# US 7,612,214 B2 · Organic amine salts of glutamic acid derivatives and their application

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- Number: US 7,612,214 B2
- Document ID: US7612214B2
- Status: Granted
- Kind: B2
- Application number: 10/992,795
- Filed: 2004-11-22
- Published: 2005-06-23
- Granted: 2009-11-03
- Earliest claimed: 2003-11-21
- Assignees: Ajinomoto Co., Inc.
- Inventors: Yusuke Amino; Kazuko Hirasawa
- Web page: https://patentgrep.com/patent/US7612214B2

## CPC

- C07D 209/20: substituted additionally by nitrogen atoms, e.g. tryptophane
- A23L 27/31: {containing amino acids, nucleotides, peptides or derivatives}
- A23L 27/32: {containing dipeptides or derivatives}
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A23L: FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF (preservation thereof A23B)

## Abstract

The present invention provides an organic amine salt of monatin, or crystal form thereof, and its application as well as a method for resolving the stereoisomers of monatin by forming its salt. The present invention further provides a salt form of monatin that is useful as a sweetening agent or as the active ingredient of a sweetener. The present invention also provides a method for preparing a salt of a particular stereoisomer of monatin with an organic amine by utilizing the difference of crystallinity or solubility of the salt of the stereoisomer of monatin with the organic amine. The present invention also relates to a use of the salt in a method for preparing a metal salt of monatin in which the organic amine is replaced by a metal such as sodium, potassium, or the like.

## Claims

### Claim 1

A crystal form of an organic amine salt of (2R,4R)-monatin, wherein said organic amine is (R)-(−)-2-phenylglycinol, and which has PXRD peaks at diffraction angles 2θ±0.2° of 5.3°, 17.4°, 18.5°, 19.0° and 21.2°.

### Claim 2 (depends on 1)

The crystal form as claimed in claim 1, wherein said organic amine salt has a chemical purity of at least 95%.

### Claim 3 (depends on 1)

The crystal form as claimed in claim 1, wherein said organic amine salt has an optical purity of at least 95%.

### Claim 4

A crystal form of an organic amine salt of (2R,4R)-monatin, wherein said organic amine is L-valinol, and which has PXRD peaks at diffraction angles 2θ±0.2° of 5.7°, 9.0°, 17.3°, 19.8° and 20.8°.

### Claim 5 (depends on 4)

The crystal form as claimed in claim 4, wherein said organic amine salt has a chemical purity of at least 95%.

### Claim 6 (depends on 4)

The crystal form as claimed in claim 4, wherein said organic amine salt has an optical purity of at least 95%.

### Claim 7 (depends on 1)

The crystal form as claimed in claim 1, which has PXRD peaks at diffraction angles 2θ±0.2° of 5.3°, 17.4°, 17.7°, 18.5°, 19.0° and 21.2°.

### Claim 8 (depends on 1)

The crystal form as claimed in claim 1, which has PXRD peaks at diffraction angles 2θ±0.2° of 5.3°, 15.2°, 17.4°, 17.7°, 18.5°, 19.0° and 21.2°.

### Claim 9 (depends on 4)

The crystal form as claimed in claim 4, which has PXRD peaks at diffraction angles 2θ±0.2° of 5.7°, 9.0°, 17.3°, 19.8°, 20.1° and 20.8°.

### Claim 10 (depends on 4)

The crystal form as claimed in claim 4, which has PXRD peaks at diffraction angles 2θ0.2° of 5.7°, 9.0°, 14.9°, 17.3°, 19.8°, 20.1° and 20.8°.

### Claim 11

A crystal form of an organic amine salt of (2R,4S)-monatin, wherein said organic amine is (R)-(−)-2-phenylglycinol, and which has PXRD peaks at diffraction angles 2θ±0.2° of 5.6°, 18.1°, 18.5°, 19.1° and 22.3°.

### Claim 12 (depends on 11)

The crystal form as claimed in claim 11, wherein said organic amine salt has a chemical purity of at least 95%.

### Claim 13 (depends on 11)

The crystal form as claimed in claim 11, wherein said organic amine salt has an optical purity of at least 95%.

### Claim 14 (depends on 11)

The crystal form as claimed in claim 11, which has PXRD peaks at diffraction angles 2θ±0.2° of 5.6°, 15.1°, 18.1°, 18.5°, 19.1° and 22.3°.

### Claim 15 (depends on 11)

The crystal form as claimed in claim 11, which has PXRD peaks at diffraction angles 2θ±0.2° of 5.6°, 7.5°, 15.1°, 18.1°, 18.5°, 19.1° and 22.3°.

### Claim 16

A crystal form of an organic amine salt of (2R,4R)-monatin, wherein said organic amine is aspartame, and which has PXRD peaks at diffraction angles 2θ±0.2° of 17.9°, 19.2°, 21.3°, 23.9° and 27.8°.

### Claim 17 (depends on 16)

The crystal form as claimed in claim 16, which has PXRD peaks at diffraction angles 2θ±0.2° of 11.9°, 17.9°, 19.2°, 21.3°, 23.9° and 27.8°.

### Claim 18 (depends on 16)

The crystal form as claimed in claim 16, which has PXRD peaks at diffraction angles 2θ±0.2° of 6.0°, 11.9°, 17.9°, 19.2°, 21.3°, 23.9° and 27.8°.

### Claim 19 (depends on 16)

The crystal form as claimed in claim 16, wherein said organic amine salt has a chemical purity of at least 95%.

### Claim 20 (depends on 16)

The crystal form as claimed in claim 16, wherein said organic amine salt has an optical purity of at least 95%.