U.S. patent application number 16/429683 was filed with the patent office on 2019-09-26 for perfume compositions.
The applicant listed for this patent is The Procter & Gamble Company. Invention is credited to Steven Louis Diersing, Marc Adam Flickinger, Virginia Tzung-Hwei Hutchins, Jianjun Justin Li, David Arthur Sturgis, Steven Michael Wujek.
Application Number | 20190292488 16/429683 |
Document ID | / |
Family ID | 59859625 |
Filed Date | 2019-09-26 |
![](/patent/app/20190292488/US20190292488A1-20190926-D00001.png)
![](/patent/app/20190292488/US20190292488A1-20190926-D00002.png)
![](/patent/app/20190292488/US20190292488A1-20190926-D00003.png)
![](/patent/app/20190292488/US20190292488A1-20190926-D00004.png)
United States Patent
Application |
20190292488 |
Kind Code |
A1 |
Sturgis; David Arthur ; et
al. |
September 26, 2019 |
PERFUME COMPOSITIONS
Abstract
A perfume composition for improved release from a cyclodextrin
complex, wherein the perfume composition includes 10% or more, by
weight of the perfume, of one or more perfume raw materials having:
a cyclodextrin complex stability constant of about 3.0 or less, a C
log P of about 2.5 or less; and a weight average molecular weight
of about 200 Daltons or less.
Inventors: |
Sturgis; David Arthur;
(Montgomery, OH) ; Li; Jianjun Justin; (West
Chester, OH) ; Flickinger; Marc Adam; (West Chester,
OH) ; Hutchins; Virginia Tzung-Hwei; (Cincinnati,
OH) ; Diersing; Steven Louis; (Cincinnati, OH)
; Wujek; Steven Michael; (Loveland, OH) |
|
Applicant: |
Name |
City |
State |
Country |
Type |
The Procter & Gamble Company |
Cincinnati |
OH |
US |
|
|
Family ID: |
59859625 |
Appl. No.: |
16/429683 |
Filed: |
June 3, 2019 |
Related U.S. Patent Documents
|
|
|
|
|
|
Application
Number |
Filing Date |
Patent Number |
|
|
15696268 |
Sep 6, 2017 |
10351796 |
|
|
16429683 |
|
|
|
|
62383637 |
Sep 6, 2016 |
|
|
|
Current U.S.
Class: |
1/1 |
Current CPC
Class: |
A61Q 13/00 20130101;
A61K 8/34 20130101; A61K 8/33 20130101; C11B 9/0015 20130101; A61K
8/4973 20130101; A61K 8/738 20130101; A61K 8/347 20130101; C11B
9/0019 20130101; A61K 8/498 20130101; C11B 9/0061 20130101; A61K
2800/56 20130101; A61K 8/37 20130101; A61K 8/44 20130101 |
International
Class: |
C11B 9/00 20060101
C11B009/00; A61K 8/44 20060101 A61K008/44; A61K 8/73 20060101
A61K008/73; A61Q 13/00 20060101 A61Q013/00; A61K 8/49 20060101
A61K008/49; A61K 8/37 20060101 A61K008/37; A61K 8/34 20060101
A61K008/34; A61K 8/33 20060101 A61K008/33 |
Claims
1. A cyclodextrin complex, comprising a cyclodextrin and a perfume
comprising perfume raw materials, wherein 10% or more, by weight of
the perfume, of the perfume raw materials have: a cyclodextrin
complex stability constant of about 3.0 or less, a C log P of about
2.5 or less; and a weight average molecular weight of about 200
Daltons or less; wherein the perfume is complexed with cyclodextrin
particles having a moisture level of less than about 10%, by weight
of the cyclodextrin particles.
2. The cyclodextrin complex of claim 1, wherein the cyclodextrin
comprises hydroxypropyl alpha-cyclodextrin, hydroxypropyl
beta-cyclodextrin, methylated-alpha-cyclodextrin,
methylated-beta-cyclodextrin, or a combination thereof.
3. The cyclodextrin complex of claim 1, wherein the percent of the
perfume that is complexed with the cyclodextrin is about 75% or
more.
4. The cyclodextrin complex of claim 1, wherein the perfume raw
materials are selected from the group consisting of: beta gamma
hexanol; cis 3 hexenyl acetate; ethyl-2-methyl butyrate;
amyl-acetate; vanillin; anethole; methyl isoeugenol; guaiacol;
floralol; 2,6-nonadien-1-ol; coumarin; and a combination
thereof.
5. The cyclodextrin complex of claim 1, wherein 10% or more of the
perfume raw materials also have an Odor Detection Threshold of
about 7 or more -log molar concentration.
6. The cyclodextrin complex of claim 1, wherein about 20% to about
100%, by weight of the perfume, of the perfume raw materials have:
a complex stability constant of about 3.0 or less, a C log P of
about 2.5 or less; and a weight average molecular weight of about
200 Daltons or less.
7. The cyclodextrin complex of claim 1, wherein the perfume raw
materials have a complex stability constant of about -1.5 to about
2.5.
8. A perfume comprising perfume raw materials, wherein 20% or more,
by weight of the perfume, of the perfume raw materials, are
selected from the group consisting of: ethyl-2-methyl butyrate;
beta gamma hexanol; iso amyl acetate; amyl acetate; cis-3-hexenyl
acetate; gamma-octalactone; ethyl vanillin; vanillin; benzaldehyde;
dimethyl anthranilate; iso-eugenyl acetate; canthoxal;
3,6-nonadien-1-ol, triplal; and combinations thereof.
9. The perfume of claim 8, wherein the perfume raw materials are
selected from the group consisting of ethyl-2-methyl butyrate; beta
gamma hexanol; iso amyl acetate; amyl acetate; cis-3-hexenyl
acetate; gamma-octalactone; ethyl vanillin; vanillin; benzaldehyde;
and combinations thereof.
10. The perfume of claim 8, wherein the perfume is part of a
cyclodextrin complex, and wherein the percent that is complexed
with the cyclodextrin is about 75% or more.
Description
CROSS REFERENCE TO RELATED APPLICATION
[0001] This application is a continuation of application Ser. No.
15/696,268, filed Sep. 6, 2017, which claims the benefit of U.S.
Provisional Application No. 62/383,637, filed Sep. 6, 2016, the
substance of which is incorporated herein by reference.
FIELD OF THE INVENTION
[0002] This application generally relates to perfume compositions
and cyclodextrin perfume complexes.
BACKGROUND OF THE INVENTION
[0003] Perfume compositions are utilized to help make products more
delightful to consumers. This is especially true for perfume
compositions and complexes that can provide a desired and
long-lasting perfume or scent each time the composition is applied
or used. However, current perfume compositions are not optimized
for release from a cyclodextrin complex and some components can
remain within the complex and unexpressed. As such, there is a need
for a perfume composition which is optimized for release from a
cyclodextrin and cyclodextrin perfume complexes made from such
optimized perfumes.
SUMMARY OF THE INVENTION
[0004] A perfume comprising perfume raw materials, wherein 10% or
more, by weight of the perfume, of the perfume raw materials have:
a cyclodextrin complex stability constant (log k) of about 3.0 or
less, a C log P of about 2.5 or less; and a weight average
molecular weight of about 200 Daltons or less.
[0005] A cyclodextrin complex, comprising a cyclodextrin and a
perfume, wherein 10% or more, by weight of the perfume, of the
perfume raw materials have: a cyclodextrin complex stability
constant of about 3.0 or less, a C log P of about 2.5 or less; and
a weight average molecular weight of about 200 Daltons or less.
[0006] These and other combinations are possible and are described
in more detail below.
BRIEF DESCRIPTION OF THE DRAWINGS
[0007] FIG. 1 is a side-by-side comparison of the cyclodextrin
complex stability constant (BCD binding strength) of a perfume
composition before and after optimization for release from a
cyclodextrin complex;
[0008] FIG. 2 is a side-by-side comparison of the cyclodextrin
complex stability constant over Log P of a perfume composition
before and after optimization for release from a cyclodextrin
complex;
[0009] FIG. 3 is a graph showing the percentage of perfume
complexed with a beta cyclodextrin that is released when measured
in accordance with the In Vitro Perfume Release Method; and
[0010] FIG. 4 is a graph showing the average scent intensity at
each assessment time point, where 1 is at application, 2 is during
the day, and 3 is at the end of the day.
DETAILED DESCRIPTION OF THE INVENTION
[0011] "Cyclodextrin complex stability constant" or "complex
stability constant" (log K) refers to the ability of a perfume raw
material to bind to a cyclodextrin. The complex stability constant
of a multitude of materials with respect to various cyclodextrins
as measured by the calorimetry technique can be found in the
literature, for example, Rekharsky and Inoue (1998), Complexation
Thermodynamics of Cyclodextrins, Chemical Review, 98, 1875-1917. In
addition, for reference, a list of perfume raw materials and their
estimated complex stability constants is included in a chart
below.
[0012] "C log P" refers to calculated log P values, which is a
measure of a compound's hydrophilicity, wherein log P is the
octanol water partitioning coefficient as computed by the Consensus
algorithm implemented in ACD/Percepta version 14.02 by Advanced
Chemistry Development, Inc. (ACD/Labs, Toronto, Canada).
[0013] "Odor Detection Threshold" refers to the lowest
concentration in the air of a certain odor compound that is
perceivable to the human sense of smell. The Odor detection
Threshold of a multitude of materials can be found in van Gernert,
L. J.; Odour Thresholds (Compilations of Odour Threshold Values in
Air, Water and Other Media; Oliemans Punter & Partners; The
Netherlands, 2011. It is in units of -log molar concentration. In
this context, human odor detection thresholds (ODTs) are expressed
as olfactory power, or p.ol (the negative log of the molar
concentration of the odorant in air at which a human first detects
the presence of the odorant). These values can be directly
transposed to other commonly used units such as ppm (volume) and
ppb (volume): thresholds of 1 ppm and 1 ppb are equivalent to
p.ol=6 and p.ol=9, respectively. Odor Detection Threshold can be
measured, for example, by the method in International Publication
Number WO 2006/138726.
[0014] "Cyclodextrin complex" refers to a complex of cyclodextrin
and perfume.
[0015] "Molecular weight," unless otherwise designated, refers to
the weight average molecular weight which can be calculated by
using the sum of the molecular weights of the elements in a
molecule. These can be found, for example, in Atomic Weights of the
Elements, Weiser, 2005.
[0016] "Room temperature as used herein refers to about 20.degree.
C.
[0017] Many consumers enjoy a good scent in a consumer product.
Scent can be delivered through a multitude of means, like direct
addition of a scent to a product or through the use of a scent
delivery agent. Scent delivery agents can enhance and/or change the
delivery of the scent. For example, some delivery agents can
encapsulate a perfume so that it can be released upon a triggering
event. Other delivery agents can help a perfume deposit onto a
target surface so that the perfume is more easily detected by the
consumer.
[0018] Perfumes are usually not a single component, but made up of
multiple perfume raw materials which combined give the overall
scent of the perfume. Each of the perfume raw materials has its own
characteristic and its own chemical properties, like molecular
weight, c Log P, etc. These properties can influence where and how
long a scent can be detected. Some of these properties are how
perfume raw materials are divided into top, middle, and base
notes.
[0019] Previously, when using a perfume in combination with a
delivery agent like a cyclodextrin, it was believed that most of
the perfume was released from the delivery agent upon the
triggering event. For cyclodextrins, the triggering event is
usually the introduction of moisture. However, it was recently
discovered that only about 4%, of a complexed perfume, was being
released from a "high" performing cyclodextrin perfume complex upon
exposure to moisture. Thus, surprisingly, most of the perfume was
remaining within the cyclodextrin and was not noticeable to the
consumer. This means there is significant room for improvement in
the efficacy of cyclodextrin perfume complexes.
[0020] An understanding of what is and what isn't releasing from a
cyclodextrin was thought helpful to improve the efficacy of the
perfume cyclodextrin complex. Since less than 5% of the perfume
compositions used in a cyclodextrin complex were efficiently
releasing from the cyclodextrin complex (see FIG. 3, Non Optimized
Composition), the perfume raw materials that were being release
from the cyclodextrins were identified to determine if there were
characteristics common among them which could be used to help
develop a perfume composition for optimized released from a
cyclodextrin.
[0021] With water being the key releasing agent, it was found that
perfume materials with more affinity with water (lower log P) had
better release from the cyclodextrin complex. Perfume materials
with a lower cyclodextrin complex stability constant (log k) also
had better release from a cyclodextrin complex. In addition, a
lower molecular weight, which may correlate with a lower
cyclodextrin complex stability constant, also correlates with a
better release. To demonstrate these characteristics as impacting
the release from the cyclodextrin composition, new perfume
compositions were created. One composition removed these higher
releasing perfume materials from the original low release
composition as a negative control check (see FIG. 3, Non Optimized
Composition minus high releasing PRM's identified vs. Non Optimized
Composition). These compositions were then complexed with a beta
cyclodextrin and tested for release. In release testing, the Non
Optimized Composition minus the high releasing PRM's had less than
one third of the release of the original Non Optimized Composition
(see FIG. 3). This helped confirm which materials were releasing
from the cyclodextrin complex.
[0022] An optimized composition was also made which utilized about
70%, by weight of the perfume composition, of perfume raw materials
with a log P, stability constant, and weight average molecular
weight believed to help with perfume release from a cyclodextrin
complex. This perfume, Optimized Composition from FIG. 3, had 4
times the release of the original composition (Non Optimized
Composition). Another perfume composition was made with 100% of the
perfume composition matching these physical property
characteristics (Example 1). This perfume composition had over 15
times the release of the Non Optimized Composition.
[0023] As noted above, one of the characteristics of a perfume raw
material that can impact its release from a cyclodextrin is its
complex stability constant. This signifies how strongly the perfume
raw material binds with the cyclodextrin. While a minimum complex
stability constant allows for a perfume raw material to bind and
stay bound, at some point the affinity of the perfume raw material
for the cyclodextrin can become so strong that it becomes difficult
to release. It is believed that a complex stability constant of
more than 3 can interfere with the release of the perfume raw
material upon a triggering event. This is not to say that perfume
raw materials with a complex stability constant above a 3 cannot be
used, just that the ability to release such materials should be
taken into consideration during perfume design. For example, FIG. 1
shows the binding complex of perfume raw materials in a perfume
composition. The graph on the left shows the make-up of a more
typical perfume, while the graph on the right shows a perfume
composition after optimization for release from a cyclodextrin. The
optimized formula showed an improvement of more than 15 times over
Non Optimized Perfume A.
[0024] Another property of a perfume raw material which can impact
its ability to release from a cyclodextrin is its C log P. C log P
is the calculation of the log P value of a compound, which is the
logarithm of its partition coefficient between n-octanol and water
(C.sub.octanol/C.sub.water). Thus log P, or if water, calculated, c
Log P, is a measure of a perfume raw material's hydrophilicity.
High log P values correspond to low hydrophilicities. It is
believed that a low log P, i.e. higher affinity for water, can
positively impact the release of a perfume raw material from a
cyclodextrin upon appropriate contact with moisture. For example,
FIG. 2 shows the binding complex of perfume raw materials in a
perfume and the C log P. The graph on the left shows the make-up of
a more typical perfume, while the graph on the right shows a
perfume composition after optimization for release from a
cyclodextrin. The optimized formula complexed with a beta
cyclodextrin showed an improvement of 15 times over the Non
Optimized Composition. For this application, it is believed a C log
P value of about 2.5 or less is optimal for release from a
cyclodextrin complex.
[0025] A third property that can impact the release of a perfume
raw material from a cyclodextrin is its weight average molecular
weight. It is believed that perfume raw materials which are smaller
in size will have less binding points to a cyclodextrin and thus
more easily released. Ideally, a perfume raw material for optimal
release will have a weight average molecular weight of about 200
Daltons or less.
[0026] A fourth property that can impact the need for efficacy is
the odor detection threshold. Odor detection threshold is the
minimum level at which a perfume raw material can be detected by
the average human nose. For a perfume raw material with a low odor
detection threshold, less of the perfume raw material needs to be
released from a cyclodextrin in order for the perfume raw material
to be noticed. This feature can allow for the use of perfume raw
materials which would otherwise be seen as too difficult to release
en masse from a cyclodextrin as only a small amount of release can
be noticeable to a consumer. Optimally, the odor detection
threshold of a perfume raw material is about 7-log molar
concentration or more.
[0027] To determine whether the release enhancement was noticeable
to consumers, an optimized beta cyclodextrin perfume complex was
placed into an invisible solid antiperspirant product and was
tested against an in market beta cyclodextrin complex with less
than 5% release in a similar product. The products were given to
over 90 consumers each to wear every day for 2 weeks. After the 2
weeks they were asked to rate the intensity of the perfume on a
scale of -2 (much too weak) to 2 (much too strong). They rated the
product they wore at application, during the day, and at the end of
the day. FIG. 4 shows on average those who wore the product with
the optimized cyclodextrin reported a higher perfume intensity at
each time point evaluated. With the single variable change of the
perfume in the cyclodextrin perfume complex between the two test
products, we believe the increase in fragrance intensity can be
attributed to the optimized perfume in the cyclodextrin perfume
complex.
[0028] Cyclodextrin
[0029] A cyclodextrin may be used for substantially "hiding" a
perfume material until a triggering mechanism has occurred, such
as, for example, perspiration, urination, or menstruation, to
"release" the perfume material. As used herein, the term
"cyclodextrin" includes any of the known cyclodextrins such as
unsubstituted cyclodextrins containing from about six to about
twelve glucose units, especially alpha-cyclodextrin,
beta-cyclodextrin, gamma-cyclodextrin, and/or mixtures thereof. For
example, cyclodextrins may be selected from the group consisting of
beta-cyclodextrin, hydroxypropyl alpha-cyclodextrin, hydroxypropyl
beta-cyclodextrin, methylated-alpha-cyclodextrin,
methylated-beta-cyclodextrin, and mixtures thereof. Cyclodextrin
complexes may be included within a product from at least about
0.1%, from about 1%, from about 2%, or from about 3%; to about 25%,
to about 20%, to about 15% or to about 10%, by weight of the
composition.
[0030] Cyclodextrin particles and cyclodextrin complexes comprising
a perfume can be formed by various methods. For example, a solvent
(e.g., water), unloaded cyclodextrin particles, and a perfume
material can be placed into a container and then mixed for a period
of time to permit loading of perfume molecules into "cavities" of
cyclodextrin molecules. The mixture may or may not be processed
further; e.g., processed through a colloid mill and/or homogenizer.
The solvent is then substantially removed, like by drying, from the
resulting mixture or slurry to yield cyclodextrin complex
particles. Different manufacturing techniques may however impart
different particle/complex characterizations, which may or may not
be desirable in the product. The particles and/or complexes can
have a low level of moisture prior to their inclusion into a
product. For example, some may have a moisture level of less than
about 20% by weight of the particles, less than about 10% by weight
of the particles, or even less than about 6% by weight of the
particles, prior to the inclusion of the volume of particles or
complexes into a composition. Other moisture levels may also be
suitable.
[0031] Spray drying a slurry or mixture of cyclodextrin-perfume
complexes is one manufacturing technique capable of producing the
cyclodextrin particles and cyclodextrin complexes having the
above-noted, low moisture levels. Table I below provides a
comparison of spray dried cyclodextrin complexes versus complexes
formed via an extruder process (kneading).
TABLE-US-00001 TABLE I Cyclodextrin Complex Moisture Level Sample %
Moisture Spray Dry Process Sample A 4.4 Spray Dry Process Sample B
3.7-4.5 Spray Dry Process Sample C 5.3 Extruder Process Sample A
27.87 Extruder Process Sample B 27.97 Extruder Process Sample C
24.00
[0032] Water content, USP (United States Pharmacopeia, current as
of Aug. 1, 2006)<921> Method I is the analytical method for
determining cyclodextrin complex moisture level, as shown in Table
I.
[0033] As one can see from Table 1, the moisture level directly
manifested by these two methods is dramatically different. It
should be understood that this comparison is not intended to
disclaim kneading/extruder processes from appended claims that do
not specify a particular complex formation process. Rather, a
kneading and extrusion method, or other method forming
particles/complexes with higher than desired moisture levels, could
utilize additional processing after their initial formation. For
example, extruded complexes may be processed through an oven or
dryer, or exposed to a controlled environment for a period of
time.
[0034] Although not wishing to be bound by theory, it is believed
that cyclodextrin particles/complexes having a relatively high
moisture level have an increased tendency to agglomerate. The
agglomerated particles may reach a size so as to become perceptible
by a consumer; that is, a consumer may characterize the composition
as being "gritty." A "gritty" composition may not be desirable to
some consumers. Microbial growth is another potential disadvantage
associated with employing cyclodextrin particles/complexes with
relatively high moisture levels into a final composition depending
on the remaining ingredients of the composition and/or storage
parameters.
[0035] The efficiency or level of complexing with a perfume
material is another parameter of cyclodextrin complexes that can
vary greatly depending on the manufacturing techniques employed.
Put another way, the percent of perfume material that is associated
with the interior of a cyclodextrin molecule compared to the
percent of perfume material that is associated with the exterior of
the cyclodextrin complex. The perfume material that is on the
exterior region of the complex is essentially free to be expressed
without the requirement of a triggering mechanism. The probability
that a consumer perceives the perfume material prior to a
triggering mechanism increases as the level of free perfume
increases. And perception of a perfume material prior to a
triggering mechanism may not be desired depending on the overall
composition design and targeted benefit associated with employment
of the cyclodextrin complexes. The percent of perfume material that
is complexed with cyclodextrin can be, for example, greater than
about 75%, in some instances greater than about 90%, and in other
instances greater than about 95%. It should be understood that
these levels of perfume complexation are directly associated with
the complex formation process itself; the percentages do not
represent a formulation design of adding a first percentage of
perfume material via a cyclodextrin complex and adding a second
percentage of neat perfume material.
[0036] Spray drying a slurry or mixture of cyclodextrin-perfume
complexes is one manufacturing technique capable of producing
cyclodextrin complexes having the above-noted levels of perfume
complexation. Table II below provides a comparison of spray dried
cyclodextrin complexes versus complexes formed via an extruder
process (kneading).
TABLE-US-00002 TABLE II Percent of Perfume Loading in Cyclodextrin
Complexes Sample Complexation Efficiency Spray Dry Process Sample A
96.6 Spray Dry Process Sample B 96.8 Spray Dry Process Sample C
96.2 Extruder Process Sample A 60.77 Extruder Process Sample B
65.47 Extruder Process Sample C 67.07
[0037] One can see from Table II that spray drying is capable of
producing cyclodextrin complexes with very little free perfume as
compared to a kneading/extruder process. The skilled artisan should
appreciate that the comparison provided in Table II is not intended
to disclaim kneading/extruder processes from appended claims that
do not specify a particular complex formation process. Rather,
additional processing steps may, for example, be employed to
eliminate free perfume associated with extruded complexes prior to
their inclusion into a composition.
[0038] The analytical method for determining the percent of perfume
complexed, as shown in Table II, determines the free perfume level
in the complex by dissolving a sample in tetrahydrofuran (THF)
adding an internal standard, and analyzing by capillary gas
chromatography (GC). The complexed perfume level is measured by
extracting the same sample in acetone containing an internal
standard, and analyzing by GC.
Complexation Efficiency=% Complexed/[% Complexed+% Free]
[0039] Perfume Compositions
[0040] A perfume composition comprises perfume raw materials. At
least a portion of the perfume raw materials may have a complex
stability constant of about 3.0 or less; about 2.5 or less, about
2.0 or less, about 1.0 or less, to about 0, to about -1, to about
-2, or any combination thereof. Some of the perfume raw material
may have a c Log P of about 2.5 or less, about 2.0 or less, about
1.5 or less, about 1.0 or less, to about -3. Some of the perfume
raw materials may have a weight average molecular weight of about
200 Daltons or less, about 180 Daltons or less, about 150 Daltons
or less, about 100 Daltons or less, to about 50 Daltons. A perfume
raw material will have an odor detection threshold. At least a
portion of the perfume raw materials in a perfume composition will
have an odor detection threshold of about 7-log molar concentration
or greater; about 8-log molar concentration or greater; about 9-log
molar concentration or greater; to about 11.5-log molar
concentration.
[0041] The perfume composition comprises about 10% or more, by
weight of the perfume, of perfume raw materials which have a
complex stability constant of about 3.0 or less, a c Log P of about
2.5 or less, and a weight average molecular weight of about 200
Daltons or less. Going further, the perfume composition may
comprise about 20% or more; about 30% or more; about 40% or more,
or about 50% or more, up to 100%; of perfume raw materials which
have a complex stability constant of about 3.0 or less, a c Log P
of about 2.5 or less, and a weight average molecular weight of
about 200 Daltons or less. In addition, a perfume composition may
also include perfume raw materials with an odor detection threshold
of about 7-log molar concentration.
[0042] A representative, non-limiting, list of perfume raw
materials that have a complex stability constant of about 3.0 or
less, a c Log P of about 2.5 or less, and a weight average
molecular weight of about 200 Daltons or less is included in the
chart below.
TABLE-US-00003 Odor Detection bCD Threshold, Complex CAS LogP
Formula Neural Net Stability Number Name (v3.0) Weight model
Constant 10031-96-6 eugenyl formate 2.35 192.21 8.84 2.71 100-52-7
Benzaldehyde 1.4 106.12 7.45 2.19 10094-40-3 2-hexen-1-yl acetate
2.21 142.20 8.20 1.45 101-39-3 alpha-methyl cinnamaldehyde 2.18
146.19 8.83 1.08 101-41-7 Methyl phenylacetate 1.89 150.18 8.02
2.14 101-48-4 Viridine (PADMA) 1.65 166.22 8.01 2.26 101-97-3 Ethyl
2-phenylacetate 2.39 164.20 8.63 2.25 103-25-3 methyl
hydrocinnamate 2.04 164.20 8.20 2.24 103-26-4 Methyl cinnamate 2.44
162.19 8.97 2.07 103-45-7 2-Phenylethyl acetate 2.07 164.20 8.15
1.54 103-54-8 Cinnamyl acetate 2.49 176.22 8.51 1.53 104-09-6 lilac
acetaldehyde 2.12 134.18 9.36 2.67 104-20-1
4-(p-Methoxyphenyl)-2-butanone 1.88 178.23 8.86 1.72 (frambinone)
104-46-1 Anethole 2.43 148.20 8.79 2.34 104-50-7 gamma-Octalactone
2.06 142.20 8.30 2.94 104-53-0 3-phenyl propionaldehyde 1.65 134.18
8.95 2.47 104-54-1 Cinnamic alcohol 1.68 134.18 8.58 2.15 104-55-2
Cinnamic aldehyde 1.92 132.16 8.56 2.37 104-62-1 Phenethyl formate
1.82 150.18 8.10 2.32 104-64-3 3-phenyl propyl formate 2.22 164.20
8.51 2.46 105-01-1 Isobutyl furylpropionate 2.34 196.25 8.60 2.30
10521-96-7 Styryl acetate 2.3 162.19 8.60 1.47 105-86-2 geranyl
formate 2.44 182.26 8.49 -1.85 10606-47-0 3-Hepten-1-ol 1.79 114.19
8.47 2.11 106-22-9 Citronellol 2.49 156.27 8.37 -0.64 106-24-1
trans-Geraniol 1.95 154.25 9.36 -2.13 106-25-2 Nerol 1.95 154.25
9.36 -2.13 106-26-3 Neral 2.33 152.24 8.48 -1.82 106-72-9 melon
heptenal (melonal) 2.09 140.23 8.09 -0.64 107-03-9 Propyl mercaptan
1.87 76.16 9.04 0.65 1073-26-3 2-Propionylpyrrole 1.37 123.15 8.13
1.88 110458-85-0 5,6-Dimethyl-1-(1- 2.36 192.30 9.46 1.27
methylethenyl)bicyclo[2.2.1]hept- 5-ene-2-methanol 1123-85-9
Hydratopic alcohol 1.85 136.19 8.19 1.99 1131-62-0
3,4-Dimethoxyacetophenone 1.7 180.20 8.15 1.63 116-26-7 Safranal
2.4 150.22 8.54 1.30 118-93-4 2-Hydroxyacetophenone 1.97 136.15
8.15 1.38 1197-06-4 cis-carveol 1.86 152.24 8.60 0.32 1205-17-0
ocean propanal (helional) 1.77 192.21 8.89 2.67 120-58-1 Isosafrol
2.01 162.19 8.45 2.52 120-72-9 Indole 2.34 117.15 8.20 2.19
120-75-2 2-Methylbenzothiazole 2.14 149.21 8.12 2.83 121-32-4 Ethyl
vanillin 1.53 166.18 10.32 2.41 121-33-5 Vanillin 1.04 152.15 9.93
2.36 121-98-2 Methyl p-anisate 1.99 166.18 8.54 2.05 122-63-4
Benzyl propionate 2.24 164.20 8.29 2.01 122-72-5 3-phenyl propyl
acetate 2.48 178.23 8.70 1.73 122-78-1 phenyl acetaldehyde 1.46
120.15 8.40 2.30 123-08-0 p-Hydroxybenzaldehyde 1.29 122.12 9.34
2.28 123-11-5 para-anisaldehyde 1.53 136.15 7.72 2.29 123-92-2
Isoamyl acetate 1.87 130.19 7.12 1.33 13327-56-5 Ethyl
3-methylthiopropionate 1.47 148.22 8.09 1.88 134-20-3 Methyl
anthranilate 1.58 151.17 8.22 1.69 13494-08-1
1,2-Cyclopentanedione, 3-ethyl- 0.5 126.16 8.29 2.72 134-96-3
Syringaldehyde 0.94 182.18 9.89 2.48 13678-68-7 furfuryl
thioacetate 1.09 156.20 8.11 1.33 13679-85-1 blackberry thiophenone
0.73 116.18 8.44 2.06 140-39-6 p-Cresyl acetate 2.17 150.18 8.10
1.67 14049-11-7 linalool oxide (pyranoid) 1.89 170.25 8.45 2.62
141-27-5 Geranial 2.33 152.24 8.48 -1.82 142653-61-0 Parmanyl 1.75
153.22 8.13 2.05 142-83-6 Sorbinaldehyde 1.29 96.13 8.57 2.29
14360-50-0 Pentyl 2-furyl ketone 2.49 166.22 9.39 2.44 150-19-6
m-Guaiacol 1.39 124.14 8.16 2.02 1504-55-8 alpha-Methylcinnamic
alcohol 1.73 148.20 8.68 0.74 (cypriol) 15111-56-5 Ethyl
cyclohex-3-enecarboxylate 1.86 154.21 8.47 2.78 1516-17-2
2,4-Hexadienyl acetate 1.75 110.16 8.30 1.36 15174-69-3
4-Hydroxy-3-methylbenzaldehyde 1.63 136.15 10.25 2.24 15186-51-3
Furan, 3-methyl-2-(3-methyl-2- 2.04 150.22 8.26 -0.46 butenyl)-
1540-28-9 n-Pentyl acetoacetate 1.63 172.22 8.04 1.79 1552-67-6
Ethyl 2-hexenoate 2.49 142.20 8.30 2.12 15679-12-6
2-Ethyl-4-methylthiazole 1.69 127.20 8.31 2.13 15679-13-7 tropical
thiazole 2.12 141.23 8.25 2.33 16251-77-7 Trifernal 2.28 148.20
8.87 2.51 1646-26-0 Coumarone 1.9 160.17 8.64 1.90 16491-25-1
2,4-Hexadienyl propionate 2.44 154.21 8.72 1.97 1679-07-8
Cyclopentyl mercaptan 2.24 102.19 9.09 1.47 1679-09-0
2-Methyl-2-butanethiol 2.45 104.21 9.16 0.79 16957-70-3
trans-2-Methyl-2-pentenoic acid 1.33 114.14 8.78 0.65
(Strawberriff) 1708-34-5 2-Hexyl-1,3-dioxolane 2.17 158.24 8.11
2.56 1708-81-2 cis-3-Hepten-1-ol 1.79 114.19 8.47 2.11 1708-82-3
3-Hexenyl acetate 2.18 142.20 8.16 1.48 17102-64-6
Trans,trans-2,4-Hexadien-1-01 0.96 98.14 8.22 2.06 1754-62-7 Methyl
Trans-Cinnamate, 99% 2.44 162.19 8.97 2.07 1759-28-0
4-Methyl-5-vinylthiazole 1.51 125.19 8.56 1.62 17626-75-4
2-Propylthiazole 1.51 127.20 8.23 1.79 18031-40-8
(S),(-)-Perillaaldehyde 2.34 150.22 9.80 1.85 18277-27-5
2-(1-Methylpropyl)thiazole 1.9 141.23 8.25 1.71 18479-68-0
(+)-P-Menth-1-en-9-ol, 97%, 2.26 154.25 8.87 1.66 mixture of
isomers 18640-74-9 Isobutyl thiazole 1.92 141.23 8.29 2.02
18829-55-5 trans-2-Heptenal 2.1 112.17 8.76 2.33 18881-04-4
(1S)-(-)-cis-Verbenol 2.03 152.24 8.09 2.61 189440-77-5 Anapear 2.3
154.21 8.78 2.20 1901-38-8 alpha-Campholenic alcohol 2.03 154.25
8.08 1.32 19788-49-9 Ethyl 2-mercaptopropionate 1.41 134.19 8.39
0.99 19819-98-8 2-Methylphenethyl alcohol 1.66 136.19 8.46 2.36
2046-17-5 Methyl 4-phenylbutyrate 2.46 178.23 8.75 2.37 20474-93-5
Allyl crotonate 1.63 126.16 8.29 2.24 2051-78-7 Allyl butyrate 1.88
128.17 8.17 2.21 2051-96-9 Benzyl lactate 1.35 180.20 8.15 1.70
20665-85-4 Vanillin isobutyrate 1.92 222.24 8.20 2.20 2111-75-3
perillaldehyde 2.34 150.22 9.80 1.85 2142-94-1 Neryl Formate 2.44
182.26 8.49 -1.85 2179-58-0 Allyl methyl disulfide 1.9 120.23 8.59
1.44 2179-60-4 Methyl propyl disulfide 2.28 122.24 8.56 1.97
21835-00-7 2-Cyclopenten-1-one, 2-hydroxy- -0.02 126.16 8.91 0.76
3,4-dimethyl- 21835-01-8 3-Ethyl-2-hydroxy-2-cyclopenten- 0.06
126.16 8.79 2.41 1-one 22104-78-5 2-Octenol-1 2.27 128.21 8.81 2.24
2217-33-6 Tetrahydrofurfuryl butyrate 1.54 172.22 8.40 2.22
22451-63-4 Allo-ocimenol 2.42 152.24 8.51 -0.99 22460-95-3
7-Octene-1,6-diol, 3,7-dimethyl- 1.33 172.27 8.27 0.79 22924-15-8
3-Ethoxybenzaldehyde 1.99 150.18 8.14 2.33 22927-13-5
2-Ethylbenzaldehyde 2.06 134.18 8.78 2.53 2305-21-7 2-hexen-1-ol
1.3 100.16 8.09 2.06 23495-12-7 Phenoxyethyl propionate 2.43 194.23
8.92 1.78 23911-56-0 Nerolione 2.02 174.20 8.74 2.04 2445-83-2
7-Methylcoumarin 2.42 160.17 8.79 2.78 2463-63-0 Butylacrolein 2.1
112.17 8.76 2.33 2497-18-9 2-Hexen-1-yl acetate 2.21 142.20 8.20
1.45 2555-49-9 Ethyl phenoxyacetate 2.04 180.20 8.36 1.93
26553-46-8 Ethyl trans-3-hexenoate 2.25 142.20 8.34 2.14 8/6/2719
N-Acetyl methyl anthranilate 1.21 193.20 8.00 1.48 27829-72-7 Ethyl
trans-2-hexenoate 2.49 142.20 8.30 2.12 27939-60-2 Vertoliff
(triplal extra) 1.8 138.21 9.24 1.71 28069-72-9
(2E,6Z)-Nona-2,6-dien-1-ol 2.43 140.23 9.59 2.24 28977-58-4
Ocimenol 2.02 152.24 8.71 -0.59 29414-56-0
2,6-Dimethyl-1,5,7-octatrienol-3 1.96 152.24 8.89 -0.76 29548-14-9
p-Menth-1-ene-9-al 2.24 152.24 9.40 1.85 30361-28-5
2,4-Octadien-1-al 2.45 124.18 9.33 2.32 30954-98-4 Propyl
anthranilate 2.47 179.22 8.88 1.87 3194-17-0 2-Pentanoylfuran 1.99
152.19 8.97 2.40 32272-48-3 4-Ethyl-2-methylthiazole 1.7 127.20
8.32 2.25 32764-98-0 Jasmolactone 2.36 168.24 8.72 2.96 33467-73-1
cis-3-Hexenyl formate 1.69 128.17 8.22 2.25 3391-86-4 1-Octenol-3
2.36 128.21 8.29 2.19 3581-91-7 4,5-Dimethylthiazole 0.91 113.18
8.10 1.30 3583-00-4 4,4-Dimethyl-5-isopropyl-1,3- 1.92 158.24 8.99
1.98 dioxolane 35926-04-6 1-Hexen-3-yl acetate 2.31 142.20 8.02
1.68 36701-01-6 Furfuryl valerate 1.89 182.22 8.39 2.12 36806-46-9
2,6-Dimethyl-6-hepten-1-ol 2.4 142.24 8.07 0.76 3681-71-8
cis-3-Hexenyl acetate 2.18 142.20 8.16 1.48 3681-82-1
trans-3-Hexenyl acetate 2.18 142.20 8.16 1.48 36880-33-8
5-Ethyl-2-thiophenecarbaldehyde 1.85 140.20 8.19 2.64 37973-51-6
2-Phenyl-1(2)propenyl-1 ester 2.47 176.22 8.82 0.44 38142-45-9
3-Cyclohexene-1-ethanol, 4- 1.84 152.24 8.62 1.58
methyl-.beta.-methylene-, (R)- 39252-02-3 Furfuryl hexanoate 2.38
196.25 8.80 2.17 39677-52-6 3-Methoxy Cinnamaldehyde 1.86 162.19
8.84 2.49 40010-99-9 3-Acetyl-5-butyldihydro-2(3H)- 1.71 184.24
8.57 2.58 furanone 40790-29-2 Pyrazine, 3-butyl-2,5-dimethyl- 2.29
164.25 8.18 2.48 409-02-9 Methyl Heptenone 2.27 126.20 8.58 2.38
4175-66-0 2,5-Dimethylthiazole 0.94 113.18 8.08 1.63 4180-23-8
(E)-anethol 2.43 148.20 8.79 2.34 41847-88-5
Phenylethyloxy-acetaldehyde 1.55 164.20 8.61 2.34 42348-12-9
3-Ethyl-2-hydroxy-4- 0.54 140.18 9.10 2.58
methylcyclopent-2-en-1-one 3/5/4313 (E,E)-2,4-heptadien-1-al 1.98
110.16 9.00 2.29 6/1/4364 Cinnamic aldehyde dimethyl acetal 2.02
178.23 8.44 2.03 4501-58-0 Campholene aldehyde 2.2 152.24 8.31 1.43
4634-89-3 cis-4-Hexenal 1.05 98.14 9.24 2.26 4643-25-8
2-Hepten-4-one 1.85 112.17 8.31 2.21 4643-27-0 2-Octen-4-one 2.42
126.20 8.70 2.43 473-67-6 Verbenol 2.03 152.24 8.09 2.61 4748-78-1
4-Ethylbenzaldehyde 2.39 134.18 9.19 2.54 491-04-3 Piperitol 2.4
154.25 8.70 1.72 491-09-8 piperitenone 2.33 150.22 8.40 -1.20
491-31-6 Isocoumarin 1.69 146.15 8.63 2.45 491-35-0 Lepidine 2.46
143.19 8.13 2.44 11/8/4940 ethyl maltol 0.17 140.14 7.44 1.94
496-77-5 Butyroin 1.29 144.21 8.36 2.22 499-44-5 Hinokitiol 1.35
164.20 9.32 2.71 50888-63-6 Pyrazine, 2-butyl-3,5-dimethyl- 2.3
164.25 8.19 2.27 53046-97-2 cis-3, cis-6-nonadienol 2.45 140.23
9.52 2.16 53398-78-0 trans-2-Hexenyl formate 1.71 128.17 8.31 2.23
53399-81-8 Ethyl 2-methyl-4-pentenoate 2.26 142.20 8.16 2.08
536-50-5 1-(4-Methylphenyl)ethanol 2 136.19 8.07 2.39 536-59-4
Perillyl alcohol 1.83 152.24 8.58 1.69 536-60-7 Cumic alcohol 2.39
150.22 8.68 2.39 5392-40-5 Citral 2.33 152.24 8.48 -1.82 5396-89-4
Benzyl acetoacetate 1.43 192.21 8.05 1.45 12/2/5406
p-Methylhydrocinnamic aldehyde 2.19 148.20 9.57 2.84 541-58-2
2,4-Dimethylthiazole 1.24 113.18 8.08 1.89 5426-78-8 Acetaldehyde
phenyl ethyl acetal 2.22 166.22 8.56 1.83 6/6/5462 Canthoxal 2.16
178.23 8.80 2.49 6/8/5466 Ethyl 3-mercaptopropionate 1.36 134.19
8.92 1.25 5471-51-2 Raspberry ketone 1.58 164.20 7.67 1.70 554-14-3
2-Methylthiophene 2.06 98.16 8.11 1.52 55722-59-3 3,6-Octadienal,
3,7-dimethyl- 2.34 152.24 8.51 -1.89 5577-44-6 2,4-Octadienal 2.45
124.18 9.33 2.32 5660-60-6 Cinnamaldehyde ethylene glycol 2.15
176.22 8.04 2.16 acetal 56805-23-3 trans-3, cis-6-nonadienol 2.45
140.23 9.52 2.16 57266-86-1 2-Heptenal, (2Z)- 2.1 112.17 8.76 2.33
57500-00-2 Methyl furfuryl disulfide 1.92 160.25 8.19 2.38 579-74-8
o-Acetylanisole 1.55 150.18 8.40 1.56 58461-27-1 Lavandulol 1.95
154.25 8.98 -1.82 585-74-0 3-Methylacetophenone 2.27 134.18 8.23
1.65 589-18-4 p-Tolyl alcohol 1.62 122.17 8.01 2.35 59020-85-8
Furfuryl thiopropionate 1.61 170.23 8.45 2.16 59021-02-2
2-Mercaptomethylpyrazine 0.34 126.18 8.26 0.66 5910-85-0
2,4-Heptadienal 1.98 110.16 9.00 2.29 5912-86-7 cis-iso-Eugenol
1.85 164.20 8.60 2.38 5925-68-8 S-Ethyl benzothioate 2.21 152.21
8.74 1.83 5932-68-3 trans-Isoeugenol 1.85 164.20 8.60 2.38 606-27-9
Methyl 2-nitrobenzoate 1.57 181.15 8.45 2.25 606-45-1 Methyl
o-methoxybenzoate 1.79 166.18 8.56 2.15 613-70-7 Guaiacyl acetate
1.55 166.18 8.18 1.57 616-44-4 3-Methylthiophene 2.23 98.16 8.51
1.52 6191-71-5 cis-4-Hepten-1-ol 1.77 114.19 8.46 2.11 6192-44-5
beta-Phenoxy ethyl acetate 1.87 180.20 8.51 1.26 61931-81-5
cis-3-Hexenyl lactate 1.34 172.22 8.20 1.76 620-23-5 meta-tolyl
aldehyde 2.13 120.15 8.79 2.38 623-15-4 4-(2-Furyl)-3-buten-2-one
1.7 136.15 8.42 1.38 624-92-0 Dimethyl disulfide 1.06 94.19 8.64
0.27 6290-14-8 Cyclopentyl isobutyrate 2.29 156.22 8.42 2.08
6314-97-2 Phenylacetaldehyde diethyl acetal 2.29 194.27 9.02 2.37
637-65-0 tetrahydrofurfuryl propionate 0.93 158.20 8.02 2.07
638-02-8 2,5-Dimethylthiophene 2.36 112.19 8.64 2.04 64988-06-3
Ethyl 2-methoxybenzyl ether 1.98 166.22 8.23 2.27 65405-67-6
p-Methoxy-alpha-methyl 2 176.22 8.85 1.16 cinnamaldehyde 65405-73-4
Geranyl oxyacetaldehyde 2.32 196.29 8.71 -1.88 67028-40-4 Ethyl
(p-tolyloxy)acetate 2.49 194.23 8.45 2.18 6728-26-3 Trans-2-Hexenal
1.57 98.14 8.41 2.26 6728-31-0 cis-4-Heptenal 1.85 112.17 9.51 2.33
67633-97-0 3-Mercapto-2-pentanone 1.37 118.19 8.86 0.23 67634-07-5
3,5,6-Trimethyl-3-cyclohexene-1- 2.37 152.24 8.63 1.97 carbaldehyde
67634-16-6 Floralol 1.83 140.23 8.38 1.50 67634-17-7
2,4-Dimethyl-3-cyclohexene-1- 1.81 140.23 8.51 1.61 methanol
67746-30-9 trans-2-Hexenal diethyl acetal 2.34 172.27 8.19 2.13
67801-65-4 3,6-ivy carbaldehyde 1.8 138.21 9.25 2.09 67845-46-9
p-Methyl phenoxy acetaldehyde 1.76 150.18 8.64 2.40 6789-80-6
(Z)-3-hexen-1-al 1.43 98.14 8.97 2.26 68039-48-5 Dimethyl
cyclohexene 1.82 138.21 9.18 1.65 carboxaldehyde 68039-49-6
2,4-Dimethyl-3-Cyclohexene-1- 1.78 138.21 9.24 1.76 carboxaldehyde
(Ligustral) 68133-76-6 cis-3-Hexenyl pyruvate 1.9 170.21 8.50 1.30
68737-61-1 3,5-ivy carbaldehyde 1.82 138.21 9.18 1.65 698-76-0
delta-Octalactone 2.03 142.20 8.24 2.83 699-10-5 Methyl benzyl
disulfide 2.47 170.29 8.45 2.96 701-70-2 1-Phenylbutan-2-ol 2.21
150.22 8.59 2.26 7452-79-1 Ethyl 2-methylbutyrate 1.91 130.19 7.27
1.75 74-93-1 Methyl mercaptan 0.58 48.10 8.63 0.43 7493-63-2 Allyl
anthranilate 2.31 177.20 8.48 1.95 7493-71-2 Allyl tiglate 1.86
140.18 8.12 0.69 75-08-1 Ethanethiol 1.37 62.13 8.87 0.63 75-18-3
dimethyl sulfide 1.24 62.13 8.33 0.86 75-33-2 2-Propanethiol 1.65
76.16 9.26 0.87 7540-51-4 (-)-Citronellol 2.49 156.27 8.37 0.64
7549-33-9 Anisyl propionate 2.23 194.23 8.45 2.08 75-66-1
tert-Butyl mercaptan 1.65 90.18 9.13 1.13 764-40-9 2,4-Pentadienal
0.7 82.10 8.16 2.37 76649-25-7 3,6-Nonadien-1-ol 2.45 140.23 9.52
2.16 774-48-1 Benzaldehyde diethyl acetal 2.03 180.25 8.57 2.35
7774-74-5 2-Thienyl mercaptan 1.77 116.20 8.00 0.81 7774-79-0
4-(p-Tolyl)-2-butanone 2.46 162.23 8.64 2.01 7774-96-1 Isoeugenyl
formate 2.35 192.21 8.84 2.71 7786-44-9 2,6-Nonadien-1-ol 2.43
140.23 9.59 2.24 7786-61-0 2-Methoxy-4-vinylphenol 2.24 150.18 8.71
2.37 7786-67-6 p-Menth-8-en-3-ol (8CI) 2.48 154.25 8.42 2.29
81925-81-7 filbert heptenone (Filbertone) 2.31 126.20 8.06 1.92
84434-18-4 Gardamide 2.16 191.27 8.08 1.98 85-91-6 Dimethyl
anthranilate 2.19 165.19 8.13 2.08 870-23-5 Allyl mercaptan 1.42
74.14 9.00 0.85 87-25-2 Ethyl anthranilate 2.05 165.19 8.58 1.84
874-66-8 cinnamon acrolein 1.29 136.15 8.09 0.92 881-68-5 Vanillin
acetate 0.95 194.19 8.11 1.94 89-79-2 Isopulegol 2.48 154.25 8.42
2.29 90-02-8 Salicylaldehyde 1.4 122.12 8.95 2.21 90-05-1 Guaiacol
1.33 124.14 8.06 1.98 90-87-9 Hydratropaldehyde dimethyl acetal
2.12 180.25 8.60 2.24 91-64-5 Coumarin 1.68 146.15 8.55 2.47
928-94-9 (Z)-2-hexen-1-ol 1.3 100.16 8.09 2.06 928-95-0
(E)-2-hexen-1-ol 1.3 100.16 8.09 2.06 928-96-1 cis-3-Hexen-1-ol 1.3
100.16 8.06 2.06 93-16-3 Methyl isoeugenol 2.05 178.23 8.70 2.49
93-29-8 Isoeugenyl acetate 2.17 206.24 8.38 1.94 93-53-8 2-phenyl
propionaldehyde 2.06 134.18 8.43 2.21 93-54-9 1-Phenyl-1-propanol
1.77 136.19 8.21 2.03 93-58-3 Methyl benzoate 1.86 136.15 8.03 2.00
93-89-0 Ethyl benzoate 2.25 150.18 8.60 2.18 93893-89-1
Citronitrile 2.34 171.24 8.57 1.27 93-92-5 Styrallyl acetate 2.2
164.20 8.18 1.54 94089-01-7 Butanoic acid, 2-methyl-, 2- 1.6 134.24
9.32 1.41 hexenyl ester, (E)- 94-86-0 Vanitrope 2.42 178.23 8.53
2.39 95-20-5 2-Methylindole 2.43 131.18 8.53 2.58 97-53-0 Eugenol
2.21 164.20 8.57 2.51
[0043] One grouping of perfume raw materials that have a complex
stability constant of about 3.0 or less, a C log P of about 2.5 or
less, and a weight average molecular weight of about 200 Daltons or
less includes beta gamma hexanol; cis 3 hexenyl acetate;
ethyl-2-methyl butyrate; amyl-acetate (isomer blends); vanillin;
anethole; methyl isoeugenol; guiacol; floralol; ethyl vanillin;
2,6-nonadien-1-ol; coumarin; and combinations thereof.
[0044] Another group of perfume raw materials that have a complex
stability constant of about 3.0 or less, a C log P of about 2.5 or
less, and a weight average molecular weight of about 200 Daltons or
less includes ethyl-2-methyl butyrate; beta gamma hexanol; iso amyl
acetate; amyl acetate; cis-3-Hexenyl acetate; gamma-Octalactone;
ethyl vanillin; vanillin; benzaldehyde; and combinations
thereof.
[0045] An additional group of perfume raw materials that have a
complex stability constant of about 3.0 or less, a C log P of about
2.5 or less, and a weight average molecular weight of about 200
Daltons or less includes dimethyl anthranilate; iso-eugenyl
acetate; canthoxal; 3,6-nonadien-1-ol, triplal; and combinations
thereof.
[0046] Some examples of perfume raw materials with an odor
detection threshold of 7-log ppb or more include can be found in
the chart above.
Examples/Combinations
[0047] A. A perfume comprising perfume raw materials, wherein 10%
or more, by weight of the perfume, of the perfume raw materials
have: a cyclodextrin complex stability constant of about -2.0 to
about 3.0, a C log P of about -3.0 to about 2.5; and a weight
average molecular weight of about 50 Daltons to about 200. [0048]
B. The perfume of paragraph B, wherein the cyclodextrin complex
stability constant is from about -2.0 to about 2.5. [0049] C. The
perfume of paragraphs A-B, wherein the perfume raw materials are
selected from the group consisting of: eugenyl formate;
benzaldehyde; 2-hexen-1-yl acetate; alpha-methyl cinnamaldehyde;
methyl phenylacetate; viridine; ethyl 2-phenylacetate; methyl
hydrocinnamate; methyl cinnamate; 2-Phenylethyl acetate; cinnamyl
acetate; lilac acetaldehyde; 4-(p-Methoxyphenyl)-2-butanone;
anethole; gamma-Octalactone; 3-phenyl propionaldehyde; cinnamic
alcohol; cinnamic aldehyde; phenethyl formate; 3-phenyl propyl
formate; isobutyl furylpropionate; styryl acetate; geranyl formate;
3-Hepten-1-ol; citronellol; trans-Geraniol; nerol; neral; melon
heptenal; propyl mercaptan; 2-Propionylpyrrole;
5,6-Dimethyl-1-(1-methylethenyl)bicyclohept-5-ene-2-methanol;
hydratopic alcohol; 3,4-Dimethoxyacetophenone; safranal;
2-Hydroxyacetophenone; cis-carveol, ocean propanal; Isosafrol;
Indole; 2-Methylbenzothiazole; Ethyl vanillin; Vanillin; Methyl
p-anisate; Benzyl propionate; 3-phenyl propyl acetate; phenyl
acetaldehyde; p-Hydroxybenzaldehyde; para-anisaldehyde; Isoamyl
acetate; Ethyl 3-methylthiopropionate; Methyl anthranilate;
1,2-Cyclopentanedione, 3-ethyl-; Syringaldehyde; furfuryl
thioacetate; blackberry thiophenone; p-Cresyl acetate; linalool
oxide (pyramid); Geranial; Parmanyl; Sorbinaldehyde; Pentyl 2-furyl
ketone; m-Guaiacol; alpha-Methylcinnamic alcohol; Ethyl
cyclohex-3-enecarboxylate; 2,4-Hexadienyl acetate;
4-Hydroxy-3-methylbenzaldehyde; Furan,
3-methyl-2-(3-methyl-2-butenyl)-; n-Pentyl acetoacetate; Ethyl
2-hexenoate; 2-Ethyl-4-methylthiazole; tropical thiazole;
Trifernal; Coumarone; 2,4-Hexadienyl propionate; Cyclopentyl
mercaptan; 2-Methyl-2-butanethiol; trans-2-Methyl-2-pentenoic acid;
2-Hexyl-1,3-dioxolane; cis-3-Hepten-1-ol; 3-Hexenyl acetate;
Trans,trans-2,4-Hexadien; methyl trans-cinnamate 99%;
4-Methyl-5-vinylthiazole; 2-Propylthiazole;
(S),(-)-Perillaaldehyde; 2-(1-Methylpropyl)thiazole;
(+)-p-menth-1-en-9-OL 97% (mixture of isomers); Isobutyl thiazole;
trans-2-Heptenal; (1S)-(-)-cis-Verbenol; Anapear; alpha-Campholenic
alcohol; Ethyl 2-mercaptopropionate; 2-Methylphenethyl alcohol;
Methyl 4-phenylbutyrate; Allyl crotonate; Allyl butyrate; Benzyl
lactate; Vanillin isobutyrate; perillaldehyde; Neryl Formate; Allyl
methyl disulfide; Methyl propyl disulfide; 2-Cyclopenten-1-one,
2-hydroxy-3,4-dimethyl-; 3-Ethyl-2-hydroxy-2-cyclopenten-1-one;
2-Octenol-1; Tetrahydrofurfuryl butyrate; Allo-ocimenol;
7-Octene-1,6-diol, 3,7-dimethyl-; 3-Ethoxybenzaldehyde;
2-Ethylbenzaldehyde; 2-hexen-1-ol; Phenoxyethyl propionate;
Nerolione; 7-Methylcoumarin; Butylacrolein; 2-Hexen-1-yl acetate;
Ethyl phenoxyacetate; Ethyl trans-3-hexenoate; N-Acetyl methyl
anthranilate; Ethyl trans-2-hexenoate; Vertoliff;
(2E,6Z)-Nona-2,6-dien-1-ol; Ocimenol;
2,6-Dimethyl-1,5,7-octatrienol-3; p-Menth-1-ene-9-al;
2,4-Octadien-1-al; Propyl anthranilate; 2-Pentanoylfuran;
4-Ethyl-2-methylthiazole; Jasmolactone; cis-3-Hexenyl formate;
1-Octenol-3; 4,5-Dimethylthiazole;
4,4-Dimethyl-5-isopropyl-1,3-dioxolane; 1-Hexen-3-yl acetate;
Furfuryl valerate; 2,6-Dimethyl-6-hepten-1-ol; cis-3-Hexenyl
acetate; trans-3-Hexenyl acetate; 5-Ethyl-2-thiophenecarbaldehyde;
2-Phenyl-1(2)propenyl-1 ester; 3-Cyclohexene-1-ethanol,
4-methyl-beta-methylene-, (R)-; Furfuryl hexanoate; 3-methoxy
cinnamaldehyde; 3-Acetyl-5-butyldihydro-2(3H)-furanone; Pyrazine,
3-butyl-2,5-dimethyl-; Methyl Heptenone; 2,5-Dimethylthiazole;
(E)-anethol; Phenylethyl oxy-acetaldehyde;
3-Ethyl-2-hydroxy-4-methylcyclopent-2-en-1-one;
(E,E)-2,4-heptadien-1-al; Cinnamic aldehyde dimethyl acetal;
Campholene aldehyde; cis-4-Hexenal; 2-Hepten-4-one; 2-Octen-4-one;
Verbenol; 4-Ethylbenzaldehyde; Piperitol; piperitenone;
Isocoumarin; Lepidine; ethyl maltol; Butyroin; Hinokitiol;
Pyrazine, 2-butyl-3,5-dimethyl-; cis-3, cis-6-nonadienol;
trans-2-Hexenyl formate; Ethyl 2-methyl-4-pentenoate;
1-(4-Methylphenyl)ethanol; Perillyl alcohol; Cumic alcohol; citral;
Benzyl acetoacetate; p-Methylhydrocinnamic aldehyde;
2,4-Dimethylthiazole; Acetaldehyde phenyl ethyl acetal; Canthoxal;
Ethyl 3-mercaptopropionate; Raspberry ketone; 2-Methylthiophene;
3,6-Octadienal, 3,7-dimethyl-; 2,4-Octadienal; Cinnamaldehyde
ethylene glycol acetal; trans-3, cis-6-nonadienol; 2-Heptenal,
(2Z)-; Methyl furfuryl disulfide; o-Acetylanisole; Lavandulol;
3-Methylacetophenone; p-Tolyl alcohol; Furfuryl thiopropionate;
2-Mercaptomethylpyrazine; 2,4-Heptadienal; cis-iso-Eugenol; S-Ethyl
benzothioate; trans-Isoeugenol; Methyl 2-nitrobenzoate; Methyl
o-methoxybenzoate; Guaiacyl acetate; 3-Methylthiophene;
cis-4-Hepten-1-ol; beta-Phenoxy ethyl acetate; cis-3-Hexenyl
lactate; meta-tolyl aldehyde; 4-(2-Furyl)-3-buten-2-one; Dimethyl
disulfide; Cyclopentyl isobutyrate; Phenylacetaldehyde diethyl
acetal; tetrahydrofurfuryl propionate; 2,5-Dimethylthiophene; Ethyl
2-methoxybenzyl ether; p-Methoxy-alpha-methyl cinnamaldehyde;
Geranyl oxyacetaldehyde; Ethyl (p-tolyloxy)acetate;
Trans-2-Hexenal; cis-4-Heptenal; 3-Mercapto-2-pentanone;
3,5,6-Trimethyl-3-cyclohexene-1-carbaldehyde; Floralol;
2,4-Dimethyl-3-cyclohexene-1-methanol; trans-2-Hexenal diethyl
acetal; 3,6-ivy carbaldehyde; p-Methyl phenoxy acetaldehyde;
(Z)-3-hexen-1-al; Dimethyl cyclohexene carboxaldehyde;
2,4-Dimethyl-3-Cyclohexene-1-carboxaldehyde; cis-3-Hexenyl
pyruvate; 3,5-ivy carbaldehyde; delta-Octalactone; Methyl benzyl
disulfide; 1-Phenylbutan-2-ol; Ethyl 2-methylbutyrate; Methyl
mercaptan; Allyl anthranilate; Allyl tiglate; Ethanethiol; dimethyl
sulfide 2-Propanethiol; (-)-Citronellol; Anisyl propionate;
tert-Butyl mercaptan; 2,4-Pentadienal; 3,6-Nonadien-1-ol;
Benzaldehyde diethyl acetal; 2-Thienyl mercaptan;
4-(p-Tolyl)-2-butanone; Isoeugenyl formate; 2,6-Nonadien-1-ol;
2-Methoxy-4-vinylphenol; p-Menth-8-en-3-ol; filbert heptenone;
Gardamide; Dimethyl anthranilate; Allyl mercaptan; Ethyl
anthranilate; cinnamon acrolein; Vanillin acetate; Isopulegol;
Salicylaldehyde; Guaiacol; Hydratropaldehyde dimethyl acetal;
Coumarin (Z)-2-hexen-1-ol; (E)-2-hexen-1-ol; cis-3-Hexen-1-ol;
Methyl isoeugenol; Isoeugenyl acetate; 2-phenyl propionaldehyde;
1-Phenyl-1-propanol; Methyl benzoate; Ethyl benzoate; Citronitrile;
Styrallyl acetate; Butanoic acid, 2-methyl-, 2-hexenyl ester, (E)-;
Vanitrope; 2-Methylindole; Eugenol; and a combination thereof.
[0050] D. The perfume of paragraphs A-B, wherein the perfume raw
materials are selected from the group consisting of: beta gamma
hexanol; cis 3 hexenyl acetate; ethyl-2-methyl butyrate;
amyl-acetate; vanillin; anethole; methyl isoeugenol; guaiacol;
floralol; 2,6-nonadien-1-ol; coumarin; and a combination thereof.
[0051] E. The perfume of any of paragraphs A-B, wherein the perfume
raw materials comprise dimethyl anthranilate; iso-eugenyl acetate;
canthoxal; 3,6-nonadien-1-ol, triplal; or a combination thereof.
[0052] F. The perfume of any of paragraphs A-B, wherein the perfume
raw materials comprise ethyl-2-methyl butyrate; beta gamma hexanol;
iso amyl acetate; amyl acetate; cis-3-hexenyl acetate;
gamma-octalactone; ethyl vanillin; vanillin; benzaldehyde; or a
combination thereof. [0053] G. The perfume of any of paragraphs
A-F, wherein 10% or more of the perfume raw materials have an Odor
Detection Threshold of about 7 or more -log molar concentration.
[0054] H. The perfume of any of paragraphs A-G, wherein 10% or more
of the perfume raw materials have an Odor Detection Threshold of
about 7 to about 11.5-log molar concentration. [0055] I. The
perfume of any of paragraphs A-H, wherein about 20% to about 100%,
by weight of the perfume, of the perfume raw materials have: a
complex stability constant of about -2.0 to about 3.0, a C log P of
about -3.0 to about 2.5; and a weight average molecular weight of
about 50 Daltons to about 200. [0056] J. The perfume of any of
paragraphs A-I, wherein about 50% to about 100%, by weight of the
perfume, of the perfume raw materials have: a complex stability
constant of about -2.0 to about 3.0, a C log P of about -3.0 to
about 2.5; and a weight average molecular weight of about 50
Daltons to about 200. [0057] K. The perfume of any of paragraphs
A-J, wherein the perfume raw materials have a complex stability
constant of about -1.5 to about 2.5. [0058] L. The perfume of any
of paragraphs A-K, wherein the perfume raw materials have a C log P
of about -3.0 to about 2.0. [0059] M. The perfume of any of
paragraphs A-L, wherein the perfume raw materials have a weight
average molecular weight of about 50 Daltons to about 180 Daltons.
[0060] N. A cyclodextrin complex, comprising a cyclodextrin and a
perfume comprising perfume raw materials, wherein 10% or more, by
weight of the perfume, of the perfume raw materials have: a
cyclodextrin complex stability constant of about -2.0 to about 3.0,
a C log P of about -3.0 to about 2.5; and a weight average
molecular weight of about 50 Daltons to about 200. [0061] O. The
cyclodextrin complex of paragraph N, wherein the cyclodextrin
complex stability constant is from about -2.0 to about 2.5. [0062]
P. The cyclodextrin complex of any of paragraphs N-O wherein the
cyclodextrin comprises an alpha-cyclodextrin, a beta-cyclodextrin,
a gamma-cyclodextrin, or a combination thereof [0063] Q. The
cyclodextrin complex of any of paragraphs N-P, wherein the
cyclodextrin comprises hydroxypropyl alpha-cyclodextrin,
hydroxypropyl beta-cyclodextrin, methylated-alpha-cyclodextrin,
methylated-beta-cyclodextrin, or a combination thereof. [0064] R.
The cyclodextrin complex of any of paragraphs N-Q, wherein the
percent of the perfume that is complexed with the cyclodextrin is
greater than about 75%. [0065] S. The cyclodextrin complex of any
of paragraphs N-R, wherein the percent of the perfume that is
complexed with the cyclodextrin is greater than about 95%. [0066]
T. The cyclodextrin complex of any of paragraphs N-S, wherein the
perfume raw materials are selected from the group consisting of:
eugenyl formate; benzaldehyde; 2-hexen-1-yl acetate; alpha-methyl
cinnamaldehyde; methyl phenylacetate; viridine; ethyl
2-phenylacetate; methyl hydrocinnamate; methyl cinnamate;
2-Phenylethyl acetate; cinnamyl acetate; lilac acetaldehyde;
4-(p-Methoxyphenyl)-2-butanone; anethole; gamma-Octalactone;
3-phenyl propionaldehyde; cinnamic alcohol; cinnamic aldehyde;
phenethyl formate; 3-phenyl propyl formate; isobutyl
furylpropionate; styryl acetate; geranyl formate; 3-Hepten-1-ol;
citronellol; trans-Geraniol; nerol; neral; melon heptenal; propyl
mercaptan; 2-Propionylpyrrole;
5,6-Dimethyl-1-(1-methylethenyl)bicyclohept-5-ene-2-methanol;
hydratopic alcohol; 3,4-Dimethoxyacetophenone; safranal;
2-Hydroxyacetophenone; cis-carveol, ocean propanal; Isosafrol;
Indole; 2-Methylbenzothiazole; Ethyl vanillin; Vanillin; Methyl
p-anisate; Benzyl propionate; 3-phenyl propyl acetate; phenyl
acetaldehyde; p-Hydroxybenzaldehyde; para-anisaldehyde; Isoamyl
acetate; Ethyl 3-methylthiopropionate; Methyl anthranilate;
1,2-Cyclopentanedione, 3-ethyl-; Syringaldehyde; furfuryl
thioacetate; blackberry thiophenone; p-Cresyl acetate; linalool
oxide (pyranoid); Geranial; Parmanyl; Sorbinaldehyde; Pentyl
2-furyl ketone; m-Guaiacol; alpha-Methylcinnamic alcohol; Ethyl
cyclohex-3-enecarboxylate; 2,4-Hexadienyl acetate;
4-Hydroxy-3-methylbenzaldehyde; Furan,
3-methyl-2-(3-methyl-2-butenyl)-; n-Pentyl acetoacetate; Ethyl
2-hexenoate; 2-Ethyl-4-methylthiazole; tropical thiazole; Trifemal;
Coumarone; 2,4-Hexadienyl propionate; Cyclopentyl mercaptan;
2-Methyl-2-butanethiol; trans-2-Methyl-2-pentenoic acid;
2-Hexyl-1,3-dioxolane; cis-3-Hepten-1-ol; 3-Hexenyl acetate;
Trans,trans-2,4-Hexadien; methyl trans-cinnamate 99%;
4-Methyl-5-vinylthiazole; 2-Propylthiazole;
(S),(-)-Perillaaldehyde; 2-(1-Methylpropyl)thiazole;
(+)-p-menth-1-en-9-OL 97% (mixture of isomers); Isobutyl thiazole;
trans-2-Heptenal; (1S)-(-)-cis-Verbenol; Anapear; alpha-Campholenic
alcohol; Ethyl 2-mercaptopropionate; 2-Methylphenethyl alcohol;
Methyl 4-phenylbutyrate; Allyl crotonate; Allyl butyrate; Benzyl
lactate; Vanillin isobutyrate; perillaldehyde; Neryl Formate; Allyl
methyl disulfide; Methyl propyl disulfide; 2-Cyclopenten-1-one,
2-hydroxy-3,4-dimethyl-; 3-Ethyl-2-hydroxy-2-cyclopenten-1-one;
2-Octenol-1; Tetrahydrofurfuryl butyrate; Allo-ocimenol;
7-Octene-1,6-diol, 3,7-dimethyl-; 3-Ethoxybenzaldehyde;
2-Ethylbenzaldehyde; 2-hexen-1-ol; Phenoxyethyl propionate;
Nerolione; 7-Methylcoumarin; Butylacrolein; 2-Hexen-1-yl acetate;
Ethyl phenoxyacetate; Ethyl trans-3-hexenoate; N-Acetyl methyl
anthranilate; Ethyl trans-2-hexenoate; Vertoliff;
(2E,6Z)-Nona-2,6-dien-1-ol; Ocimenol;
2,6-Dimethyl-1,5,7-octatrienol-3; p-Menth-1-ene-9-al;
2,4-Octadien-1-al; Propyl anthranilate; 2-Pentanoylfuran;
4-Ethyl-2-methylthiazole; Jasmolactone; cis-3-Hexenyl formate;
1-Octenol-3; 4,5-Dimethylthiazole;
4,4-Dimethyl-5-isopropyl-1,3-dioxolane; 1-Hexen-3-yl acetate;
Furfuryl valerate; 2,6-Dimethyl-6-hepten-1-ol; cis-3-Hexenyl
acetate; trans-3-Hexenyl acetate; 5-Ethyl-2-thiophenecarbaldehyde;
2-Phenyl-1(2)propenyl-1 ester; 3-Cyclohexene-1-ethanol,
4-methyl-beta-methylene-, (R)-; Furfuryl hexanoate; 3-methoxy
cinnamaldehyde; 3-Acetyl-5-butyldihydro-2(3H)-furanone; Pyrazine,
3-butyl-2,5-dimethyl-; Methyl Heptenone; 2,5-Dimethylthiazole;
(E)-anethol; Phenylethyl oxy-acetaldehyde;
3-Ethyl-2-hydroxy-4-methylcyclopent-2-en-1-one;
(E,E)-2,4-heptadien-1-al; Cinnamic aldehyde dimethyl acetal;
Campholene aldehyde; cis-4-Hexenal; 2-Hepten-4-one; 2-Octen-4-one;
Verbenol; 4-Ethylbenzaldehyde; Piperitol; piperitenone;
Isocoumarin; Lepidine; ethyl maltol; Butyroin; Hinokitiol;
Pyrazine, 2-butyl-3,5-dimethyl-; cis-3, cis-6-nonadienol;
trans-2-Hexenyl formate; Ethyl 2-methyl-4-pentenoate;
1-(4-Methylphenyl)ethanol; Perillyl alcohol; Cumic alcohol; citral;
Benzyl acetoacetate; p-Methylhydrocinnamic aldehyde;
2,4-Dimethylthiazole; Acetaldehyde phenyl ethyl acetal; Canthoxal;
Ethyl 3-mercaptopropionate; Raspberry ketone; 2-Methylthiophene;
3,6-Octadienal, 3,7-dimethyl-; 2,4-Octadienal; Cinnamaldehyde
ethylene glycol acetal; trans-3, cis-6-nonadienol; 2-Heptenal,
(2Z)-; Methyl furfuryl disulfide; o-Acetylanisole; Lavandulol;
3-Methylacetophenone; p-Tolyl alcohol; Furfuryl thiopropionate;
2-Mercaptomethylpyrazine; 2,4-Heptadienal; cis-iso-Eugenol; S-Ethyl
benzothioate; trans-Isoeugenol; Methyl 2-nitrobenzoate; Methyl
o-methoxybenzoate; Guaiacyl acetate; 3-Methylthiophene;
cis-4-Hepten-1-ol; beta-Phenoxy ethyl acetate; cis-3-Hexenyl
lactate; meta-tolyl aldehyde; 4-(2-Furyl)-3-buten-2-one; Dimethyl
disulfide; Cyclopentyl isobutyrate; Phenylacetaldehyde diethyl
acetal; tetrahydrofurfuryl propionate; 2,5-Dimethylthiophene; Ethyl
2-methoxybenzyl ether; p-Methoxy-alpha-methyl cinnamaldehyde;
Geranyl oxyacetaldehyde; Ethyl (p-tolyloxy)acetate;
Trans-2-Hexenal; cis-4-Heptenal; 3-Mercapto-2-pentanone;
3,5,6-Trimethyl-3-cyclohexene-1-carbaldehyde; Floralol;
2,4-Dimethyl-3-cyclohexene-1-methanol; trans-2-Hexenal diethyl
acetal; 3,6-ivy carbaldehyde; p-Methyl phenoxy acetaldehyde;
(Z)-3-hexen-1-al; Dimethyl cyclohexene carboxaldehyde;
2,4-Dimethyl-3-Cyclohexene-1-carboxaldehyde; cis-3-Hexenyl
pyruvate; 3,5-ivy carbaldehyde; delta-Octalactone; Methyl benzyl
disulfide; 1-Phenylbutan-2-ol; Ethyl 2-methylbutyrate; Methyl
mercaptan; Allyl anthranilate; Allyl tiglate; Ethanethiol; dimethyl
sulfide 2-Propanethiol; (
-)-Citronellol; Anisyl propionate; tert-Butyl mercaptan;
2,4-Pentadienal; 3,6-Nonadien-1-ol; Benzaldehyde diethyl acetal;
2-Thienyl mercaptan; 4-(p-Tolyl)-2-butanone; Isoeugenyl formate;
2,6-Nonadien-1-ol; 2-Methoxy-4-vinylphenol; p-Menth-8-en-3-ol;
filbert heptenone; Gardamide; Dimethyl anthranilate; Allyl
mercaptan; Ethyl anthranilate; cinnamon acrolein; Vanillin acetate;
Isopulegol; Salicylaldehyde; Guaiacol; Hydratropaldehyde dimethyl
acetal; Coumarin (Z)-2-hexen-1-ol; (E)-2-hexen-1-ol;
cis-3-Hexen-1-ol; Methyl isoeugenol; Isoeugenyl acetate; 2-phenyl
propionaldehyde; 1-Phenyl-1-propanol; Methyl benzoate; Ethyl
benzoate; Citronitrile; Styrallyl acetate; Butanoic acid,
2-methyl-, 2-hexenyl ester, (E)-; Vanitrope; 2-Methylindole;
Eugenol; and a combination thereof. [0067] U. The cyclodextrin
complex of any of paragraphs N-S, wherein the perfume raw materials
are selected from the group consisting of: beta gamma hexanol; cis
3 hexenyl acetate; ethyl-2-methyl butyrate; amyl-acetate; vanillin;
anethole; methyl isoeugenol; guaiacol; floralol; 2,6-nonadien-1-ol;
coumarin; and a combination thereof. [0068] V. The cyclodextrin
complex of any of paragraphs N-S, wherein the perfume raw materials
comprise ethyl-2-methyl butyrate; beta gamma hexanol; iso amyl
acetate; amyl acetate; cis-3-hexenyl acetate; gamma-octalactone;
ethyl vanillin; vanillin; benzaldehyde; or a combination thereof.
[0069] W. The cyclodextrin complex of any of paragraphs N-S,
wherein the perfume raw materials comprise dimethyl anthranilate;
iso-eugenyl acetate; canthoxal; 3,6-nonadien-1-ol, triplal; or a
combination thereof. [0070] X. The cyclodextrin complex of any of
paragraphs N-W, wherein the 10% or more of the perfume raw
materials have an Odor Detection Threshold of about 7 or more -log
molar concentration. [0071] Y. The cyclodextrin complex of any of
paragraphs N-X, wherein 10% or more of the perfume raw materials
have an Odor Detection Threshold of about 7 to about 11.5-log molar
concentration. [0072] Z. The cyclodextrin complex of any of
paragraphs N-Y, wherein about 20% to about 100%, by weight of the
perfume, of the perfume raw materials have: a complex stability
constant of about -2.0 to about 3.0, a C log P of about -3.0 to
about 2.5; and a weight average molecular weight of about 50
Daltons to about 200. [0073] AA. The cyclodextrin complex of any of
paragraphs N-Z, wherein about 50% to about 100%, by weight of the
perfume, of the perfume raw materials have: a complex stability
constant of about 0 to about 3, a C log P of about -3.0 to about
2.5; and a weight average molecular weight of about 50 to about 200
Daltons or less. [0074] BB. The cyclodextrin complex of any of
paragraphs N-AA, wherein the perfume raw materials have a complex
stability constant of about -1.5 to about 2.5. [0075] CC. The
cyclodextrin complex of any of paragraphs N-BB, wherein the perfume
raw materials have a C log P of about -3.0 to about 2.0. [0076] DD.
The cyclodextrin complex of any of paragraphs N-CC, wherein the
perfume raw materials have a weight average molecular weight of
about 180 Daltons or less. [0077] EE. A perfume comprising perfume
raw materials, wherein 20% or more, by weight of the perfume, of
the perfume raw materials, are selected from the group consisting
of: ethyl-2-methyl butyrate; beta gamma hexanol; iso amyl acetate;
amyl acetate; cis-3-hexenyl acetate; gamma-octalactone; ethyl
vanillin; vanillin; benzaldehyde; dimethyl anthranilate;
iso-eugenyl acetate; canthoxal; 3,6-nonadien-1-ol, triplal; and
combinations thereof. [0078] FF. The perfume of paragraph EE,
wherein the perfume raw materials are selected from the group
consisting of ethyl-2-methyl butyrate; beta gamma hexanol; iso amyl
acetate; amyl acetate; cis-3-hexenyl acetate; gamma-octalactone;
ethyl vanillin; vanillin; benzaldehyde; and combinations thereof.
[0079] GG. The perfume of paragraph EE, wherein the perfume raw
materials are selected from the group consisting of dimethyl
anthranilate; iso-eugenyl acetate; canthoxal; 3,6-nonadien-1-ol,
triplal; and combinations thereof. [0080] HH. The perfume of any of
paragraphs EE-GG, wherein about 20% to about 100%, by weight of the
perfume, of the perfume raw materials have: a complex stability
constant of about -2.0 to about 3.0, a C log P of about -3.0 to
about 2.5; and a weight average molecular weight of about 50
Daltons to about 200. [0081] II. The perfume of any of paragraphs
EE-HH, wherein about 50% to about 100%, by weight of the perfume,
of the perfume raw materials have: a complex stability constant of
about -2.0 to about 3.0, a C log P of about -3.0 to about 2.5; and
a weight average molecular weight of about 50 Daltons to about 200.
[0082] JJ. The perfume of any of paragraphs EE-HH, wherein about
50% to about 100% of the perfume raw materials have a complex
stability constant of about -1.5 to about 2.5. [0083] KK. The
perfume of any of paragraphs EE-JJ, wherein about 50% to about 100%
of the perfume raw materials have a C log P of about 2.0 or less.
[0084] LL. The perfume of any of paragraphs EE-KK, wherein about
20% to about 100% of the perfume raw materials have a weight
average molecular weight of about 180 Daltons or less. [0085] MM.
The perfume of any of paragraphs EE-LL, wherein the perfume is part
of a cyclodextrin complex. [0086] NN. The perfume of any of
paragraph MM, wherein the cyclodextrin comprises an
alpha-cyclodextrin, a beta-cyclodextrin, a gamma-cyclodextrin, or a
combination thereof. [0087] OO. The perfume of any of paragraphs
MM-NN, wherein the cyclodextrin comprises hydroxypropyl
alpha-cyclodextrin, hydroxypropyl beta-cyclodextrin,
methylated-alpha-cyclodextrin, methylated-beta-cyclodextrin, or a
combination thereof. [0088] PP. The perfume of any of paragraphs
MM-OO, wherein the percent of the perfume that is complexed with
the cyclodextrin is about 75% or more. [0089] QQ. The perfume of
any of paragraphs MM-PP, wherein the percent of the perfume that is
complexed with the cyclodextrin is about 95% or more. [0090] RR.
The perfume of any of paragraphs N-DD and MM-QQ, wherein the
cyclodextrin comprises beta-cyclodextrin.
Examples
[0091] Exemplary perfume compositions in accordance with the
invention can include:
TABLE-US-00004 Material % by weight of perfume composition
Cis-3-hexen-1-ol 5-50% Cis-3-hexenyl acetate 5-50% Ethyl
2-methylbutyrate 5-50% Isoamyl acetate 5-50% Vanillin 5-50%
Additional information about the perfume raw materials in the
example can be found in the table below:
TABLE-US-00005 Odor Detection Weight threshold Cyclo- average (-log
dextrin molecular molar stability CAS weight concen- constant
Number Name cLogP (Dalton) tration) (log K) 123-92-2 Isoamyl 1.87
130 7.12 0.33 acetate 121-33-5 Vanillin 1.04 152 9.93 1.36
7452-79-1 Ethyl 2- 1.91 130 7.27 0.75 methylbutyrate 928-96-1
Cis-3-hexen-1- 1.3 100 8.06 1.06 ol 3681-71-8 Cis-3-hexenyl 2.18
142 8.16 0.48 acetate
[0092] The perfume composition can be made by blending all of the
perfume raw materials together until a homogenous solution is
formed.
[0093] This exemplary composition can then be formed into a
cyclodextrin complex by mixing 10 parts cyclodextrin with 10 (or
more) parts water, and 1 part (or less) of the perfume composition.
After the mixing, the slurry will be more viscous than at the start
of mixing--the change in viscosity is believed to be due to the
formation of the cyclodextrin perfume complex. The mixture is then
dried (or spray dried) to remove the water and leave the
cyclodextrin and perfume complex as a powder. The cyclodextrin can
be, for example, a beta cyclodextrin.
In Vitro Perfume Release Method
Released Perfume (RP) Sample
[0094] About 500 milligrams of a cyclodextrin perfume complex is
weighed into a glass scintillation vial. About 1 milliliter of
water is added to the vial. The vial is then capped tightly and
vortexed for about 30 seconds to create a slurry. The RP sample is
then placed into a 37 degrees Celsius oven to incubate for 4 hours.
The sample vial is removed from the oven and allowed to cool to
room temperature. 10 milliliters of hexane is then added to the
vial. The vial is capped tightly and mixed by hand shaking for
about 10 seconds and then mixed on high speed with a vortex mixer
for about 30 seconds to extract perfume components liberated by the
water incubation step. After allowing solids to settle, an aliquot
of the sample is transferred to a 2 milliliter autosampler vial for
analysis.
Total Perfume (TP) Sample
[0095] Another 500 milligrams of the same cyclodextrin perfume
complex used to create the RP sample is weighed into a
scintillation vial. About 10 milliliters of acetone is added to the
vial. This sample is then capped tightly and vortexed for about 30
seconds to disperse the sample. The total sample is then placed
into a 70 degrees Celsius oven for 4 hours. The sample is removed
from the oven and allowed to cool to room temperature. After
allowing solids to settle, an aliquot of the sample is transferred
to a 2 milliliter autosampler vial for analysis.
Analysis
[0096] The RP and TP samples are analyzed using liquid injection
gas chromatography with a mass selective detector. The injection
port is heated to 270 degrees Celsius and operated in split mode
with a split ratio of about 20:1. The carrier gas is helium and
delivered at a constant flowrate of about 1.2 milliliters per
minute. The oven temperature is ramped from an initial temperature
of 50 degrees Celsius to a final temperature of 250 degrees Celsius
at a rate of 10 degrees Celsius per minute. The final temperature
is held for 2 minutes. The mass selective detector is operated in
scanning mode and perfume components are identified using NIST mass
spectral library searching. The chromatogram from the TP sample is
used to identify a specific mass to charge ratio for each perfume
component and extracted ion peak areas for each perfume component
are obtained. The RP chromatogram is correspondingly processed.
Results Calculation
[0097] Individual perfume component peak areas per unit of sample
weight from the RP sample are divided by the corresponding peak
areas per unit of sample weight from the TP sample. The resulting
ratio is multiplied by 100 to calculate a release percentage for
each individual perfume material. The release percentages from all
perfume components are averaged to calculate a composite release
value for a given complex sample.
[0098] The dimensions and values disclosed herein are not to be
understood as being strictly limited to the exact numerical values
recited. Instead, unless otherwise specified, each such dimension
is intended to mean both the recited value and a functionally
equivalent range surrounding that value. For example, a dimension
disclosed as "40 mm" is intended to mean "about 40 mm."
[0099] Every document cited herein, including any cross referenced
or related patent or application and any patent application or
patent to which this application claims priority or benefit
thereof, is hereby incorporated herein by reference in its entirety
unless expressly excluded or otherwise limited. The citation of any
document is not an admission that it is prior art with respect to
any invention disclosed or claimed herein or that it alone, or in
any combination with any other reference or references, teaches,
suggests or discloses any such invention. Further, to the extent
that any meaning or definition of a term in this document conflicts
with any meaning or definition of the same term in a document
incorporated by reference, the meaning or definition assigned to
that term in this document shall govern.
[0100] While particular embodiments of the present invention have
been illustrated and described, it would be obvious to those
skilled in the art that various other changes and modifications can
be made without departing from the spirit and scope of the
invention. It is therefore intended to cover in the appended claims
all such changes and modifications that are within the scope of
this invention.
* * * * *