# US 11,028,034 B2 · Method for producing rotundone-containing mixtures

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- Number: US 11,028,034 B2
- Document ID: US11028034B2
- Status: Granted
- Kind: B2
- Application number: 16/488,408
- Filed: 2017-02-27
- Published: 2020-08-06
- Granted: 2021-06-08
- Earliest claimed: 2017-02-27
- Assignees: Symrise AG
- Applicants: Symrise AG
- Inventors: Michael Backes; Tobias Vössing; Nadine Heinemeier; Lars Meier; Dietmar Schatkowski; Willi Krieger; Katharina Reichelt; Susanne Otte-Hölscher
- Web page: https://patentgrep.com/patent/US11028034B2

## CPC

- C07C 45/34: in unsaturated compounds
- A23L 27/203: {Alicyclic compounds}
- A23L 33/105: Plant extracts, their artificial duplicates or their derivatives
- C07C 1/24: by elimination of water
- C12G 3/07: Flavouring with wood extracts, e.g. generated by contact with wood; Wood pretreatment therefor
- C07C 49/653: polycyclic
- C07C 2602/30: Azulenes; Hydrogenated azulenes
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- A23L: FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF (preservation thereof A23B)
- C12G: WINE; PREPARATION THEREOF; ALCOHOLIC BEVERAGES (beer C12C); PREPARATION OF ALCOHOLIC BEVERAGES NOT PROVIDED FOR IN SUBCLASSES C12C OR C12H

## Abstract

The present invention relates to, according to a primary aspect, a method for manufacturing a mixture comprising rotundone. A further aspect of the present invention relates to mixtures containing rotundone as well as their use for generating, imparting or modifying, preferably enhancing, one or several taste and/or olfactory impressions. Moreover, the invention relates to a pharmaceutical preparation for nutrition, for oral care or for pleasure or a cosmetic pharmaceutical preparation or a pharmaceutical preparation intended for oral consumption or an intermediate good for manufacturing a pharmaceutical preparation for nutrition, for oral care or for pleasure or a cosmetic pharmaceutical preparation or a pharmaceutical preparation intended for oral consumption comprising a mixture according to the invention and furthermore to a method for manufacturing said preparation or intermediate good.

## Claims

### Claim 1

A method for manufacturing a mixture comprising rotundone comprising:
a) reacting wood oil(s), extract(s) and/or natural resin(s) containing guaiol and bulnesol with one or several organic acid(s),
b) separating a guaiene containing fraction from a mixture obtained in a),
c) oxidizing the separated guaiene containing fraction of b),
d) optionally, heating an oxidized mixture obtained in c), and
e) separating a rotundone containing fraction from the mixture obtained in c) or d), if present, to obtain a rotundone containing mixture.

### Claim 2 (depends on 1)

A method according to claim 1, wherein the organic acid(s) used in a) is or are selected from the group consisting of citric acid, malic acid, tartaric acid, and oxalic acid.

### Claim 3 (depends on 1)

A method according to claim 1, wherein in a) the weight ratio of wood oil(s), extract(s) and/or natural resin(s) containing guaiol and bulnesol to organic acid or organic acids is between 50:1 to 3:1.

### Claim 4 (depends on 1)

A method according to claim 1, wherein the reaction in a) takes place in the presence of a co-solvent or several co-solvents.

### Claim 5 (depends on 1)

A method according to claim 1, wherein a reaction temperature of the reaction in a) is between 160 and 260° C., and/or the reaction time of the reaction in a) is between 1 and 20 h, and/or the reaction in a) is conducted at normal pressure or at negative pressure.

### Claim 6 (depends on 1)

A method according to claim 1, wherein the separation of the guaiene containing fraction from the mixture obtained or provided in a) takes place in b) by distillation.

### Claim 7 (depends on 1)

A method according to claim 1, wherein the oxidation of the guaiene containing fraction of b) takes place in c) with ambient air and/or pure oxygen as oxidizing agent and/or at a temperature of 60 to 150° C., and/or with a gas amount of oxidizing agent from ≥10 to ≤10001/h, per kg of precursor and/or over a period of time of 10 to 60 h.

### Claim 8 (depends on 1)

A method according to claim 1, wherein a peroxide number of the mixture obtained in c) or d), if present, is <30 meq O/kg.

### Claim 9 (depends on 1)

A method according to claim 1, wherein one or more entrainer(s) selected from the group consisting of triacetin and triethylcitrate in a weight ratio of mixture obtained in c) or d), if present, to entrainer(s) of 4:1 to 1:4, is or are added to the mixture in e) before and/or during distillation, and/or one or more co-solvent(s) selected from the group consisting of polyethylene glycols and palatinol Z, is or are added in a weight ratio of mixture obtained in c) or d), if present, to co-solvent(s) of 10:1 to 1:5.

### Claim 10 (depends on 1)

A method according to claim 1, wherein the separation of the rotundone containing fraction from the mixture obtained in c) or d), if present, takes place in e) by distillation.

### Claim 11 (depends on 1)

A rotundone containing mixture comprising rotundone, bulnesene, guaiene, guaiol and bulnesol as well as optionally triethylcitrate and/or triacetin, wherein the rotundone containing mixture is producible according to the method of claim 1.

### Claim 12 (depends on 11)

A method for generating, imparting or modifying one or several taste and/or olfactory impression(s) comprising incorporating a rotundone containing mixture of claim 11 into a composition.

### Claim 13 (depends on 11)

A preparation or intermediate good comprising a mixture according to claim 11.

### Claim 14 (depends on 13)

A preparation or intermediate good according to claim 13, further comprising one or several (further) flavouring and/or odorous substance(s), wherein the total amount of the rotundone containing mixture is sufficient to modify one or several taste and/or olfactory impressions of the (further) flavouring and/or odorous substance(s).

### Claim 15 (depends on 13)

A method for manufacturing a preparation or intermediate good according to claim 13 comprising:
providing the rotundone containing mixture as well as one or several further components, wherein the further component or several further components is/are selected from the group consisting of flavouring and odorous substances, and
mixing the rotundone containing mixture with the further component(s).

### Claim 16 (depends on 1)

The method according to claim 1, wherein the wood oil(s), extract(s) and/or natural resin(s) of a) contain 15 to 45% by weight guaiol and 25 to 55% by weight bulnesol.

### Claim 17 (depends on 1)

The method according to claim 1 comprising d) heating the oxidized mixture obtain in c) for 1 to 3 hours at 110 to 150° C.

### Claim 18 (depends on 6)

The method according to claim 6, wherein the wherein the separation of the guaiene containing fraction from the mixture obtained or provided in a) takes place in b) by distillation at 1.0 to 20.0 mbar and a sump temperature of 90 to 175° C.

### Claim 19 (depends on 7)

A method according to claim 7, wherein the oxidation of the guaiene containing fraction of b) takes place in c) with ambient air and/or pure oxygen as oxidizing agent at a temperature of 60 to 150° C. with a gas amount of oxidizing agent from ≥10 to ≤10001/h, per kg of precursor over a period of time of 10 to 60 h.

### Claim 20 (depends on 8)

A method according to claim 8, wherein the peroxide number of the mixture obtained in c) or d), if present, is <20 meq O/kg.