Process for preparing sphingolipids

Patent metadata

Field	Value
Publication number	US-11939612-B2
Application number	US-202117497484-A
Country	US
Kind code	B2
Filing date	Oct 8, 2021
Priority date	Mar 29, 2018
Publication date	Mar 26, 2024
Grant date	Mar 26, 2024

Abstract

The invention provides a process for preparing sphingolipids, compositions comprising sphingolipids and further components, and for the use of the compositions.

First claim

The invention claimed is:

1. A cosmetic formulation comprising a composition, comprising:
A) at least one sphingolipid of the general formula I

B) at least one lysosphingolipid of the general formula II

C) at least one triglyceride of the general formula III

D) at least one diglyceride of the general formula IV

E) at least one monoglyceride of the general formula V

where
R 1 is the same or different and independently represents a linear or branched alkyl chain having 2 to 55 carbon atoms that optionally contains one or more multiple bonds and/or aromatic or heteroaromatic rings, is optionally interrupted by oxygen atoms or ester or amide functionalities and is optionally substituted by at least one further group selected from alkyl, hydroxyl, keto or amine groups,
R 2 is the same or different and independently represents H, phosphocholine, serine, ethanolamine or a sugar, and
X represents CH═CH, CH 2 —CH 2 or CH 2 —HCOH,
wherein based on the total composition, the components are present as follows:
A) 30% by weight to 98% by weight,
B) 0.01% by weight to 60% by weight,
C) 0.01% by weight to 60% by weight,
D) 0.1% by weight to 30% by weight,
E) 0.1% by weight to 30% by weight.

2. A cosmetic formulation comprising a composition comprising:
A) at least one sphingolipid of the general formula I

B) at least one lysosphingolipid of the general formula II

C) at least one triglyceride of the general formula III

D) at least one diglyceride of the general formula IV

E) at least one monoglyceride of the general formula V

where
R 1 is the same or different and independently represents a linear or branched alkyl chain having 2 to 55 carbon atoms that optionally contains one or more multiple bonds and/or aromatic or heteroaromatic rings, is optionally interrupted by oxygen atoms or ester or amide functionalities and is optionally substituted by at least one further group selected from alkyl, hydroxyl, keto or amine groups,
R 2 is the same or different and independently represents H, phosphocholine, serine, ethanolamine or a sugar, and
X represents CH═CH, CH 2 —CH 2 or CH 2 —HCOH,
wherein the components are present in the composition as follows:
A) 30 parts by weight to 98 parts by weight,
B) 0.01 part by weight to 60 parts by weight,
D) 0.1 part by weight to 30 parts by weight,
E) 0.1 part by weight to 30 parts by weight,
and, based on the overall composition,
C) 60% by weight to 98% by weight.

3. The formulation according to claim 1 , wherein
R 2 ═H and X═CH 2 —CH 2 and
R 1 is selected from the group consisting of cocyol radicals, palmitoyl radicals, oleyl radicals, linoleyl radicals, linolenyl radicals, ricinoyl radicals, stearyl radicals, erucyl radicals and polyunsaturated fatty acyl radicals.

4. The formulation according to claim 1 , wherein
R 2 is selected from the group consisting of sugar and H, and
X is CH 2 —CH 2
wherein based on the total composition, the components are present as follows:
A) 50% by weight to 90% by weight,
B) 0.01% by weight to 45% by weight,
C) 0.01% by weight to 45% by weight,
D) 0.1% by weight to 20% by weight,
E) 0.1% by weight to 20% by weight.

5. The formulation according to claim 1 , wherein
R 2 is H, and
X is CH 2 —CH 2
wherein based on the total composition, the components are present as follows:
A) 65% by weight to 85% by weight,
B) 0.5% by weight to 10% by weight,
C) 0.01% by weight to 10% by weight,
D) 2% by weight to 15% by weight, and
E) 2% by weight to 15% by weight.

6. The formulation according to claim 2 , wherein
R 2 ═H and X═CH 2 —CH 2 and
R 1 is selected from the group consisting of cocyol radicals, palmitoyl radicals, oleyl radicals, linoleyl radicals, linolenyl radicals, ricinoyl radicals, stearyl radicals, erucyl radicals and polyunsaturated fatty acyl radicals.

7. The formulation according to claim 2 , wherein
R 2 is selected from the group consisting of sugar and H, and
X is CH 2 —CH 2 —
wherein based on the total composition, the components are present as follows:
A) 50% by weight to 90% by weight,
B) 0.01% by weight to 45% by weight,
C) 0.01% by weight to 45% by weight,
D) 0.1% by weight to 20% by weight,
E) 0.1% by weight to 20% by weight.

8. The formulation according to claim 2 , wherein
R 2 is H, and
X is CH 2 —CH 2
wherein based on the total composition, the components are present as follows:
A) 65% by weight to 85% by weight,
B) 0.5% by weight to 10% by weight,
C) 0.01% by weight to 10% by weight,
D) 2% by weight to 15% by weight, and
E) 2% by weight to 15% by weight.

9. The formulation according to claim 1 , wherein the at least one sphingolipid of the general formula I is formed by reaction of
a sphinganine of the general formula II,

wherein
R 2 =H and X=CH 2 -CH 2 ,

with
a second component selected from the group consisting of olive oil, castor oil, rapeseed oil, sesame oil, palm kernel oil, palm oil, almond oil, sorbitan monooleate, sorbitan monolaurate, sorbitan trioleate, soya oil, glycol distearate, and cetyltriglyceride.

Assignees

• Evonik Operations Gmbh

Inventors

• Eckstein Marrit Friederike
• Van Logchem Monica Desiree
• Wenk Hans Henning
• Schrader Annika
• Maczkiewitz Ursula
• Hierath Claudia
• Karacocuk Sunay
• Seifert Andreas

Classifications

• C12P13/02 Primary

  Amides, e.g. chloramphenicol {or polyamides; Imides or polyimides; Urethanes, i.e. compounds comprising N-C=O structural element or polyurethanes (peptides C12P21/00 or C07K)} · CPC title

• A61K8/68

  Sphingolipids, e.g. ceramides, cerebrosides, gangliosides · CPC title

• A61K8/92

  Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof · CPC title

• C07H15/00

  Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals · CPC title

• A61Q5/12

  Preparations containing hair conditioners · CPC title