COMPOSE PARFUME A BASE D'ACETONIDE

ACETONIDE FRAGRANCE COMPOUND

Abrégé français

On divulgue un nouveau composé de 3A, 5, 6, 7, 8, 8B-hexahydro-2,2,6,6,7, 8,8-heptaméthyle de 4H-indéno¬4,5-D|-1;3-dioxole ainsi que l'utilisation de ce composé comme parfum. Ce composé parfumant peut être utilisé dans la création de formulations de parfum et comme parfum dans des articles comme les eaux de toilette et les eaux de parfum, les eaux de Cologne et les produits de soins personnels.

Abrégé anglais

A novel compound 4H-indeno[4,5-D]-1;3-dioxole, 3A, 5, 6, 7, 8, 8B -hexahydro - 2,2,6,6,7, 8,8 -heptamethyl is dislosed as well as the use of the compound as a fragrance chemical. The fragrance compound is suitable for use in creating fragrances, and scents in items such as perfumes, colognes and personal care products.

Revendications

The embodiments of the invention in which an exclusive property or privilege
is claimed are defined as follows:
1. A method for modifying a fragrance through the addition of an olfactory
acceptable
amount of 4H-indeno[4,5-D]-1,3-dioxole, 3A, 5, 6, 7, 8, 8B -hexahydro -
2,2,6,6,7, 8,8 -
heptamethyl.
2. The method of claim 1 wherein the fragrance is incorporated into a product
selected
from perfumes, colognes, candles, toilet waters, cosmetic products, personal
care products,
fabric care products, cleaning products and air fresheners.
3. The method of claim 2 wherein the cleaning product is selected from the
group
consisting of soaps, detergents, dishwashing compositions, scrubbing compounds
and
window cleaners.
4. The method of claim 2 wherein the product is a personal care product.
5. The method of claim 1 wherein the olfactory acceptable amount is from about
0.005
to about 20 weight percent.
6. The method of claim 1 wherein the olfactory acceptable amount is from about
0.1 to
about 10 weight percent.
7. The method of claim 1 wherein the olfactory acceptable amount is from about
0.5 to
about 5 weight percent.
8. The compound 4H-indeno[4,5-D]-1,3-dioxole, 3A, 5, 6, 7, 8, 8B-hexahydro-
2,2,6,6,7,
8,8 -heptamethyl.
9. A fragrance formulation comprising an olfactory effective amount of the
compound
of claim 8.
10. The fragrance formulation of claim 9 which is incorporated into a product
selected
from the group selected from perfumes, colognes, toilet waters, personal care
products,
cosmetics, cleaning products, candles and air fresheners.

11. The fragrance formulation of claim 10 wherein the cleaning product is
selected from
detergents, fabric conditioners, dishwashing compositions, scrubbing compounds
and window
cleaners.
12. The fragrance formulation of claim 10 wherein the personal care product is
selected
from soaps, bath and shower gels, body washes, and hair care products.
13. A process for making the compound of claim 8 comprising the reaction of 2H-
indeno[4,5]-boxirene, 1A,3,4,5,6,6B-hexahydro-4,4,5,6,6-pentamethylindan,
4,5,epoxy-
4,5,6,7-tetrahydro-1,1,2,3,3-pentamethyl and acetone.
14. The process of claim 13 conducted in the presence of BF3#Et2O.
11

Description

CA 02484354 2010-12-06
ACETONIDE FRAGRANCE COMPOUND
Field of the Invention
The present invention is directed to a novel compound and the use of this
novel
compound as a fragrance chemical suitable for incorporation in fine
fragrances, cosmetics,
toiletries and related applications.
Background of the Invention
There is an ongoing need in the fragrance industry to provide new chemicals to
give
perfumers and other persons ability to create new fragrances for perfumes,
colognes and
personal care products.
US Patent No. 4,902,840 discloses the use of substituted tetrahydroindane
derivatives
as useful fragrance chemicals. U.S. Patent 6,303,798 discloses the use of
4,4a,5,6,7,8,9,9b-
octahydro-7,7,8,9,9-pentamethyl-indano[4,5-d] -dioxin as a fragrance chemical.
Despite this disclosure and numerous other patents on fragrance materials,
there is a
continuing need to provide additional fragrance materials such that perfumers
may create new
fragrances for various applications.
Summary of the Invention
The present invention provides a novel chemical, and the use of this chemical
to
enhance the fragrance of perfumes, toilet waters, colognes, personal products
and the like. In
addition, the present invention is directed to the use of the novel chemical
to enhance
fragrance in perfumes, toilet waters, colognes, personal products and the
like.
1

CA 02484354 2004-10-08
More specifically, the present invention is directed to the novel compound,
4,4a,5,6,7,8,9,9b-octahydro-7,7,8,9,9-pentamethyl-indano[4,5-d]-dioxin, which
is
understood to be represented by the formula below.
Despite this disclosure and numerous other patents on fragrance materials,
there is a
continuing need to provide additional fragrance materials such that perfumers
may create
new fragrances for various applications.
Summary of the Invention
The present invention is directed to the compound 4H-indeno[4,5-D]-l,3-
dioxole,
3A, 5, 6, 7, 8, 8B -hexahydro - 2,2,6,6,7, 8,8 -heptamethyl use of 4H-
indeno[4,5-D]-l,3-
dioxole, 3A, 5, 6, 7, 8, 8B -hexahydro - 2,2,6,6,7, 8,8 -heptamethyl as a
fragrance chemical
to enhance fragrance in perfumes, toilet waters, colognes, personal products
and the like.
More specifically, the present invention is direct to the compound having the
structure set
forth below as well as a method for enhancing a perfume by incorporating an
olfactory
acceptable amount of compounds ofthe formula:
O
These and other embodiments of the present invention will be apparent by
reading
the following specification.
IFF-62 Specification -2-

CA 02484354 2004-10-08
Retailed Description of the Invention
The compound 4H-indeno[4,5-D]-1,3-dioxole, 3A, 5, 6, 7, 8, 8B -hexahydro -
2,2,6,6,7, 8,8 -heptamethyl is well suited for incorporation in fragrance
formulations. The
preparation ofthe 4H-indeno[4,5-D]-1,3-dioxole, 3A, 5, 6, 7, 8, 8B -hexahydro-
2,2,6,6,7,8,8-heptamethyl is set forth in Example 1 below.
We have discovered that 4H-indeno[4,5-D]-1,3-dioxole, 3A, 5, 6, 7, 8, 8B -
hexahydro- 2,2,6,6,7, 8,8 -heptamethyl has a woody or mossy, odor or note,
that is well
suited for use as a fragrance chemical.
Those with skill in the art will appreciate that novel compound ofthe present
invention has various isomers. As used throughout this specification 4H-
indeno[4,5-D]-l,3-
dioxole, 3A, 5, 6, 7, 8, 8B -hexahydro - 2,2,6,6,7, 8,8 -heptamethyl includes
various
isomers and isomer blends. The isomers include, but are not limited to the
isomers set forth
below:
IFF-62 Specification -3-

CA 02484354 2004-10-08
-4-C) -4- 0 0
0 0 0
4-ol _)_0
0 0- o.
__~Lo _~Lo
0, o,
These isomers can be prepared by techniques known in the art. Such techniques
include but
are not limited to stereoselective dihydroxylation. Other techniques for
separating the
isomers include distillation and other techniques suitable for separating
isomers. The
present invention contemplates the use of the stereoisomer mixtures as well as
the
preparation and/or isolation of the selective isomers.
The use of this novel compound is widely applicable in current perfumery
products,
including the preparation of perfumes and colognes, the perfuming of personal
care
products, such as soaps, bath and shower gels, body washes, and hair care
products as well
as air fresheners, candles and cosmetic products including but not limited to
mascara, make-
up, eyebrow liner, eyebrow pencil, rouge, cake make-up and the like. The
compound can
IFF-62 Specification -4-

CA 02484354 2010-12-06
also be used to perfume candles and cleaning agents, such as, but not limited
to soaps,
detergents, dishwashing materials, scrubbing compositions, window cleaners,
and the like.
In these preparations, the compound of the present invention can be used alone
or in
combination with other fragrance compositions, solvents, adjuvants and the
like. Those with
skill in the art will appreciate the nature and variety of the other
ingredients that can be used
in combination with the compound of the present invention.
Many types of fragrances can be employed in the present invention, the only
limitation being the compatibility with the other components being employed.
Suitable
fragrances include but are not limited to fruits such as almond, apple,
cherry, grape, pear,
pineapple, orange, strawberry, raspberry; musk, flower scents such as lavender-
like, roselike,
iris-like, and carnation-like. Other pleasant scents include herbal and
woodland scents derived
from pine, spruce and other forest smells. Fragrances may also be derived from
various oils,
such as essential oils, or from plant materials such as peppermint, spearmint
and the like.
A list of suitable fragrances is provided in U.S. Patent No. 4,534,891.
Another source
of suitable fragrances is found in Perfumes, Cosmetics and Soaps, Second
Edition, edited by
W. A. Poucher, 1959. Among the fragrances provided in this treatise are
acacia, cassie,
chypre, cyclamen, fern, gardenia, hawthorn, heliotrope, honeysuckle, hyacinth,
jasmine, lilac,
lily, magnolia, mimosa, narcissus, freshly-cut hay, orange blossom, orchid,
reseda, sweet pea,
trefle, tuberose, vanilla, violet, wallflower, and the like.
As used herein olfactory effective amount is understood to mean the amount of
fragrance ingredient in perfume compositions the individual component will
contribute to its
particular olfactory characteristics, but the olfactory effect of the perfume
composition will be
the sum of the effects of each of the perfume or fragrance ingredients. Thus
the 30 ingredients
of the invention can be used to alter the aroma characteristics of the perfume
composition by
modifying the olfactory reaction contributed by another ingredient in the
5

CA 02484354 2004-10-08
composition. The amount will vary depending on many factors including other
ingredients,
their relative amounts and the effect that is desired.
The level of compound of the invention employed in the perfumed article varies
from about 0.005 to. about 20 weight percent, preferably from about 0.01 to
about 10 and
most preferably from about 0.5 to about 5 weight percent. In addition to the
fragrance
compound ofthe present invention, other agents can be used in conjunction with
the
fragrance. Well known materials such as surfactants, emulsifiers, and polymers
to
encapsulate the fragrance can also be employed without departing from the
scope of the
present invention.
Another method of reporting the level of the fragrance compound of the
invention
in the perfumed composition, i.e., the compounds as a weight percentage ofthe
materials
added to impart the desired fragrance. The compounds of the invention can
range widely
from 0.005 to about 10 weight percent of the perfumed composition, and
preferably from
about 0.1 to about 5 weight percent. Those with skill in the art will be able
to employ the
desired level of the compound of the invention to provide the desired
fragrance and
intensity.
The following are provided as specific embodiments ofthe present invention.
Other
modifications of this invention will be readily apparent to those .skilled in
the. art, without
departing from the scope of this invention. As used herein all percentages are
weight
percent unless noted to the contrary.
IFF-62 Specification -6-
- :n, ..'F.Y. Y{v-~ SYI`-C Sfl lA r.. JA nmx

CA 02484354 2010-12-06
EXAMPLE 1
PREPARATION OF 4H-INDENO14,5-D1-1,3-DIOXOLE, 3 A, 5,6,7,8, 8B -
HEXAHYDRO - 2,2,6,6,7,8,8 -HEPTAMETHYL
A three liter, four neck flask equipped with a stirrer with stir shaft,
thermometer,
thermowatch, water condenser, addition funnel and isopropyl alcohol / dry ice
cooling bath
was charged with 15 grams of BF3#Et2O and 500 grams of acetone. Five hundred
grams of the
epoxide, 2H-indeno[4,5]-boxirene, 1A,3,4,5,6,6B-hexahydro-4,4,5,6,6-
pentamethylindan,
4,5,epoxy-4,5,6,7-tetrahydro-1,1,2,3,3-pentamethyl (48% by weight) was fed to
the reaction
flask over a period of two hours. Synthesis of the above epoxy material is
described in U.S.
Patent 4,902,840. The resulting reaction was exothermic and the cooling bath
was used to
control the reaction temperature to 25-30 C. After the epoxide addition was
concluded the
reaction was allowed to age for an additional 30 minutes. Water was added to
quench the
reaction and the layers were separated. The organic phase was washed with
saturated Na2CO3
solution. The crude product was recovered [about 513 grams] and was distilled
to provide 133
grams of the acetonide, which is about a 43% theoretical yield.
1H NMR (360 MHz, CDC13) 4.55 (d, 1H), 4.27 (m, 1H), 2.07 (m, 1H), 1.89 (m,
2H), 1.69
(m, 1H), 1.54 (q, 1H), 1.38 (s, 6H), 1.05 (s, 3H), 1.01 (s, 3H), 0.95 (d, 3H),
0.87 (s, 3H), 0.86
(s, 3H).
7

CA 02484354 2004-10-08
EXAMPLE 2
FRAGRANCE COMPOSITIQN CONTAINING THE COMPOUND OF THE
PRESENT. INVENTION
DPG is understood to mean dipropylene glycol. Unless noted to the contrary all
of
the following fragrance materials are available from International Flavors &
Fragrances
Inc., New York, NY.
Material Parts
ARMOISE ESSENCE 5.0
AMBRETTOLIDE 1% in DPG 30
Citronellol 40
Alpha-damascone 10% DEP (Firmenich) 1
Dimethyl benzyl carbinyl butyrate 2
DPG 88
4-Ethyloctanal 20
FLOROL (Firmenich) 6
FRUCTONE 11
Galbasconel%(DPG) 60
Ginger Oil 1.0
Iso cyclo Citral I% DPG 1.0
KOAVONE (IFF) 36
LIFFAROME "PFG" 10% in DPG 40
Litsea cubeba oil 15
MAGNOLAN (Haarman & Reimer) 9
IFF-62 Specification -8-

CA 02484354 2004-10-08
Material Parts
Magnolia flower oil 10% in DEP 4.0
MAGNOLAN 9.0
Phenyl acetaldehyde (50%) 2.5
Phenyl ethyl alcohol 130
Rose oxide 10% in DPG 13
Triplal Extra 5.5
VELOUTONE 10% in DPG (Firmenich) 25
TOTAL 550.0
The compound ofthe present invention was admixed in DPG to form a 10%
solution. Ninety parts ofthe second solution was admixed with the above
fragrance
formulation. The resulting formulation was described as having a green, mossy
note,
partially through the incorporation of4H-indeno[4,5-D]-1,3-dioxole, 3A, 5, 6,
7, 8, 8B -
hexahydro - 2,2,6,6,7, 8,8 -heptamethyl.
The above fragrance formulation was presented to demonstrate the effectiveness
of
the compound of the present invention in enhancing, improving or modifying the
performance of the formulations in which it is incorporated.
IFF-62 Specification -9-