Synthesis of deuterated γ-lactones for use in stable isotope dilution assays

Journal of Agricultural and Food Chemistry

Volumn 52, Issue 23, 2004, Pages 7075-7083

  Hislop, J O Anna ^a   Hunt, Martin B ^a   Fielder, Simon ^a   Rowan, Daryl D ^a  

^a THE NEW ZEALAND INSTITUTE FOR PLANT AND FOOD RESEARCH LIMITED   (New Zealand)

Author keywords

decalactone; dodecalactone; Lactones; octalactone; Deuterium; Flavor compounds; Isotope labeling; SIDA; Synthesis

Indexed keywords

3,3,4 2 H 3 GAMMA DECALACTONE; 3,3,4 2 H 3 GAMMA DODECALACTONE; 3,3,4 2 H 3 GAMMA OCTALACTONE; 4 HYDROXYDEC 2 YNOIC ACID METHYL ESTER; 4 HYDROXYPROPARGYLIC ACID; 4 TERT BUTYLDIMETHYLSILOXYDEC 2 YNOIC ACID METHYL ESTER; [2,2,3,3, 2 H 4] 4 TERT BUTYLDIMETHYLSILOXYDECANOIC ACID METHYL ESTER; [2,2,3,3, 2 H 4] GAMMA DECALACTONE; [2,2,3,3, 2 H 4] GAMMA DODECALACTONE; [2,2,3,3, 2 H 4] GAMMA OCTALACTONE; DEUTERIUM; GAMMA DECALACTONE; GAMMA LACTONE DERIVATIVE; LACTONE DERIVATIVE; STABLE ISOTOPE; UNCLASSIFIED DRUG;

ADDITION REACTION; ALKYLATION; ARTICLE; CHEMICAL STRUCTURE; ISOTOPE DILUTION ASSAY; SYNTHESIS;

DEUTERIUM; INDICATOR DILUTION TECHNIQUES; ISOTOPE LABELING; LACTONES;

EID: 8444235045     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf048885b     Document Type: Article

References (23)

1. Derail, C.; Hofmann, T.; Schieberle, P. Differences in key odorants of handmade juice of yellow-flesh peaches (Prunus persica L.) induced by the workup procedure. J. Agric. Food Chem. 1999, 47, 4742-4745.
2. Engle, K.-H.; Flath, R. A.; Buttery, R. G.; Mon, T. R.; Ramming, D. W.; Teranishi, R. Investigation of volatile constituents in nectarines. 1. Analytical and sensory characterization of aroma components in some nectarine cultivars. J. Agric. Food Chem. 1988, 36, 549-553.
3. Aznar, M.; López, R.; Cacho, J. F.; Ferreira, V. Identification and quantification of impact odorants of aged red wines from Rioja. GC-olfactometry, quantitative GC-MS, and odor evaluation of HPLC fractions. J. Agric. Food Chem. 2001, 49, 2924-2929.
4. Bendall, J. G. Aroma compounds of fresh milk from New Zealand cows fed different diets. J. Agric. Food Chem. 2001, 49, 4825-4832.
5. 18 in dairy products, margarine and coconut. Lebensm.-Unters. -Forschung 1995, 201, 55-61.
6. Haffner, T.; Tressl, R. Biosynthesis of (R)-γ-decanolactone in the yeast Sporobolomyces odorus. J. Agric. Food Chem. 1996, 44, 1218-1223.
7. Fenaroli, C. Fenaroli's Handbook of Flavour Ingredients; Furia, T. E., Bellanca, N., Eds.; CRC Handbook; The Chemical Rubber Co.: Cleveland, OH, 1971.
8. Grosch, W. Detection of potent odorants in foods by aroma extract dilution analysis. Trends Food Sci. Technol. 1993, 4, 68-73.
9. Collins, I. Saturated and unsaturated lactones. J. Chem. Soc., Perkin Trans. 1 1999, 1377-1395.
10. Heiba, E. I.; Dessau, R. M.; Rodewald, P. G. Oxidation by metal salts. X. One-step synthesis of γ-lactones from olefins. J. Am. Chem. Soc. 1974, 96, 7977-7981.
11. Curran, D. P.; Ko, S. B. Additions of electrophilic radicals to electron rich alkenes by the atom transfer method, surmounting potentially reversible radical atom transfer reactions by irreversible ionic reactions. Tetrahedron Lett. 1998, 39, 6629-6632.
12. Yorimitsu, H.; Wakabayashi, K.; Shinokubo, H.; Oshima, K. Radical addition of 2-iodoalkanamide or 2-iodoalkanoic acid to alkenols using a water-soluble radical initiator in water. A facile synthesis of γ-lactones. Tetrahedron Lett. 1999, 40, 519-522.
13. Haffner, T.; Tressl, R. Stereospecific metabolism of isomeric epoxyoctadecanoic acids in the lactone-producing yeast Sporidiobolus salmonicolor. Lipids 1998, 33, 47-58.
14. Pollnitz, A. P.; Jones, G. P.; Sefton, M. A. Determination of oak lactones in barrel-aged wines and in oak extracts by stable isotope dilution analysis. J. Chromatogr. A 1999, 857, 239-246.
15. Milo, C.; Reineccius, G. A. Identification and quantification of potent odorants in regular-fat and low-fat mild cheddar cheese. J. Agric. Food Chem. 1997, 45, 3590-3594.
16. Schieberle, P.; Gassenmeier, K.; Guth, H.; Sen, A.; Grosch, W. Character impact odour compounds of different kinds of butter. Lebensm.-Wiss. -Technol. 1993, 26, 3247-356.
17. Midland, M. M.; Tramontan, A. The synthesis of naturally occurring 4-alkyl and 4-alkenyl-γ-lactones using the asymmetric reducing agent β-3-pinanyl-9-borabicyclo[3.3.1]nonane. Tetrahedron Lett. 1980, 21, 3549-3552.
18. Herrmann, J. L.; Berger, M. H.; Schlessinger, R. H. A total synthesis of racemic Avenaciolide. J. Am. Chem. Soc. 1979, 101, 1544-1549.
19. Mohrig, J. R.; Dabora, S. L.; Foster, T. F.; Schultz, S. C. Stereospecific synthesis of 2-deuterio-3-hydroxybutanoate esters. Regiochemistry and stereochemistry of homogeneous hydrogenation with Wilkinson's catalyst. J. Org. Chem. 1984, 49, 5179-5182.
20. Sirokman, G.; Molner, A.; Bartok, M. Synthesis of deuterium-labeled alkenes. J. Labelled Compd. Radiopharm. 1998, 27, 1-11.
21. Burns, D. H.; Miller, J. D.; Chan, H.-K.; Delaney, M. O. Scope and utility of a new soluble copper catalyst [CuBr-LiSPh-LiBr-THF]: A comparison with other copper catalysts in their ability to couple one equivalent of a Grignard reagent with an alkyl sulfonate. J. Am. Chem. Soc. 1997, 119, 2125-2133.
22. Wong, N. P.; Parks, O. W. Simple technique for extracting flavor compounds from fatty foods. J. Dairy Sci. 1994, 51, 1768-1769.
23. Yorimitsu, H.; Wakabayashi, K.; Shinokubo, H.; Oshima, K. Radical addition of 2-iodoalkanamide or 2-iodoalkanoic acid to alkenes with a water-soluble radical initiator in aqueous media: facile synthesis of γ-lactones. Bull. Chem. Soc. Jpn. 2001, 74, 1963-1970.