CA1212224A - Tobacco musk compounds - Google Patents
Tobacco musk compoundsInfo
- Publication number
- CA1212224A CA1212224A CA000431638A CA431638A CA1212224A CA 1212224 A CA1212224 A CA 1212224A CA 000431638 A CA000431638 A CA 000431638A CA 431638 A CA431638 A CA 431638A CA 1212224 A CA1212224 A CA 1212224A
- Authority
- CA
- Canada
- Prior art keywords
- tobacco
- per million
- flavor
- parts per
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
- A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
- A24B15/18—Treatment of tobacco products or tobacco substitutes
- A24B15/28—Treatment of tobacco products or tobacco substitutes by chemical substances
- A24B15/30—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances
- A24B15/34—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a carbocyclic ring other than a six-membered aromatic ring
-
- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
- A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
- A24B15/18—Treatment of tobacco products or tobacco substitutes
- A24B15/28—Treatment of tobacco products or tobacco substitutes by chemical substances
- A24B15/30—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances
- A24B15/36—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring
- A24B15/40—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring having only oxygen or sulfur as hetero atoms
- A24B15/403—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring having only oxygen or sulfur as hetero atoms having only oxygen as hetero atoms
Landscapes
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Manufacture Of Tobacco Products (AREA)
Abstract
UNITED STATES PATENT APPLICATION
OF
ANDREW MCMURTRIE
EZRA D. ALFORD
THOMAS J. CRAVOTTA
FOR
TOBACCO MUSK COMPOUNDS
ABSTRACT OF THE DISCLOSURE
An improved tobacco product composition including macrocyclic musk compounds selected from the groups consisting of cyclohexadecen-7-olide, cyclopentadecanolide, 3-methylcyclopentadecanone, cycloheptadecen-9-one or cyclopertadecanone to provide enhanced aroma and flavor and a method for producing the same.
OF
ANDREW MCMURTRIE
EZRA D. ALFORD
THOMAS J. CRAVOTTA
FOR
TOBACCO MUSK COMPOUNDS
ABSTRACT OF THE DISCLOSURE
An improved tobacco product composition including macrocyclic musk compounds selected from the groups consisting of cyclohexadecen-7-olide, cyclopentadecanolide, 3-methylcyclopentadecanone, cycloheptadecen-9-one or cyclopertadecanone to provide enhanced aroma and flavor and a method for producing the same.
Description
SLY
¦ BACKGROUND OF THY INVENTION
The present invention relates to novel tobacco products, foreign copyist and processes for producing the novel tobacco pr~d~c~s. The invention relates principally Jo a process for improving the flavor and aroma of tobacco and tobacco smoke Additionally a sweet flavor is imparted to the tobacco smoke.
Addition of flavors to tobacco to enhance the aroma of a tobacco product as well as the smoke from the tobacco product is well known in the art and such flavorings are known to provide enhanced attractiveness of the tobacco product as far as the ultimate consumer is concerned.
Considerable efforts as relocate Dye outwore or or art teachings have been made and are being exerted by the manufacturers of tobacco products to provide a product that it acceptable to the customer and provides satisfying aroma and flavor.
It is the general practice in the tobacco industry to prepare blends of domestic and other tobaccos to provide a smoking tobacco which has a pleasing flavor and aroma before and during smoking. In many instances such procedure, are expensive and prohibited when certain types of tobacco are in short supply. Additionally, the ever increasing cost of tobacco raw material make the development of procedures for
¦ BACKGROUND OF THY INVENTION
The present invention relates to novel tobacco products, foreign copyist and processes for producing the novel tobacco pr~d~c~s. The invention relates principally Jo a process for improving the flavor and aroma of tobacco and tobacco smoke Additionally a sweet flavor is imparted to the tobacco smoke.
Addition of flavors to tobacco to enhance the aroma of a tobacco product as well as the smoke from the tobacco product is well known in the art and such flavorings are known to provide enhanced attractiveness of the tobacco product as far as the ultimate consumer is concerned.
Considerable efforts as relocate Dye outwore or or art teachings have been made and are being exerted by the manufacturers of tobacco products to provide a product that it acceptable to the customer and provides satisfying aroma and flavor.
It is the general practice in the tobacco industry to prepare blends of domestic and other tobaccos to provide a smoking tobacco which has a pleasing flavor and aroma before and during smoking. In many instances such procedure, are expensive and prohibited when certain types of tobacco are in short supply. Additionally, the ever increasing cost of tobacco raw material make the development of procedures for
2 0 Utah zing less desirable tobaccos even more important.
Jo SLY
In the prior art US. Patent No. vinyls, et at teaches the use of alpha-pryone compounds to cite. the organoleptic characteristics of tobacco products.
US. Patent No 3, 8B4,247~Dietrich, en at, teaches flavoring with ~utyro~a~ton~s derivatives to flavor the tobacco and tobacco smote.
US. Patent Nos. 3,380,457; 3,372,700; 3,372,701;
Jo SLY
In the prior art US. Patent No. vinyls, et at teaches the use of alpha-pryone compounds to cite. the organoleptic characteristics of tobacco products.
US. Patent No 3, 8B4,247~Dietrich, en at, teaches flavoring with ~utyro~a~ton~s derivatives to flavor the tobacco and tobacco smote.
US. Patent Nos. 3,380,457; 3,372,700; 3,372,701;
3,372,699; and 3,251,366-Shumacher, et at teach the use of various flavorings for tobaccos.
US. Patent Jo. laughingly teaches the use of various hexane based raw materials as flavoring components, while US. Patent Nos. 4,076,854; 4,135,520-Light, et at teaches tobacco flavoring with cyclohexadine derivatives.
USE Patent No. dimly teaches improvement of tobacco properties by the addition of 3-Isopropyl-cyclopen-2-en-1-one.
US. Patent No. Lotte, et at, teaches the use of hydroxy cyclohexenone derivatives in tobacco products while US. Patent No. 4,130,508 and 4,154,763-Light, et at teaches the use of cyclohexadine derivatives and a tobacco flavor ant.
US. Patent No. 4,183,363-Flynn teacups the use of 2-hydroxymethylenecyclohexanone as a flavor ant.
US. Patent No. 4,022,920-Doornbos, et at. r teaches use of amadori rearrangement compounds to provide a creamy buttery avow or aroma which is utilized in food.
1~21Z;~
SUMMARY OF THE INVENTION
The prevent invention relates to the use of non~nitro~e~ous muckrake ask compound as additives to tobacco to impure toe aria and other characteristics of S tobacco, tobacco smote, and flavor.
More particularly, it has been found that the use of the macrocylic musk compounds as as additive to tobacco products unexpectedly increases the body of the smoke, smooths the smoke flavor, and decreases mouth dryness.
More particularly, it has been found that the addition of macrocylic musk compounds to tobacco in accordance with the present invention, such as burley, flue cured tobacco, or oriental tobacco or even reconstituted tobacco or tobacco substitutes such as various vegetable leaves imparts amelioration properties and adds a unique characteristic musk flavor and aroma to the tobacco and the tobacco smoke.
The compounds within the scope of the present invention may be applied at any point during the processing of the tobacco or tobacco substitute product as well as any paper, plug wrap, tipping, filter, or package to achieve the desired effect.
No prior art disclosure is known relating to the use of musk or musk type products or non-nitrogenous macrocylic compounds as flavor ants or aroma imparting vehicles for tobacco products.
More particularly the present invention provides an improved tobacco product composition incl~ldin~ macro cyclic us compounds selected from the props consisting of issue cyclohexadecen-7~olide, cyclopentadecanolide, 3-methylcy~lopentadecanone~ cycloheptadecen-9-one or cyclopetadecanone to provide enhanced aroma and flavor and a method for producing the same.
lulled RESCRIPT OFF'' THE Invention In accordance with the present invention it has been found that macrocylic musk compounds including particularly:
cyclohexadecen-7-olide SAmbrettolide~
~CN2~7 SCHICK
cyclopentadecanolide (Exaltolide) US oh it 3-Methylcyclopentadecanone-l (Muscon) SHEA ) fH--CH3 O C SHEA
cycloheptadecen-9-one-1 (Civettone) OH - (SHEA
cyclopentadecanone Exalt one oh (1~2)1 I O
are particularly useful to impart desirable characteristics to tobacco smoke.
r 5 SWAHILI
The five previous compounds are included in two groups, namely lactones (ambrettolide and exaltolide) as jell as non-lactones mu scone civettone and exalt one).
Mach of the companies is recognized to have isomers, however evaluation of these products show little difference between the isomers of the materials and it is believed that all isomers impart similar effects in the use of the materials as flavorance for tobaccos.
It has been further found that addition of the macrocylic musk compounds previously noted to tobaccos as well as tobacco like products such as reconstituted tobacco and tobacco substitutes imparts amelioration properties and a unique characteristic and pleasant musk flavor and aroma to the tobacco and the tobacco smoke.
It has further been found that the flavor ant may be added to the tobacco product at any point during the processing including top flavor casing, top dressing or application of the stems and/or reconstituted tobacco sheet.
To evaluate the flavor ants a blend of tobacco as shown in Table I was prepared.
TABLE I
Percentage Component of Blend Flue Cured Tobacco 27.6 Burley Tobacco 26.2 Oriental tobacco 10.6 tobacco Stems 12.4 Reconstituted Tobacco 13.3 Expanded Tobacco 9.9 22~
The flavor ants within the scope of the present invention were added to the blend as discussed hereinafter.
Both filter ventilated and non-filtered cigarettes were evaluated inn ye blend It was found that neither cellulose acetate filtration nor ventilation affected the flavoring qualities of the musk compounds in the tobacco products.
The tests were conducted in accordance with a procedure where selected of the components ambrettolide, exaltolide, muscon, civettone, and exalt one were dissolved in ethanol.
The test procedure involved generally dissolving the flavor an as previously described in an ethanol solution of selected concentration. Using 2 10 micro liter syringe the solutions were injected into the tobacco sections of the cigarettes formed from the previously noted blend where each cigarette had a tobacco weight of 686 milligrams.
Several test samples were prepared using solutions of flavor ant and ethanol so that cigarettes were provided having test levels of lo parts per million, 50 parts per million, lo parts per million, 5 parts per million, l part per million and .01 part per million of the components within the scope of the present invention. The cigarettes were aged for two to three days and then smoked to determine the optimum application levels.
While effects were noted even at the 0.1 parts per lZlZZZ~
million level, the optimum for the various components were found to ye as follows:
ambre~toLide 2-5 parts per million exaltolide Z 5 parts per million mu scone 2-5 parts per million civettone 3-5 parts per million exalt one 4-9 parts per million Specific organoleptic effects were perceived upon smoking the cigarettes and the following was noted:
AMBRETTOL IRE
The optimum application range of ambrettolide was found to be Jo minimum of 2 to 5 parts per million based on the weight of the tobacco in the cigarette. The material provided ameliorating and soothing effect on the smoke flavor and character. A pleasant characteristic musk type pack aroma was imparted. It was found that the material is satisfactory between the 0.1 to 50 parts per million level to provide an organoleptic effects.
EXULTED
2 to 5 parts per million of exaltolide was found to be the optimum application rate based on the weight of the tobacco. An ameliorating soothing effect was noted on the smoke flavor and character. Also increased smoke body was noted along with added sweetness and decreased dryness. Top mixture provided a pleasant characteristic musk type pack aroma. It was found that the concentration of exaltolide at 0.1 parts per million provide some effect and the lZ12~Z~
concentrate can be increased to So part per million where the desired orqanoleptic effects are still noted.
MCKEE
The optimum level of mu scone was found to be 2-5 parts per million based on the weight of the tobacco. In those concentrations the ~nu~COQe provide an ameliorate smoothing effect on smoke flavor and character with increased smoke body. Added sweet fruity flavor and decreased dryness was also nutted. Pleasant characteristic musk type aroma was imparted to the cigarette. It was further found that the additive level can vary from 0.1 to 50 parts per million to achieve the desired effects.
CIVETTONE
It was found that 3-5 parts per million of civettone was the optimum application level based on the weight of the tobacco. An ameliorating smoothing effect was noted on smoke flavor and character. also the smoke had added body and a heavy, sweet flavor was imparted. Once again the material provided pleasant characteristic musk type pack aroma. It was found that as in previous cases effects were noted where the additive level varied from 0.1 to 50 parts per million.
EXALT ONE
The optimum level of exalt one was found to be 4-9 parts per million but the level can Mary from 0.1 to 75 parts per million end still provide the characteristic ameliorating smooth effect on the smoke flavored characteristics with increased smoke heady. the blend l;~lZZ24 further provides decreased dryness with a pleasant musk type aroma.
The same musk compound as described previously was applied to pipe tobacco closed of a blend consisting of:
COMPANY PERCENTAGE OF BLEND
Burley 7 4 %
Stems 26%
The effects perceived from smoking pipe tobacco with the applied materials were generally the same as those found in cigarettes where the optimum application levels for pipe tobacco is 1~20 parts per million with a range of 0.1-100 parts per million providing evidences of the desired effects.
A similar test was conducted using oxahexadecanolide having two oxygen atoms in the ring structure of the molecule and the results were generally unsatisfactory. For example, at the 5 parts per million application level the effect of the additive was an increase in nasal, throat, mouth irritation.
The foregoing are but a few examples of preparations in accordance with the present invention and it is recognized that other preparations also within the scope so the present invention will occur to those skilled in the art upon reading the disclosure set forth herein before.
US. Patent Jo. laughingly teaches the use of various hexane based raw materials as flavoring components, while US. Patent Nos. 4,076,854; 4,135,520-Light, et at teaches tobacco flavoring with cyclohexadine derivatives.
USE Patent No. dimly teaches improvement of tobacco properties by the addition of 3-Isopropyl-cyclopen-2-en-1-one.
US. Patent No. Lotte, et at, teaches the use of hydroxy cyclohexenone derivatives in tobacco products while US. Patent No. 4,130,508 and 4,154,763-Light, et at teaches the use of cyclohexadine derivatives and a tobacco flavor ant.
US. Patent No. 4,183,363-Flynn teacups the use of 2-hydroxymethylenecyclohexanone as a flavor ant.
US. Patent No. 4,022,920-Doornbos, et at. r teaches use of amadori rearrangement compounds to provide a creamy buttery avow or aroma which is utilized in food.
1~21Z;~
SUMMARY OF THE INVENTION
The prevent invention relates to the use of non~nitro~e~ous muckrake ask compound as additives to tobacco to impure toe aria and other characteristics of S tobacco, tobacco smote, and flavor.
More particularly, it has been found that the use of the macrocylic musk compounds as as additive to tobacco products unexpectedly increases the body of the smoke, smooths the smoke flavor, and decreases mouth dryness.
More particularly, it has been found that the addition of macrocylic musk compounds to tobacco in accordance with the present invention, such as burley, flue cured tobacco, or oriental tobacco or even reconstituted tobacco or tobacco substitutes such as various vegetable leaves imparts amelioration properties and adds a unique characteristic musk flavor and aroma to the tobacco and the tobacco smoke.
The compounds within the scope of the present invention may be applied at any point during the processing of the tobacco or tobacco substitute product as well as any paper, plug wrap, tipping, filter, or package to achieve the desired effect.
No prior art disclosure is known relating to the use of musk or musk type products or non-nitrogenous macrocylic compounds as flavor ants or aroma imparting vehicles for tobacco products.
More particularly the present invention provides an improved tobacco product composition incl~ldin~ macro cyclic us compounds selected from the props consisting of issue cyclohexadecen-7~olide, cyclopentadecanolide, 3-methylcy~lopentadecanone~ cycloheptadecen-9-one or cyclopetadecanone to provide enhanced aroma and flavor and a method for producing the same.
lulled RESCRIPT OFF'' THE Invention In accordance with the present invention it has been found that macrocylic musk compounds including particularly:
cyclohexadecen-7-olide SAmbrettolide~
~CN2~7 SCHICK
cyclopentadecanolide (Exaltolide) US oh it 3-Methylcyclopentadecanone-l (Muscon) SHEA ) fH--CH3 O C SHEA
cycloheptadecen-9-one-1 (Civettone) OH - (SHEA
cyclopentadecanone Exalt one oh (1~2)1 I O
are particularly useful to impart desirable characteristics to tobacco smoke.
r 5 SWAHILI
The five previous compounds are included in two groups, namely lactones (ambrettolide and exaltolide) as jell as non-lactones mu scone civettone and exalt one).
Mach of the companies is recognized to have isomers, however evaluation of these products show little difference between the isomers of the materials and it is believed that all isomers impart similar effects in the use of the materials as flavorance for tobaccos.
It has been further found that addition of the macrocylic musk compounds previously noted to tobaccos as well as tobacco like products such as reconstituted tobacco and tobacco substitutes imparts amelioration properties and a unique characteristic and pleasant musk flavor and aroma to the tobacco and the tobacco smoke.
It has further been found that the flavor ant may be added to the tobacco product at any point during the processing including top flavor casing, top dressing or application of the stems and/or reconstituted tobacco sheet.
To evaluate the flavor ants a blend of tobacco as shown in Table I was prepared.
TABLE I
Percentage Component of Blend Flue Cured Tobacco 27.6 Burley Tobacco 26.2 Oriental tobacco 10.6 tobacco Stems 12.4 Reconstituted Tobacco 13.3 Expanded Tobacco 9.9 22~
The flavor ants within the scope of the present invention were added to the blend as discussed hereinafter.
Both filter ventilated and non-filtered cigarettes were evaluated inn ye blend It was found that neither cellulose acetate filtration nor ventilation affected the flavoring qualities of the musk compounds in the tobacco products.
The tests were conducted in accordance with a procedure where selected of the components ambrettolide, exaltolide, muscon, civettone, and exalt one were dissolved in ethanol.
The test procedure involved generally dissolving the flavor an as previously described in an ethanol solution of selected concentration. Using 2 10 micro liter syringe the solutions were injected into the tobacco sections of the cigarettes formed from the previously noted blend where each cigarette had a tobacco weight of 686 milligrams.
Several test samples were prepared using solutions of flavor ant and ethanol so that cigarettes were provided having test levels of lo parts per million, 50 parts per million, lo parts per million, 5 parts per million, l part per million and .01 part per million of the components within the scope of the present invention. The cigarettes were aged for two to three days and then smoked to determine the optimum application levels.
While effects were noted even at the 0.1 parts per lZlZZZ~
million level, the optimum for the various components were found to ye as follows:
ambre~toLide 2-5 parts per million exaltolide Z 5 parts per million mu scone 2-5 parts per million civettone 3-5 parts per million exalt one 4-9 parts per million Specific organoleptic effects were perceived upon smoking the cigarettes and the following was noted:
AMBRETTOL IRE
The optimum application range of ambrettolide was found to be Jo minimum of 2 to 5 parts per million based on the weight of the tobacco in the cigarette. The material provided ameliorating and soothing effect on the smoke flavor and character. A pleasant characteristic musk type pack aroma was imparted. It was found that the material is satisfactory between the 0.1 to 50 parts per million level to provide an organoleptic effects.
EXULTED
2 to 5 parts per million of exaltolide was found to be the optimum application rate based on the weight of the tobacco. An ameliorating soothing effect was noted on the smoke flavor and character. Also increased smoke body was noted along with added sweetness and decreased dryness. Top mixture provided a pleasant characteristic musk type pack aroma. It was found that the concentration of exaltolide at 0.1 parts per million provide some effect and the lZ12~Z~
concentrate can be increased to So part per million where the desired orqanoleptic effects are still noted.
MCKEE
The optimum level of mu scone was found to be 2-5 parts per million based on the weight of the tobacco. In those concentrations the ~nu~COQe provide an ameliorate smoothing effect on smoke flavor and character with increased smoke body. Added sweet fruity flavor and decreased dryness was also nutted. Pleasant characteristic musk type aroma was imparted to the cigarette. It was further found that the additive level can vary from 0.1 to 50 parts per million to achieve the desired effects.
CIVETTONE
It was found that 3-5 parts per million of civettone was the optimum application level based on the weight of the tobacco. An ameliorating smoothing effect was noted on smoke flavor and character. also the smoke had added body and a heavy, sweet flavor was imparted. Once again the material provided pleasant characteristic musk type pack aroma. It was found that as in previous cases effects were noted where the additive level varied from 0.1 to 50 parts per million.
EXALT ONE
The optimum level of exalt one was found to be 4-9 parts per million but the level can Mary from 0.1 to 75 parts per million end still provide the characteristic ameliorating smooth effect on the smoke flavored characteristics with increased smoke heady. the blend l;~lZZ24 further provides decreased dryness with a pleasant musk type aroma.
The same musk compound as described previously was applied to pipe tobacco closed of a blend consisting of:
COMPANY PERCENTAGE OF BLEND
Burley 7 4 %
Stems 26%
The effects perceived from smoking pipe tobacco with the applied materials were generally the same as those found in cigarettes where the optimum application levels for pipe tobacco is 1~20 parts per million with a range of 0.1-100 parts per million providing evidences of the desired effects.
A similar test was conducted using oxahexadecanolide having two oxygen atoms in the ring structure of the molecule and the results were generally unsatisfactory. For example, at the 5 parts per million application level the effect of the additive was an increase in nasal, throat, mouth irritation.
The foregoing are but a few examples of preparations in accordance with the present invention and it is recognized that other preparations also within the scope so the present invention will occur to those skilled in the art upon reading the disclosure set forth herein before.
Claims (11)
1. A process for altering the organoleptic properties of tobacco comprising the step of adding to a selected quantity of tobacco product a flavoring composition comprising a small but effective quantity of a non-nitrogenous macrocyclic musk compound in the range of 0.1 to 100 parts per million based on the weight of the tobacco product.
2. The process as claimed in claim 1, wherein said macrocyclic musk compound has the structure:
wherein X is from 12 to 18 inclusive.
wherein X is from 12 to 18 inclusive.
3. The process as claimed in claim 2, wherein said compound is added to said tobacco product in the range of 2-5 part per million.
4. The process as claimed in claim 2, wherein said macrocyclic musk compound is cyclohexadecen-7-olide.
5. The process as claimed in claim 3, wherein said macrocyclic musk compound is cyclopentadecanolide.
6. The process as claimed in claim 1, wherein said macrocyclic musk compound has the structure:
wherein X is from 12 to 18 inclusive consistign of alkenyl and alkyl group.
wherein X is from 12 to 18 inclusive consistign of alkenyl and alkyl group.
7. The process as claimed in claim 6, wherein said compound is added to said tobacco product in the range of 2-5 parts per million.
8. The process as claimed in claim 6, wherein said macrocyclic musk compound is:
3-methylcyclopentacdecanone
3-methylcyclopentacdecanone
9. The process as claimed in claim 6, wherein said macrocyclic musk compound is cycloheptadecen-9-one-1.
10. The process as claimed in claim 6, wherein said macrocyclic musk compound is cyclopentadecanone.
11. The process as claimed in claim 1, wherein said macrocyclin musk compound has the structure:
and X + Y is from 10 to 16 inclusive.
and X + Y is from 10 to 16 inclusive.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US39421182A | 1982-07-01 | 1982-07-01 | |
| US394,211 | 1982-07-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1212224A true CA1212224A (en) | 1986-10-07 |
Family
ID=23558017
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000431638A Expired CA1212224A (en) | 1982-07-01 | 1983-06-30 | Tobacco musk compounds |
Country Status (5)
| Country | Link |
|---|---|
| AU (1) | AU544089B2 (en) |
| BR (1) | BR8303494A (en) |
| CA (1) | CA1212224A (en) |
| DE (1) | DE3323456A1 (en) |
| GB (1) | GB2122869A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2159933T5 (en) * | 1997-01-24 | 2014-12-03 | Givaudan Nederland Services B.V. | Mixtures of macrocyclic musk |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH585522A5 (en) * | 1973-09-05 | 1977-03-15 | Firmenich & Cie | |
| GB1414545A (en) * | 1973-12-31 | 1975-11-19 | Brown & Williamson Tobacco | Deposition of flavourant on tobacco |
| GB1596251A (en) * | 1976-09-15 | 1981-08-26 | Int Flavors & Fragrances Inc | Alpha-oxy (oxo) sulphides ethers and mercaptan compounds and their use in food and perfume compositions |
| CH635810A5 (en) * | 1978-12-21 | 1983-04-29 | Firmenich & Cie | UNSATURATED ALICYCLIC COMPOUNDS, PROCESS FOR THEIR PREPARATION AND THEIR USE. |
| US4183965A (en) * | 1978-12-26 | 1980-01-15 | International Flavors & Fragrances Inc. | 2- and 3-Cyclotetradecen-1-ones as bitterness depressants |
-
1983
- 1983-06-16 AU AU15835/83A patent/AU544089B2/en not_active Ceased
- 1983-06-28 GB GB08317537A patent/GB2122869A/en not_active Withdrawn
- 1983-06-29 DE DE19833323456 patent/DE3323456A1/en not_active Ceased
- 1983-06-30 BR BR8303494A patent/BR8303494A/en unknown
- 1983-06-30 CA CA000431638A patent/CA1212224A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AU1583583A (en) | 1984-01-05 |
| BR8303494A (en) | 1984-02-07 |
| AU544089B2 (en) | 1985-05-16 |
| GB8317537D0 (en) | 1983-08-03 |
| GB2122869A (en) | 1984-01-25 |
| DE3323456A1 (en) | 1984-01-05 |
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