Bioflavours Natural γ -Decalactone and other Lactones Prof. Dr. Jürgen Rabenhorst A collaborative MOOC-Project by: part of the Hochschule OWL, 10.04.2017
What are Lactones?
What are Lactones? • Cyclic esters of γ‐ and δ‐hydroxy acids • Chain length from C8 to C12 (of Interest for Flavours)
What are Lactones? • Cyclic esters of γ‐ and δ‐hydroxy acids • Chain length from C8 to C12 (of Interest for Flavours) • Most important: γ‐Decalactone
Flavour profile of γ‐Decalactone • Oily‐peachy • Extraordinarily tenacious odour • Very powerful creamy‐fruity taste
Flavour profile of γ‐Decalactone • Oily‐peachy • Extraordinarily tenacious odour • Very powerful creamy‐fruity taste • Peachy character: < 5 ppm
Usage of γ‐Decalactone • Fruit and dairy flavours • Numerous beverages
Current market situation • Synthetic production ≈ 500 tons/ year • Natural production ≈ 10 tons/ year
Fermentation process • Yarrowia lipolytica , • reclassified to Yarrowia deformans (2016) • Has obtained GRAS status by FDA (Generally recognized as safe) [A. Braga, I. Belo; World J Microbiol Biotechnol (2016) 32; p. 169; DOI: 10.1007/s11274-016-2116-2]
From Castor oil to γ‐Decalactone
Degradation of Castor oil – possible by‐products γ-decalactone 12-hydroxyoctadec-9-enoic acid 6-hydroxy dodec-3-enoic acid 4 ß-oxidation CH 3 -(CH 2 ) 5 CH 3 -(CH 2 ) 5 (CH 2 ) 7 -COOH COOH COOH OH OH O 2 FAD 4 CH 3 COSCoA POX 1-6 H 2 O 2 FADH 2 COOH dec-2-enolide H 2 O MFE1 3-hydroxy-γ-decalactone MFE1 COOH COOH dec-3-enolide NAD NADH 2 HSCoA POT1 R-CO-SCoA + CH 3 -CO-SCoA β-oxidation
From Castor oil to γ‐Decalactone • Product concentration > 12 g/l in 2 1/2 days was reached with a not genetically engineered strain [EP1123409B1]
γ‐Dodecalactone • Peach, butter and fatty odour
γ‐Dodecalactone • Peach, butter and fatty odour • Use of 10‐hydroxystearic acid instead of Ricinoleic acid
γ‐Dodecalactone • Peach, butter and fatty odour • Use of 10‐hydroxystearic acid instead of ricinolic acid • Produced by Oleate hydratases • Introduction of Oleate hydratase gene of Stenotrophomonas maltophilia into E. coli results in a product concentration of over 40 g/L [J.-U. An, Y.-C. Joo, D.-K. Oh; Applied and Environmental Microbiology (2013); 79 nr. 8; p. 2636–2641; DOI: 10.1128/AEM.02602-12]
γ‐Octalactone • Cardillo et al. (patent from 1990), they disclosed a process to produce 1 g/L of γ‐Octalactone from 10 g/L coconut oil with Cladosporium suaveolens • γ‐Octalactone has a sweet‐herbaceous coconut‐like odour
δ‐Decalactone and δ‐Dodecalactone δ‐Dodecalactone δ‐Decalactone
δ‐Decalactone and δ‐Dodecalactone • δ‐Decalactone very powerful and tenacious sweet creamy, nut‐like odour with a heavy fruity undertone Taste is creamy, sweet coconut‐peach‐milk‐like below 2 ppm.
δ‐Decalactone and δ‐Dodecalactone • δ‐Decalactone very powerful and tenacious sweet creamy, nut‐like odour with a heavy fruity undertone Taste is creamy, sweet coconut‐peach‐milk‐like below 2 ppm. • Production process for δ‐Decalactone and δ‐Dodecalactone: Usage of unsaturated lactones in the Massoia Bark oil as substrate They are hydrated with a reductase present in baker’s yeast [EP0425001B1]
δ‐Decalactone and δ‐Dodecalactone • Recently published: alternative process for δ‐Decalactone
δ‐Decalactone and δ‐Dodecalactone • Recently published: alternative process for δ‐Decalactone Hydroxylation of linoleic acid to 13‐hydroxy‐9(Z)‐ octadecenoic acid as an intermediate • with a Linoleate‐13‐hydratase from Lactobacillus acidophilus
δ‐Decalactone and δ‐Dodecalactone • Recently published: alternative process for δ‐Decalactone Hydroxylation of linoleic acid to 13‐hydroxy‐9(Z)‐ octadecenoic acid as an intermediate • with a Linoleate‐13‐hydratase from Lactobacillus acidophilus than metabolized by Yarrowia lipolytica to δ‐Decalactone [W.-R. Kang, M.-J. Seo, J.-U. An, K.-C. Shin, D.-K. Oh; Biotechnol Lett (2016) 38; p. 817–823; DOI: 10.1007/s10529-016-2041-3]
A collaborative MOOC-Project by: part of the
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