US4211242A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Composition of matter comprising more than 50% trans, trans-Δ-damascone for augmenting or enhancing the aroma and taste of a smoking tobacco
Assignee: International Flavors and Fragrances Inc
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Filing: 1977-11-15
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Granted: 1980-07-08
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Expires: 1997-11-15
Abstract
Abstract Described is a process for augmenting or enhancing the aroma and taste of a smoking tobacco comprising adding to said smoking tobacco an organoleptic property modifying quantity of a composition of matter comprising more than 50% trans,trans-Δ-damascone and in addition a process for augmenting or enhancing the aroma and taste of a smoking tobacco comprising adding to said smoking tobacco in an organoleptic property modifying quantity a product produced according to the process of (i) reacting 1-alpha-acetyl-2-alpha,6,6-trimethyl-3-cyclohexene with strong base in aqueous ethanol at reflux thereby producing 1-alpha-acetyl-2-beta,6,6-trimethyl-3-cyclohexene; (ii) reacting the 1-alpha-acetyl-2-beta,6,6-trimethyl-3-cyclohexene with n-methyl aniline Grignard thereby forming a first organometallic compound; (iii) reacting said first organometallic compound with acetaldehyde thereby forming a second organometallic compound; (iv) reacting said second organometallic compound with acid in order to hydrolyze said second organometallic compound thereby forming a hydroxy ketone having the structure: ##STR1## in admixture with other compounds; (v) dehydrating said hydroxy ketone in admixture with other compounds thereby forming a mixture having a major proportion of trans, trans-Δ-damascone having the structure: ##STR2## in admixture with cis, trans-Δ-damascone having the structure: ##STR3## and in admixture with other compounds; and in addition smoking tobacco products containing same.
Inventors
- 👤 Braja D. Mookherjee
- 👤 Robert W. Trenkle
- 👤 Richard A. Wilson
- 👤 Frederick L. Schmitt
- 👤 Manfred H. Vock
- 👤 Edward J. Granda
- 👤 Joacquin Vinals
- 👤 Jacob Kiwala
- 👤 William L. Schreiber
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 01:36
CPC Classifications
C; C11; C11D; C11D3/00; C11D3/0005; C11D3/0084; A; A24; A24B; A24B15/00; A24B15/18; A24B15/28; A24B15/30; A24B15/34; C07; C07C; C07C403/00; C07C403/14; C07C403/16; C07C45/00; C07C45/61; C07C45/67; C07C45/68; C07C45/69; C07C45/72; C07C49/00; C07C49/527; C07C49/543; C07C49/573; C11B; C11B9/00; C11B9/0026; C11B9/0034; C07B; C07B2200/00; C07B2200/09; C07C2601/00; C07C2601/12; C07C2601/16
Claims Analysis
Total Claims: 9
Claim 1
Independent Claim
51 words
A process for augmenting or enhancing the aroma and taste of a smoking tobacco comprising adding to said tobacco an organoloptic property modifying quantity of a composition of matter consisting essentially of 80 to 85 percent of a synthetically produced trans, trans-Δ-damascone and 20-15 percent of a synthetically produced cis, trans-Δ-damascone.
Claim 2
Dependent Claim
51 words
A process for augmenting or enhancing the aroma and taste of a smoking tobacco comprising adding to said tobacco an organoloptic property modifying quantity of a composition of matter consisting essentially of 80 to 85 percent of a synthetically produced trans, trans-Δ-damascone and 20-15 percent of a synthetically produced cis, trans-Δ-damascone.
Claim 3
Dependent Claim
170 words
A process for augmenting or enhancing the aroma and taste of a smoking tobacco comprising adding to said smoking tobacco in an organoleptic property modifying quantity, a product produced according to the process of (i) reacting 1-α-acetyl-2-α, 6,6-trimethyl-3-cyclohexene with strong base in aqueous ethanol at reflux thereby producing 1-α-acetyl-2-β, 6,6-trimethyl-3-cyclohexene; (ii) reacting the 1-α-acetyl-2-β, 6,6-trimethyl-3-cyclohexene with n-methyl aniline Grignard thereby forming a first organometallic compound; (iii) reacting said first organometallic compound with acetaldehyde thereby forming a second organometallic compound; (iv) reacting said second organometallic compound with acid in order to hydrolyze said second organometallic compound thereby forming a hydroxy ketone having the structure: ##STR29## in admixture with other compounds; (v) dehydrating said hydroxy ketone in admixture with other compounds thereby forming a mixture having a major proportion of trans, trans-Δ-damascone having the structure: ##STR30## in admixture with cis, trans-Δ-damascone having the structure: ##STR31## and in admixture with other compounds wherein said mixture contains 80 to 85 percent of the trans, trans-Δ-damascone and 20 to 15 percent of the cis, trans-Δ-damascone.
Claim 4
Dependent Claim
170 words
A process for augmenting or enhancing the aroma and taste of a smoking tobacco comprising adding to said smoking tobacco in an organoleptic property modifying quantity, a product produced according to the process of (i) reacting 1-α-acetyl-2-α, 6,6-trimethyl-3-cyclohexene with strong base in aqueous ethanol at reflux thereby producing 1-α-acetyl-2-β, 6,6-trimethyl-3-cyclohexene; (ii) reacting the 1-α-acetyl-2-β, 6,6-trimethyl-3-cyclohexene with n-methyl aniline Grignard thereby forming a first organometallic compound; (iii) reacting said first organometallic compound with acetaldehyde thereby forming a second organometallic compound; (iv) reacting said second organometallic compound with acid in order to hydrolyze said second organometallic compound thereby forming a hydroxy ketone having the structure: ##STR29## in admixture with other compounds; (v) dehydrating said hydroxy ketone in admixture with other compounds thereby forming a mixture having a major proportion of trans, trans-Δ-damascone having the structure: ##STR30## in admixture with cis, trans-Δ-damascone having the structure: ##STR31## and in admixture with other compounds wherein said mixture contains 80 to 85 percent of the trans, trans-Δ-damascone and 20 to 15 percent of the cis, trans-Δ-damascone.
Claim 5
Dependent Claim
54 words
A smoking tobacco product comprising (i) smoking tobacco and (ii) intimately mixed with said smoking tobacco a composition suitable for augmenting or enhancing the organoleptic properties of said smoking tobacco which composition consists essentially of 80 to 85 percent of a synthetically produced trans, trans-Δ-damascone and 20-15 percent of a synthetically produced cis, trans-Δ-damascone.
Claim 6
Dependent Claim
54 words
A smoking tobacco product comprising (i) smoking tobacco and (ii) intimately mixed with said smoking tobacco a composition suitable for augmenting or enhancing the organoleptic properties of said smoking tobacco which composition consists essentially of 80 to 85 percent of a synthetically produced trans, trans-Δ-damascone and 20-15 percent of a synthetically produced cis, trans-Δ-damascone.
Claim 7
Dependent Claim
29 words
The composition of claim 3 wherein the composition containing said synthetically produced trans, trans-Δ-damascone is added to the smoking tobacco in an amount between 250 ppm and 1,500 ppm.
Claim 8
Dependent Claim
38 words
A process of augmenting or enhancing the aroma and taste of a smoking tobacco comprising adding to said tobacco an organoleptic property modifying quantity of a composition matter consisting essentially of a substantially pure synthetically produced trans, trans-Δ-damascone.
Claim 9
Dependent Claim
38 words
A process of augmenting or enhancing the aroma and taste of a smoking tobacco comprising adding to said tobacco an organoleptic property modifying quantity of a composition matter consisting essentially of a substantially pure synthetically produced trans, trans-Δ-damascone.
References Cited (Backward Citations)
US3887625A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-07-08 | 1984-01-07 | 1984-07-08 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-07-08 | 1988-01-07 | 1988-07-08 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-07-08 | 1992-01-07 | 1992-07-08 | $7700.00 | Window Closed / Lapsed |