46, 668–672 (1998)

    Article  CAS  Google Scholar 

  • Schieberle, P. Primary odorants in popcorn. J. Agric. Food Chem. 39, 1141–1144 (1991)

    Article  CAS  Google Scholar 

  • Schmarr, H.-G. Ph. D. Thesis, University Frankfurt/Main, Germany (1992)

    Google Scholar 

  • Schmarr, H.-G.; Schellenberg, A.; Engel, K.-H., manuscript in preparation

    Google Scholar 

  • Shibamoto, T.; Tang, C. S. Minor tropical fruits—mango, papaya, passion fruit and guava. In: Morton, I. D., MacLeod, A. J. (Eds.) Food Flavors. Part C. The Flavor of Fruits. Elsevier, Amsterdam, 1990, p. 221–280

    Google Scholar 

  • Singer, G., Heusinger, G., Fröhlich, O., Schreier, P.; Mosandl, A. Chirality evaluation of 2-methyl-4-propyl-1,3oxathiane from the yellow passion fruit. J. Agric. Food Chem. 34, 1029–1033 (1986)

    Article  CAS  Google Scholar 

  • Takeoka, G. R.; Buttery, R. G.; Teranishi, R.; Flath, R. A.; Güntert, M. Identification of additional pineapple volatiles. J. Agric. Food Chem. 39, 1848–1851 (1991)

    Article  CAS  Google Scholar 

  • Tominaga, T.; Darriet, P.; Dubourdieu, D. Identification de l’acétate de 3-mercaptohexanol, composé à forte odeur de buis, intervenant dans l’arôme des vins de Sauvignon. Vitis 35, 207–210 (1996)

    CAS  Google Scholar 

  • Tominaga, T.; Murat, M.-L.; Dubourdieu, D. Development of a method for analyzing the volatile thiols involved in the characteristic aroma of wines made from Vitis vinifera L. cv. Sauvignon blanc. J. Agric. Food Chem. 46, 1044–1048 (1998a)

    Article  CAS  Google Scholar 

  • Tominaga, T.; Furrer, A.; Henry, R.; Dubourdieu, D. Identification of new volatile thiols in the aroma of Vitis vinifera L. var. Sauvignon blanc wines. Flavor Fragr. J. 13, 159–162 (1998b)

    Article  CAS  Google Scholar 

  • Tominaga, T.; Peyrot des Gachons, C.; Dubourdieu, D. New type of flavor precursors in Vitis vinifera L. cv. Sauvignon blanc: S-cysteine conjugates. J. Agric. Food Chem. 46, 5215–5219 (1998c)

    Article  CAS  Google Scholar 

  • Tressl, R.; Engel, K.-H. Formation and analysis of optically active aroma compounds. In: Schreier, P. (Ed.) Analysis of Volatiles. Walter de Gruyter, Berlin, New York, 1984, p. 323–342

    Google Scholar 

  • Tressl, R.; Engel, K.-H. Biogenesis of chiral aroma components and their analytical characterization at trace level. In: Adda, J. (Ed.) Progress in Flavor Research 1984. Elsevier Science Publishers B.V., Amsterdam, 1985, p. 441–455

    Google Scholar 

  • Tressl, R.; Engel, K.-H.; Albrecht, W. Detection of Adulteration by Investigation of Aroma and Flavor Components. In: Nagy, S.; Attaway, J. A.; Rhodes, M. E. (Eds.) Adulteration of Fruit Juice Beverages. Marcel Dekker, Inc., New York, Basel, 1988, pp. 67–80

    Google Scholar 

  • Umano, K.; Hagi, Y.; Nakahara, K.; Shoji, A.; Shibamoto, T. Volatile constituents of green and ripened pineapple (Ananas comosus [L.] Merr.). J. Agric. Food Chem. 40, 599–603 (1992)

    Article  CAS  Google Scholar 

  • Weber, B.; Haag, H.-P; Mosandl, A. LIX. 3-Mercaptohexyl-und 3-Methylthiohexylalkanoate—Struktur und Eigenschaften der Enantiomere. Z. Lebensm. Unters. Forsch. 195, 426–428 (1992)

    Article  CAS  Google Scholar 

  • Weber, B.; Dietrich, A.; Maas, B.; Marx, A.; Olk, J.; Mosandl, A. LXVI. Enantiomeric distribution of the chiral sulphur-containing alcohols in yellow and purple passion fruits. Z. Lebensm. Unters. Forsch. 199, 48–50 (1994)

    Article  CAS  Google Scholar 

  • Weber, B.; Maas, B.; Mosandl, A. Stereoisomeric Flavor Compounds. 72. Stereoisomeric distribution of some chiral sulfur-containing trace components of yellow passion fruits. J. Agric. Food Chem. 43, 2438–2441 (1995)

    Article  CAS  Google Scholar 

  • Werkhoff, P.; Güntert, M.; Krammer, G.; Sommer, H.; Kaulen, J. Vacuum headspace method in aroma research: flavor chemistry of yellow passion fruits. J. Agric. Food Chem. 46, 1076–1093 (1998)

    Article  CAS  Google Scholar 

  • Werkhoff, P.; Brüning, J.; Güntert, M.; Kaulen, J.; Krammer, G.; Sommer, H. Potent mercapto/methylthio-substituted aldehydes and ketones in cooked beef liver. Adv. Food Sci. 18, 19–27 (1996)

    CAS  Google Scholar 

  • Whitfield, F. B.; Last, J. H. The flavor of the passion fruit—a review. In: Brunke, E. J. (Ed.) Progress in Essen-tial Oil Research. De Gruyter, Berlin, 1986, p. 3–48

    Google Scholar 

  • Winter, M.; Klöti, R. Über das Aroma der gelben Passionsfrucht (Passiflora edulis f. flavicarpa). HeIv. Chim. Acta 55, 1916–1921 (1972)

    Article  CAS  Google Scholar 

  • Winter, M.; Furrer, A.; Willhalm, B.; Thommen, W. Identification and synthesis of two new organic sulfur compounds from the yellow passion fruit (Passiflora edulis f. flavicarpa). HeIv. Chim. Acta 59, 1613–1620 (1976)

    Article  CAS  Google Scholar 

  • Winter, M.; Willhalm, B. Ger. Offen 2,338,680 (1972)

    Google Scholar 

  • Winter, M. Ger. Offen. 2,534,162 (1976)

    Google Scholar 

  • Wong, K. C.; Tie, D. Y. Volatile constituents of durian (Dario zibethinus Murr.). Flavor Fragr. J. 10, 79–83 (1995)

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Lehrstuhl für Allgemeine Lebensmitteltechnologie, Technische Universität München, Am Forum 2, D-85354, Freising-Weihenstephan, Germany

    Karl-Heinz Engel

Authors
  1. Karl-Heinz Engel
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. Formerly of United States Department of Agriculture, Agricultural Research Service, Albany, California, USA

    Roy Teranishi

  2. Formerly of Massachusetts Institute of Technology, Cambridge, Massachusetts, USA

    Emily L. Wick

  3. Mount Holyoke College, South Hadley, Massachusetts, USA

    Emily L. Wick

  4. Formerly of United States Department of Agriculture, Agricultural Research Service, Beltsville, Maryland, USA

    Irwin Hornstein

  5. United States Agency for International Development, Washington, D.C., USA

    Irwin Hornstein

Rights and permissions

Reprints and permissions

Copyright information

© 1999 Springer Science+Business Media New York

About this chapter

Cite this chapter

Engel, KH. (1999). The Importance of Sulfur-Containing Compounds to Fruit Flavors. In: Teranishi, R., Wick, E.L., Hornstein, I. (eds) Flavor Chemistry. Springer, Boston, MA. https://doi.org/10.1007/978-1-4615-4693-1_23

Download citation

  • DOI: https://doi.org/10.1007/978-1-4615-4693-1_23

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-1-4613-7125-0

  • Online ISBN: 978-1-4615-4693-1

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation