Structure-Odor Activity Studies on Monoterpenoid Mercaptans Synthesized by Changing the Structural Motifs of the Key Food Odorant 1-p-Menthene-8-thiol

Journal of Agricultural and Food Chemistry

Volumn 64, Issue 19, 2016, Pages 3849-3861

  Schoenauer, Sebastian ^a   Schieberle, Peter ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

1 p menthene derivatives; 1 p menthene 8 thiol; mercaptan; mercapto monoterpenoids; p menthane derivatives; structure odor activity

Indexed keywords

AROMATIC COMPOUNDS; CHAINS; CITRUS FRUITS; FRUIT JUICES; UNSATURATED COMPOUNDS;

1-P-MENTHENE-8-THIOL; GRAPEFRUIT JUICE; MERCAPTAN; MERCAPTO GROUPS; MONOTERPENOIDS; P-MENTHANE; STRUCTURAL MOTIFS; SULFUR CONTAINING COMPOUND;

ODORS;

FRAGRANCE; TERPENE; THIOL DERIVATIVE;

CHEMICAL STRUCTURE; CHEMISTRY; ELECTROSPRAY MASS SPECTROMETRY; FOOD; MASS FRAGMENTOGRAPHY;

FOOD; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; MOLECULAR STRUCTURE; MONOTERPENES; ODORANTS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SULFHYDRYL COMPOUNDS;

EID: 84970024514     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/acs.jafc.6b01645     Document Type: Article

References (28)

1. Kuroiwa, Y.; Hashimoto, N.; Hashimoto, H.; Kokubo, E.; Nakagawa, K. Factors essential for the evolution of sunstruck flavor Proc. Am. Soc. Brew. Chem. 1963, 181-193
2. Engel, K.-H.; Tressl, R. Identification of new sulfur-containing volatiles in yellow passion fruits (Passiflora edulis f. flavicarpa) J. Agric. Food Chem. 1991, 39 (12) 2249-2252 10.1021/jf00012a030
3. Tominaga, T.; Furrer, A.; Henry, R.; Dubourdieu, D. Identification of new volatile thiols in the aroma of Vitis vinifera L. var. Sauvignon blanc wines Flavour Fragrance J. 1998, 13 (3) 159-162 10.1002/(SICI)1099-1026(199805/06)13:3<159::AID-FFJ709>3.0.CO;2-7
4. Steinhaus, M.; Sinuco, D.; Polster, J.; Osorio, C.; Schieberle, P. Characterization of the aroma-active compounds in pink guava (Psidium guajava L.) by application of the aroma extract dilution analysis J. Agric. Food Chem. 2008, 56 (11) 4120-4127 10.1021/jf8005245
5. Demole, E.; Enggist, P.; Ohloff, G. 1-p-Menthene-8-thiol: a powerful flavor impact constituent of grapefruit juice (Citrus paradise Mac Fayden) Helv. Chim. Acta 1982, 65 (6) 1785-1794 10.1002/hlca.19820650614
6. Hinterholzer, A.; Schieberle, P. Identification of the most odour-active volatiles in fresh, hand-extracted juice of Valencia Late oranges by odour dilution techniques Flavour Fragrance J. 1998, 13, 49-55 10.1002/(SICI)1099-1026(199801/02)13:1<49::AID-FFJ691>3.0.CO;2-S
7. Serot, T.; Prost, C.; Visan, L.; Burcea, M. Identification of the main odor-active compounds in musts from French and Romanian hybrids by three olfactometric methods J. Agric. Food Chem. 2001, 49, 1909-1914 10.1021/jf0012291
8. Gürbüz, O.; Rouseff, J.; Talcott, S. T.; Rouseff, R. Identification of Muscadine wine sulfur volatiles: pectinase versus skin-contact maceration J. Agric. Food Chem. 2013, 61, 532-539 10.1021/jf304074m
9. Plaza, M. L.; Marshall, M. R.; Rouseff, R. L. Volatile composition and aroma activity of guava puree before and after thermal and dense phase carbon dioxide treatments J. Food Sci. 2015, 80 (2) 218-227 10.1111/1750-3841.12736
10. Lamparsky, D.; Schudel, P. p-Menthane-8-thiol-3-one, a new component of buchu leaf oil Tetrahedron Lett. 1971, 12, 3323-3326 10.1016/S0040-4039(01)97168-0
11. Cannon, R. J.; Kazimierski, A.; Curto, N. L.; Li, J.; Trinnaman, L.; Janczuk, A. J.; Agyemang, D.; da Costa, N. C.; Chen, M. Z. Identification, synthesis, and characterization of novel sulfur-containing volatile compounds from the in-depth analysis of Lisbon lemon peels (Citrus limon L. Burm. f. cv. Lisbon) J. Agric. Food Chem. 2015, 63, 1915-1931 10.1021/jf505177r
12. Wannagat, U.; Damrath, V.; Schliephake, A.; Harder, U. Sila-substituted perfumes and isosteric compounds of perfumes. XI. Comparison of carbinols and silanols with thiocarbinols and silanethiols Monatsh. Chem. 1987, 118, 779-788 10.1007/BF00809228
13. Polak, E.; Fetison, G.; Fombon, A.-M.; Skalli, A. Structure-odor relationships for catty-smelling mercapto compounds in humans J. Agric. Food Chem. 1988, 36 (2) 355-359 10.1021/jf00080a028
14. Node, M.; Kumar, K.; Nishide, K.; Ohsugi, S.-i.; Miyamoto, T. Odorless substitutes for foul-smelling thiols: syntheses and applications Tetrahedron Lett. 2001, 42, 9207-9210 10.1016/S0040-4039(01)02024-X
15. Sakoda, Y.; Hayashi, S. Relationship of odour and chemical structure in 1- and 2-alkyl alcohols and thiols Spec. Publ.-R. Soc. Chem. 2002, 277, 15-24 10.1039/9781847550071-00015
16. Polster, J.; Schieberle, P. Structure-odor correlations in homologous series of alkanethiols and attempts to predict odor thresholds by 3D-QSAR studies J. Agric. Food Chem. 2015, 63, 1419-1432 10.1021/jf506135c
17. Meilgaard, M. C. Flavor chemistry of beer. II. Flavor and threshold of 239 aroma volatiles Tech. Q.-Master Brew. Assoc. Am. 1975, 12, 151-168
18. Wakabayashi, M.; Wakabayashi, H.; Nörenberg, S.; Kubota, K.; Engel, K.-H. Comparison of odour thresholds and odour qualities of the enantiomers of 4-mercapto-2-alkanones and 4-acetylthio-2-alkanones Flavour Fragrance J. 2015, 30, 171-178 10.1002/ffj.3228
19. Nishio, T. Direct conversation of alcohols into thiols J. Chem. Soc.; Perkin Trans. 1 1993, 1113-1117 10.1039/p19930001113
20. Engel, W.; Bahr, W.; Schieberle, P. Solvent assisted flavor evaporation. A new and versatile technique for the careful and direct isolation of aroma compounds from complex food matrices Eur. Food Res. Technol. 1999, 209, 237-241 10.1007/s002170050486
21. Simian, H.; Robert, F.; Blank, I. Identification and synthesis of 2-heptanethiol, a new flavor compound found in bell peppers J. Agric. Food Chem. 2004, 52 (2) 306-310 10.1021/jf035008h
22. Ott, F.; Kindel, G. Use of certain isopropyl methylcyclohexene thiols as fragrances and/or flavors. US20100310479A1, 2010.
23. Helminger, D.; Lamparsky, D.; Schudel, P.; Wild, J.; Sigg-Gruetter, T. 3,7-Dimethyl-octa-2,6-dienylmercaptan perfume composition. US3975311A, 1976.
24. Sigg-Gruetter, T.; Wild, J. Thiolinalool for perfumes and flavors. DE2404154A1, 1974.
25. Ullrich, F.; Grosch, W. Identification of the most intense volatile flavour compounds formed during autoxidation of linoleic acid Z. Lebensm.-Unters. Forsch. 1987, 184, 277-282 10.1007/BF01027663
26. Teranishi, R.; Buttery, R. G.; Guadagni, D. G. Odor quality and chemical structure in fruit and vegetable flavors Ann. N.Y. Acad. Sci. 1974, 237, 209-216 10.1111/j.1749-6632.1974.tb49855.x
27. Czerny, M.; Christlbauer, M.; Christlbauer, M.; Fischer, A.; Granvogl, M.; Hammer, M.; Hartl, C.; Hernandez, N. M.; Schieberle, P. Re-investigation on odour thresholds of key food aroma compounds and development of an aroma language based on odour qualities of defined aqueous odorant solutions Eur. Food Res. Technol. 2008, 228, 265-273 10.1007/s00217-008-0931-x
28. Jabalpurwala, F.; Lin, J.; Rouseff, R. L. 1-p-Menthen-8-thiol, the grapefruit character impact volatile, is a thermally generated artifact in citrus juices. In Abstracts of Papers, 250th ACS National Meeting & Exposition, Boston, MA, USA, Aug 16-20, 2015; p 295.