Field of the Invention
The present invention relates to new chemical entities
and the incorporation and use of the a novel compound and the use of this new molecule
as fragrance chemicals.
Background of the Invention
U.S. Patent Numbers 2,947,780 and 6,632, 788 among various
other patents disclose cyclic chemicals that are suitable for use as fragrance chemicals.
Those with skill in the art appreciate how differences in the chemical structure
of the molecule can result in significant differences in the odor, notes and characteristics
of a molecule. These variations and the ongoing need to discover and use the new
chemicals in the development of new fragrances allow perfumers to apply the new
compounds in creating new fragrances.
Summary of the Invention
The present invention provides a novel molecule, and the
use of the molecule 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 chemicals to enhance fragrance in perfumes, toilet waters,
colognes, personal products and the like.
More specifically, the present invention is directed to
the novel compound, cyclohexanbutanol, 4-(hydroxymethyl)- alpha, alpha-dimethyl
-, set forth below:
Another embodiment of the invention is a method for enhancing
a fragrance by incorporating an olfactory acceptable amount of cyclohexanbutanol,
4-(hydroxymethyl)- alpha, alpha-dimethyl -. These and other embodiments of the present
invention will be apparent by reading the following specification.
Detailed Description of the Invention
The novel compound of the present invention can be prepared
as described more completely in the examples that follow.
Cyclohexanbutanol, 4-(hydroxymethyl)- alpha, alpha-dimethyl
-, has a fatty, floral, fresh fragrance, with green notes.
The use of the compound of the present invention is widely
applicable in current perfumery products, including the preparation of perfumes
and colognes, the perfuming of personal care products such as soaps, shower gels,
and hair care products as well as air fresheners and cosmetic preparations. The
present invention can also be used to perfume cleaning agents, such as, but not
limited to detergents, dishwashing materials, scrubbing compositions, window cleaners
and the like. In these preparations, the compounds of the present invention can
be used alone or in combination with other perfuming compositions, solvents, adjuvants
and the like. The nature and variety of the other ingredients that can also be employed
are known to those with skill in the art.
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, rose-like, iris-like, 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. Pat.
No. 4,534,891, the contents of which are incorporated by reference as if set forth
in its entirety. 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.
Olfactory effective amount is understood to mean the amount
of compound 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 perfumes or fragrance
ingredients. Thus the compounds of the invention can be used to alter the aroma
characteristics of the perfume composition, or by modifying the olfactory reaction
contributed by another ingredient in the 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
fragranced article varies from about 0.005 to about 10 weight percent, preferably
from about 0.5 to about 8 and most preferably from about 1 to about 7 weight percent.
In addition to the compounds other agents can be used in conjunction with the fragrance.
Well known materials such as surfactants, emulsifiers, 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 compounds
of the invention in the perfumed composition, i.e., the compounds as a weight percentage
of the materials added to impart the desired fragrance. The compounds of the invention
can range widely from 0.005 to about 70 weight percent of the perfumed composition,
preferably from about 0.1 to about 50 and most preferably from about 0.2 to about
25 weight percent. Those with skill in the art will be able to employ the desired
level of the compounds of the invention to provide the desired fragrance and intensity.
All U.S. patents and patent applications cited herein are
incorporated by reference as if set forth in their entirety. The reader is directed
to read them now and to read their content as part of the disclosure of this patent
The following are provided as specific embodiments of the
present invention. Other modifications of this invention will be readily apparent
to those skilled in the art. Such modifications are understood to be within the
scope of this invention. As used herein all percentages are weight percent unless
otherwise noted, ml is understood to be milliliters, DPG is dipropylene glycol,
g is understood to be grams. All of the fragrance ingredients used in the following
examples are available from International Flavors & Fragrances Inc., Hazlet, N.J.,
PREPARATION OF CYCLOHEXANBUTANOL, 4-(HYDROXYMETHYL)- ALPHA, ALPHA-DIMETHYL -
1200 grams of LYRAL (IFF) was fed into an 18 inch column
that contained palladium and Al2O3 (18grams). Isopropyl alcohol
(260 grams) was fed to the column as well as hydrogen at a temperature of 120ºC
and 600 pounds per square inch.
The reaction was allowed to run for approximately 27 hours.
The NMR data for the resulting product was the following:
USE OF THE COMPOUND IN A FRAGRANCE
- 1.2 ppm (s,6H), 1.23-1.8 ppm (m, 14H), 1.97ppm (bs, 1H), 2.5 ppm (bs, 1H),
- 3.48 ppm (d, 2H)
A fragrance was prepared according to the following formulation,
all weights are in grams:
Hexyl Cinnamic Aldehyde
4-(Hydroxymethyl)- Alpha, Alpha-Dimethyl -
Indolarome 10% DPG
Iso E Super
Phenyl Ethyl Alcohol
This fragrance was described as having a floral note which
was enhanced by the incorporation of the cyclohexanbutanol, 4-(hydroxymethyl)- alpha,