IP Library Granted Patent US 12,005,095
Granted Patent B2
US 12,005,095 · App. 17/177,016 · Granted Jun 11, 2024

Eutectic extraction solvents, extraction methods by eutectigenesis using said solvents, and extracts derived from said extraction methods

Inventors: Alexis Lavaud (Sorgues, FR); Michael Laguerre (Montfavet, FR); Simona Birtic (Cavaillon, FR); Anne Sylvie Fabiano Tixier (Rochefort du Gard, FR); Marc Roller (Morieres les Avignon, FR); Farid Chemat (Morieres les Avignon, FR); Antoine Charles Bily (Vedene, FR)
Assignees: Givaudan France Naturals SAS; AVIGNON UNIVERSITÉ
A61K36/736A23L33/105A61K36/11A61K36/23A61K36/31A61K36/53A61K36/63A61K36/88B01D11/02B01D11/0288A61K2236/331
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Quick Facts
Patent No.
US 12,005,095
App. No.
17/177,016
Granted
Jun 11, 2024
Kind
B2
Abstract

A eutectic extraction solvent for extracting plant (e.g. vegetable) and/or animal and/or prokaryotic biological material, wherein the solvent is a clear, stable and fluid mixture comprising: (a) betaine or a hydrated form of betaine; (b) at least one hydrogen bond donor compound selected from the group consisting of polyols and organic acids; and (c) water with the proviso that the eutectic extraction solvent does not contain any exogenous sugar and/or amine salt and/or anion.

Claims (27)

1. A eutectic extraction solvent for extracting plant biological material, wherein the eutectic extraction solvent is a clear, stable and fluid mixture comprising:

(a) betaine (trimethyl glycine) or a hydrated form of betaine;

(b) at least one hydrogen bond donor compound selected from the group consisting of polyols and organic acids; and

(c) water;

wherein the ratio of betaine or a hydrated form of betaine to the at least one hydrogen bond donor is from 1:1.5 to 1:3 and the proportion of water added to the mixture is from 15 to 30% by weight;

with the proviso that the eutectic extraction solvent does not contain any one or more of exogenous sugar, exogenous amine salt, or exogenous anion.

2. The eutectic extraction solvent according to claim 1 , wherein the polyols are selected from the group consisting of glycerol, erythritol, mannitol, sorbitol, ethylene glycol, propylene glycol, ribitol, aldonitol, propanediol, and pentylene glycol.

3. The eutectic extraction solvent according to claim 2 , wherein the organic acids are selected from the group consisting of lactic acid, malic acid, maleic acid, pyruvic acid, fumaric acid, succinic acid, citric acid, acetic acid, aconitic acid, tartric acid, ascorbic acid, malonic acid, oxalic acid, glucuronic acid, neuraminic acid, sialic acid, shikimic acid, phytic acid, galacturonic acid, iduronic acid, hyaluronic acid, hydroxycitric acid, and lactone derivatives.

4. The eutectic extraction solvent according to claim 1 , wherein the organic acids are selected from the group consisting of lactic acid, malic acid, maleic acid, pyruvic acid, fumaric acid, succinic acid, citric acid, acetic acid, aconitic acid, tartric acid, ascorbic acid, malonic acid, oxalic acid, glucuronic acid, neuraminic acid, sialic acid, shikimic acid, phytic acid, galacturonic acid, iduronic acid, hyaluronic acid, hydroxycitric acid, and lactone derivatives.

5. The eutectic extraction solvent according to claim 1 , wherein the polyol is propylene glycol, propanediol, or pentylene glycol.

6. The eutectic extraction solvent according to claim 1 , wherein the organic acid is lactic acid.

7. A method for extracting natural biological compounds from plant biological material, wherein the method comprises the following steps:

a. immersing, while stirring, a ground or unground biological material in a eutectic extraction solvent as defined in claim 1 , then

b. macerating or percolating or infusing the mixture obtained in step a. at a temperature between 20 and 60° C.; then

c. filtering the extraction product obtained at step b., thereby obtaining a natural biological liquid extract derived from the plant biological material.

8. The method according to claim 7 , wherein the plant biological material is selected from the group consisting of cherry blossom, horsetail, plantain, saffron flowers, chrismum, rose of Jerico, rosemary, Selaginella pulvinata, Tillandsia usnoides and olive leaves.

9. A natural biological liquid extract comprising plant biological material obtained by the extraction method according to claim 8 .

10. The natural biological liquid extract comprising plant biological material obtained by the extraction method according to claim 7 .

11. The liquid extract according to claim 10 , wherein the eutectic extraction solvent is present in the liquid extract in an amount of from about 0.01 to about 50% by weight, or from about 0.1 to about 25% by weight.

12. The liquid extract according to claim 10 , wherein the liquid extract comprises biological compounds extracted from plant biological material selected from the group consisting of cherry blossom, horsetail, plantain, saffron flowers, chrismum, rose of Jerico, rosemary, olive leaves, Selaginella pulvinata and Tillandsia usnoides.

13. A natural biological liquid extract derived from cherry blossom according to claim 12 .

14. A pharmaceutical composition comprising a liquid extract according to claim 12 .

15. A pharmaceutical composition comprising a liquid extract according to claim 10 .

16. The pharmaceutical composition according to claim 15 , wherein the composition is suitable for oral or parenteral administration, or for topical, rectal, nasal, auricular, vaginal and/or ocular application.

17. The liquid extract according to claim 10 , wherein liquid extraction comprises the eutectic extraction solvent.

18. The liquid extract according to claim 17 , wherein the eutectic extraction solvent is present in the liquid extract in an amount of from about 0.1 to about 25% by weight.

19. The method according to claim 7 , wherein the extraction product obtained at step c. comprises one or more biological compounds selected from the group of phenolic compounds including phenolic acids and esters, flavonoids, secoiridoids, stilbenes and phenolic alcohols, antioxidants, carotenoids, alkaloids, lipids, phenylpropanoids, flavourings and taste modifiers, fragrances, biocides, antimicrobials, proteins, enzymes, colourings, pigments, surfactants and terpenoids including saponins.

Assignments (6)
CHANGE OF NAME Recorded Aug 16, 2023
From: NATUREX SA
To: GIVAUDAN FRANCE NATURALS SAS
Reel/Frame 064615/0626 →
CHANGE OF NAME Recorded Jun 6, 2023
From: NATUREX
To: NATUREX SA
Reel/Frame 063875/0077 →
CHANGE OF NAME Recorded Jul 6, 2022
From: UNIVERSITE D'AVIGNON ET DES PAYS DE VAUCLUSE
To: AVIGNON UNIVERSITÉ
Reel/Frame 060612/0973 →
CORRECTIVE ASSIGNMENT TO CORRECT THE APPLICATION NUMBER FROM 17/177,106 TO 17/177,016 PREVIOUSLY RECORDED AT REEL: 056587 FRAME: 0187. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Jul 14, 2021
From: FABIANO TIXIER, ANNE SYLVIE; CHEMAT, FARID
To: UNIVERSITE D'AVIGNON ET DES PAYS DE VAUCLUSE
Reel/Frame 056862/0743 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 14, 2021
From: LAVAUD, ALEXIS; LAGUERRE, MICHAEL; BIRTIC, SIMONA; ROLLER, MARC; BILY, ANTOINE CHARLES
To: NATUREX
Reel/Frame 056587/0138 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 14, 2021
From: FABIANO TIXIER, ANNE SYLVIE; CHEMAT, FARID
To: UNIVERSITE D'AVIGNON ET DES PAYS DE VAUCLUSE
Reel/Frame 056587/0187 →
Priority Claims (2)
FR 1553092 · Apr 10, 2015 · national
FR 1562033 · Dec 8, 2015 · national
Continuity (2)
Continuation 15564985
Related Publication 20210205394A1 · Jul 8, 2021