# US 11,306,054 B2 · Propanediol monoacetate mononitrate

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- Number: US 11,306,054 B2
- Document ID: US11306054B2
- Status: Granted
- Kind: B2
- Application number: 16/770,730
- Filed: 2018-12-11
- Published: 2021-06-03
- Granted: 2022-04-19
- Earliest claimed: 2017-12-13
- Assignees: Dsm IP Assets B.V.
- Applicants: Dsm IP Assets B.V.
- Inventors: Christine Mendrok-Edinger; Peter Riebel; Angela Wildermann
- Web page: https://patentgrep.com/patent/US11306054B2

## CPC

- C07C 203/04: having nitrate groups bound to acyclic carbon atoms
- A61K 8/40: containing nitrogen (quinones containing nitrogen A61K8/355)
- A61P 17/06: Antipsoriatics
- A61P 17/08: Antiseborrheics
- A61P 17/10: Anti-acne agents
- A61P 31/04: Antibacterial agents
- A61Q 17/005: {Antimicrobial preparations}
- A61Q 5/006: {Antidandruff preparations}
- A61Q 15/00: Anti-perspirants or body deodorants (deodorisation of air A61L9/00)
- A61Q 19/00: Preparations for care of the skin
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- 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)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61Q: SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS

## Abstract

The present invention relates to propanediol monoacetate mononitrate as well as the use thereof as antimicrobial agent, in particular for cosmetic applications.

## Claims

### Claim 1

Propanediol monoacetate mononitrate of formula (I)

### Claim 2

A method to improve preservation of a product by inhibiting microbial degradation thereof, wherein the method comprises adding an anti-microbial effective amount of 1,3-propanediol monoacetate mononitrate to the product.

### Claim 3

A method to maintain skin homeostasis and/or balance skin microbiome which comprises contacting the skin with an effective amount of 1,3-propanediol monoacetate mononitrate.

### Claim 4

A deodorant product which comprises 1,3-propanediol monoacetate mononitrate as a deodorant active compound.

### Claim 5

An anti-acne product which comprises 1,3-propanediol monoacetate mononitrate as an anti-acne agent.

### Claim 6

A method for treating skin conditions selected from the group consisting of Pityriasis versicolor, dandruff formation, seborrheic dermatitis, atopic dermatitis and psoriasis, wherein the method comprises applying to skin in need thereof an effective treatment amount of 1,3-propanediol monoacetate mononitrate.

### Claim 7

A cosmetic or pharmaceutical composition comprising 1,3-propanediol monoacetate mononitrate.

### Claim 8 (depends on 7)

The cosmetic or pharmaceutical composition according to claim 7, wherein the 1,3-propanediol monoacetate mononitrate is an antimicrobial agent.

### Claim 9 (depends on 7)

The cosmetic or pharmaceutical composition according to claim 7, wherein the 1,3-propanediol monoacetate mononitrate is an antifungal and/or antibacterial agent.

### Claim 10 (depends on 9)

The cosmetic or pharmaceutical composition according to claim 9, wherein the 1,3-propanediol monoacetate mononitrate is an agent that inhibits the growth of microbes selected from the group consisting of S. epidermis, C. xerosis, M. furfur, and P. acnes and mixtures thereof.

### Claim 11 (depends on 7)

The cosmetic or pharmaceutical composition according to claim 7, wherein the 1,3-propanediol monoacetate mononitrate is present in an amount of about 0.005 to 2 wt. %, based on the total weight of the composition.

### Claim 12 (depends on 7)

The cosmetic or pharmaceutical composition according to claim 7, wherein the 1,3-propanediol monoacetate mononitrate is present an amount of 0.01 to 1 wt. %, based on the total weight of the composition.

### Claim 13 (depends on 7)

The cosmetic or pharmaceutical composition according to claim 7, wherein the 1,3-propanediol monoacetate mononitrate is present in an amount of 0.05 to 0.75 wt. %, based on the total weight of the composition.

### Claim 14 (depends on 7)

The cosmetic or pharmaceutical composition according to claim 7, wherein the 1,3-propanediol monoacetate mononitrate is present in an amount of 0.1 to 0.5 wt. %, based on the total weight of the composition.

### Claim 15

A non-therapeutic method for killing and/or inhibiting growth of microbial cells, wherein the method comprises contacting the microbial cells with an effective amount of 1,3-propanediol monoacetate mononitrate.

### Claim 16 (depends on 15)

The method according to claim 15, wherein the microbial cells are fungal and/or bacterial cells.

### Claim 17

A process for preparing 1,3-propanediol monoacetate mononitrate, wherein the process comprises reacting 1,3-propandiol monoacetate with nitrosulfuric acid.

### Claim 18 (depends on 17)

The process according to claim 17, wherein the process is carried out in an inert organic solvent.