Ethyl 3-mercaptobutyrate as a flavoring or fragrance agent and methods for preparing and using same

• US 20020150662A1
• Filed: 12/04/2001
• Published: 10/17/2002
• Est. Priority Date: 04/19/2000
• Status: Abandoned Application

• Current Assignee: Bush Boake Allen, Inc. (International Flavors & Fragrances Incorporated)
• Original Assignee: Bush Boake Allen, Inc. (International Flavors & Fragrances Incorporated)
• Inventors: Dewis, Mark Lawrence, Edwards, David John, Kendrick, Lesley, Wright, Maria
• Application Number:
  US10/007,095
• Publication Number:
  US 20020150662A1
• Time in Patent Office: Days
• US Class Current: 426/534
• CPC Class Codes: A23G 3/36 characterised by the composition containing organic or inorganic compounds
• CPC Class Codes: A23G 3/48 containing plants or parts thereof, e.g. fruits, seeds, extracts containing gums A23G3/42
• CPC Class Codes: A23G 4/06 characterised by the composition containing organic or inorganic compounds
• CPC Class Codes: A23G 4/068 containing plants or parts thereof, e.g. fruits, seeds, extracts containing gums A23G4/10
• CPC Class Codes: A23L 27/2022 containing sulfur
• CPC Class Codes: A23L 27/29 Fruit flavours
• CPC Class Codes: C11B 9/0011 containing S

Abstract

This invention pertains to a method for flavoring an ingestible composition with a flavoring agent in organoleptically purified form, unaccompanied by substances of natural origin present in mango. The flavoring agent may be used in a wide variety of ingestible vehicles such as chewing gum compositions, hard and soft confections, dairy products, beverage products including juice drinks and juice products, green vegetable and chicken products, and the like. The present invention also pertains to an ingestible composition comprising an ingestible vehicle and an organoleptically effective amount of the purified flavoring agent. The present invention further pertains to ethyl 3-mercaptobutyrate represented by the formula, CH₃(SH)CHCH₂COOCH₂CH₃, in purified form, unaccompanied by substances of natural origin present in mango. The present invention still further pertains to a method to confer, enhance, improve, or modify the odor properties of a perfuming composition or a perfumed article, which comprises adding to the perfuming composition or perfumed article, ethyl 3-mercaptobutyrate represented by the formula, CH₃(SH)CHCH₂COOCH₂CH₃. The present invention still further pertains to a perfuming composition or a perfumed article containing as an active perfuming ingredient, ethyl 3-mercaptobutyrate represented by the formula, CH₃(SH)CHCH₂COOCH₂CH₃. The present invention also pertains to a method for preparing ethyl 3-mercaptobutyrate which comprises reacting ethyl crotonate with sodium hydrogen sulfide and sodium bicarbonate to form the disulfide dimer of ethyl 3-mercaptobutyrate followed by reducing the disulfide dimer to yield ethyl 3-mercaptobutyrate.

Claims

1. A method for flavoring an ingestible composition which comprises admixing an ingestible vehicle with an organoleptically effective amount of ethyl 3-mercaptobutyrate represented by the formula, CH₃(SH)CHCH₂COOCH₂CH₃, in purified form, unaccompanied by substances of natural origin present in mango.

2. The method according to claim 1, wherein ethyl 3-mercaptobutyrate is present in the ingestible composition in an amount from about 0.001% to about 1%, by weight.

3. The method according to claim 2, wherein ethyl 3-mercaptobutyrate is present in the ingestible composition in an amount from about 0.1% to about 0.50%, by weight.

4. The method according to claim 1, wherein the ingestible composition is a beverage product.

5. The method according to claim 1, wherein the ingestible composition is a confectionery composition.

6. The method according to claim 1, wherein the ingestible composition is a chewing gum.

7. An ingestible composition comprising:

(i) an ingestible vehicle; and

(ii) an organoleptically effective amount of ethyl 3-mercaptobutyrate represented by the formula, CH₃(SH)CHCH₂COOCH₂CH₃, in purified form, unaccompanied by substances of natural origin present in mango.

8. The ingestible composition according to claim 7, wherein ethyl 3-mercaptobutyrate is present in the ingestible composition in an amount from about 0.001% to about 1%, by weight.

9. The ingestible composition according to claim 8, wherein ethyl 3-mercaptobutyrate is present in the ingestible composition in an amount from about 0.1% to about 0.50%, by weight.

10. The ingestible composition according to claim 7, wherein the ingestible composition is a beverage product.

11. The ingestible composition according to claim 7, wherein the ingestible composition is a confectionery composition.

12. The ingestible composition according to claim 7, wherein the ingestible composition is a chewing gum.

15. The method according to claim 14, wherein ethyl 3-mercaptobutyrate is present in the perfuming composition or perfumed article in an amount from about 0.001% to about 1%, by weight.

16. The method according to claim 15, wherein ethyl 3-mercaptobutyrate is present in the perfuming composition or perfumed article in an amount from about 0.1% to about 0.50%, by weight.

18. The perfumed article according to claim 17, in the form of a perfume or a cologne, a soap, a bath or shower gel, a shampoo or other hair care product, a body deodorant, an air freshener, a detergent or fabric softener, or a household cleaner.

13. Ethyl 3-mercaptobutyrate represented by the formula, CH₃(SH)CHCH₂COOCH₂CH₃, in purified form, unaccompanied by substances of natural origin present in mango.

14. A method to confer, enhance, improve, or modify the odor properties of a perfuming composition or a perfumed article, which comprises adding to the perfuming composition or perfumed article, ethyl 3-mercaptobutyrate represented by the formula, CH₃(SH)CHCH₂COOCH₂CH₃.

17. A perfuming composition or a perfumed article containing as an active perfuming ingredient, ethyl 3-mercaptobutyrate represented by the formula, CH₃(SH)CHCH₂COOCH₂CH₃.

19. A method for preparing ethyl 3-mercaptobutyrate which comprises reacting ethyl crotonate with sodium hydrogen sulfide and sodium bicarbonate to form the disulfide dimer of ethyl 3-mercaptobutyrate followed by reducing the disulfide dimer of ethyl 3-mercaptobutyrate to yield ethyl 3-mercaptobutyrate.