# US 10,767,198 B2 · Method for producing branched aldehydes

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- Number: US 10,767,198 B2
- Document ID: US10767198B2
- Status: Granted
- Kind: B2
- Application number: 15/779,214
- Filed: 2015-11-28
- Published: 2019-12-05
- Granted: 2020-09-08
- Earliest claimed: 2015-11-28
- Assignees: Symrise AG
- Applicants: Symrise AG
- Inventors: Marco A. Fraatz; Holger Zorn; Johanna Rost; Michael Goldmann; Egon Gross; Jakob Ley; Katrin Geissler; Torsten Geissler; Michael Backes; Fabia Hentschel; Jens-Michael Hilmer
- Web page: https://patentgrep.com/patent/US10767198B2

## CPC

- C12P 7/24: containing a carbonyl group
- C12P 7/64: Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
- A23L 27/00: Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L 27/2052: {having oxygen or sulfur as the only hetero atoms}
- A23L 27/26: Meat flavours
- C07C 45/27: by oxidation (with ozone C07C45/40)
- C12N 9/0083: {Miscellaneous (1.14.99)}
- C12P: FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE {(brewing of beer C12C; producing vinegar C12J; producing specific peptides or proteins C07K; producing enzymes C12N9/00; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; measuring or testing processes involving enzymes or microorganisms C12Q; measuring or testing processes involving nucleic acid amplification reactions C12Q1/6844; fermentation processes to form a food composition, A21 or A23; compounds in general, see the relevant compound class, e.g. C01, C07)}
- A23L: FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF (preservation thereof A23B)
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C12N: MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA (microbiological testing media C12Q1/00)

## Abstract

A method for producing branched aldehydes is proposed, the method comprising the following steps: (a) providing a culture of one or more fungi of the genus Conidiobolus and producing biomass containing branched carboxylic acids in free and/or bound form; (b) extracting the biomass from step (a) to produce a first intermediate containing free and/or bound carboxylic acids; (c) optionally chemically, enzymatically or microbially hydrolyzing the bound carboxylic acids from the first intermediate; (d) treating the first intermediate with a reducing agent of a chemical nature to convert the free and/or bound carboxylic acids into the corresponding alcohols and optionally separating one or more alcohols from interfering by-products and producing the chemically produced second intermediate containing these alcohols as a mixture or in enriched form; (e) treating the first intermediate with a reducing agent of a biological nature to convert the free and/or bound carboxylic acids into the corresponding aldehydes having the same number of carbon atoms compared to the free and/or bound carboxylic acids or into the corresponding aldehydes having a reduced number of carbon atoms by one compared to the free and/or bound carboxylic acids and producing the biologically produced second intermediate containing these aldehydes; (f) treating the chemically produced second intermediate with an oxidizing agent of a chemical nature to convert the free and/or bound alcohols into the corresponding aldehydes; and optionally (g) removing interfering by-components from the fractions obtainable after step(s) (d) and/or (e) and/or (f).

## Claims

### Claim 1

A method for producing branched aldehydes comprising:
(a) providing a culture of one or more fungi of the genus Conidiobolus, wherein the one or more fungi is selected from the group consisting the species of C. denaeosporus and C. heterosporus, and producing biomass containing branched carboxylic acids in free form and/or bound form;
(b) extracting the biomass from step (a) to produce a first intermediate containing free and/or bound carboxylic acids;
(c) optionally chemically, enzymatically, or microbially hydrolyzing the bound carboxylic acids from the first intermediate;
and
(d) treating the first intermediate with a reducing agent of a chemical nature to convert the free and/or bound carboxylic acids into the corresponding alcohols and optionally separating one or more alcohols from interfering by-products and producing the chemically produced second intermediate containing these alcohols as a mixture or in enriched form;
and
(e) treating the chemically produced second intermediate with an oxidizing agent of a chemical nature to convert the free and/or bound alcohols into the corresponding aldehydes;
or
(f) treating the first intermediate with a reducing agent of a biological nature to convert the free and/or bound carboxylic acids into the corresponding aldehydes having the same number of carbon atoms compared to the free and/or bound carboxylic acids or into the corresponding aldehydes having a reduced number of carbon atoms by one compared to the free and/or bound carboxylic acids and producing the biologically produced second intermediate containing these aldehydes;
and optionally
(g) removing interfering by-components from the fractions obtainable after step(s) (d) and/or (e) and/or (f).

### Claim 2 (depends on 1)

The method according to claim 1, wherein the branched aldehydes have 12 to 18 carbon atoms.

### Claim 3 (depends on 1)

The method according to claim 1, wherein the branched aldehydes have a branched methyl group.

### Claim 4 (depends on 1)

The method according to claim 1, wherein the aldehydes include 12-methyltridecanal, 12-methyltetradecanal, 14-methylpentadecanal, 16-methyloctadecanal, or mixtures thereof.

### Claim 5 (depends on 1)

The method according to claim 1, wherein the first intermediate is subjected to hydrolysis before reduction.

### Claim 6 (depends on 1)

The method according to claim 1, wherein, in step (d), the reduction is carried out with lithium alanate or sodium borohydride.

### Claim 7 (depends on 1)

The method according to claim 1, wherein, in step (f), the reduction is carried out by a biological system.

### Claim 8 (depends on 7)

The method according to claim 7, wherein the reduction is carried out with an aldehyde dehydrogenase.

### Claim 9 (depends on 7)

The method according to claim 7, wherein the reduction is carried out with an α-dioxygenase.

### Claim 10 (depends on 7)

The method according to claim 7, wherein the reduction is carried out with purified enzyme Nsp-CAR and/or MmFad9.

### Claim 11 (depends on 7)

The method according to claim 7, wherein the reduction is carried out with a whole cell extract of cells expressing Nsp-CAR and/or MmFad9.

### Claim 12 (depends on 7)

The method according to claim 7, wherein the reduction is carried out with viable cells capable of expressing the enzymes Nsp-CAR and/or MmFad9.

### Claim 13 (depends on 1)

The method according to claim 1, wherein the reduction is carried out at a temperature in the range from 15 to 25° C.

### Claim 14 (depends on 1)

The method according to claim 1, wherein, in step (e), 2,2,6,6-tetramethylpiperidinyloxyl (TEMPO) is used as the oxidizing agent.

### Claim 15 (depends on 14)

The method according to claim 14, wherein the TEMPO is used together with an alkali bromide and an alkali hypochlorite.

### Claim 16 (depends on 15)

The method according to claim 15, wherein the TEMPO, the alkali bromide, and the alkali hypochlorite are used in a molar ratio of about 1:(2 to 10):(10 to 40).

### Claim 17 (depends on 1)

The method according to claim 1, wherein the oxidation is carried out at a temperature in the range from −5 to +10° C.

### Claim 18 (depends on 1)

The method according to claim 1, wherein the reduction product, the oxidation product, or both are subjected to a distillation step.