Abstract: The purpose of the present invention is to provide a method for obscuring (masking) the odor of p-cresol using olfactory receptor antagonism without affecting the flavor of a food or beverage. The present invention uses a specific concentration of ambrettolide, isoambrettolide, pentalide, muscone, civetone, d-2-decenolactone, cinnamic aldehyde, ß-caryophyllene oxide, sclareolide, and ethyl maltol in a food or beverage.
Technical Field
The present invention relates to a food and/or beverage having a flavor of citrus
fruit or ginger. Specifically, the present invention relates to a food and/or beverage in
which a deteriorated odor (off-flavor) caused by deterioration of the aromatic components
of citrus fruit or ginger is masked.
10 Background Art
A food and/or beverage having a citrus fruit flavor is favored by many people
because moderately sweet and sour taste is combined with a refreshing aroma peculiar to
citrus fruits to provide a unique refreshing feeling. In addition, ginger has a sweet and
refreshing scent and a refreshing pungent taste, and thus has been widely used since
15 ancient times to remove the odor of meat and fish and to impart a unique flavor to food
and/or beverage. However, it is known that the refreshing aroma peculiar to citrus fruits
or ginger is lost over time, and instead deteriorated odor (off-flavor) is generated, which
impairs the quality of food and/or beverage.
20
Citral is an aromatic component widely contained in citrus fruits or ginger, and
is an important aromatic component having a characteristic lemon-like aroma.
citral is known to decrease with heating or over time and produce an off-flavor.
is known as one of the substances that cause off-flavors.
However,
p-Cresol
As a method of masking an off-flavor, Patent Literature 1 describes a method of
containing a specific amount of cineol or cis-3-hexenol, and Patent Literature 2 describes
25 a method of adding one or more selected from the group consisting of ethylpyruvate,
methyl jasmonate, methyl dihydro jasmonate, diethyl malonate, methyl beta naphthyl
ketone, maltol isobutyrate, menthol, lauric acid, acetoin, cinnamyl acetate, benzyl acetate,
and a-terpineol.
It is known that ambrettolide, isoambrettolide, cyclopentadecanolide, civetone,
30 muscone, 8-2-decenolactone, ethyl maltol, cinnamic aldehyde, ~-caryophyllene oxide,
1
and the like are used in masking compositions for hair cosmetics for masking unpleasant
odors such as substrate odors, amine odors, ammonia odors, sulfur odors, acid odors, rust
odors, tobacco odors, animal odors, and halogen odors (Patent Literature 3). Sclareolide
is known to be used as an aroma/flavor imparting or modulating agent in flavor
5 compositions for oral products (Patent Literature 4). ~-Caryophyllene oxide is known
to be used as an aroma/flavor imparting or modulating agent in citrus-like flavor
compositions (Patent Literature 5). Ethyl maltol and the like are known to make fruit
flavor-derived off-flavor less noticeable in clear beverages containing fruit flavors (Patent
Literature 6).
10 On the other hand, in the fragrant cosmetics field, a method of suppressing urine
odor has been provided by specifically inhibiting the activity of the olfactory receptor
OR9Q2 for p-cresol (Patent Literature 7).
Citation List
15 Patent Literatures
Patent Literature 1: Japanese Patent Application Publication No. 2016-36319
Patent Literature 2: Japanese Patent Application Publication No. 2015-180715
Patent Literature 3: Japanese Patent Application Publication No. 2003-137758
Patent Literature 4: Japanese Patent Application Publication No. 2004-18431
20 Patent Literature 5: Japanese Patent Application Publication No. 2004-168936
Patent Literature 6: Japanese Patent Application Publication No. 2016-127818
Patent Literature 7: Japanese Patent Application Publication No. 2017-101224
Summary of Invention
25 Problems to be solved by the invention
30
The present invention relates to providing a method of making less noticeable
(masking) p-cresol odor without affecting the flavor of citrus-flavored food and/or
beverage or ginger-flavored food and/or beverage.
Means for solution of the problems
The present inventors used olfactory receptor antagonism, and have found that
2
among the antagonist substances of the olfactory receptor OR9Q2 for p-cresol,
ambrettolide, isoambrettolide, pentalide, muscone, civetone, 8-2-decenolactone,
cinnamic aldehyde, ~-caryophyllene oxide, sclareolide, and ethyl maltol suppress the pcresol
odor in citrus-flavored beverages at a specific concentration without impairing the
5 flavor of the product.
The present invention includes the contents [ 1] to [ 11] below.
[ 1] A method of masking an off-flavor of citral or a citral-containing product,
including:
adding one or more selected from the group consisting of ambrettolide,
10 isoambrettolide, pentalide, muscone, civetone, 8-2-decenolactone, cinnamic aldehyde,
~-caryophyllene oxide, sclareolide, and ethyl maltol to a citral-containing product.
[2] The masking method according to [1], in which the off-flavor is p-cresol.
[3] The masking method according to [1] or [2], in which the citral-containing
product is a citrus-flavored food and/or beverage or a ginger-flavored food and/or
15 beverage.
20
[ 4] A flavor composition for masking an off-flavor of a citral-containing
product, including: one or more selected from the group consisting of ambrettolide,
isoambrettolide, pentalide, muscone, civetone, 8-2-decenolactone, cinnamic aldehyde,
~-caryophyllene oxide, sclareolide, and ethyl maltol.
cresol.
[5] The flavor composition according to [4], which is citrus-like or ginger-like.
[6] The flavor composition according to [4] or [5], in which the off-flavor is p-
[7] The flavor composition according to any one of [4] to [6], in which the
citral-containing product is a citrus-flavored food and/or beverage or a ginger-flavored
25 food and/or beverage.
30
[8] A citral-containing product including: 0.01 ppt to 10 ppm of one or more
selected from the group consisting of ambrettolide, isoambrettolide, pen tali de, muscone,
civetone, 8-2-decenolactone, cinnamic aldehyde, ~-caryophyllene oxide, sclareolide,
and ethyl maltol.
[9] The product according to [8], in which the citral-containing product is a
3
citrus-flavored food and/or beverage or a ginger-flavored food and/or beverage.
[1 OJ The product according to [8] or [9], further including: 10 ppb to 1 ppm of
p-cresol.
[ 11] A method of producing a citral-containing product including: blending a
5 citral-containing product with 0.01 ppt to 10 ppm of one or more selected from the
group consisting of ambrettolide, isoambrettolide, pentalide, muscone, civetone, 8-2-
decenolactone, cinnamic aldehyde, B-caryophyllene oxide, sclareolide, and ethyl maltol.
Advantageous Effects of Invention
According to the present invention, by imparting a citrus-flavored food and/or
10 beverage or ginger-flavored food and/or beverage with a specific amount of one or more
selected from the group consisting of ambrettolide, isoambrettolide, pentalide, muscone,
civetone, 8-2-decenolactone, cinnamic aldehyde, B-caryophyllene oxide, sclareolide, and
ethyl maltol, it is possible to mask off-flavor caused by deterioration of the aromatic
components of citrus fruit or ginger. As a result, even when a food and/or beverage with
15 easily deteriorating aromatic components of citrus fruit or ginger produce deteriorated
components due to long-term storage or the like, it is possible to provide a food and/or
beverage with a flavor of citrus fruit or ginger that is closer to the design immediately
after production.
20 Brief Description of Drawings
Fig. 1 is a graph illustrating the effects of adding 1-oxacycloheptadecan-7 -en-2-
one to suppress the response of the olfactory receptor OR9Q2 for p-cresol.
Fig. 2 is a graph illustrating the effects of adding 1-oxacycloheptadecan-8-en-2-
one to suppress the response of the olfactory receptor OR9Q2 for p-cresol.
25 Fig. 3 is a graph illustrating the effects of adding isoambrettolide to suppress the
response of the olfactory receptor OR9Q2 for p-cresol.
Fig. 4 is a graph illustrating the effects of adding muscone to suppress the
response of the olfactory receptor OR9Q2 for p-cresol.
Fig. 5 is a graph illustrating the effects of adding civetone to suppress the
30 response of the olfactory receptor OR9Q2 for p-cresol.
4
5
Fig. 6 is a graph illustrating the effects of adding pentalide to suppress the
response of the olfactory receptor OR9Q2 for p-cresol.
Fig. 7 is a graph illustrating the effects of adding 8-2-decenolactone to suppress
the response of the olfactory receptor OR9Q2 for p-cresol.
Fig. 8 is a graph illustrating the effects of adding cinnamic aldehyde to suppress
the response of the olfactory receptor OR9Q2 for p-cresol.
Fig. 9 is a graph illustrating the effects of adding ~-caryophyllene oxide to
suppress the response of the olfactory receptor OR9Q2 for p-cresol.
Fig. 10 is a graph illustrating the effects of adding sclareolide to suppress the
10 response of the olfactory receptor OR9Q2 for p-cresol.
15
Fig. 11 is a graph illustrating the effects of adding ethyl maltol to suppress the
response of the olfactory receptor OR9Q2 for p-cresol.
Description of Embodiments
A method of searching for an antagonist substance of the olfactory receptor
OR9Q2 for p-cresol is a method of searching for candidate substances for p-cresol odor
suppressing materials from among test substances using an olfactory receptor polypeptide
responsive to p-cresol by the following steps.
(i) A step of bringing p-cresol into contact with an olfactory receptor polypeptide selected
20 from the group consisting ofOR9Q2 and polypeptides containing an amino acid sequence
having 80% or more identity with the amino acid sequence of the polypeptide OR9Q2
and being responsive to p-cresol to measure the response of the olfactory receptor
polypeptide to p-cresol,
(ii) a step of mixing p-cresol with a test substance to measure the response of the olfactory
25 receptor polypeptide used in step (i), and
(iii) comparing the measurement results in steps (i) and (ii) to select the test substance
that suppresses the response as a candidate substance for the p-cresol odor suppressing
material.
Each step is described below.
30
5
The olfactory receptor polypeptide used is an olfactory receptor polypeptide
selected from the group consisting of OR9Q2 and polypeptides containing an amino acid
sequence having 80% or more identity with the amino acid sequence of any polypeptide
thereof and being responsive to p-cresol.
5 OR9Q2 is a polypeptide that is registered as NM_001005283 in GenBank, and
composed of an amino acid sequence (SEQ ID NO: 2) encoded by the DNA having the
base sequence set forth in SEQ ID NO: 1.
The olfactory receptor used may be an olfactory receptor polypeptide selected
from the group consisting of polypeptides containing an amino acid sequence having 80%
10 or more, preferably 85% or more, more preferably 90% or more, further preferably 95%
or more, and particularly preferably 98% or more identity with the amino acid sequence
of this polypeptide (that is, SEQ ID NO: 2) and being responsive top-cresol.
Olfactory receptor polypeptides may be used alone or in combination of two or
more kinds.
15 The method of measuring the response of the olfactory receptor polypeptide is
not particularly limited. For example, it may be brought into contact with p-cresol to
measure the response of the olfactory receptor polypeptide on cells isolated from a living
body expressing the olfactory receptor polypeptide, or it may be brought into contact with
p-cresol to measure the response of the olfactory receptor polypeptide on cells in which
20 the olfactory receptor polypeptide has been artificially expressed by genetic engineering.
The contact time between the olfactory receptor polypeptide and p-cresol depends on the
concentration of p-cresol and cannot be generally specified, but is usually 2 to 4 hours.
The same is true when the test substance is mixed with p-cresol and brought into contact
with the olfactory receptor polypeptide.
25 Also, the 20 N -terminal amino acid residues of bovine rhodopsin may be
incorporated together with the olfactory receptor polypeptide. Incorporation of the 20
N-terminal amino acid residues of bovine rhodopsin can promote cell membrane
expression of the olfactory receptor polypeptide.
Bovine rhodopsin is registered in GenBank as NM 001014890. Bovine
30 rhodopsin is a polypeptide composed of an amino acid sequence (SEQ ID NO: 4) encoded
6
by the DNAs 1 to 1047 of the base sequence set forth in SEQ ID NO: 3.
Further, instead of bovine rhodopsin, one may use a polypeptide containing an
amino acid sequence having 80% or more, preferably 85% or more, more preferably 90%
or more, further preferably 95% or more, and particularly preferably 98% or more identity
5 with the amino acid sequence set forth in SEQ ID NO: 3 and capable of promoting cell
membrane expression of the olfactory receptor polypeptide.
10
Note that amino acid residues of not only bovine rhodopsin but also other
polypeptides may be used as long as they can promote cell membrane expression of
olfactory receptor polypeptides.
The method of measuring the response of the olfactory receptor polypeptide is
not particularly limited, and any method used in the art may be used. It is known, for
example, that when an aromatic compound binds to an olfactory receptor polypeptide, it
activates intracellular G protein, and the G protein activates adenylate cyclase, converts
ATP to cyclic AMP (cAMP), and increases intracellular cAMP level. Therefore,
15 measuring the cAMP level makes it possible to measure the response of the olfactory
receptor polypeptide. As a method of measuring the cAMP level, the ELISA method,
the reporter gene assay method, or the like is used. Among them, it is preferable to
measure the response of the olfactory receptor polypeptide by the reporter gene assay
method using a luminescent substance such as luciferase.
20 The response of the olfactory receptor polypeptide may be evaluated using the
Fold Increase value, obtained by dividing the measurement result in the presence of pcresol
by the measurement result in the absence ofp-cresol, as an index. For example,
when measuring the response of an olfactory receptor polypeptide by the reporter gene
assay method using a luminescent substance such as luciferase, evaluation can be
25 performed using p-cresol at a concentration that gives a Fold Increase value of preferably
2 or more, more preferably 4 or more, and further preferably 10 or more.
As a method of measuring the response of the olfactory receptor polypeptide,
one can use a method similar to that presented in step (i), except that p-cresol is mixed
30 with the test substance and brought into contact with the olfactory receptor polypeptide.
7
For example, the response of the olfactory receptor polypeptide may be measured on cells
isolated from a living body expressing the olfactory receptor polypeptide, or the response
of the olfactory receptor polypeptide may be measured on cells in which the olfactory
receptor polypeptide has been artificially expressed by genetic engineering. In order to
5 properly compare the measurement results in steps (i) and (ii), the measurement
conditions in steps (i) and (ii) are preferably the same, except for the presence or absence
of the test substance.
Step (iii) compares the measurement results in steps (i) and (ii), and selects test
10 substances with suppressed responses as candidate substances for p-cresol odor
suppressing materials.
If a suppression in response is observed by comparing the measurement results,
the test substance used in step (ii) can be evaluated as a candidate substance for a p-cresol
odor suppressing material.
15 All of ambrettolide, isoambrettolide, pentalide, muscone, civetone, 8-2-
decenolactone, cinnamic aldehyde, B-caryophyllene oxide, sclareolide, and ethyl maltol
used in the present invention, which were found by the above methods, are known
aromatic components, and commercially available products can be used.
There are two kinds of aroma components,. 1-oxacycloheptadecan-7 -en-2-one
20 and 1-oxacycloheptadecan-8-en-2-one, which are distributed under the name of
ambrettolide, and any one of them can be used alone, or a mixture thereof in any ratio can
be used.
Ambrettolide, isoambrettolide, civetone, and cinnamic aldehyde have cis and
trans structural isomers, and any one of them can be used alone, or a mixture thereof in
25 any ratio can be used.
Muscone, 8-2-decenolactone, and sclareolide have optical isomers, which may
be racemates or specific optical isomers.
By adding one or more selected from the group consisting of ambrettolide,
isoambrettolide, pentalide, muscone, civetone, 8-2-decenolactone, cinnamic aldehyde,~-
30 caryophyllene oxide, sclareolide, and ethyl maltol to a citral-containing product, it is
8
possible to mask an off-flavor of citra! or citral-containing product. In addition, a flavor
composition containing one or more selected from the group consisting of ambrettolide,
isoambrettolide, pentalide, muscone, civetone, 8-2-decenolactone, cinnamic aldehyde,~caryophyllene
oxide, sclareolide, and ethyl maltol can be used for masking an off-flavor
5 of a citral-containing product.
Here, the citral-containing product is not particularly limited as long as it
contains citra!. Citral-containing products include citrus beverages, citrus confectionery,
citrus seasonings, ginger-containing foods, grated ginger, and the like.
Also, for citrus beverages, the content ofp-cresol in the citral-containing product
10 1s preferably 100 ppt to 500 ppb, more preferably 1 ppb to 50 ppb. For citrus
confectionery and citrus seasonings, it is preferably 1 ppb to 10 ppm, more preferably 50
ppb to 500 ppb. For ginger~containing foods and grated ginger, it is preferably 10 ppb
to 10 ppm, more preferably 100 ppb to 1 ppm.
In the fragrance composition of the present invention, the "citrus-like flavor
15 composition" is a composition used for the purpose of imparting or enhancing a flavor
reminiscent of citrus fruits to a food and/or beverage. The citrus fruits include, for
example, oranges such as Valencia orange, navel orange, and blood orange, grapefruits,
sour-flavored citrus fruits such as lemon, lime, citrus depress a, daidai, yuzu, kabosu,
sudachi, citron, and buddha's hand, miscellaneous citruses such as natsumikan, hassaku
20 orange, hyuganatsu, oro blanco, shiranui, tangors such as iyokan and tankan, tangelos such
as Seminole, pomelos such as buntan, Rutaceae such as mandarin orange, unshu mikan,
ponkan, and kishu mikan, and kumquats such as kinkan, but are not limited to the citrus
fruits listed here. In the flavor composition of the present invention, the "ginger-like
flavor composition" is a composition used for the purpose of imparting or enhancing a
25 flavor reminiscent of ginger to a food and/or beverage.
Other ingredients that can be blended in the flavor composition of the present
invention include various synthetic flavors, natural flavors, natural essential oils, plant
extracts, and the like. For example, natural essential oils, natural flavors, synthetic
flavors, and the like described in "Patent Office Gazette, Collection of Well-known Prior
30 Arts (Flavors), Part II Food Flavors, p 88-131, issued on January 14, 2000" can be
9
mentioned.
The flavor composition of the present invention can contain a commonly used
solvent such as water or ethanol; a retaining agent such as ethylene glycol, propylene
glycol, dipropylene glycol, hexylene glycol, glycerin, triethyl citrate, medium-chain fatty
5 acid triglyceride, medium-chain fatty acid diglyceride, or an animal or vegetable oil
and/ or fat, and the like, if necessary.
10
In the citral-containing product of the present invention, the "citrus-flavored food
and/or beverage" refers to a food and/or beverage having an aroma and taste reminiscent
of citrus fruits.
The citrus-flavored food and/or beverage includes, for example,
confectionery, snacks, sweet buns, cookies, fresh confectionery, western
confectionery, chocolate, chocolate confectionery, foods made mainly from milk and the
like, and foods partially containing citrus ingredients such as filling cream, flower paste,
whipped cream, candy, gummy candy, and jelly (which may be referred to as "citrus
15 confectionery" in the present specification);
animal and vegetable oils and/or fats; agricultural foods and processed agricultural foods;
meat and processed meat foods; fish meat and processed marine products; dairy products;
steamed rice such as retort-packed rice and sprouted brown rice; noodles such as instant
noodles, dried noodles, and chilled noodles; bread such as steamed pork buns and side
20 dish bread; soup foods; cooked and processed foods such as retort pouch foods, pasta
sauces, canned foods, and frozen and chilled foods; plant-based alternative foods;
seasonings such as sauces, soy sauce, tare sauces, tsuyu sauce, mayonnaise, ketchup,
dressings, tube products, soup base, Chinese seasonings, Western seasonings, and various
roux and spices (which may be referred to as "citrus seasoning" in the present
25 specification);
30
beverages and alcoholic beverages containing citrus fruit juice, and beverages that
partially use citrus ingredients such as citrus cocktails, citrus RTD (ready to drink), citrus
RTS (ready to serve) (which may be referred to as "citrus drink" in the present
specification), for example, sangria.
no fruit juice may be contained.
In addition, as long as a citrus flavor can be felt,
For example, it may be a food and/or beverage
10
containing an extract containing aromatic components extracted from citrus fruits, or a
food and/or beverage containing a flavor that artificially reproduces the characteristic
aromatic components of citrus fruits. Examples include citrus fruit juices, citrus fruitflavored
refreshing beverages, refreshing confectionery, chewing gums, and infused
5 liquors obtained by soaking citrus fruit in alcohol. The beverage may or may not be
carbonated. Moreover, alcohol (ethanol) may or may not be contained.
In the citral-containing product of the present invention, the "ginger-flavored
food and/or beverage" refers to a food having an aroma and taste reminiscent of ginger.
The ginger-flavored food and/or beverage includes, for example,
10 ginger-containing beverages, animal and vegetable oils and/or fats; agricultural foods and
processed agricultural foods; meat and processed meat foods; fish meat and processed
marine products; dairy products; steamed rice such as retort-packed rice and sprouted .
brown rice; noodles such as instant noodles, dried noodles, and chilled noodles; bread
such as steamed pork buns and side dish bread; soup foods; cooked and processed foods
15 such as retort pouch foods, pasta sauces, canned foods, and frozen and chilled foods;
plant-based alternative foods; seasonings such as sauces, soy sauce, tare sauces, tsuyu
sauce, mayonnaise, ketchup, dressings, tube products, soup base, Chinese seasonings,
Western seasonings, and various roux and spices; snacks (which may be referred to as
"ginger-containing food" in the present specification). Moreover, if ginger flavor can be
20 felt, no ginger may be used. For example, it may be a food and/or beverage containing
an extract containing aromatic components extracted from ginger, or a food and/or
beverage containing a flavor that artificially reproduces the characteristic aromatic
components of ginger.
The content of one or more selected from the group consisting of ambrettolide,
25 isoambrettolide, pentalide, muscone, civetone, 8-2-decenolactone, cinnamic aldehyde,~caryophyllene
oxide, sclareolide, and ethyl maltol in the citrus-like flavor composition or
ginger-like flavor composition of the present invention varies depending on other
components to be blended and cannot be generally specified, but can generally be in a
concentration range of 0.01 ppm or more and 10000 ppm or less, preferably 0.1 ppm or
30 more and 1000 ppm or less in total, based on the weight of the flavor composition.
11
When the content of one or more selected from the group consisting of ambrettolide,
isoambrettolide, pentalide, muscone, civetone, 8-2-decenolactone, cinnamic aldehyde,~caryophyllene
oxide, sclareolide, and ethyl maltol is less than 0.01 ppm, it is impossible
to obtain the effect of masking the off-flavor of citrus-flavored food and/or beverage or
5 ginger-flavored food and/or beverage. When the content exceeds 10000 ppm, the citrus
flavor or ginger flavor is impaired, which is undesirable.
In addition, the content of one or more selected from the group consisting of
ambrettolide, isoambrettolide, pentalide, muscone, civetone, 8-2-decenolactone,
cinnamic aldehyde, ~-caryophyllene oxide, sclareolide, and ethyl maltol to be contained
10 in a citral-containing product such as the citrus-flavored food and/or beverage or gingerflavored
food and/or beverage can be in a concentration range from 0.01 ppt to 10 ppm,
preferably from 1 ppt to 100 ppb in total, based on the weight of the citral-containing
product. When the content of one or more selected from the group consisting . of
ambrettolide, isoambrettolide, pentalide, muscone, civetone, 8-2-decenolactone,
15 cinnamic aldehyde, ~-caryophyllene oxide, sclareolide, and ethyl maltol is less than 0.01
ppt, it is impossible to obtain the effect of masking the deteriorated odor of citrus-flavored
food and/or beverage or ginger-flavored food and/or beverage. When the content
exceeds 1 0 ppm, the citrus flavor or ginger flavor is impaired, which is undesirable.
The present invention is described in more detail with reference to Examples
20 below, but the present invention is not limited to these Examples.
Examples
(Measurement of Olfactory Receptor Response to p-Cresol)
(1) Olfactory Receptor Gene Cloning
The human olfactory receptor gene was obtained by cloning from Human
25 Genomic DNA: Female (Promega) by PCR method based on the sequence information
registered in GenBank. The 20 N-terminal amino acid residues of bovine rhodopsin
were incorporated into the pME18S vector, and the obtained human olfactory receptor
gene was incorporated downstream thereof to obtain a human olfactory receptor gene
expression vector.
What is claimed is:
1. A method of masking an off-flavor of citral or a citral-containing product, comprising:
adding one or more selected from the group consisting of ambrettolide,
isoambrettolide, pentalide, muscone, civetone, 8-2-decenolactone, cinnamic aldehyde, B-
5 caryophyllene oxide, sclareolide, and ethyl maltol to a citral-containing product.
2. The masking method according to claim 1, wherein the off-flavor is p-cresol.
3. The masking method according to claim 1 or 2, wherein the citral-containing product
10 is a citrus-flavored food and/or beverage or a ginger-flavored food and/or beverage.
4. A flavor composition for masking an off-flavor of a citral-containing product,
compnstng:
one or more selected from the group consisting of ambrettolide, isoambrettolide,
15 pentalide, muscone, civetone, 8-2-decenolactone, cinnamic aldehyde, B-caryophyllene
oxide, sclareolide, and ethyl maltol.
5. The flavor composition according to claim 4, which is citrus-like or ginger-like.
20 6. The flavor composition according to claim 4 or 5, wherein the off-flavor is p-cresol.
25
30
7. The flavor composition according to any one of claims 4 to 6, wherein the citralcontaining
product is a citrus-flavored food and/or beverage or a ginger-flavored food
and/ or beverage.
8. A citral-containing product comprising:
0.01 ppt to 10 ppm of one or more selected from the group consisting of
ambrettolide, isoambrettolide, pentalide, muscone, civetone, 8-2-decenolactone,
cinnamic aldehyde, B-caryophyllene oxide, sclareolide, and ethyl maltol.
31
9. The product according to claim 8, wherein the citral-containing product is a citrusflavored
food and/or beverage or a ginger-flavored food and/or beverage.
10. The product according to claim 8 or 9, further comprising: 10 ppb to 1 ppm of p-
5 cresol.
11. A method of producing a citral-containing product comprising:
blending a citral-containing product with 0.01 ppt to 10 ppm of one or more
selected from the group consisting of ambrettolide, isoambrettolide, pentalide, muscone,
10 civetone, 8-2-decenolactone, cinnamic aldehyde, ~-caryophyllene oxide, sclareolide, and
ethyl maltol.
| # | Name | Date |
|---|---|---|
| 1 | 202217070044-TRANSLATIOIN OF PRIOIRTY DOCUMENTS ETC. [05-12-2022(online)].pdf | 2022-12-05 |
| 2 | 202217070044-STATEMENT OF UNDERTAKING (FORM 3) [05-12-2022(online)].pdf | 2022-12-05 |
| 3 | 202217070044-Sequence Listing in txt [05-12-2022(online)].txt | 2022-12-05 |
| 4 | 202217070044-Sequence Listing in PDF [05-12-2022(online)].pdf | 2022-12-05 |
| 5 | 202217070044-PROOF OF RIGHT [05-12-2022(online)].pdf | 2022-12-05 |
| 6 | 202217070044-PRIORITY DOCUMENTS [05-12-2022(online)].pdf | 2022-12-05 |
| 7 | 202217070044-POWER OF AUTHORITY [05-12-2022(online)].pdf | 2022-12-05 |
| 8 | 202217070044-NOTIFICATION OF INT. APPLN. NO. & FILING DATE (PCT-RO-105-PCT Pamphlet) [05-12-2022(online)].pdf | 2022-12-05 |
| 9 | 202217070044-FORM 1 [05-12-2022(online)].pdf | 2022-12-05 |
| 10 | 202217070044-DRAWINGS [05-12-2022(online)].pdf | 2022-12-05 |
| 11 | 202217070044-DECLARATION OF INVENTORSHIP (FORM 5) [05-12-2022(online)].pdf | 2022-12-05 |
| 12 | 202217070044-COMPLETE SPECIFICATION [05-12-2022(online)].pdf | 2022-12-05 |
| 13 | 202217070044.pdf | 2022-12-24 |
| 14 | 202217070044-FORM 3 [23-05-2023(online)].pdf | 2023-05-23 |
| 15 | 202217070044-FORM 3 [13-12-2023(online)].pdf | 2023-12-13 |
| 16 | 202217070044-FORM 3 [18-12-2023(online)].pdf | 2023-12-18 |
| 17 | 202217070044-FORM 3 [04-03-2024(online)].pdf | 2024-03-04 |
| 18 | 202217070044-FORM 18 [06-03-2024(online)].pdf | 2024-03-06 |