# US 12,005,095 B2 · Eutectic extraction solvents, extraction methods by eutectigenesis using said solvents, and extracts derived from said extraction methods

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- Number: US 12,005,095 B2
- Document ID: US12005095B2
- Status: Granted
- Kind: B2
- Application number: 17/177,016
- Filed: 2021-02-16
- Published: 2021-07-08
- Granted: 2024-06-11
- Earliest claimed: 2015-04-10
- Assignees: Givaudan France Naturals SAS; Avignon Université
- Applicants: Givaudan France Naturals SAS; Avignon Université
- Inventors: Alexis Lavaud; Michael Laguerre; Simona Birtic; Anne Sylvie Fabiano Tixier; Marc Roller; Farid Chemat; Antoine Charles Bily
- Web page: https://patentgrep.com/patent/US12005095B2

## CPC

- A61K 36/736: Prunus, e.g. plum, cherry, peach, apricot or almond
- A23L 33/105: Plant extracts, their artificial duplicates or their derivatives
- A61K 36/11: Pteridophyta or Filicophyta (ferns)
- A61K 36/23: Apiaceae or Umbelliferae (Carrot family), e.g. dill, chervil, coriander or cumin
- A61K 36/31: Brassicaceae or Cruciferae (Mustard family), e.g. broccoli, cabbage or kohlrabi
- A61K 36/53: Lamiaceae or Labiatae (Mint family), e.g. thyme, rosemary or lavender
- A61K 36/63: Oleaceae (Olive family), e.g. jasmine, lilac or ash tree
- A61K 36/88: Liliopsida (monocotyledons)
- A61P 17/16: Emollients or protectives, e.g. against radiation
- A61P 17/18: Antioxidants, e.g. antiradicals (preparations for protection against sunlight A61Q17/00)
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P 39/06: Free radical scavengers or antioxidants
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- B01D 11/02: of solids
- B01D 11/0288: {Applications, solvents}
- A61K 2236/331: using water, e.g. cold water, infusion, tea, steam distillation or decoction
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A23L: FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF (preservation thereof A23B)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- B01D: SEPARATION (separating solids from solids by wet methods B03B, B03D; by pneumatic jigs or tables B03B; by other dry methods B07; magnetic or electrostatic separation of solid materials from solid materials or fluids, separation by high-voltage electric fields B03C; centrifuges, vortex apparatus B04; presses per se for squeezing-out liquid from liquid-containing material B30B9/02; treatment of water C02F, e.g. softening by ion-exchange C02F1/42; {arrangements of air intake cleaners in gas turbine plants F02C7/05} ; arrangements or mounting of filters in air-conditioning, air-humidification or ventilation F24F13/28)

## 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

### Claim 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.

### Claim 2 (depends on 1)

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.

### Claim 3 (depends on 2)

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.

### Claim 4 (depends on 1)

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.

### Claim 5 (depends on 1)

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

### Claim 6 (depends on 1)

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

### Claim 7 (depends on 1)

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.

### Claim 8 (depends on 7)

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.

### Claim 9 (depends on 8)

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

### Claim 10 (depends on 7)

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

### Claim 11 (depends on 10)

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.

### Claim 12 (depends on 10)

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.

### Claim 13 (depends on 12)

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

### Claim 14 (depends on 12)

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

### Claim 15 (depends on 10)

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

### Claim 16 (depends on 15)

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.

### Claim 17 (depends on 10)

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

### Claim 18 (depends on 17)

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.

### Claim 19 (depends on 7)

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.