Use of novel mixtures of (e/z) cyclopentadecenone isomers, the production and use thereof as flavoring substance

Patent metadata

Field	Value
Publication number	US-2018290959-A1
Application number	US-201615766407-A
Country	US
Kind code	A1
Filing date	Oct 7, 2016
Priority date	Oct 8, 2015
Publication date	Oct 11, 2018
Grant date	—

Abstract

The present invention relates to novel mixtures of cyclopentadecenone isomers, preparation thereof and use thereof as aroma substances, particularly as fragrances, and also aroma substance compositions and agents comprising said mixtures.

First claim

1 .- 20 . (canceled)

21 . A method for preparing a macrocyclic keto compound of formula X

wherein A is a cycloaliphatic hydrocarbon residue having m ring carbon atoms, where m is an integer from 13 to 17, and optionally has n C═C double bonds, where n is an integer equal to 1, 2 or 3, the method comprising)
a) Oxidatively decarbonylating a cycloaliphatic carbaldehyde compound of formula XI

where A is as defined above; wherein the compound of formula XI is reacted in the presence of a Cu(II) catalyst and molecular oxygen; and optionally
b) Isolating at least one compound of formula X from the reaction mixture.

22 . The method as claimed in claim 21 , wherein the catalyst is formed in situ by adding a ligand to a Cu(II) salt.

23 . The method as claimed in claim 21 , wherein m is 15 and/or n is 1 in the compounds of formula X and XI.

24 . The method as claimed in claim 21 , wherein (E/Z)-cyclopentadec-8-enyl-1-carbaldehyde or a mixture of (E/Z)-cyclopentadec-8-enyl- and (E/Z)-cyclopentadec-7-enyl-1-carbaldehyde, or a mixture comprising this compound, is used.

25 . The method as claimed in claim 24 , wherein at least one compound is obtained selected from the group consisting of (E/Z)-cyclopentadec-8-en-1-one and the regioisomers thereof.

26 . The method as claimed in claim 25 , wherein at least one compound is obtained selected from compounds of formulae I and III and regioisomers thereof of formulae II and IV

27 . The method as claimed in claim 21 , wherein a reaction product is used in stage a) obtained from the dinitrogen monoxide oxidation of a cycloaliphatic compound of formula XII

where A′ is a cycloaliphatic hydrocarbon residue having m+1 ring carbon atoms, where m is an integer from 13 to 17, and optionally has n+1 C═C double bonds, and where n is an integer equal to 1, 2 or 3.

28 . The method as claimed in claim 27 , wherein m is 15 and n is 1 in the compound of formula XII.

29 . The method as claimed in claim 28 , wherein the compound of formula XII is cyclohexadeca-1,9-diene.

30 . A method for preparing Globanone ((E/Z)-cyclohexadec-8-en-1-one), comprising
a) oxidizing cyclohexadeca-1,9-diene with dinitrogen monoxide, wherein a reaction mixture is obtained, which comprises a mixture comprising Globanone and at least one cyclopentadecenyl carbaldehyde compound, particularly selected from (E/Z)Application cyclopentadec-8-enyl-1-carbaldehydes; wherein unreacted cyclohexadeca-1,9-diene is optionally removed; b) subjecting the reaction mixture from stage a) to an oxidative decarbonylation reaction as claimed in claim 21 ; and c) separating Globanone from the cyclopentadecenones I thus formed.

31 . The method as claimed in claim 21 , wherein the oxidative decarbonylation is carried out in the presence or absence of a solvent.

32 . A substance or substance mixture comprising at least one macrocyclic keto compound of formula X

wherein A is a cycloaliphatic hydrocarbon residue having m ring carbon atoms, where m is an integer from 13 to 17, and optionally has n C═C double bonds, where n is an integer equal to 1, 2 or 3.

33 . The substance mixture as claimed in claim 32 comprising at least two compounds selected from the group consisting of (E/Z)-cyclopentadec-8-en-1-one and the regioisomers thereof.

34 . The substance mixture as claimed in claim 33 comprising at least two compounds selected from compounds of formulae I and III and regioisomers thereof of formula II:

or comprising at least two compounds selected from the group consisting of compounds of the following formulae I and III and optionally regioisomers thereof of the formulae II and IV

35 . A fragrance composition comprising at least one substance or substance mixture as claimed in claim 31 as an aroma chemical.

36 . The composition as claimed in claim 35 of a mixture essentially comprising (E)cyclopentadec-8-en-1-one (I) and (Z)-cyclopentadec-8-en-1-one (III).

37 . The composition as claimed in claim 36 , wherein the molar ratio of (I) to (III) is in the range of approximately 1:1 to approximately 5:1.

38 . The composition as claimed in claim 35 wherein the aroma chemical generates a musk note in the fragrance composition.

39 . A fragrance composition comprising at least one substance or one substance mixture prepared according to the method as claimed in claim 21 .

40 . An agent comprising at least one substance or one substance mixture according to the definition in claim 32 .

Assignees

• Basf Se

Inventors

• Thrun Frauke
• Teles Joaquim Henrique
• Werner Albert
• Pelzer Raff

Classifications

• A61Q13/00

  Formulations or additives for perfume preparations (essential oils or perfumes per se C11B9/00) · CPC title

• C11B9/0038

  the ring containing more than six carbon atoms · CPC title

• C07C49/607 Primary

  of a seven-to twelve-membered ring · CPC title

• C07C45/54

  of compounds containing doubly bound oxygen atoms, e.g. esters · CPC title

• C07C2601/18

  with a ring being at least seven-membered · CPC title