Production of cis-pellitorin and use as a flavouring
View Patent ↗The invention describes a process for the production of 2E,4Z-decadienoic acid-N-isobutylamide (cis-pellitorine) and its use as a pungent principle and aromatic substance having a heat-generating effect, preferably in preparations used for foodstuffs, oral hygiene or luxury foodstuffs.
1. Process for the production of 2E,4Z-decadienoic acid-N-isobutylamide (cis-pellitorine), characterised in that a 2E,4Z-decadienoic acid ester is reacted with isobutylamine in the presence of an enzyme catalyst, and then isolating the mixture by physico-chemical methods.
2. A sensory ingredient mixture containing at least 80 wt. % of 2E,4Z-decadienoic acid-N-iso-butylamide and at least two other N-isobutylamides of decanoic acid, 2E-decenoic acid, 2E,4E-decadienoic acid, 2Z,4E-decadienoic acid, 2Z,4Z-decadienoic acid, 2E,4Z,7Z-decatrienoic acid, 3Z,5E-decadienoic acid or 3Z,5E,7Z-decatrienoic acid.
3. A sensory agent comprising 2E,4Z-decadienoic acid-N-isobutylamide or a mixture according to claim 2 as an aromatic substance.
4. A sensory agent according to claim 3 , wherein said aromatic substance comprises a pungent principle or aromatic substance having a heat-generating effect.
5. A food stuff preparation comprising a sensory agent according to claim 3 .
6. An oral hygiene composition comprising a sensory agent according to claim 3 .
7. Preparations useful for foodstuffs, oral hygiene or luxury foodstuffs, containing 2E,4Z-decadienoic acid isobutylamide or a mixture comprising at least 80 wt. % of 2E,4Z-decadienoic acid-N-isobutylamide and at least two other N-isobutylamides of decanoic acid, 2E-decenoic acid, 2E,4E-decadienoic acid, 2Z,4E-decadienoic acid, 2Z,4Z-decadienoic acid, 2E,4Z,7Z-decatrienoic acid, 3Z,5E-decadienoic acid or 3Z,5E,7Z-decatrienoic acid.
8. Preparations according to claim 7 , containing at least one other pungent-tasting or heat-generating substance.
9. Preparations according to claim 7 , containing at least one pungent-tasting plant extract.
10. Preparations according to claim 7 , containing at least one other pungent-tasting or heat-generating substance and at least one pungent-tasting plant extract.
11. Preparations according to claim 7 in the form of a semi-finished product.
12. Preparations according to claim 7 in the form of a perfume, an aromatic composition, a flavouring composition, and a spice mix.
13. Preparations according to claim 7 containing at least 80 wt. % of 2E,4Z-decadienoic acid-N-isobutylamide and at least two other N-isobutylamides of decanoic acid, 2E-decenoic acid, 2E,4E-decadienoic acid, 2Z,4E-decadienoic acid, 2Z,4Z-decadienoic acid 2E,4Z,7Z-decatrienoic acid, 3Z,5E-decadienoic acid or 3Z,5E,7Z-decatrienoic acid.
14. Preparations according to claim 7 containing 2E,4Z-decadienoic acid-N-iso-butylamide.
15. The process of claim 1 , further comprising saponifying unreacted 2E,4Z-decadienoic acid ester.
16. The process of claim 1 , wherein the catalyst is an enzyme having lipase activity.
17. The process of claim 16 , wherein the enzyme is on a support.
18. The process of claim 1 , wherein the mixture is isolated by a process selected from the group consisting of crystallization, chromatography, distillation and co-distillation.