Bioflavours Natural -Decalactone and other Lactones Prof. Dr. Jrgen - - PowerPoint PPT Presentation

Hochschule OWL, 10.04.2017

Bioflavours

Natural γ-Decalactone and other Lactones

A collaborative MOOC-Project by: part of the

• Prof. Dr. Jürgen Rabenhorst

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

CH3-(CH2)5 COOH COOH COOH (CH2)7-COOH NAD HSCoA OH NADH2 12-hydroxyoctadec-9-enoic acid CH3COSCoA 4 CH3-(CH2)5 OH COOH 6-hydroxy dodec-3-enoic acid COOH γ-decalactone ß-oxidation 4 FAD FADH2 H2O2 O2 H2O dec-2-enolide dec-3-enolide 3-hydroxy-γ-decalactone R-CO-SCoA + CH3-CO-SCoA β-oxidation

POX 1-6 MFE1 MFE1 POT1

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

• ver 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
• 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

δ‐Decalactone and δ‐Dodecalactone

[EP0425001B1]

• 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)‐
• ctadecenoic acid as an intermediate
• with a Linoleate‐13‐hydratase from Lactobacillus

acidophilus

δ‐Decalactone and δ‐Dodecalactone

δ‐Decalactone and δ‐Dodecalactone

• Recently published:
• alternative process for δ‐Decalactone
• Hydroxylation of linoleic acid to 13‐hydroxy‐9(Z)‐
• ctadecenoic 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