# US 10,865,334 B2 · Process for extracting materials from biological material

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- Number: US 10,865,334 B2
- Document ID: US10865334B2
- Status: Granted
- Kind: B2
- Application number: 14/451,845
- Filed: 2014-08-05
- Published: 2014-11-20
- Granted: 2020-12-15
- Earliest claimed: 2010-06-07
- Assignees: Universiteit Leiden
- Applicants: Universiteit Leiden
- Inventors: Jacob van Spronsen; Geert-Jan Witkamp; Frank Hollman; Young Hae Choi; Robert Verpoorte
- Web page: https://patentgrep.com/patent/US10865334B2

## CPC

- C09K 3/00: Materials not provided for elsewhere
- B01D 11/0288: {Applications, solvents}
- B01D 11/04: of solutions which are liquid
- C07D 311/62: with oxygen atoms directly attached in position 3, e.g. anthocyanidins
- C07H 17/07: Benzo[b]pyran-4-ones
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- 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)
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07H: SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS (derivatives of aldonic or saccharic acids C07C, C07D; aldonic acids, saccharic acids C07C59/105, C07C59/285; cyanohydrins C07C255/16; glycals C07D; compounds of unknown constitution C07G; polysaccharides, derivatives thereof C08B; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; sugar industry C13)

## Abstract

The invention is directed to a process for extracting materials from biological material, which process is characterized in that the naturally occurring biological material is treated with an extractant consisting of a deep eutectic solvent of natural origin or a an ionic liquid of natural origin to produce a biological extract of natural origin dissolved in the said solvent or ionic liquid.

## Claims

### Claim 1

A process for extracting materials from a biological material, comprising:
treating the biological material with an extractant comprising a deep eutectic solvent to produce a biological extract dissolved in said extractant, wherein the deep eutectic solvent comprises a first component and a second component, wherein the first component consists of at least one naturally occurring organic acid; and wherein the second component is selected from the group consisting of (i) at least one mono- or dimeric sugar or sugar alcohol selected from the group consisting of sucrose, glucose, fructose, lactose, maltose, galactose, raffinose, xylose, mannose, trehalose, sorbitol, erythritol, rhamnose, inositol, xylitol, ribitol, and adonitol, (ii) an amino acid selected from the group consisting of alanine, glutamic acid, glutamate, proline and serine, or (iii) 1,2-propanediol, or wherein the deep eutectic solvent comprises at least two sugars selected from the group consisting of glucose, fructose, sucrose and lactose; or wherein the deep eutectic solvent comprises (i) choline or betaine and (ii) said first component or said second component; and wherein the molar ratio of the components of the deep eutectic solvent is between 1:1 and 5:1; wherein the biological extract comprises a flavonoid or an anthocyanin; and wherein said biological material originates from a source selected from the group consisting of plants, insects, animals, and micro-organisms.

### Claim 2 (depends on 1)

The process of claim 1, wherein the said naturally occurring organic acid is selected from the group consisting of: malic acid, maleic acid, citric acid, lactic acid, pyruvic acid, fumaric acid, succinic acid, acetic acid, aconitic acid, tartaric acid, ascorbic acid, malonic acid, oxalic acid, glucuronic acid, neuraminic acid and sialic acids.

### Claim 3 (depends on 1)

The process of claim 1, wherein the deep eutectic solvent further comprises water.

### Claim 4 (depends on 1)

The process of claim 1, wherein the deep eutectic solvent has a melting point below 25° C.

### Claim 5 (depends on 1)

The process of claim 1, wherein the biological extract is recovered from said deep eutectic solvent.

### Claim 6 (depends on 1)

The process of claim 1, wherein the deep eutectic solvent is selected from the group consisting of malic acid:β-alanine:water (1:1:3), proline:malic acid:water (1:1:3), fructose:glucose:sucrose:water (1:1:1:11), fructose:glucose:malic acid (1:1:1) and lactose:glucose:water (5:1:2).

### Claim 7 (depends on 1)

The process of claim 1, wherein the flavonoid is rutin, quercetin or quercitrin.

### Claim 8

A process for extracting materials from a biological material, comprising:
treating the biological material with an extractant consisting of a deep eutectic solvent to produce a biological extract dissolved in said extractant, wherein the deep eutectic solvent comprises (i) alanine and malic acid, (ii) fructose and sucrose, (iii) fructose and glucose, (iv) proline and sucrose, (v) malic acid and glucose, (vi) malic acid and sucrose, (vii) citric acid and sucrose, (viii) lactose and glucose or (ix) glucose and; wherein the molar ratio of the components of the deep eutectic solvent is between 1:1 and 5:1; wherein the biological extract comprises galanthamine or paclitaxel; and wherein said biological material originates from a source selected from the group consisting of plants, insects, animals and micro-organisms.