Back to results
US 12,030,852 B2Granted
Method for producing fatty alcohol esters of hydroxycarboxylic acids
AssigneeIoi Oleo GmbH
InventorsDirk Lochmann, Sebastian Reyer, Michael Stehr
Life of this patent
Estimating the term…
Abstract
The invention relates to a method for producing fatty alcohol esters of 3-hydroxybutyric acid and their acylated derivatives, as well as the products thus obtained and their use.
Claims14
A method for producing fatty alcohol esters of 3-hydroxybutyric acid,
- (A) wherein, according to a first synthesis route (A), at least one compound of the general formula (Ia)
- CH3—CH(OH)—CH2—C(O)OR1 (Ia)
- wherein, in the general formula (Ia), the radical R1 represents hydrogen or C1-C4-alkyl,
- is reacted with at least one fatty alcohol (II) selected from C10-C30-fatty alcohols,
- wherein the reaction is carried out in the absence of any solvents,
- wherein the reaction is carried out in the presence of an enzyme as a catalyst, wherein the catalyst is recycled after the reaction, and
- wherein during the reaction, the compound according to the general formula (IVa)
- R1—OH (IVa)
- is formed simultaneously, wherein, in general formula (IVa), the radical R1 represents hydrogen or C1-C4-alkyl, wherein the compound according to the general formula (IVa) is continuously withdrawn from the reaction;
- or else
- (B) wherein, according to a second synthesis route (B), which is alternative to synthesis route (A), at least one compound of the general formula (Ib)
- CH3—CH(OR2)—CH2—C(O)—O—C(O)—CH2—CH(OR2)—CH3 (Ib)
- wherein, in the general formula (Ib), the radical R2 represents an acyl group selected from an acetyl group of formula —C(O)—CH3 or a propionyl group of formula —C(O)—C2H5,
- is reacted with at least one fatty alcohol (II) selected from C10-C30-fatty alcohols, followed by hydrolysis of the acyl group;
- so that, as a reaction product (III), in each case a C10-C30-fatty alcohol ester of 3-hydroxybutyric acid is obtained.
12 more elements
A fatty alcohol ester of acylated 3-hydroxybutyric acid,
- wherein the fatty alcohol ester of acylated 3-hydroxybutyric acid is a fatty alcohol ester of acylated 3-hydroxybutyric acid of the general formula (IIIa)
- CH3—CH(OR2)—CH2—C(O)OR3 (IIIa)
- wherein, in the general formula (IIIa),
- R2 represents an acyl group selected from an acetyl group of formula —C(O)—CH3 and a propionyl group of formula —C(O)—C2H5,
- the radical R3 represents a 1-decanyl radical, a 1-dodecanyl radical, a 1-tetradecanyl radical, a 1-hexadecanyl radical, a 1-heptadecanyl radical, a 1-octadecanyl radical, a 1-eicosanyl radical, a 1-docosanyl radical, a 1-tetracosanyl radical, a 1-hexacosanyl radical, a 1-octacosanyl radical, a 1-tricontanyl radical, a cis-9-hexadecen-1-yl radical, a cis-9-octadecen-1-yl radical, a trans-9-octadecen-1-yl radical, a cis-11-octadecen-1-yl radical, a cis, cis-9,12-octadecadien-1-yl radical or a 6,9,12-octadecatrien-1-yl radical.
2 more elements
A pharmaceutical composition,
- wherein the pharmaceutical composition comprises at least one of (i) and (ii):
- (i) a fatty alcohol ester of 3-hydroxybutyric acid, wherein the fatty alcohol ester of 3-hydroxybutyric acid corresponds to the general formula (III′)
- CH3—CH(OH)—CH2—C(O)OR3 (III′)
- wherein the radical R3 represents a 1-tetradecanyl radical, a 1-hexadecanyl radical, a 1-heptadecanyl radical, a 1-octadecanyl radical, a 1-eicosanyl radical, a 1-docosanyl radical, a 1-tetracosanyl radical, a 1-tricontanyl radical, a cis-9-hexadecen-1-yl radical, a cis-9-octadecen-1-yl radical, a trans-9-octadecen-1-yl radical, a cis-11-octadecen-1-yl radical, a cis, cis-9,12-octadecadien-1-yl radical or a 6,9,12-octadecatrien-1-yl radical;
- (ii) a fatty alcohol ester of acylated 3-hydroxybutyric acid, wherein the fatty alcohol ester of acylated 3-hydroxybutyric acid is a fatty alcohol ester of acylated 3-hydroxybutyric acid of the general formula (IIIa)
- CH3—CH(OR2)—CH2—C(O)OR3 (IIIa)
- wherein, in the general formula (IIIa),
- R2 represents an acyl group selected from an acetyl group of formula —C(O)—CH3 and a propionyl group of formula —C(O)—C2H5,
- the radical R3 represents a 1-decanyl radical, a 1-dodecanyl radical, a 1-tetradecanyl radical, a 1-hexadecanyl radical, a 1-heptadecanyl radical, a 1-octadecanyl radical, a 1-eicosanyl radical, a 1-docosanyl radical, a 1-tetracosanyl radical, a 1-hexacosanyl radical, a 1-octacosanyl radical, a 1-tricontanyl radical, a cis-9-hexadecen-1-yl radical, a cis-9-octadecen-1-yl radical, a trans-9-octadecen-1-yl radical, a cis-11-octadecen-1-yl radical, a cis, cis-9,12-octadecadien-1-yl radical or a 6,9,12-octadecatrien-1-yl radical.
6 more elements
A method of treating a human suffering from a disease,
- wherein the method comprises a step of administering to said human an efficient dose of a pharmaceutical composition, wherein the pharmaceutical composition comprises at least one of (i) and (ii):
- (i) a fatty alcohol ester of 3-hydroxybutyric acid, wherein the fatty alcohol ester of 3-hydroxybutyric acid corresponds to the general formula (III′)
- CH3—CH(OH)—CH2—C(O)OR3 (III′)
- wherein the radical R3 represents a 1-tetradecanyl radical, a 1-hexadecanyl radical, a 1-heptadecanyl radical, a 1-octadecanyl radical, a 1-eicosanyl radical, a 1-docosanyl radical, a 1-tetracosanyl radical, a 1-tricontanyl radical, a cis-9-hexadecen-1-yl radical, a cis-9-octadecen-1-yl radical, a trans-9-octadecen-1-yl radical, a cis-11-octadecen-1-yl radical, a cis, cis-9,12-octadecadien-1-yl radical or a 6,9,12-octadecatrien-1-yl radical;
- (ii) a fatty alcohol ester of acylated 3-hydroxybutyric acid, wherein the fatty alcohol ester of acylated 3-hydroxybutyric acid is a fatty alcohol ester of acylated 3-hydroxybutyric acid of the general formula (IIIa)
- CH3—CH(OR2)—CH2—C(O)OR3 (IIIa)
- wherein, in the general formula (IIIa),
- R2 represents an acyl group selected from an acetyl group of formula —C(O)—CH3 and a propionyl group of formula —C(O)—C2H5,
- the radical R3 represents a 1-decanyl radical, a 1-dodecanyl radical, a 1-tetradecanyl radical, a 1-hexadecanyl radical, a 1-heptadecanyl radical, a 1-octadecanyl radical, a 1-eicosanyl radical, a 1-docosanyl radical, a 1-tetracosanyl radical, a 1-hexacosanyl radical, a 1-octacosanyl radical, a 1-tricontanyl radical, a cis-9-hexadecen-1-yl radical, a cis-9-octadecen-1-yl radical, a trans-9-octadecen-1-yl radical, a cis-11-octadecen-1-yl radical, a cis, cis-9,12-octadecadien-1-yl radical or a 6,9,12-octadecatrien-1-yl radical.
6 more elements
A food product,
- wherein the food product comprises at least one of (i) and (ii):
- (i) a fatty alcohol ester of 3-hydroxybutyric acid, wherein the fatty alcohol ester of 3-hydroxybutyric acid corresponds to the general formula (III′)
- CH3—CH(OH)—CH2—C(O)OR3 (III′)
- wherein the radical R3 represents a 1-tetradecanyl radical, a 1-hexadecanyl radical, a 1-heptadecanyl radical, a 1-octadecanyl radical, a 1-eicosanyl radical, a 1-docosanyl radical, a 1-tetracosanyl radical, a 1-tricontanyl radical, a cis-9-hexadecen-1-yl radical, a cis-9-octadecen-1-yl radical, a trans-9-octadecen-1-yl radical, a cis-11-octadecen-1-yl radical, a cis, cis-9,12-octadecadien-1-yl radical or a 6,9,12-octadecatrien-1-yl radical;
- (ii) a fatty alcohol ester of acylated 3-hydroxybutyric acid, wherein the fatty alcohol ester of acylated 3-hydroxybutyric acid is a fatty alcohol ester of acylated 3-hydroxybutyric acid of the general formula (IIIa)
- CH3—CH(OR2)—CH2—C(O)OR3 (IIIa)
- wherein, in the general formula (IIIa),
- R2 represents an acyl group selected from an acetyl group of formula —C(O)—CH3 and a propionyl group of formula —C(O)—C2H5,
- the radical R3 represents a 1-decanyl radical, a 1-dodecanyl radical, a 1-tetradecanyl radical, a 1-hexadecanyl radical, a 1-heptadecanyl radical, a 1-octadecanyl radical, a 1-eicosanyl radical, a 1-docosanyl radical, a 1-tetracosanyl radical, a 1-hexacosanyl radical, a 1-octacosanyl radical, a 1-tricontanyl radical, a cis-9-hexadecen-1-yl radical, a cis-9-octadecen-1-yl radical, a trans-9-octadecen-1-yl radical, a cis-11-octadecen-1-yl radical, a cis, cis-9,12-octadecadien-1-yl radical or a 6,9,12-octadecatrien-1-yl radical.
6 more elements
Dependencies are inferred from the claim text.