U.S. patent application number 13/369420 was filed with the patent office on 2013-06-27 for novel decenal mixtures and their use in perfume compositions.
The applicant listed for this patent is Edward Mark Arruda, Anubhav P.S. Narula, Franc T. Schiet. Invention is credited to Edward Mark Arruda, Anubhav P.S. Narula, Franc T. Schiet.
Application Number | 20130165532 13/369420 |
Document ID | / |
Family ID | 48538347 |
Filed Date | 2013-06-27 |
United States Patent
Application |
20130165532 |
Kind Code |
A1 |
Narula; Anubhav P.S. ; et
al. |
June 27, 2013 |
NOVEL DECENAL MIXTURES AND THEIR USE IN PERFUME COMPOSITIONS
Abstract
The present invention relates to a novel decenal mixture and the
incorporation and use of this mixture as a fragrance material. The
novel decenal mixture contains decenals that are represented by the
formula set forth below: ##STR00001## wherein the broken line
represents one double bond and two single bonds.
Inventors: |
Narula; Anubhav P.S.;
(Hazlet, NJ) ; Arruda; Edward Mark; (Easton,
PA) ; Schiet; Franc T.; (Naarden, NL) |
|
Applicant: |
Name |
City |
State |
Country |
Type |
Narula; Anubhav P.S.
Arruda; Edward Mark
Schiet; Franc T. |
Hazlet
Easton
Naarden |
NJ
PA |
US
US
NL |
|
|
Family ID: |
48538347 |
Appl. No.: |
13/369420 |
Filed: |
February 9, 2012 |
Related U.S. Patent Documents
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Application
Number |
Filing Date |
Patent Number |
|
|
61579642 |
Dec 22, 2011 |
|
|
|
Current U.S.
Class: |
514/772 ;
510/101; 512/27 |
Current CPC
Class: |
A61K 8/33 20130101; A61Q
13/00 20130101; A61K 2800/591 20130101 |
Class at
Publication: |
514/772 ; 512/27;
510/101 |
International
Class: |
A61K 8/33 20060101
A61K008/33; C11D 3/50 20060101 C11D003/50; A61Q 13/00 20060101
A61Q013/00 |
Claims
1. (canceled)
2. A fragrance formulation comprising a mixture of dec-6-enal,
dec-7-enal, and dec-8-enal, wherein the mixture contains about
8-22% by weight of dec-6-enal, about 20-43% by weight of
dec-7-enal, and about 35-59% by weight of dec-8-enal.
3. The fragrance formulation of claim incorporated into a product
selected from the group consisting of a perfume, a cologne, toilet
water, a cosmetic product, a personal care product, a fabric care
product, a cleaning product, and an air freshener.
4. The fragrance formulation of claim 3, wherein the cleaning
product is selected from the group consisting of a detergent, a
dishwashing composition, a scrubbing compound, and a window
cleaner.
5. The fragrance formulation of claim 3, wherein the mixture is
incorporated at a level of from about 0.005 to about 50 weight
percent of the product.
6. The fragrance formulation of claim 3, wherein the mixture is
incorporated at a level of from about 0.5 to about 25 weight
percent of the product.
7. The fragrance formulation of claim 3, wherein the mixture is
incorporated at a level of from about 1 to about 10 weight percent
of the product.
8. (canceled)
9. A method of improving, enhancing or modifying a fragrance
formulation through the addition of an olfactory acceptable amount
of a mixture of dec-6-enal, dec-7-enal, and dec-8-enal, wherein the
mixture contains about 8-22% by weight of dec-6-enal, about 20-43%
by weight of dec-7-enal, and about 35-59% by weight of
dec-8-enal.
10. The method of claim 9, wherein the olfactory acceptable amount
is from about 0.005 to about 50 weight percent of the fragrance
formulation.
11. The method of claim 9, wherein the olfactory acceptable amount
is from about 0.5 to about 25 weight percent of the fragrance
formulation.
12. The method of claim 9, wherein the olfactory acceptable amount
is from about 1 to about 10 weight percent of the fragrance
formulation.
13. (canceled)
14. A fragrance product comprising a mixture of dec-6-enal,
dec-7-enal, and dec-8-enal, wherein the mixture contains about
8-22% by weight of dec-6-enal, about 20-43% by weight of
dec-7-enal, and about 35-59% by weight of dec-8-enal.
Description
STATUS OF RELATED APPLICATIONS
[0001] This application claims priority to U.S. provisional patent
application Ser. No. 61/579,642, filed Dec. 22, 2011, the contents
of which are incorporated herein by reference.
FIELD OF THE INVENTION
[0002] The present invention relates to novel decenal mixtures and
the incorporation and use of these mixtures as fragrance
materials.
BACKGROUND OF THE INVENTION
[0003] There is an ongoing need in the fragrance industry to
provide chemicals with strong odors so that less fragrance is
needed to accomplish the desired odor effect. This, therefore,
gives perfumers and other persons the freedom to create new
fragrances for perfumes, colognes and personal care products
without the limitation of cost. In addition to odor strength,
practical considerations such as the scale of synthesis operation
may also determine the applicability of identified fragrance
molecules in commercial use. However, whether the production of a
given fragrance molecule can be carried out at a commercial scale
is sometimes unpredictable. For these reasons, continuous effort
has been made in fragrance industry to investigate and develop
economical processes for making fragrance molecules that possess
high strength.
[0004] One skilled person recognizes and appreciates the
combinations of existing fragrance ingredients that possess
superior effect when compared to individual ingredients. Such
combinations are considered unexpected and inventive (See, for
example, U.S. Pat. No. 7,767,640 and U.S. Pat. No. 7,846,886).
[0005] Dec-6-enal is identified as a flavorant in dry parsley (See,
Masanetz et al.). Dec-7-enal is employed to reduce the alcohol odor
and alcohol sting, but it acts differently from a traditional
perfume, wherein a traditional perfume overpowers the alcohol odor
or sting by making compositions smell like the perfume (See, U.S.
Pat. No. 5,843,881). Dec-8-enal falls under a generic structure
that is disclosed as having potential fragrance use (See, U.S.
Publication No. 2011/0142776). However, the generic structure as
taught covers a wide range of compounds and the synthetic method as
described cannot lead to the synthesis of dec-8-enal.
[0006] Thus, dec-6-enal, dec-7-enal, and dec-8-enal were each
individually reported since early 1990's with various flavor and
fragrance properties. They were extracted from natural resources or
synthesized via methods that required multi-steps and suffered from
long reaction times leading to complex and expensive procedures. To
date, none of dec-6-enal, dec-7-enal, and dec-8-enal has achieved
commercial importance as a fragrance material. More importantly,
nothing set forth in the prior art discloses a mixture of
dec-6-enal, dec-7-enal, and dec-8-enal having specified ratios.
[0007] The present invention has discovered a convenient and
economical process that provides a novel mixture of dec-6-enal,
dec-7-enal, and dec-8-enal. The present invention has further
surprisingly and unexpectedly discovered that this novel decenal
mixture, only when in specified mixing ratios, possesses desirable
fragrance properties of high strength that are suitable for
fragrance application.
SUMMARY OF THE INVENTION
[0008] The present invention provides a novel decenal mixture and
its unexpected advantageous use in enhancing, improving or
modifying the fragrance of perfumes, colognes, toilet water, fabric
care products, personal products and the like.
[0009] More specifically, the novel decenal mixture contains
decenals that are represented by Formula I set forth below:
##STR00002##
wherein the broken line represents one double bond and two single
bonds.
[0010] Another embodiment of the present invention relates to a
fragrance composition comprising the novel mixture provided
above.
[0011] Another embodiment of the present invention relates to a
fragrance product comprising the novel mixture provided above.
[0012] Another embodiment of the present invention relates to a
method of improving, enhancing or modifying a fragrance formulation
through the addition of an olfactory acceptable amount of the novel
mixture provided above.
[0013] Another embodiment of the present invention relates to a
method of making the novel mixture provided above.
[0014] These and other embodiments of the present invention will be
apparent by reading the following specification.
DETAILED DESCRIPTION OF THE INVENTION
[0015] The decenals of the present invention may be represented by
the following structures:
##STR00003##
[0016] Those with the skill in the art will appreciate that
[0017] Formula II is dec-6-enal;
[0018] Formula III is dec-7-enal; and
[0019] Formula IV is dec-8-enal.
[0020] The present invention relates to a mixture of dec-6-enal,
dec-7-enal, and dec-8-enal.
[0021] The present invention further relates to a mixture of
dec-6-enal (.about.8-22% by weight), dec-7-enal (.about.20-43%),
and dec-8-enal (.about.35-59%) that possesses desirable and useful
fragrance properties.
[0022] The decenals of the present invention can be prepared from
9-decenol (Rosalva, commercially available at International Flavors
& Fragrances Inc.) according to the reaction scheme below, the
details of which are specified in the Examples. Materials were
purchased from Aldrich Chemical Company unless noted otherwise.
##STR00004##
[0023] Additionally, specific ratios of dec-6-enal (Formula II),
dec-7-enal (Formula III), and dec-8-enal (Formula IV) were
obtained.
[0024] It has been surprisingly and unexpectedly found that there
exist criticality to the mixing ratios of dec-6-enal, dec-7-enal,
and dec-8-enal. Specifically, only a decenal mixture containing
dec-6-enal (.about.8-22% by weight), dec-7-enal (.about.20-43%),
and dec-8-enal (.about.35-59%) has been found to possess desirable
and useful fragrance properties of high strength while a mixing
ratio outside the specified ranges will cause off-notes and render
the decenal mixture unsuitable for fragrance use. Thus, the present
invention relates to the surprising and unexpected discovery of the
criticality of the mixing ratios in the dec-6-enal, dec-7-enal, and
dec-8-enal mixture.
[0025] Those with skill in the art will recognize that, if needed,
the isomeric products obtained as described above can be further
separated using techniques known to those with skill in the art.
Suitable techniques include, for example, distillation and
chromatography such as high performance liquid chromatography,
referred to as HPLC, particularly silica gel chromatograph, and gas
chromatography trapping known as GC trapping. Yet, commercial
products are mostly offered as isomeric mixtures.
[0026] The use of the decenal mixtures 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,
fabric care products, 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.
[0027] In these preparations, the decenal mixtures 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.
[0028] 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.
[0029] The decenal mixtures of the present invention can be used in
combination with a complementary fragrance compound. The term
"complementary fragrance compound" as used herein is defined as a
fragrance compound selected from the group consisting of
2-[(4-methylphenyl)methylene]-heptanal (Acalea), iso-amyl oxyacetic
acid allylester (Allyl Amyl Glycolate),
(3,3-dimethylcyclohexyl)ethyl ethyl propane-1,3-dioate (Applelide),
(E/Z)-1-ethoxy-1-decene (Arctic al),
2-ethyl-4-(2,2,3-trimethyl-3-cyclo-penten-1-yl)-2-buten-1-ol
(Bacdanol),
2-methyl-3-[(1,7,7-trimethylbicyclo[2.2.1]hept-2-yl)oxy]
exo-1-propanol (Bornafix),
1,2,3,5,6,7-hexahydro-1,1,2,3,3-pentamethyl-4H-inden-4-one
(Cashmeran), trimethylcyclopentenylmethyloxabicyclooctane
(Cassiffix), 1,1-dimethoxy-3,7-dimethyl-2,6-octadiene (Citral DMA),
3,7-dimethyl-6-octen-1-ol (Citronellol),
3A,4,5,6,7,7A-hexahydro-4,7-methano-1H-inden-5/6-yl acetate
(Cyclacet), 3A,4,5,6,7,7A-hexahydro-4,7-methano-1H-inden-5/6-yl
propinoate (Cyclaprop),
3A,4,5,6,7,7A-hexahydro-4,7-methano-1G-inden-5/6-yl butyrate
(Cyclobutanate),
1-(2,6,6-trimethyl-3-cyclohexen-1-yl)-2-buten-1-one (Delta
Damascone), 3-(4-ethylphenyl)-2,2-dimethyl propanenitrile
(Fleuranil), 3-(O/P-ethylphenyl) 2,2-dimethyl propionaldehyde
(Floralozone), tetrahydro-4-methyl-2-(2-methylpropyl)-2H-pyran-4-ol
(Floriffol),
1,3,4,6,7,8-hexahydro-4,6,6,7,8,8-hexamethylcyclopenta-gamma-2-benzopyran
(Galaxolide), 1-(5,5-dimethyl-1-cyclohexen-1-yl)pent-4-en-1-one
(Galbascone), E/Z-3,7-dimethyl-2,6-octadien-1-yl acetate (Geranyl
Acetate), .alpha.-methyl-1,3-benzodioxole-5-propanal (Helional),
1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-1,6-heptadien-3-one
(Hexalon), (Z)-3-hexenyl-2-hydroxybenzoate (Hexenyl Salicylate,
CIS-3), 4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one (Ionone
.alpha.),
1-(1,2,3,4,5,6,7,8-octahydro-2,3,8,8-tetramethyl-2-naphthalenyl)-ethan-1--
one (Iso E Super), methyl 3-oxo-2-pentylcyclopentaneacetate
(Kharismal), 2,2,4-trimethyl-4-phenyl-butanenitrile (Khusinil),
3,4,5,6,6-pentamethylhept-3-en-2-one (Koavone),
3/4-(4-hydroxy-4-methyl-pentyl) cyclohexene-1-carboxaldehyde
(Lyral),
3-methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one
(Methyl Ionone .gamma.), 1-(2,6,6-trimethyl-2-cyclohexen-1-yl)
pent-1-en-3-one (Methyl Ionone .alpha. Extra, Methyl Ionone N),
3-methyl-4-phenylbutan-2-ol (Muguesia), cyclopentadec-4-en-1l-one
(Musk Z4),
3,3,4,5,5-pentamethyl-11,13-dioxatricyclo[7.4.0.0<2,6>]tridec--
2(6)-ene (Nebulone), 3,7-dimethyl-2,6-octadien-1-yl acetate (Neryl
Acetate), 3,7-dimethyl-1,3,6-octatriene (Ocimene),
ortho-tolylethanol (Peomosa), 3-methyl-5-phenylpentanol
(Phenoxanol), 1-methyl-4-(4-methyl-3-pentenyl)
cyclohex-3-ene-1-carboxaldehyde (Precyclemone B),
4-methyl-8-methylene-2-adamantanol (Prismantol),
2-ethyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol
(Sanjinol),
2-methyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol
(Santaliff), Terpineol, 2,4-dimethyl-3-cyclohexene-1-carboxaldehyde
(Triplal), decahydro-2,6,6,7,8,8-hexamethyl-2H-indeno [4,5-B] furan
(Trisamber), 2-tert-butylcyclohexyl acetate (Verdox),
4-tert-butylcyclohexyL acetate (Vertenex), acetyl cedrene
(Vertofix), 3,6/4,6-dimethylcyclohex-3-ene-1-carboxaldehyde
(Vertoliff), and (3Z)-1-[(2-methyl-2-propenyl)oxy]-3-hexene
(Vivaldie).
[0030] The terms "fragrance formulation", "fragrance composition",
and "perfume composition" mean the same and refer to a consumer
composition that is a mixture of compounds including, for example,
alcohols, aldehydes, ketones, esters, ethers, lactones, nitriles,
natural oils, synthetic oils, and mercaptans, which are admixed so
that the combined odors of the individual components produce a
pleasant or desired fragrance. The fragrance formulation of the
present invention is a consumer composition comprising the decenal
mixtures of the present invention. The fragrance formulation of the
present invention comprises the decenal mixtures of the present
invention and further a complementary fragrance compound as defined
above.
[0031] The term "fragrance product" means a consumer product that
adds a fragrance or masks a malodor. Fragrance products may
include, for example, perfumes, colognes, personal care products
such as soaps, shower gels, and hair care products, fabric
products, air fresheners, cosmetic preparations, and perfume
cleaning agents such as detergents, dishwashing materials,
scrubbing compositions, and window cleaners. The fragrance product
of the present invention is a consumer product that contains the
decenal mixtures of the present invention. The fragrance product of
the present invention contains the decenal mixtures of the present
invention and further a complementary fragrance compound as defined
above.
[0032] The term "improving" in the phrase "improving, enhancing or
modifying a fragrance formulation" is understood to mean raising
the fragrance formulation to a more desirable character. The term
"enhancing" is understood to mean making the fragrance formulation
greater in effectiveness or providing the fragrance formulation
with an improved character. The term "modifying" is understood to
mean providing the fragrance formulation with a change in
character.
[0033] Olfactory acceptable 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
decenal mixtures 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.
[0034] The amount of the decenal mixtures of the present invention
employed in a fragrance formulation varies from about 0.005 to
about 70 weight percent, preferably from 0.005 to about 50 weight
percent, more preferably from about 0.5 to about 25 weight percent,
and even more preferably from about 1 to about 10 weight percent.
Those with skill in the art will be able to employ the desired
amount to provide desired fragrance effect and intensity. In
addition to the decenal mixtures of the present invention, other
materials can also be used in conjunction with the fragrance
formulation. 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.
[0035] When used in a fragrance formulation these ingredients
provide powerful, clean, aldehydic, crispy, green, ambrette seed
like, sweet, bright, and melon notes to make the fragrance
formulation more desirable and noticeable, and add the perception
of value. The odor qualities found in this material assist in
beautifying and enhancing the finished accord as well as improving
the performance of the other materials in the fragrance.
[0036] 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,
ppm is understood to stand for parts per million, g is understood
to be gram, mg is understood to be milligram, and mmHg be
millimeters (mm) of mercury (Hg). IFF as used in the examples is
understood to mean International Flavors & Fragrances Inc., New
York, N.Y., USA.
EXAMPLE I
##STR00005##
[0037] Preparation of 6,7,8-Decene-1-ol (Mixture of 6-Decene-1-ol,
7-Decene-1-ol, and 8-Decene-1-ol)
[0038] A reaction flask was charged with toluene (500 g), 9-decenol
(Rosalva) (500 g), and rhodium trichloride (RhCl.sub.3) (1.25 g).
Water (2 g) was added. The reaction mixture was heated with
stirring to about 65-80.degree. C. The reaction mixture was heated
for about 20 hours till a steady state of 6,7,8-decene-1-ol isomers
was reached. The reaction mixture was then cooled. The organic
layer was transferred to a rush-over distillation flask and Primol
oil (15 g) was added. Toluene was then removed at atmospheric
pressure. The crude product was distilled to afford
6,7,8-decene-1-ol (463 g) having a boiling point of 98.degree. C.
at a pressure of 3.2 mmHg The broken line in the above formula of
6,7,8-decene-1-ol represents one double bond and two single
bonds.
[0039] 6,7,8-Decene-1ol was described as having aldehydic, green,
floral, rosy, and waxy notes.
EXAMPLE II
##STR00006##
[0041] Preparation of Dec-6-enal (Formulas II), Dec-7-enal
(Formulas III), And Dec-8-enal (Formulas IV)
[0042] A reaction flask was charged with Primol oil (100 g) and
Pricat catalyst (25 g, commercially available at Johnson Matthey
Catalysts). The reaction mixture was heated with stirring to about
250-290.degree. C. The mixture of 6,7,8-decene-1ol (238 g,
synthesized as above in EXAMPLE I) was then added slowly while the
temperature was maintained at about 290-295.degree. C. The reaction
was vented properly during the reaction. After the reaction was
completed, the reaction mixture was transferred into a distillation
flask and further fractional distillation afforded the mixture of
Formulas II, III, and IV (141 g) having a boiling point of
80.degree. C. at a pressure of 6.8-7.8mmHg It was surprisingly
found that the double bond position along the carbon chain could be
specified and only careful control of the reaction conditions in
both steps (EXAMPLEs I and II) would lead to the desired decenal
isomers.
[0043] Dec-6-enal:
[0044] .sup.1H NMR: 9.76 ppm (br, 1H), 5.30-5.50 ppm (m, 2H), 2.42
ppm (t, 2H, J=7.4 Hz), 1.90-2.13 ppm (m, 4H), 1.54-1.73 ppm (m,
2H), 1.20-1.45 ppm (m, 4H), 0.88 ppm (t, 3H, J=7.4 Hz)
[0045] Dec-7-enal:
[0046] .sup.1H NMR: 9.76 ppm (br, 1H), 5.30-5.50 ppm (m, 2H), 2.42
ppm (t, 2H, J=7.4 Hz), 1.90-2.13 ppm (m, 4H), 1.54-1.73 ppm (m,
4H), 1.20-1.45 ppm (m, 2H), 0.96 ppm (t, 3H, J=7.4 Hz)
[0047] Dec-8-enal:
[0048] .sup.1H NMR: 9.76 ppm (br, 1H), 5.30-5.50 ppm (m, 2H), 2.42
ppm (t, 2H, J=7.4 Hz), 1.90-2.13 ppm (m, 2H), 1.63 ppm (br, s, 3H),
1.54-1.73 ppm (m, 2H), 1.20-1.45 ppm (m, 6H)
EXAMPLE III
Preparation And Evaluation of Dec-6-enal, Dec-7-enal, And
Dec-8-enal Mixture of Different Ratios
[0049] The decenal mixture (synthesized as above in EXAMPLE II) was
further carefully distilled through a GOODLOE column with high
theoretical plates to afford a series of decenal mixture of
different mixing ratios.
[0050] The following specific mixture samples were evaluated for
odor properties:
TABLE-US-00001 Decenal Mixture (% by weight) Sample Dec-6-enal
Dec-7-enal Dec-8-enal Odor Profile 1 3 46 51 Off notes, too
lactonic 2 2 33 65 Off notes, too fruity and too coconut 3 27 43 30
Dirty off notes, solventy, and phenolic 4 20 25 55 Strong, clean,
aldehydic, and crispy 5 22 20 58 Strong, clean, aldehydic, crispy,
and slightly green 6 9 38 53 Strong, clean, aldehydic, crispy
slightly green, bright, and melon 7 22 43 35 Strong, clean,
aldehydic, crispy, green, ambrette seed-like, and slightly sweet 8
12 31 47 Powerful, very clean, aldehydic, crispy, green, ambrette
seed-like, sweet, bright, and melon 9 19 33 40 Strong, clean,
aldehydic, crispy, slightly green, and slightly sweet 10 15 33 43
Strong, clean, aldehydic, crispy, slightly green, and slightly
sweet
[0051] The above evaluation yielded unexpected finding, samples
4-10 were surprisingly superior to samples 1, 2, and 3. There was
criticality to the mixing ratios of dec-6-enal, dec-7-enal, and
dec-8-enal. Specifically, only a decenal mixture containing
dec-6-enal (.about.8-22% by weight), dec-7-enal (.about.20-43%),
and dec-8-enal (.about.35-59%) were found to possess desirable
fragrance properties of high strength while a mixing ratio outside
the defined ranges caused off-notes which rendered the decenal
mixture unsuitable for fragrance use. Thus, the present invention
made surprising and unexpected discovery of the criticality of the
mixing ratios in dec-6-enal, dec-7-enal, and dec-8-enal
mixture.
EXAMPLE IV
[0052] The fragrance formula exemplified as follows demonstrated
that the addition of the mixture of dec-6-enal (22%), dec-7-enal
(43%), and dec-8-enal (35%) (Sample 7 as described in EXAMPLE III)
provided clean, aldehydic, crispy, green, ambrette seed-like, and
slightly sweet characters to the fragrance formula.
TABLE-US-00002 Ingredient Parts (g) Benzophenone 100 Cinnamic
Alcohol 50 Damascone, Delta 5 Decanol, n- 30 Dimethyl Benzyl
Carbinyl Acetate 50 Diphenyl Oxide 20 Dodecanol, n- 15 Ethyl Methyl
Phenyl Glycidate 5 Eugenol 10 Geraniol 60 Guaiacwood Oil 20 Ionone
Alpha 10 Iso E Super .RTM. 60 Methyl Ionone Gamma 65 Octanol, n- 10
Phenoxanol .RTM. 200 Phenyl Acetaldehyde Dimethyl Acetal 7 Phenyl
Ethyl Alcohol 100 Phenyl Methyl Carbinyl Acetate 20 Rose Oxide 5
Vertenex .RTM. 150 Decenal Mixture (Sample 7) 8 Total 1000
EXAMPLE V
[0053] The fragrance formula exemplified as follows demonstrated
that the addition of the mixture of dec-6-enal (15%), dec-7-enal
(33%), and dec-8-enal (43%) (Sample 10 as described in EXAMPLE III)
provided clean, aldehydic, crispy, slightly green, and slightly
sweet characters to the fragrance formula.
TABLE-US-00003 Ingredient Parts (g) Agrumea (Schiff base of Triplal
.RTM. 10 and Methyl Anthranilate) Allyl Cyclohexyl Proprionate 10
Ambroxan 2 Benzophenone 5 Cyclacet .RTM. 40 Cyclaprop .RTM. 40
Damascone Delta 8 Dihydro Myrcenol 65 Dimethyl Benzyl Carbinyl
Acetate 10 Diola 4 Diphen Oxide 2 Dodecanal, n- 2 Eugenol 4
Geraniol 60 Hexenyl Isobutyrate, Cis-3- 6 Hexyl Cinnamic Aldehyde
70 Ionone Alpha 4 Iso E Super .RTM. 100 Koavone .RTM. 20 Lavandin
Oil Grosso 20 Methyl Beta Naphtyl Ketone 2 Methyl Ionone Gamma 30
Nerol 30 Petitgrain Oil 2 Phenoxanol .RTM. 20 Phenoxy Ethyl
Isobutyrate 8 Phenyl Ethyl Alcohol 50 Prenyl Acetate 12 Rose Oxide
2 Sage Oil French 2 Salicynalva 90 Sanjinol 4 Phenyl Methyl
Carbinyl Acetate 15 Tetrahydro Myrcenol 50 Trimofix O 5
Undecalactone Gamma 20 Undecavertol 5 Verdox 70 Vertenex .RTM. HC
50 Vertofix .RTM. Coeur 30 Vertoliff 12 Violiff 5 Decenal Mixture
(Sample 10) 4 Total 1000
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