Language selection

Search

Patent 1212224 Summary

Third-party information liability

Some of the information on this Web page has been provided by external sources. The Government of Canada is not responsible for the accuracy, reliability or currency of the information supplied by external sources. Users wishing to rely upon this information should consult directly with the source of the information. Content provided by external sources is not subject to official languages, privacy and accessibility requirements.

Claims and Abstract availability

Any discrepancies in the text and image of the Claims and Abstract are due to differing posting times. Text of the Claims and Abstract are posted:

  • At the time the application is open to public inspection;
  • At the time of issue of the patent (grant).
(12) Patent: (11) CA 1212224
(21) Application Number: 1212224
(54) English Title: TOBACCO MUSK COMPOUNDS
(54) French Title: TABAC AU MUSC
Status: Term Expired - Post Grant
Bibliographic Data
(51) International Patent Classification (IPC):
  • A24B 15/40 (2006.01)
  • A24B 15/34 (2006.01)
(72) Inventors :
  • MCMURTRIE, ANDREW (United States of America)
  • ALFORD, EZRA D. (United States of America)
  • CRAVOTTA, THOMAS J. (United States of America)
(73) Owners :
  • BROWN & WILLIAMSON TOBACCO CORPORATION
(71) Applicants :
  • BROWN & WILLIAMSON TOBACCO CORPORATION (United States of America)
(74) Agent: MITCHES & CO.
(74) Associate agent:
(45) Issued: 1986-10-07
(22) Filed Date: 1983-06-30
Availability of licence: N/A
Dedicated to the Public: N/A
(25) Language of filing: English

Patent Cooperation Treaty (PCT): No

(30) Application Priority Data:
Application No. Country/Territory Date
394,211 (United States of America) 1982-07-01

Abstracts

English 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.


Claims

Note: Claims are shown in the official language in which they were submitted.


- 11 -
The embodiments of the invention in which an exclusive
property or privilege is claimed are defined as follows:
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:
< IMG >
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:
< IMG >
wherein X is from 12 to 18 inclusive consistign of alkenyl and
alkyl group.

- 12 -
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
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:
< IMG >
and X + Y is from 10 to 16 inclusive.

Description

Note: Descriptions are shown in the official language in which they were submitted.


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
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;
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.

Representative Drawing

Sorry, the representative drawing for patent document number 1212224 was not found.

Administrative Status

2024-08-01:As part of the Next Generation Patents (NGP) transition, the Canadian Patents Database (CPD) now contains a more detailed Event History, which replicates the Event Log of our new back-office solution.

Please note that "Inactive:" events refers to events no longer in use in our new back-office solution.

For a clearer understanding of the status of the application/patent presented on this page, the site Disclaimer , as well as the definitions for Patent , Event History , Maintenance Fee  and Payment History  should be consulted.

Event History

Description Date
Inactive: IPC from MCD 2006-03-11
Inactive: Expired (old Act Patent) latest possible expiry date 2003-10-07
Grant by Issuance 1986-10-07

Abandonment History

There is no abandonment history.

Owners on Record

Note: Records showing the ownership history in alphabetical order.

Current Owners on Record
BROWN & WILLIAMSON TOBACCO CORPORATION
Past Owners on Record
ANDREW MCMURTRIE
EZRA D. ALFORD
THOMAS J. CRAVOTTA
Past Owners that do not appear in the "Owners on Record" listing will appear in other documentation within the application.
Documents

To view selected files, please enter reCAPTCHA code :



To view images, click a link in the Document Description column (Temporarily unavailable). To download the documents, select one or more checkboxes in the first column and then click the "Download Selected in PDF format (Zip Archive)" or the "Download Selected as Single PDF" button.

List of published and non-published patent-specific documents on the CPD .

If you have any difficulty accessing content, you can call the Client Service Centre at 1-866-997-1936 or send them an e-mail at CIPO Client Service Centre.

({010=All Documents, 020=As Filed, 030=As Open to Public Inspection, 040=At Issuance, 050=Examination, 060=Incoming Correspondence, 070=Miscellaneous, 080=Outgoing Correspondence, 090=Payment})


Document
Description 
Date
(yyyy-mm-dd) 
Number of pages   Size of Image (KB) 
Abstract 1993-07-28 1 17
Claims 1993-07-28 2 44
Drawings 1993-07-28 1 13
Descriptions 1993-07-28 9 304