U.S. patent application number 15/305686 was filed with the patent office on 2017-03-02 for unsaturated macrocyclic epoxide as perfuming ingredient.
This patent application is currently assigned to Firmenich SA. The applicant listed for this patent is Firmenich SA. Invention is credited to Peter FANKHAUSER.
Application Number | 20170058236 15/305686 |
Document ID | / |
Family ID | 50513808 |
Filed Date | 2017-03-02 |
United States Patent
Application |
20170058236 |
Kind Code |
A1 |
FANKHAUSER; Peter |
March 2, 2017 |
UNSATURATED MACROCYCLIC EPOXIDE AS PERFUMING INGREDIENT
Abstract
The present invention relates to a compound of formula (I) in
the form of any one of its stereoisomers or a mixture thereof which
is useful as perfuming ingredients. ##STR00001##
Inventors: |
FANKHAUSER; Peter; (Meyrin,
CH) |
|
Applicant: |
Name |
City |
State |
Country |
Type |
Firmenich SA |
Geneva 8 |
|
CH |
|
|
Assignee: |
Firmenich SA
Geneva 8
CH
|
Family ID: |
50513808 |
Appl. No.: |
15/305686 |
Filed: |
April 17, 2015 |
PCT Filed: |
April 17, 2015 |
PCT NO: |
PCT/EP2015/058435 |
371 Date: |
October 21, 2016 |
Current U.S.
Class: |
1/1 |
Current CPC
Class: |
A61Q 19/002 20130101;
A61L 9/01 20130101; A61L 2/00 20130101; C11D 3/50 20130101; A61Q
15/00 20130101; A61Q 13/00 20130101; C11D 3/001 20130101; A61K
8/4973 20130101; C11B 9/0076 20130101; A61L 9/00 20130101 |
International
Class: |
C11B 9/00 20060101
C11B009/00; A61K 8/49 20060101 A61K008/49; C11D 3/00 20060101
C11D003/00; A61Q 13/00 20060101 A61Q013/00; C11D 3/50 20060101
C11D003/50; A61Q 15/00 20060101 A61Q015/00; A61Q 19/00 20060101
A61Q019/00 |
Foreign Application Data
Date |
Code |
Application Number |
Apr 24, 2014 |
EP |
14165739.5 |
Claims
1. In a perfuming composition or perfuming consumer product, the
improvement which comprises including therein a perfuming
ingredient of a compound of formula (I) ##STR00003## in the form of
any one of its stereoisomers or of any mixture thereof and wherein
the dotted line represents a carbon-carbon single or double
bond.
2. The improvement according to claim 1, wherein the compound (I)
is in the form of a composition of matter comprising predominantly
the following stereoisomers:
(1RS,4E,8E,12RS)-13-oxabicyclo[10.1.0]trideca-4,8-diene, also
referred to as isomer (A);
(1RS,4E,8E,12SR)-13-oxabicyclo[10.1.0]trideca-4,8-diene, also
referred to as isomer (B); and
(1RS,4E,8Z,12RS)-13-oxabicyclo[10.1.0]trideca-4,8-diene, also
referred to as isomer (C).
3. The improvement according to claim 1, wherein the compound (I)
is in the form of a composition of matter comprising essentially,
or even consisting of, the isomers (A), (B) and (C) in the
following weight %: (A) being comprised between 0% and 5%,
preferably between 0% and 3%; (B) being comprised between 5% and
30%, preferably between 7% and 22%; and (C) being comprised between
65% and 90%, preferably between 72% and 85%.
4. The improvement according to claim 1, wherein the compound (I)
is in the form of a composition of matter comprising essentially,
or even consisting of, the isomers (A), (B) and (C) in the
following weight%: (A) being comprised between 50% and 75%,
preferably between 60% and 70%; (B) being comprised between 0% and
5%, preferably between 0% and 3%; and (C) being comprised between
20% and 50%, preferably between 27% and 40%.
5. The improvement according to claim 1, wherein the compound (I)
is in the form of a composition of matter comprising essentially,
or even consisting of, the isomers (A), (B) and (C) in the
following weight ratio: (A)/(C)/(B)=1/80/19 obtainable from
epoxydation of compound (II-a); (A)/(C)/(B)=63/36/1 obtainable from
epoxydation of compound (II-b); or (A)/((C)+(B))=99/1 obtainable
from epoxydation of compound (II-c).
6. The improvement according to claim 1, wherein the compound of
formula (I) is obtainable by the process comprising the step of
treating cyclododaca-1,5,9-triene in the form of any one of its
stereoisomers or of any mixture thereof with an epoxidizing agent
and optionally monohydrogenating one double bond.
7. The improvement according to claim 1, wherein the
cyclododecatriene is in the form of a mixture of isomer (1Z,4E,8E)
and isomer (1E,4E,8E) comprising at least 98% w/w of the isomer
(1Z,4E,8E), the rest being the isomer (1E,4E,8E) or
cyclododecatriene is in the form of a mixture comprising at least
30% w/w of the isomer (1Z,5E,9E), at most 75 w/w of the isomer
(1E,5E,9E) and at most 5% w/w of the isomer (1Z,5Z,9E).
8. A perfuming composition comprising i) at least one compound of
formula (I), as defined in claim 1; ii) at least one ingredient
selected from the group consisting of a perfumery carrier and a
perfumery base; and iii) optionally at least one perfumery
adjuvant.
9. A perfuming consumer product comprising at least one compound of
formula (I), as defined in claim 1.
10. A perfuming consumer product according to claim 9,
characterized in that the perfumery consumer product is a perfume,
a fabric care product, a body-care product, an air care product or
a home care product.
11. A perfuming consumer product according to claim 9,
characterized in that the perfumery consumer product is a fine
perfume, a cologne, an after-shave lotion, a liquid or solid
detergent, a fabric softener, a fabric refresher, an ironing water,
a paper, a bleach, a shampoo, a coloring preparation, a hair spray,
a vanishing cream, a deodorant or antiperspirant, a perfumed soap,
shower or bath mousse, oil or gel, a hygiene product, an air
freshener, a "ready to use" powdered air freshener, a wipe, a dish
detergent or hard-surface detergent.
12. The perfuming composition of claim 8, wherein the compound (I)
is in the form of a composition of matter comprising essentially,
or even consisting of, the isomers (A), (B) and (C) in the
following weight%: (A) being comprised between 0% and 5%,
preferably between 0% and 3%; (B) being comprised between 5% and
30%, preferably between 7% and 22%; and (C) being comprised between
65% and 90%, preferably between 72% and 85%.
13. The perfuming composition of claim 8, wherein the compound (I)
is in the form of a composition of matter comprising essentially,
or even consisting of, the isomers (A), (B) and (C) in the
following weight%: (A) being comprised between 50% and 75%,
preferably between 60% and 70%; (B) being comprised between 0% and
5%, preferably between 0% and 3%; and (C) being comprised between
20% and 50%, preferably between 27% and 40%.
14. The perfuming composition of claim 8, wherein the compound (I)
is in the form of a composition of matter comprising essentially,
or even consisting of, the isomers (A), (B) and (C) in the
following weight ratio: (A)/(C)/(B)=1/80/19 obtainable from
epoxydation of compound (II-a); (A)/(C)/(B)=63/36/1 obtainable from
epoxydation of compound (II-b); or (A)/((C)+(B))=99/1 obtainable
from epoxydation of compound (II-c).
15. The perfuming consumer product of claim 9, wherein the compound
(I) is in the form of a composition of matter comprising
essentially, or even consisting of, the isomers (A), (B) and (C) in
the following weight%: (A) being comprised between 0% and 5%,
preferably between 0% and 3%; (B) being comprised between 5% and
30%, preferably between 7% and 22%; and (C) being comprised between
65% and 90%, preferably between 72% and 85%.
16. The perfuming consumer product of claim 9, wherein the compound
(I) is in the form of a composition of matter comprising
essentially, or even consisting of, the isomers (A), (B) and (C) in
the following weight%: (A) being comprised between 50% and 75%,
preferably between 60% and 70%; (B) being comprised between 0% and
5%, preferably between 0% and 3%; and (C) being comprised between
20% and 50%, preferably between 27% and 40%.
17. The perfuming consumer product of claim 9, wherein the compound
(I) is in the form of a composition of matter comprising
essentially, or even consisting of, the isomers (A), (B) and (C) in
the following weight ratio: (A)/(C)/(B)=1/80/19 obtainable from
epoxydation of compound (II-a); (A)/(C)/(B)=63/36/1 obtainable from
epoxydation of compound (II-b); or (A)/((C)+(B))=99/1 obtainable
from epoxydation of compound (II-c).
Description
TECHNICAL FIELD
[0001] The present invention relates to the field of perfumery.
More particularly, it concerns a compound of formula (I), in the
form of any one of its stereoisomers or of any mixture thereof, and
its use as perfuming ingredient. Therefore, following what is
mentioned herein, the present invention comprises the invention's
compound as part of a perfuming composition or of a perfuming
consumer product.
PRIOR ART
[0002] The compounds 13-oxabicyclo[10.1.0]trideca-4,8-diene and
13-oxabicyclo[10.1.0]tridec-4-ene are known as such and are
respectively reported for example in WO 2012/175437 or in WO
2004/078738 and in GB 960305 or in J. Mol. Catal. 1991, 69 (1),
95-103. The prior art reports the invention's compound always as
chemical products or as intermediates, but never discloses or
suggests any organoleptic properties of the compound of formula
(I), or any use of said compound in the field of perfumery.
[0003] The perfumery ingredient having the closest chemical
structure is 1,4,8-trimethyl-13-oxabicyclo[10.1.0]trideca-4,8-diene
(also known as Cedroxyde.RTM., from Firmenich SA). However, said
prior art compound not only differs from the present compound by at
least three methyl groups, but is also differs by its olfactive
properties. Such prior art compound does not suggest any
organoleptic properties of the compound of formula (I), or any use
of said compound in the field of perfumery.
DESCRIPTION OF THE INVENTION
[0004] We have now surprisingly discovered that a compound of
formula (I)
##STR00002## [0005] in the form of any one of its stereoisomers or
of any mixture thereof and wherein the dotted line represents a
carbon-carbon single or double bond; can be used as perfuming
ingredient, for instance to impart odor notes of the woody,
cedar/ambery type and optionally also thujonic aromatic type.
[0006] For the sake of clarity, by the expression "wherein the
dotted line represents a carbon-carbon single or double bond", or
the similar, it is meant the normal meaning understood by a person
skilled in the art, i.e. that the whole bonding (solid and dotted
lines) between the carbon atoms connected by said dotted line is a
carbon-carbon single or double bond.
[0007] The invention's compound possesses one or two carbon-carbon
double bonds as well as two fused rings, and each of said moiety
can have two different stereochemistries (e.g. E or Z; (RS;RS) or
(RS,SR)), and the compound may even be chiral or not. Therefore the
compound of formula (I) can be in the form of a composition of
matter comprising, or consisting of, the various stereoisomers.
[0008] The invention's compound can be in a racemic form or
enantioenriched (if chiral).
[0009] In particular, for compound of formula (I) wherein the
dotted line represents a carbon-carbon double bond; i.e. compound
of formula (I) having two carbon-carbon double bonds, each
carbon-carbon double bond of said compound, independently from each
other, can be in a configuration Z or E or a mixture thereof. For
the sake of clarity, by the expression "each carbon-carbon double
bond of said compound, independently from each other, can be in a
configuration Z or E or a mixture thereof" it is meant also a
composition of matter comprising the various (E,E), (E,Z), (Z,E)
and (Z,Z) isomers. For compound of formula (I) wherein the dotted
line represents a carbon-carbon single bond, the carbon-carbon
double bond of said compound can be in a configuration Z or E or a
mixture thereof.
[0010] The same applies to the epoxy moiety. The epoxy moiety can
be in a configuration (1RS,12RS) or (1RS,12SR) or a mixture
thereof. For the sake of clarity, by the expression "(1RS,12RS)" it
is meant an equimolar mixture of (1R,12R) and (1S,12S) and by the
expression "(1RS,12SR)" it is meant an equimolar mixture of
(1R,12S) and (1S,12R). As non-limiting example one may cite the
following stereoisomers:
(1RS,4E,8Z,12RS)-13-oxabicyclo[10.1.0]trideca-4,8-diene or
(1RS,4E,8E,12RS)-13-oxabicyclo[10.1.0]trideca-4,8-diene.
[0011] In other words, said compound (I) can be in the form of an
essentially pure stereoisomer (i.e. the (1RS,4E,8Z,12RS) one) or in
the form of a composition of matter comprising several
stereoisomers, e.g. in a mixture comprising the stereoisomers
(4E,8E), (4Z,8E) and (4E,8Z) in various w/w ratio.
[0012] According to a preferred embodiment, the compound of formula
(I) is 13-oxabicyclo[10.1.0]trideca-4,8-diene (wherein the dotted
line represents a carbon-carbon double bond).
[0013] According to any embodiment, the compound of formula (I), in
particular in the form of a mixture of stereoisomers, can also be
better defined by the process for obtaining to it. Indeed, the
compound of formula (I) is obtainable by the process comprising the
step of treating cyclododaca-1,5,9-triene in the form of any one of
its stereoisomers or of any mixture thereof with an epoxidizing
agent and optionally monohydrogenating one double bond.
[0014] Cyclododeca-1,5,9-triene, a known and commercially product,
possesses 3 carbon-carbon double bonds which can have different
stereochemistries (i.e. can be in a E or Z configuration).
[0015] According to any one of the above embodiments of the
invention, cyclododeca-1,5,9-triene is in the form of a mixture of
isomers (1E,5E,9E), (1Z,5E,9E) and (1Z,5Z,9E).
[0016] According to a preferred embodiment,
cyclododaca-1,5,9-triene is in the form of a mixture of isomer
(1Z,5E,9E) and isomer (1E,5E,9E) comprising at least 90% w/w of the
isomer (1Z,5E,9E), most preferably comprising at least 95% w/w of
the isomer (1Z,5E,9E), even more preferably comprising at least 98%
w/w of the isomer (1Z,5E,9E), the rest being the isomer (1E,5E,9E).
Cyclododaca-1,5,9-triene in a form of a mixture comprising at least
98% of isomer (1Z,5E,9E) and at most 2% of isomer (1E,5E,9E), also
here-referred as compound (II-a), are commercially available from
Evonik Industries.
[0017] According to a particular embodiment,
cyclododeca-1,5,9-triene is in the form of a mixture comprising at
least 95% w/w of the isomer (1E,5E,9E) also here-referred as
compound (II-c) which is commercially available from Sigma-Aldrich
Co..
[0018] According to another particular embodiment,
cyclododaca-1,5,9-triene is in the form of a mixture comprising at
least 30% w/w of the isomer (1Z,5E,9E), at most 75% w/w of the
isomer (1E,5E,9E) and at most 5% w/w of the isomer (1Z,5Z,9E), also
here-referred as compound (II-b). An isomerization of the
commercially available (1Z,5E,9E)-cyclododaca-1,5,9-triene allows
to increase the proportion of isomer (1E,4E,8E). The person skilled
in the art is well aware of isomerization conditions reported in
the literature and will be able to select the best conditions in
order to obtain the desired isomeric mixture. Moreover, the person
skilled in the art is able to mix the commercially available
quality of cyclododecatriene in order to obtain a cyclododecatriene
in the desired form of mixture of isomers.
[0019] For the sake of clarity, by the term "epoxidizing agent" and
similar, it is meant the normal meaning in the art, i.e. a reactant
able to react with a double bond to form an epoxide. Specific, and
non-limiting, examples of epoxidizing agent is selected from the
group consisting of C.sub.2-8 peroxy acids, such as peracetic acid,
ethaneperoxoic acid, buthaneperoxoic acid, 2-ethylhexaneperoxoic
acid, butanediperoxoic acid, perbenzoic acid, para-methylperbenzoic
acid, methoxyperbenzoic acid, meta-chloroperbenzoic acid,
para-chloroperbenzoic acid or ortho-chloroperbenzoic acid, hydrogen
peroxide, dioxygen, alkyl peroxide such as tert-butylhydroperoxide
and a mixture thereof. The reaction is optionally catalyzed by a
transitional metal. An overview of epoxydation condition could be
found in March's "Advanced Organic Chemistry", 5.sup.th edition
2001, pg 1051-1054). The person skilled in the art is able to
select the most appropriate epoxidizing agent.
[0020] As a person skilled in the art knows, said epoxidizing agent
can be in a pure form or diluted in a solvent. Typically it can be
used an aqueous solution having a concentration ranging from 10% to
50% w/w, preferably between 30% and 40%, the % being relative to
the total weight of the solution. However other solvent can be
used, such a C.sub.1-10 carboxylic acid (preferably the
corresponding carboxylic acid, i.e. acetic acid in case of
peracetic acid), a C.sub.6-10 alkane or cycloalkane, a C.sub.3-10
ester.
[0021] According to any embodiment of the invention, said
epoxidizing agent is selected amongst the solutions containing
between 10% to 50% w/w, preferably between 30% and 40%, the % being
relative to the total weight of the solution, of a C.sub.2-8 peroxy
acid.
[0022] For the sake of clarity, by the term "monohydrogenating one
double bond", it is meant the normal meaning in the art, i.e. the
selective hydrogenation of one double bond. This reaction is well
known in the art, and the person skilled in the art will be able to
select the appropriate condition in odor to hydrogenate mainly one
double bond.
[0023] Without being bound by theory, we believe that the
invention's compound obtainable by such a process is in the form of
a composition of matter comprising predominantly (i.e. at least 90%
w/w) the following stereoisomers: [0024]
(1RS,4E,8E,12RS)-13-oxabicyclo[10.1.0]trideca-4,8-diene (also
referred to as isomer (A)); [0025]
(1RS,4E,8E,12SR)-13-oxabicyclo[10.1.0]trideca-4,8-diene (also
referred to as isomer (B)); [0026]
(1RS,4E,8Z,12RS)-13-oxabicyclo[10.1.0]trideca-4,8-diene (also
referred to as isomer (C)).
[0027] According to a particular embodiment of the invention, said
compound (I) is in the form of a composition of matter comprising
essentially, or even consisting of, the isomers (A), (B) and (C) in
the following weight%: [0028] (A) being comprised between 0% and
5%, preferably between 0% and 3%; [0029] (B) being comprised
between 5% and 30%, preferably between 7% and 22%; and [0030] (C)
being comprised between 65% and 90%, preferably between 72% and
85%.
[0031] Alternatively, according to a particular embodiment of the
invention, said compound (I) is in the form of a composition of
matter comprising essentially, or even consisting of, the isomers
(A), (B) and (C) in the following weight%: [0032] (A) being
comprised between 50% and 75%, preferably between 60% and 70%;
[0033] (B) being comprised between 0% and 5%, preferably between 0%
and 3%; and [0034] (C) being comprised between 20% and 50%,
preferably between 27% and 40%.
[0035] According to a particular embodiment of the invention, said
compound (I) is in the form of a composition of matter comprising
essentially, or even consisting of, the isomers (A), (B) and (C) in
the following weight ratio: [0036] (A)/(C)/(B)=1/80/19 (also
referred to as compound (I-a)) obtainable from epoxydation of
compound (II-a); [0037] (A)/(C)/(B)=63/36/1 (also referred to as
compound (I-b)) obtainable from epoxydation of compound (II-b); or
[0038] (A)/((C)+(B))=99/1 (also referred to as compound (I-c))
obtainable from epoxydation of compound (II-c).
[0039] For the sake of clarity, by the expression "comprising
essentially" it is meant at least 80% w/w, or even 90% w/w, of the
composition is made of the listed materials.
[0040] As specific examples of the invention's compound, one may
cite, as non-limiting example, the compound (I-a). Said compound
has a unique odor having a duality characterized by a fresh top
note woody, aromatic type of reminiscent of thuja leaves and a
middle, bottom note of the woody cedar/ambery type as well as a
slightly earthy aspect. The presence of such fresh, raising top
note of the woody, aromatic type is an exceptional feature of said
invention's compound, since in general the woody notes are
associated with middle to bottom notes. The overall olfactive
impression of said compound is a very natural, raising and impact
woody note which marries perfectly with the classical woody notes
used in the art of perfumery.
[0041] Said compound (I-a) represents a particularly appreciated
embodiment of the invention.
[0042] When the odor of the invention's compound is compared with
that of the prior art compounds, e.g. Cedroxyde.RTM., then the
invention's compound distinguishes themselves by having an aromatic
note and as well as being by having a clear top note contribution,
all aspect which are absent in the prior art compound(s). Said
differences lend the invention's compound and the prior art
compound(s) to be each suitable for different uses, i.e. to impart
different organoleptic impressions.
[0043] As mentioned above, the invention concerns the use of a
compound of formula (I) as perfuming ingredient. In other words, it
concerns a method to confer, enhance, improve or modify the odor
properties of a perfuming composition or of a perfumed article,
which method comprises adding to said composition or article an
effective amount of at least a compound of formula (I). By "use of
a compound of formula (I)" it has to be understood here also the
use of any composition containing a compound (I) and which can be
advantageously employed in perfumery industry.
[0044] Said compositions, which in fact can be advantageously
employed as perfuming ingredients, are also an object of the
present invention.
[0045] Therefore, another object of the present invention is a
perfuming composition comprising: [0046] i) as perfuming
ingredient, at least one invention's compound as defined above;
[0047] ii) at least one ingredient selected from the group
consisting of a perfumery carrier and a perfumery base; and [0048]
iii) optionally at least one perfumery adjuvant.
[0049] By "perfumery carrier" we mean here a material which is
practically neutral from a perfumery point of view, i.e. that does
not significantly alter the organoleptic properties of perfuming
ingredients. Said carrier may be a liquid or a solid.
[0050] As liquid carrier one may cite, as non-limiting examples, an
emulsifying system, i.e. a solvent and a surfactant system, or a
solvent commonly used in perfumery. A detailed description of the
nature and type of solvents commonly used in perfumery cannot be
exhaustive. However, one can cite as non-limiting examples solvents
such as dipropyleneglycol, diethyl phthalate, isopropyl myristate,
benzyl benzoate, 2-(2-ethoxyethoxy)-1-ethanol or ethyl citrate,
which are the most commonly used. For the compositions which
comprise both a perfumery carrier and a perfumery base, other
suitable perfumery carriers than those previously specified, can be
also ethanol, water/ethanol mixtures, limonene or other terpenes,
isoparaffins such as those known under the trademark Isopar.RTM.
(origin: Exxon Chemical) or glycol ethers and glycol ether esters
such as those known under the trademark Dowanol.RTM. (origin: Dow
Chemical Company).
[0051] As solid carriers one may cite, as non-limiting examples,
absorbing gums or polymers, or yet encapsulating materials.
Examples of such materials may comprise wall-forming and
plasticizing materials, such as mono, di- or trisaccharides,
natural or modified starches, hydrocolloids, cellulose derivatives,
polyvinyl acetates, polyvinylalcohols, proteins or pectins, or yet
the materials cited in reference texts such as H. Scherz,
Hydrokolloide: Stabilisatoren, Dickungs- and Geliermittel in
Lebensmitteln, Band 2 der Schriftenreihe Lebensmittelchemie,
Lebensmittelqualitat, Behr's Verlag GmbH & Co., Hamburg, 1996.
The encapsulation is a well-known process to a person skilled in
the art, and may be performed, for instance, using techniques such
as spray-drying, agglomeration or yet extrusion; or consists of a
coating encapsulation, including coacervation and complex
coacervation technique.
[0052] By "perfumery base" we mean here a composition comprising at
least one perfuming co-ingredient.
[0053] Said perfuming co-ingredient is not of formula (I).
Moreover, by "perfuming co-ingredient" it is meant here a compound,
which is used in a perfuming preparation or a composition to impart
a hedonic effect. In other words such a co-ingredient, to be
considered as being a perfuming one, must be recognized by a person
skilled in the art as being able to impart or modify in a positive
or pleasant way the odor of a composition, and not just as having
an odor.
[0054] The nature and type of the perfuming co-ingredients present
in the base do not warrant a more detailed description here, which
in any case would not be exhaustive, the skilled person being able
to select them on the basis of his general knowledge and according
to intended use or application and the desired organoleptic effect.
In general terms, these perfuming co-ingredients belong to chemical
classes as varied as alcohols, lactones, aldehydes, ketones,
esters, ethers, acetates, nitriles, terpenoids, nitrogenous or
sulphurous heterocyclic compounds and essential oils, and said
perfuming co-ingredients can be of natural or synthetic origin.
Many of these co-ingredients are in any case listed in reference
texts such as the book by S. Arctander, Perfume and Flavor
Chemicals, 1969, Montclair, N.J., USA, or its more recent versions,
or in other works of a similar nature, as well as in the abundant
patent literature in the field of perfumery. It is also understood
that said co-ingredients may also be compounds known to release in
a controlled manner various types of perfuming compounds.
[0055] According to any one of the invention's embodiments, said
perfuming composition can be one wherein the perfumery base
comprises, or consists of, ingredients currently used to impart
woody notes. Such ingredients imparting woody notes are well known
to a person skilled in the art and can be easily retrieved in any
perfumery text book or pertinent literature (e.g. the Arctander
book cited above, or in the patent literature).
[0056] Although an exhaustive list of such ingredients imparting
woody notes would impossible, one may cite as non-limiting examples
the following ones:
[0057] methyl cedryl ketone, Vertofix.RTM. (trademark owned by
International Flavors &Fragrances, USA,
1-(octahydro-2,3,8,8-tetramethyl-2-naphthalenyl)-1-ethanone, Iso E
Super.RTM., Cedar oil, patchouli oil, cypriol oil,
trans-1-(2,2,6-trimethyl-1-cyclohexyl)-3-hexanol, Norlimbanol.RTM.,
1-(2,2,3,6-tetramethyl-cyclohexyl)-3-hexanol, Limbanol.RTM.,
(1'R,E)-2-ethyl-4-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl)-2-buten-
1-ol,
3,3-dimethyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol,
2-ethyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol,
5,5,9,13-tetramethyl-14,16-dioxatetracyclo[11.2.1.0(1,10).0(4,9)]hexadeca-
ne,
{1-methyl-2-[(1',2',2'-trimethylbicyclo[3.1.0]hex-3'-yl)methyl]cyclopr-
opyl}methanol,
3-methyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol,
(1R,3S,7R,8R,10S,13R)-5,5,7,9,9,13-hexamethyl-4,6-dioxatetracyclo[6.5.1.0-
(1,10).0(3,7)]tetradecane, Ambrocenide.RTM. (trademark owned by
Symrise AG, Germany)
perhydro-2,6,6,7,8,8-hexamethylindeno[4,5-b]furan, Trisamber.RTM.,
2-(2,2,7,7-tetramethyl-tricyclo[6.2.1.0(1,6)]undec-4/5-en-5-yl)-1-propano-
l, Ambermax.RTM. (trademark owned by Givaudan SA, Switzerland),
Casmirone.RTM. and 4,8-cyclododecadien-1-one.
[0058] In such embodiment, the invention's compound can be used in
amounts comprised between about 5% to 50% w/w, relative to the
total amount of ingredients imparting woody notes.
[0059] By "perfumery adjuvant" we mean here an ingredient capable
of imparting additional added benefit such as a color, a particular
light resistance, chemical stability, etc. A detailed description
of the nature and type of adjuvant commonly used in to perfuming
bases cannot be exhaustive, but it has to be mentioned that said
ingredients are well known to a person skilled in the art.
[0060] An invention's composition consisting of at least one
compound of formula (I) and at least one perfumery carrier
represents a particular embodiment of the invention as well as a
perfuming composition comprising at least one compound of formula
(I), at least one perfumery carrier, at least one perfumery base,
and optionally at least one perfumery adjuvant.
[0061] It is useful to mention here that the possibility to have,
in the compositions mentioned above, more than one compound of
formula (I) is important as it enables the perfumer to prepare
accords, perfumes, possessing the odor tonality of various
compounds of the invention, creating thus new tools for his
work.
[0062] For the sake of clarity, it is also understood that any
mixture resulting directly from a chemical synthesis, e.g. a
reaction medium without an adequate purification, in which the
compound of the invention would be involved as a starting,
intermediate or end-product could not be considered as a perfuming
composition according to the invention as far as said mixture does
not provide the inventive compound in a suitable form for
perfumery. Thus, unpurified reaction mixtures are generally
excluded from the present invention unless otherwise specified.
[0063] Furthermore, the invention's compound can also be
advantageously used in all the fields of modem perfumery, i.e. fine
or functional perfumery, to positively impart or modify the odor of
a consumer product into which said compound (I) is added.
Consequently, another object of the present invention is
represented by a perfuming consumer product comprising, as
perfuming ingredient, at least one compound of formula (I), as
defined above.
[0064] The invention's compound can be added as such or as part of
an invention's perfuming composition.
[0065] For the sake of clarity, it has to be mentioned that, by
"perfuming consumer product" it is meant a consumer product which
is expected to deliver at least a pleasant perfuming effect to the
surface to which it is applied (e.g. skin, hair, textile, or home
surface). In other words, a perfuming consumer product according to
the invention is a perfumed consumer product which comprises the
functional formulation, as well as optionally additional benefit
agents, corresponding to the desired consumer product, e.g. a
detergent or an air freshener, and an olfactive effective amount of
at least one invention's to compound. For the sake of clarity, said
perfuming consumer product is a non-edible product.
[0066] The nature and type of the constituents of the perfumery
consumer product do not warrant a more detailed description here,
which in any case would not be exhaustive, the skilled person being
able to select them on the basis of his general knowledge and
according to the nature and the desired effect of said product.
[0067] Non-limiting examples of suitable perfumery consumer product
can be a perfume, such as a fine perfume, a cologne or an
after-shave lotion; a fabric care product, such as a liquid or
solid detergent, a fabric softener, a fabric refresher, an ironing
water, a paper, or a bleach; a body-care product, such as a hair
care product (e.g. a shampoo, a coloring preparation or a hair
spray), a cosmetic preparation (e.g. a vanishing cream or a
deodorant or antiperspirant), or a skin-care product (e.g. a
perfumed soap, shower or bath mousse, oil or gel, or a hygiene
product); an air care product, such as an air freshener or a "ready
to use" powdered air freshener; or a home care product, such as a
wipe, a dish detergent or hard-surface detergent.
[0068] Some of the above-mentioned consumer products may represent
an aggressive medium for the invention's compound, so that it may
be necessary to protect the latter from premature decomposition,
for example by encapsulation or by chemically bounding it to
another chemical which is suitable to release the invention's
ingredient upon a suitable external stimulus, such as an enzyme,
light, heat or a change of pH.
[0069] The proportions in which the compound according to the
invention can be incorporated into the various aforementioned
articles or compositions vary within a wide range of values. These
values are dependent on the nature of the article to be perfumed
and on the desired organoleptic effect as well as the nature of the
co-ingredients in a given base when the compound according to the
invention are mixed with perfuming co-ingredients, solvents or
additives commonly used in the art.
[0070] For example, in the case of perfuming compositions, typical
concentrations are in the order of 0.001% to 30% by weight, or even
more, of the compound of the invention based on the weight of the
composition into which they are incorporated. Concentrations lower
than these, such as in the order of 0.01% to 10% by weight, can be
used when these compounds are incorporated into perfumed articles,
percentage being relative to the weight of the article.
[0071] The invention's compound can be prepared from
cyclododecatriene according to a to method as described
herein-below in the Examples or as described in WO2009117498,
EP1170291, WO2004078738, EP0965575, WO2012175437 and J. Mol. Catal.
1991, 69 (1), 95-103.
EXAMPLES
[0072] The invention will now be described in further detail by way
of the following examples, wherein the abbreviations have the usual
meaning in the art, the temperatures are indicated in degrees
centigrade (.degree. C.).
Example 1
[0073] Preparation of Compound of Formula (I)
[0074] To a mixture of sodium carbonate (160 g, 1.23 mol, 2.9
equiv.) in toluene (1000 mL) was added cyclododeca-1,5,9-triene
(II-a) (500 g, 3.1 mol, 1 equiv.). The mixture was cooled down to
0.degree. C. and peracetic acid (1000 mL, 3.9 mol, 1 equiv.)) was
added dropwise over a 5 min-period. The reaction mixture was slowly
warm to room temperature and stirred overnight. Then, the reaction
mixture was cooled down to 0.degree. C. and was poured onto an
aqueous solution of NaHSO.sub.3. The organic layer was washed with
an aqueous solution of NaHCO.sub.3 then with water and finally with
brine. The combined organic extracts were dried over sodium sulfate
and the solvent was evaporated. The residue was purified by
distillation under reduced pressure (0.07 mbar, 110.degree. C.) to
provide a stereoisomers mixture of
13-oxabicyclo[10.1.0]trideca-4,8-diene. Based on analysis, the
stereoisomers mixtures consists of 80% of
(1RS,4E,8Z,12RS)-13-oxabicyclo[10.1.0]trideca-4,8-diene, 19% of
(1RS,4E,8E,12SR)-13-oxabicyclo[10.1.0]trideca-4,8-diene and 1% of
(1RS,4E,8E,12RS)-13-oxabicyclo[10.1.0]trideca-4,8-diene.
Example 2
Preparation of a Perfuming Composition
[0075] A perfuming composition for masculine cologne was prepared
by admixing the following ingredients:
TABLE-US-00001 Parts by weight Ingredient 50 10%* C 10 aldehyde 20
Ambrettolide .RTM. .sup.1) 100 Ambrox .RTM. .sup.2) 10 Amione .RTM.
.sup.3) 50 Bergamot essential oil 120 (Ethoxymethoxy)cyclododecane
50 10%* Calone .RTM. .sup.4) 10 Cardamon essential oil 40 Cashmeran
.RTM. .sup.5) 70 8-Methoxy-2,6,6,8-tetramethyl-
tricyclo[5.3.1.0(1,5)]undecane 20 Coumarine 10 Cypress oil 400
Dihydromyrcenol 700 Exaltolide .RTM. .sup.6) 100
2-Methyl-4-(2,2,3-trimethyl-3- cyclopenten-1-yl)-4-penten-1-ol 2000
Habanolide .RTM. .sup.7) 1000 Hedione .RTM. .sup.8) HC 250
3-(1,3-Benzodioxol-5-yl)-2-methylpropanal 500 Helvetolide .RTM.
.sup.9) 40 Hivernal .RTM. .sup.10) 400 Hydroxycitronellal 1600 Iso
EC .RTM. .sup.11) Super 200 Lyral .RTM. .sup.12) 300 Mandarin
essential oil 70 Crystal moss 250 Muscenone .RTM..sup.13) Delta 30
Myrrhone .RTM. .sup.14) 20 Cis-3-Hexenol 80 Orange essential oil 50
1%* 2,6,6-Trimethyl-1,3-cyclohexadiene- 1-carbaldehyde 40 Amyl
salicylate 60 Salicynile .RTM. .sup.15) 40 10%* Vanilline 700
Vertofix .RTM. .sup.16) Coeur 20 Ionone Beta 100 Vulcanolide .RTM.
.sup.17) 9500 *in dipropyleneglycol **in isopropyle myristate
.sup.1) 16-hexadecanolide .sup.a) .sup.2)
(-)-(8R)-8,12-epoxy-13,14,15,16-tetranorlabdane .sup.a) .sup.3)
allyl ionone .sup.b) .sup.4) 7-methyl-2H,4H-1,5-benzodioxepin-3-one
.sup.a) .sup.5)
1,2,3,5,6,7-hexahydro-1,1,2,3,3-pentamethyl-4-indenone .sup.c)
.sup.6) pentadecanolide .sup.a) .sup.7) pentadecenolide .sup.a)
.sup.8) methyl cis-dihydrojasmonate .sup.a) .sup.9)
(1S,1'R)-2-[1-(3',3'-dimethyl-1'-cyclohexyl)ethoxy]-2-methylpropyl
propanoate .sup.a) .sup.10) 3-(3,3/1,1-dimethyl-5-indanyl)propanal
.sup.a) .sup.11)
1-(octahydro-2,3,8,8-tetramethyl-2-naphthalenyl)-1-ethanone .sup.c)
.sup.12)
4/3-(4-hydroxy-4-methylpentyl)-3-cyclohexene-1-carbaldehyde .sup.c)
.sup.13) 3-methyl-5-cyclopentadecen-1-one .sup.a) .sup.14)
4-(2,2,C-3,T-6-tetramethyl-R-1-cyclohexyl)-3-buten-2-one .sup.a)
.sup.15) (2Z)-2-phenyl-2-hexenenitrile .sup.a) .sup.16) methyl
cedryl ketone .sup.c) .sup.17)
trans-5,6,7,8-tetrahydro-3,5,5,6,7,8,8-heptamethyl-2-naphthalenec-
arbaldehyde .sup.a) .sup.a) origin: Firmenich SA, Geneva,
Switzerland .sup.b) origin: Givaudan-Roure SA, Vernier, Switzerland
.sup.c) origin: International Flavors & Fragrances, USA
[0076] The addition of 500 parts by weight of Compound (I-a) to the
above-described cologne imparted to the latter an amazing woody,
aromatic top note, completing and complementary to the note
imparted by Iso E.RTM. Super (which impact essentially the bottom
notes).
[0077] The addition of the same amount of Cedroxyde.RTM. provided a
different effect, devoid of the woody top note, as well as of the
aromatic effect.
Example 3
Preparation of a Perfuming Composition
[0078] A perfuming composition for a detergent was prepared by
admixing the following ingredients:
TABLE-US-00002 Parts by weight Ingredient 150
1-Methyl-1-phenylethyl acetate 1000 Hexylcinnamic aldehyde 20
9-Undecenal 10 Methyl anthranilate 150 Benzyl benzoate 50 10%*
Raspberry ketone 750 Citronellol 80 Citronellyl nitrile 200
Clearwood .TM. .sup.1) 50 10%* Ethyl (2e,4z)-2,4-decadienoate 10
Estragole 50 10%* Ethylvanilline 60 Ethyl
tricyclo[5.2.1.0.(2,6)]decane-2-carboxylate 1000 70%** Galaxolide
.RTM. .sup.2) 500 Habanolide .RTM. .sup.3) 400 Hedione .RTM.
.sup.4) 60 10%* Indocolore .TM. .sup.5) 300 Alpha iso methylionone
1000 Lilial .RTM. .sup.6) 500 Linalool 800 Lorysia .RTM. .sup.7) 30
10%* 2-Ethyl methylbutyrate 50 Methylnaphthylketone 150 Muscenone
.RTM. .sup.8) Delta 60 50%** Natactone .TM. .sup.9) 600 Phenethylol
800 Orange essential oil 200 Wardia .RTM. .sup.10) 500 Terpineol 50
10%* Vanilline 100 Ylang oil 20
2,4-Dimethyl-3-cyclohexene-1-carbaldehyde 9700 *in
dipropyleneglycol **in isopropyle myristate .sup.1) terpenic
fraction of Patchouli oil, obtained by fermentation of sugars
.sup.a) .sup.2)
1,3,4,6,7,8-hexahydro-4,6,6,7,8,8-hexamethyl-cyclopenta-g-2-benzop-
yrane .sup.c) .sup.3) pentadecenolide .sup.a) .sup.4) methyl
cis-dihydrojasmonate.sup.a) .sup.5) 1-phenylvinyl acetate .sup.a)
.sup.6) 3-(4-tert-butylphenyl)-2-methylpropanal .sup.b) .sup.7)
4-(1,1-dimethylethyl)-1-cyclohexyl acetate .sup.a) .sup.8)
3-methyl-5-cyclopentadecen-1-one .sup.a) .sup.9)
(6R)-perhydro-3,6-dimethyl-benzo[b]furan-2-one .sup.a) .sup.10)
compounded perfumery base .sup.a) .sup.a) origin: Firmenich SA,
Geneva, Switzerland .sup.b) origin: Givaudan-Roure SA, Vernier,
Switzerland .sup.c) origin: International Flavors & Fragrances,
USA
[0079] The addition of 300 parts by weight of Compound (I-a) to the
above-described composition imparted to the latter an amazing
woody, ambery and aromatic top note, completing and complementary
to the Patchouli note imparted by Clearwood.TM. (which impact
essentially the bottom notes).
[0080] The addition of the same amount of Cedroxyde.RTM. provided a
different effect, devoid of the woody top note, as well as of the
aromatic effect.
* * * * *