Flavoring with cyclic acetals of 2-methyl-2-pentenal

• US 4,159,347 A
• Filed: 09/05/1978
• Issued: 06/26/1979
• Est. Priority Date: 08/24/1977
• Status: Expired due to Term

• Current Assignee: International Flavors & Fragrances Incorporated
• Original Assignee: International Flavors & Fragrances Incorporated
• Inventors: Yoshida, Takao, Vock, Manfred H.
• Primary Examiner(s): Golian, Joseph M.
• Application Number:
  US05/939,911
• Time in Patent Office: 294 Days
• Field of Search: 426/3, 426/536
• US Class Current: 426/3
• CPC Class Codes: A23G 4/06 characterised by the composition containing organic or inorganic compounds
• CPC Class Codes: A23L 27/2052 having oxygen or sulfur as the only hetero atoms
• CPC Class Codes: A61K 8/4973 with oxygen as the only hetero atom
• CPC Class Codes: A61Q 11/00 Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
• CPC Class Codes: C07D 317/12 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms

Abstract

Processes and compositions are described for the use in foodstuff, chewing gum, toothpaste and medicinal product flavor and aroma augmenting, modifying, enhancing and imparting compositions and as foodstuff, chewing gum, toothpaste and medicinal product aroma imparting materials of cyclic acetals of 2-methyl-2-pentenal having the generic structure: ##STR1## wherein R represents either hydrogen or methyl and the wavy lines signify that the cyclic acetal moiety is in either a "cis" or "trans" configuration with respect to the ethyl moiety bonded to the ethylenic moiety of the molecule. Addition of one or more cyclic acetals of 2-methyl-2-pentenal to foodstuffs, chewing gums, toothpastes and/or medicinal products produces sweet, fruity, gooseberry, green, aniseed, licorice, floral and herbal aroma characteristics and sweet, fruity, gooseberry, green, spearmint-like, aniseed, licorice, floral and herbal flavor characteristics with albedo-like flavor nuances.

Claims

1. A process for augmenting or enhancing the flavor of a foodstuff comprising adding to said foodstuff from 0.5 parts per million up to about 100 parts per million based on the total weight of foodstuff of a compound having the structure:

##STR20## wherein R is selected from the group consisting of hydrogen and methyl and the wavy lines represent a "cis" or "trans" configuration with respect to the carbon-carbon double bond of the ethyl moiety with respect to the dioxolane moiety.

2. The process of claim 1 wherein in the compound added to said foodstuff, R is methyl.

3. A flavor formulation comprising (i) from about 0.1% up to about 15% by weight based on the total weight of said flavoring composition of a cyclic acetal of 2-methyl-2-pentenal having the structure:

##STR21## wherein R is selected from the group consisting of hydrogen and methyl and the wavy lines represent "cis" or "trans" configuration around the carbon-carbon double bond of said compound of the ethyl moiety with respect to the dioxolane moiety and (ii) the remainder of said composition being a material selected from the group consisting of;

Oil of Cubeb;

Phellandrene;

Oil of Coriander;

Clove Oil;

p1 Cardamon Oil;

Spearmint Oil;

Anethole;

Peppermint Oil;

Oil of Pimento leaf;

Oil of Patchouli;

Alpha-Pinene;

Beta-Pinene;

Beta-caryophyllene;

Dihydrocarveol;

Piperonal;

Piperine;

Chavicine;

Piperidine;

Oil of Black Pepper;

Black Pepper Oleoresin;

Capsicum; and

Oil of Nutmeg

4. The composition of claim 3 wherein R is methyl.

5. A chewing gum comprising a chewing gum base and added thereto the composition of claim 3.