Synthesis of 1,3-olein-2-palmitin (OPO)

Patent metadata

Field	Value
Publication number	US-11261401-B2
Application number	US-201816637401-A
Country	US
Kind code	B2
Filing date	Jul 26, 2018
Priority date	Aug 11, 2017
Publication date	Mar 1, 2022
Grant date	Mar 1, 2022

Abstract

The present invention concerns a highly selective process for the preparation of an ingredient comprising 1,3-Olein-2-palmitin (OPO), a triglyceride present in human breast milk. The present invention also relates to 1,3-Olein-2-palmitin (OPO) ingredient obtainable by the process.

First claim

The invention claimed is:

1. A process for preparation of a 1,3-Olein-2-palmitin ingredient, the process comprising:
subjecting 2-oxopropane-1,3-diyl dioleate to a reduction reaction under an anhydrous condition in a solvent system comprising tetrahydrofurane and in the presence of sodium borohydride to yield 2-hydroxypropane-1,3-diyl dioleate;
partially removing and replacing the tetrahydrofurane with a solvent which is not miscible with water;
adding acidulated water to inactivate the sodium borohydrate to form an inactivated mixture;
separating an organic phase of the inactivated mixture;
evaporating the solvent to recover the 2-hydroxypropane-1,3-diyl dioleate; and
reacting the 2-hydroxypropane-1,3-diyl dioleate with palmitoyl chloride to yield the 1,3-Olein-2-palmitin.

2. The process according to claim 1 comprising:
reacting 1,3-dihydroxyacetone with oleic acid or oleoyl chloride to yield the 2-oxopropane-1,3-diyl dioleate.

3. The process according to claim 1 comprising reacting 1,3-dihydroxyacetone in chloroform with oleoyl chloride in the presence of 2,6-lutidine at a temperature ranging from 0° C. to 25° C. to yield the 2-oxopropane-1,3-diyl dioleate.

4. The process according to claim 1 , wherein the solvent system consists of the tetrahydrofurane.

5. The process according to claim 1 , wherein the solvent system is selected from the group consisting of the tetrahydrofurane, the tetrahydrofurane/MeOH, the tetrahydrofurane/EtOH, and the tetrahydrofurane/MeOH/EtOH.

6. The process according to claim 1 , wherein the reduction reaction is performed at a temperature lower than 25° C.

7. The process according to claim 1 comprising reacting 1,3-dihydroxyacetone in chloroform with oleoyl chloride in the presence of pyridine or a pyridine derivative at a temperature ranging from 0° C. to 25° C. to yield the 2-oxopropane-1,3-diyl dioleate.

8. A 1,3-Olein-2-palmitin ingredient comprising a palmitic acid content at sn-2 position greater than 70% of a total palmitic content and by having a weight ratio of 1,3-Olein-2-palmitin to 3-(Palmitoyloxy)-1,2-propanediyl (9Z,9′Z)bis(-9-octadecenoate) or to 1-(Palmitoyloxy)-2,3-propanediyl (9Z,9′Z)bis(-9-octadecenoate) equal or higher than 90:10.

9. The 1,3-Olein-2-palmitin ingredient according to claim 8 , wherein the palmitic acid content at sn-2 position is equal or greater than 75% of the total palmitic content.

10. The 1,3-Olein-2-palmitin ingredient according to claim 8 , wherein the weight ratio of the 1,3-Olein-2-palmitin to the 3-(Palmitoyloxy)-1,2-propanediyl (9Z,9′Z)bis(-9-octadecenoate) or to the 1-(Palmitoyloxy)-2,3-propanediyl (9Z,9′Z)bis(-9-octadecenoate) is equal or greater than 92:8.

11. The 1,3-Olein-2-palmitin ingredient according to claim 8 , wherein the weight ratio of the 1,3-Olein-2-palmitin to the 3-(Palmitoyloxy)-1,2-propanediyl (9Z,9′Z)bis(-9-octadecenoate), or to the 1-(Palmitoyloxy)-2,3-propanediyl (9Z,9′Z)bis(-9-octadecenoate) is equal or greater than 95:5.

12. The 1,3-Olein-2-palmitin ingredient according to claim 8 , wherein the weight ratio of the 1,3-Olein-2-palmitin to the 3-(Palmitoyloxy)-1,2-propanediyl (9Z,9′Z)bis(-9-octadecenoate) or to the 1-(Palmitoyloxy)-2,3-propanediyl (9Z,9′Z)bis(-9-octadecenoate) is equal or greater than 98:2.

13. The 1,3-Olein-2-palmitin ingredient according to claim 8 , wherein the palmitic acid content at sn-2 position is equal or greater than 80% of the total palmitic content.

Assignees

• Nestle Sa

Inventors

• Destaillats Frederic
• Giuffrida Francesca
• Patin Amaury

Classifications

• C07C29/132

  by reduction of an oxygen containing functional group · CPC title

• C11C3/003 Primary

  by esterification of fatty acids with alcohols (C11C3/02 takes precedence) · CPC title

• C07C29/136

  of >C=O containing groups, e.g. —COOH · CPC title

• C11C3/08

  with fatty acids · CPC title

• A23D9/02 Primary

  characterised by the production or working-up · CPC title