U.S. patent application number 14/306725 was filed with the patent office on 2014-10-02 for pyridine derivatives with umami flavour.
The applicant listed for this patent is Givaudan S.A.. Invention is credited to Andrew DANIHER, Adri DE KLERK, Yili WANG, Cornelis WINKEL.
Application Number | 20140295045 14/306725 |
Document ID | / |
Family ID | 42711889 |
Filed Date | 2014-10-02 |
United States Patent
Application |
20140295045 |
Kind Code |
A1 |
WANG; Yili ; et al. |
October 2, 2014 |
Pyridine Derivatives With Umami Flavour
Abstract
A compound (including salts thereof) according to Formula I
##STR00001## in which R.sup.1 is H, methyl or ethyl; R.sup.2 is H,
OH, fluorine, C.sub.1-C.sub.4 linear or branched alkyl,
C.sub.1-C.sub.6 alkoxy wherein the alkyl group is linear or
branched, or a C.sub.3-C.sub.5 cycloalkyl moiety; R.sup.3 is H,
methoxy, methyl or ethyl; or R.sup.2 and R.sup.3 together form a
bridging moiety --O--CH.sub.2--O-- between the phenyl carbon atoms
to which they are connected; R.sup.4 is OH or methoxy; and R.sup.5
and R.sup.6 are independently H or methyl; R.sup.1, R.sup.2,
R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are such that, (i) when
R.sup.2 and R.sup.3 together form a bridging moiety
--O--CH.sub.2--O-- between the phenyl carbon atoms to which they
are connected, R.sup.1, R.sup.5, R.sup.6 are H, and R.sup.4 is OH;
and (ii) when R.sup.4 is OH and R.sup.1-R.sup.3 are H, at least one
of R.sup.5, R.sup.6 is methyl, which compound or salt thereof
provides umami flavour.
Inventors: |
WANG; Yili; (Mason, OH)
; DANIHER; Andrew; (Cincinnati, OH) ; DE KLERK;
Adri; (Made, NL) ; WINKEL; Cornelis; (Bussum,
NL) |
|
Applicant: |
Name |
City |
State |
Country |
Type |
Givaudan S.A. |
Vernier |
|
CH |
|
|
Family ID: |
42711889 |
Appl. No.: |
14/306725 |
Filed: |
June 17, 2014 |
Related U.S. Patent Documents
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Application
Number |
Filing Date |
Patent Number |
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13381393 |
Jan 19, 2012 |
|
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PCT/EP2010/059916 |
Jul 9, 2010 |
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14306725 |
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61224604 |
Jul 10, 2009 |
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61235452 |
Aug 20, 2009 |
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Current U.S.
Class: |
426/537 ;
546/283.7; 546/340 |
Current CPC
Class: |
C07D 213/46 20130101;
C07D 405/00 20130101; A23L 27/2054 20160801; A23L 27/203 20160801;
A23L 27/2052 20160801; C07D 405/06 20130101; A23L 27/2024 20160801;
A23L 27/70 20160801; C07D 405/10 20130101; C07D 213/50
20130101 |
Class at
Publication: |
426/537 ;
546/340; 546/283.7 |
International
Class: |
A23L 1/226 20060101
A23L001/226; C07D 405/10 20060101 C07D405/10; C07D 213/50 20060101
C07D213/50 |
Claims
1. A umami flavouring compound according to Formula I or salt
thereof ##STR00015## in which R.sup.1 comprises H, methyl or ethyl;
R.sup.2 comprises H, OH, fluorine, C.sub.1-C.sub.4 linear or
branched alkyl, C.sub.1-C.sub.6 alkoxy wherein the alkyl group is
linear or branched, or a C.sub.3-C.sub.5 cycloalkyl moiety; R.sup.3
comprises H, methoxy, methyl or ethyl; or R.sup.2 and R.sup.3
together form a bridging moiety --O--CH.sub.2--O-- between the
phenyl carbon atoms to which they are connected; R.sup.4 comprises
OH or methoxy; and R.sup.5 and R.sup.6 independently comprise H or
methyl; R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are
such that, (i) when R.sup.2 and R.sup.3 together form a bridging
moiety --O--CH.sub.2--O-- between the phenyl carbon atoms to which
they are connected, R.sup.1, R.sup.5, R.sup.6 are H, and R.sup.4 is
OH; and (ii) when R.sup.4 is OH and R.sup.1-R.sup.3 are H, at least
one of R.sup.5 or R.sup.6 is methyl, which compound or salt thereof
provides umami flavouring.
2. The umami flavouring compound according to claim 1, in which
R.sup.3 is selected from H and methoxy.
3. The umami flavouring compound according to claim 1, in which
R.sup.2 comprises H, OH, fluorine, methyl, C.sub.1-C.sub.6 alkoxy
wherein the alkyl group is linear or branched, or a C.sub.3-C.sub.5
cycloalkyl moiety.
4. The umami flavouring compound according to claim 1, in which
R.sup.2 consists of a C.sub.3-C.sub.5 cycloalkyl moiety.
5. The umami flavouring compound according to claim 1, in which
R.sup.1 comprises H or methyl, R.sup.2 comprises methyl, methoxy or
isobutyloxy, R.sup.3 is H, R.sup.4 is OH, and R.sup.5 and R.sup.6
are H.
6. The umami flavouring compound according to claim 5, selected
from the group consisting of:
1-(2-hydroxy-4,5-dimethylphenyl)-3-(pyridine-2-yl)propan-1-one;
1-(2-hydroxy-4-methylphenyl)-3-(pyridin-2-yl)propan-1-one;
1-(2-hydroxy-4-methoxyphenyl)-3-(pyridin-2-yl)propan-1-one;
1-(2-hydroxy-4-isobutoxyphenyl)-3-(pyridine-2-yl)propan-1-one; and
mixtures thereof.
7. A method of providing umami flavour to a consumable composition,
comprising the addition to the composition of at least one umami
flavouring compound according to claim 1, which compound provides
umami flavour.
8. A consumable composition having an umami flavour, comprising a
product base and at least one umami flavouring compound according
to claim 1, which compound provides umami flavour.
9. The consumable composition according to claim 8, in which the
umami flavouring compound is present at a concentration of from
about 0.01 to about 100 ppm.
10. The consumable composition according to claim 8, in which the
umami flavouring compound is present at a concentration of from
about 0.1 to about 50 ppm.
11. The consumable composition according to claim 8, in which the
umami flavouring compound is present at a concentration of from
about 0.2 to about 10 ppm.
Description
[0001] This application is a continuation of co-pending U.S. Ser.
No. 13/381,393, having a 371(c) date of Jan. 19, 2012, which is a
national stage application of International Application No.
PCT/EP2010/059916, filed Jul. 9, 2010, which claims priority from
U.S. Provisional Patent Application Ser. No. 61/224,604, filed Jul.
10, 2009, and from U.S. Provisional Patent Application Ser. No.
61/235,452, filed Aug. 20, 2009, from which applications priority
is claimed, and which are incorporated herein by reference.
[0002] This disclosure relates to chemical compounds and to their
use in flavouring.
[0003] Umami is a flavour sensation generally associated with Asian
cuisine. In addition, improved umami taste helps make low salt
products more palatable. Umami flavour has traditionally been
achieved by the addition of monosodium glutamate (MSG) to
foodstuffs. However, the presence of MSG in foodstuffs is not
universally welcome, and there is an interest in the achievement of
umami taste without MSG.
[0004] It has been found that certain compounds confer desirable
umami taste sensations on compositions intended to be taken orally.
There is therefore provided a compound (including salts thereof)
according to Formula I
##STR00002##
[0005] in which
[0006] R.sup.1 is selected from H, methyl and ethyl;
[0007] R.sup.2 is selected from H, OH, fluorine, C.sub.1-C.sub.4
linear or branched alkyl, C.sub.1-C.sub.6 alkoxy wherein the alkyl
group is linear or branched, or comprises or consists of a
C.sub.3-C.sub.5 cycloalkyl moiety;
[0008] R.sup.3 is selected from H, methoxy, methyl and ethyl;
[0009] or R.sup.2 and R.sup.3 together form a bridging moiety
--O--CH.sub.2--O-- between the phenyl carbon atoms to which they
are connected;
[0010] R.sup.4 is selected from OH and methoxy; and
[0011] R.sup.5 and R.sup.6 are independently selected from H and
methyl;
[0012] R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6
being selected such that,
[0013] (i) when R.sup.2 and R.sup.3 together form a bridging moiety
--O--CH.sub.2--O-- between the phenyl carbon atoms to which they
are connected, R.sup.1, R.sup.5, R.sup.6 are H, and R.sup.4 is OH;
and
[0014] (ii) when R.sup.4 is OH and R.sup.1-R.sup.3 are H, at least
one of R.sup.5, R.sup.6 is methyl.
[0015] In a particular embodiment, R.sup.3 is selected from H and
methoxy.
[0016] In a particular embodiment, R.sup.2 is selected from H, OH,
fluorine, methyl, C.sub.1-C.sub.6 alkoxy wherein the alkyl group is
linear or branched, or comprises or consists of a C.sub.3-C.sub.5
cycloalkyl moiety.
[0017] In a further particular embodiment, R.sup.2 is selected from
methyl, methoxy and isobutyloxy, R.sup.3 is H, R.sup.4 is OH and
R.sup.5 and R.sup.6 are H.
[0018] In a further particular embodiment, the compound (including
salts thereof) of Formula I is selected from the group consisting
of:
[0019]
1-(2-hydroxy-4,5-dimethylphenyl)-3-(pyridine-2-yl)propan-1-one;
##STR00003##
[0020]
1-(2-hydroxy-4-methylphenyl)-3-(pyridin-2-yl)propan-1-one;
##STR00004##
[0021] 1-(2-hydroxy-4-methoxyphenyl)-3-(pyridin-2-yl)propan-1-one;
and
##STR00005##
[0022]
1-(2-hydroxy-4-isobutoxyphenyl)-3-(pyridine-2-yl)propan-1-one.
##STR00006##
[0023] Other particular embodiments include (but are not limited
to):
##STR00007## ##STR00008##
[0024] The compounds may be made by methods well known to the art.
Non-limiting examples of suitable methods include:
[0025] 1. Claisen-Schmidt condensation of an aromatic aldehyde with
a substituted acetophenone. The base used for this condensation is
sodium methoxide in methanol.
[0026] The reactions were performed in an organic solvent (in
particular, THF). The obtained intermediate was hydrogenated in
methanol with hydrogen and 10% palladium on carbon as a
catalyst.
[0027] 2. Friedel-Craft acylation of the substituted phenol with
2-pyridinyl-propionic acid derivatives.
[0028] 3. A one-step reaction of 2-hydroxyacetophenone with
pyridin-2-ylmethanol and RuCl.sub.2(Me.sub.2SO).sub.4 as a catalyst
in dioxane solvent.
[0029] 4. A one-step reaction of 2-hydroxyacetophenone with
isonicotinaldehyde was used with RuCl.sub.2(PPh.sub.3).sub.3 as a
catalyst in dioxane slovent.
[0030] Not all of these methods will work for all compounds, but
the selection of a particular method for a given compound is well
known within the skill of the art.
[0031] The compounds hereinabove described may be used individually
or in combinations, either with other such compounds, or other
umami flavourants, or both. Other umami flavorants include, but are
not limited to MSG, GMP (guanosine monophosphate) and IMP (inosine
mono phosphate). There is therefore also provided a method of
adding umami flavour to a consumable composition, comprising the
addition to the composition of at least one compound of the Formula
I.
[0032] By "consumable composition" is meant any composition that is
taken into the mouth for ultimate spitting out or ingestion. The
composition may be in any physical form, solid, liquid or gaseous.
Non-limiting examples include all food products, food additives,
nutraceuticals, pharmaceuticals and any product placed in the mouth
including (but not limited to) chewing gum, oral care products, and
oral hygiene products including but not limited to, cereal
products, rice products, tapioca products, sago products, baker's
products, biscuit products, pastry products, bread products,
confectionery products, dessert products, gums, chewing gums,
flavor or flavor-coated food/beverage containers, yeast products,
baking-powder, salt and spice products, snack foods, savoury
products, mustard products, vinegar products, sauces (condiments),
soups, seasonings, ready-to-eat meals, gravies, nuts & nut
products, tobacco products, cigars, cigarettes, processed foods,
vegetable products, meat and meat products, egg products, milk and
dairy products, yoghourts, cheese products, butter and butter
substitute products, milk substitute products, soy products, edible
oils and fat products, medicaments, beverages, carbonated
beverages, alcoholic drinks such as beers, wines and spirits,
non-alcoholic drinks such as soft drinks, including forms requiring
reconstitution including, without limitation, beverage powder, milk
based beverage powder, sugar-free beverage powder, beverage syrup,
beverage concentrate, coffee and tea, food extracts, plant
extracts, meat extracts, condiments, gelatins, pharmaceutical and
non-pharmaceutical gums, tablets, lozenges, drops, emulsions,
elixirs, syrups and other preparations for making beverages, and
combinations thereof.
[0033] There is therefore provided an umami-flavored consumable
composition comprising a product base and at least one compound as
hereinabove described. By "product base" is meant the combination
of all the usual art-recognised ingredients required for the
particular consumable composition.
[0034] The concentrations at which the compounds hereinabove
described may be used will naturally vary, depending on the taste
desired, the nature of the other ingredients and the desired
end-use. Typically the concentration will vary between 0.01-100
ppm, but it is to be emphasised that this is only an indication of
a typical useful concentration, and that there will be
circumstances in which it may be possible to formulate outside this
range. More particular ranges are 0.1-50 ppm and 0.2-10 ppm.
[0035] The form in which the compounds hereinabove described may be
used may vary. In addition to powders, liquids, solutions,
dispersions or emulsions, they may be used in spray-dried or
encapsulated forms.
[0036] The umami-flavoured consumable compositions may also contain
any of the standard ingredients used in making such compositions,
in art-recognised quantities. Non-limiting examples include food
additives such as sweeteners, emulsifiers, yeast extracts,
hydrolyzed vegetable proteins, short chain peptides, amino acids,
fermented products, enzyme digests, Maillard reaction products and
botanical extracts.
[0037] In addition to at least one of the subject compounds, the
umami flavor may contain flavoring materials well known to those
skilled in the art, including the materials on the FEMA GRAS list
and the EU positive list. Flavor materials commonly provide aroma
which in itself, can help improve the overall umami profile of the
product. However, some flavor materials also have taste effects
which, when used with the compounds hereinabove described, improve
or enhance the umami taste sensation or improve the overall
profile.
[0038] In addition, other materials on the approved list of flavor
materials provide a umami taste or umami-like character or may
enhance the overall umami taste. Some examples from the FEMA GRAS
which may be used with the subject compounds include items, such
as,
N1-(2-methoxy-4-methylbenzyl)-N2-(2-(pyridin-2-yl)ethyl)oxalamide
(FEMA #4231), N-(heptan-4-yl)benz0[D][1,3]dioxole-5-carboxamide
(FEMA#4232),
N1-(2,4-dimethoxybenzyl)-N2-(2-(pyridin-2-yl)ethyl)oxalamide
(FEMA#4233),
N1-(2-methoxy-4-methylbenzyl)-N2-(2-(5-methylpyridin-2-yl)ethyl)oxalamide
(FEMA #4234), N-gluconyl ethanolamine(FEMA #4254), N-gluconyl
ethanolamine phosphate (FEMA #4255), N-lactoyl ethanolamine (FEMA
#4256), N-lactoyl ethanolamine phosphate (FEMA #4257),
N-3,7-dimethyl-2,6-octadienylcyclopropylcarboxamide (FEMA #4267)
and gamma amino-butyric acid.
[0039] There now follows a series of non-limiting examples, which
describe particular embodiments.
EXAMPLE 1
Synthesis of
1-(2-hydroxy-4,5-dimethylphenyl)-3-(pyridine-2-yl)propan-1-one
##STR00009##
[0041] To a stirring solution of picolinaldehyde (1.52 g, 14.1
mmol) in THF (50 ml) and 7 ml 25% wt NaOMe was added
1-(2-hydroxy-4,5-dimethylphenyl)ethanone in 5 ml THF dropwise at
room temperature (2.33 g, 14.1 mmol). The solution was continuously
stirred at room temperature for 5 hours, and then water was added
to the reaction flask. The aqueous layer was acidified to pH=7
using 1N HCl and extracted three times with EtOAc.
[0042] The organic layers combined and dried (Na.sub.2SO.sub.4).
The solvent was removed in vacuo and the residue chromatographed on
silica gel (15% EtOAc/Hex) to yield 1.17 g of yellow product
(32%).
[0043] .sup.1H NMR (300 MHz, CDCl.sub.3): .delta. 12.64 (s, 1H),
8.75 (d, J=5.1 Hz, 1H), 8.29 (d, J=15.9 Hz, 1H), 7.88-7.78 (m, 3H),
7.52 (d, J=8.4 Hz, 1H), 7.35 (d, d, d, J=1.5, 6.0, 9.0 Hz, 1H),
6.85 (s, 3H), 2.31 (s, 3H), 2.28 (s, 3H).
[0044] In a 250 ml round-bottom flask,
(E)-1-(2-hydroxy-4,5-dimethylphenyl)-3-(pyridine-2-yl)prop-2-en-1-one
(1.17 g, 4.62 mmol) and 0.18 g of 10% Pd/C were mixed together in
wet EtOAc. Hydrogenation was conducted at atmospheric pressure,
then the catalyst was filtered off. The crude product was purified
by chromatography on silica gel (20% EtOAc/hexane) to provide 0.58
g (47.7%) of final compound.
[0045] .sup.1H NMR (300 MHz, CDCl.sub.3): .delta. 12.12 (s, 1H),
8.55 (d, J=5.1 Hz, 1H), 7.62 (d, d, d, J=2.1, 7.5, 9.6 Hz, 1H),
7.56 (s, 1H), 7.27 (d, J=7.5 Hz, 1H), 7.14 (d, d, J=4.5, 5.7 Hz,
1H), 6.77 (s, 1H), 3.52 (t, J=7.8 Hz, 2H), 3.25 (t, J=7.5 Hz, 2H),
2.26 (s, 3H), 2.21 (s, 3H).
EXAMPLE 2
Synthesis of
1-(2,4-dihydroxyphenyl)-3-(pyridine-2-yl)propan-1-one
##STR00010##
[0047] A mixture of resorcinol (2.2 g, 20 mmol),
3-pyridin-2-yl-propionic acid sulphuric acid salt (5 g, 20 mmol)
and 50 ml boron trifluoride diethyl etherate (BF.sub.3.Et.sub.2O)
was stirred at 90 C for 5 hours under N.sub.2 (monitored by TLC).
The reaction mixture was poured into 10% aqueous NaOAc solution and
allowed to stand for 30 min and the solution was neutralized to
pH=7 by 1M HCl and was extracted with EtOAc (3.times.50 ml). The
combined EtOAc layer was washed with water, brine and dried over
Na.sub.2SO.sub.4. The residue obtained after evaporation of the
solvent was chromatographed over silica gel column using
hexane-EtOAc mixture (1:1) as eluent to give mixture of products,
which was then recrystalized in hot MTBE/Hex to afford final
product (24%) with >97% purity.
[0048] .sup.1H NMR (300 mHz, CD.sub.3OD) .delta. 8.46-8.44 (d,d,d,
J=5.1, 1.8, 0.9 Hz, 1H), 7.78-7.72 (d, d, d, J=9.9, 7.8, 2.1 Hz,
1H), 7.78-7.75 (d, J=8.7 Hz, 1H), 7.40-7.37 (d, J=8.1 Hz, 1H),
7.29-7.23 (d,d, d, J=6.3, 4.8, 1.2 Hz, 1H), 6.38-6.34 (d, d, J=9.0,
2.4 Hz, 1H), 6.26-6.25 (d, J=2.4 Hz, 1H), 3.41 (t, J=7.5 Hz, 2H),
3.18 (t, J=8.4 Hz, 2H).
EXAMPLE 3
1-(2-hydroxy-4-methylphenyl)-3-(pyridin-2-yl)propan-1-one
[0049] The title compound was synthesized using the same procedure
as described in example 1.
[0050] .sup.1H NMR (300 MHz, CDCl.sub.3): .delta. 12.29 (s, 1H),
8.53 (d, J=4.5 Hz, 1H), 7.63 (d, d, d, J=3.0, 9.6, 11.7 Hz, 1H),
7.26 (d, J=7.2 Hz, 1H), 7.14 (d, d, d, J=1.2, 5.4,7.8 Hz, 1H), 6.79
(s, 1H), 6.71 (d, d, J=1.8, 8.4 Hz, 1H), 3.53 (t, J=7.2 Hz, 2H),
3.24 (t, J=7.2 HZ, 2H), 2.36 (s, 3H).
EXAMPLE 4
1-(2-hydroxy-4-methoxyphenyl)-3-(pyridin-2-yl)propan-1-one
[0051] The title compound was synthesized using the same procedure
as described in example 1.
[0052] .sup.1H NMR (300 MHz, CDCl.sub.3): .delta. 12.77 (s, 1H),
8.53 (d, J=4.8 Hz, 1H), 7.72 (d, d, J=2.7, 8.7 Hz,1H), 7.60 (d, d,
d, J=2.1, 7.5, 9.6 Hz, 1H), 7.23 (d, J=8.1 Hz, 1H), 7.12 (d, d, d,
J=1.5, 4.8, 6.3 Hz, 1H), 6.44-6.41 (m, 2H), 3.83 (s, 3H), 3.45 (t,
J=7.5 Hz, 3=2H), 3.22 (t, J=7.8 Hz, 2H).
EXAMPLE 5
1-(2-hydroxyphenyl)-3-(5-methylpyridin-2-yl)propan-1-one
[0053] The title compound was synthesized using the same procedure
as described in example 1.
[0054] .sup.1H NMR (300 MHz, CDCl.sub.3): .delta. 12.25 (s, 1H),
8.36 (d, J=3.0 Hz, 1H), 7.85 (d, d, J=1.8, 8.4 Hz, 1H), 7.49-7.43
(m, 2H), 7.20 (d, J=9.0 Hz, 1H), 6.97 (d, d, J=2.1, 8.1 Hz, 1H),
6.89 (d, d, J=7.5, 8.1 Hz, 1H), 3.57 (t, J=6.9 Hz, 2H), 3.23 (t,
J=6.9 Hz, 2H), 2.32 (s, 3H).
EXAMPLE 6
1-(4-ethoxy-2-hydroxyphenyl)-3-(pyridine-2-yl)propan-1-one
[0055] The title compound was synthesized using the same procedure
as described in example 1.
[0056] .sup.1H NMR (300 MHz, CDCl.sub.3): .delta. 12.71 (s, 1H),
8.53 (d, J=5.4 Hz, 1H), 7.73 (d, J=8.7 Hz, 1H), 7.63 (d, d, d,
J=1.8, 7.5, 9.6 Hz, 1H), 7.28 (d, J=8.1 Hz, 1H), 7.15 (d, d, J=4.8,
6.3 Hz, 1H), 6.44-6.40 (m, 2H), 4.06 (q, J=7.5 Hz, 2H), 3.48 (t,
J=7.8 Hz, 2H), 3.24 (t, J=7.8 Hz, 2H), 1.42 (t, J=7.5 Hz, 3H).
EXAMPLE 7
1-(2-hydroxy-3,5-dimethylphenyl)3-(pyridine-2-yl)propan-1-one
[0057] The title compound was synthesized using the same procedure
as described in example 1.
[0058] .sup.1H NMR (300 MHz, CDCl.sub.3): .delta. 12.40 (s, 1H),
8.55 (bd, J=5.2 Hz, 1H), 7.64 (d, d, d, J=1.8, 8.1, 10.2 Hz, 1H),
7.49 (s, 1H), 7.29 (d, J=8.1 Hz, 1H), 7.18-7.14 (m, 2H), 3.57 (t,
J=7.5 Hz, 2H), 3.26 (t, J=7.8 Hz, 2H), 2.28 (s, 3H), 2.24 (s,
3H).
EXAMPLE 8
1-(2-hydroxy-5-methylphenyl)-3-(pyridine-2-yl)propan-1-one
[0059] The title compound was synthesized using the same procedure
as described in example 1.
[0060] .sup.1H NMR (300 MHz, CDCl.sub.3): .delta. 12.09 (s, 1H),
8.52 (d, J=4.8 Hz, 1H), 7.62-7.57 (m, 2H), 7.28-7.23 (m, 2H), 7.12
(d, d, J=4.8, 7.5 Hz, 1H), 6.86 (d, J=8.4 Hz, 1H), 3.54 (t, J=6.9
Hz, 2H), 3.23 (t, J=6.9 Hz, 2H), 2.28 (s, 3H).
EXAMPLE 9
1-(5-ethyl-2-hydroxyphenyl)-3-(pyridine-2-yl)propan-1-one
[0061] The title compound was synthesized using the same procedure
as described in example 1.
[0062] .sup.1H NMR (300 MHz, CDCl.sub.3): .delta. 12.11 (s, 1H),
8.54 (d, J=3.3 Hz, 1H), 7.67-7.61(m, 2H), 7.32 (d,d, J=2.1, 8.1 Hz,
1H), 7.16 (d, d, J=6.3, 8.4 Hz, 1H), 6.92 (d, J=8.7 Hz, 1H), 3.59
(t, J=6.6 Hz, 2H), 3.27 (t, J=6.6 Hz, 2H), 2.61 (q, J=8.7 Hz, 2H),
1.23 (t, J=7.5 Hz, 3H).
EXAMPLE 10
1-(2-hydroxyphenyl)-3-(3-methylpyridin-2-yl)propan-1-one
[0063] The title compound was synthesized using the same procedure
as described in example 1.
[0064] .sup.1H NMR (300 MHz, CDCl.sub.3): .delta. 12.31 (s, 1H),
8.34 (d, J=6.3 Hz, 1H), 7.91 (d, J=6.3 Hz, 1H), 7.49-7.44 (m, 2H),
7.09-7.04 (m, 1H), 6.98 (d, J=9.0 Hz, 1H), 6.91 (, d, d, J=7.5, 7.5
Hz, 1H), 3.61 (t, J=7.5 Hz, 2H), 3.23 (t, J=7.5 Hz, 2H), 2.39 (s,
3H).
EXAMPLE 11
1-(2-hydroxy-3,5-dimethylphenyl)3-(pyridine-2-yl)propan-1-one
[0065] The title compound was synthesized using the same procedure
as described in example 2.
[0066] .sup.1H NMR (300 MHz, CDCl.sub.3): 12.40 (s, 1H), 8.55 (bd,
J=5.2 Hz, 1H), 7.64 (d, d, d, J=1.8, 8.1, 10.2 Hz, 1H), 7.49 (s,
1H), 7.29 (d, J=8.1 Hz, 1H), 7.18-7.14 (m, 2H), 3.57 (t, J=7.5 Hz,
2H), 3.26 (t, J=7.8 Hz, 2H), 2.28 (s, 3H), 2.24 (s, 3H).
EXAMPLE 12
1-(2-hydroxy-4-isobutoxyphenyl)-3-(pyridine-2-yl)propan-1-one
##STR00011##
[0068] Step1: To a stirred solution of
1-(2,4-dihydroxyphenyl)ethanone (3.2 g, 21.03 mmol) and
K.sub.2CO.sub.3 in 100 mL of acetone at room temperature, the
1-iodo-2-methylpropane (3.6 ml, 21.03 mmol) was added dropwise. The
mixture was refluxed for 8 hrs, and then the reaction was kept in
54.degree. C. for overnight. The reaction was cooled down to room
temperature and quenched by 1N HCl to pH=7. The aqueous layer was
extracted 3.times. with EtOAc, the organic layers were combined,
washed with water, brine and dried (Na.sub.2SO.sub.4). The solvent
was removed in vacuo and the residue chromatographed on silica gel
5% EtOAc/Hex to give 1.1 g (25%) of product.
[0069] .sup.1H NMR (300 MHz, CDCl.sub.3): .delta. 12.67 (s, 1H),
7.55 (d, J=8.7 Hz, 1H), 6.36 (d, d, J=2.4, 8.7 Hz, 1H), 6.32 (d,
J=2.4 Hz, 1H), 3.68 (d, J=6.6 Hz, 2H), 2.48 (s, 3H), 2.09-21.95 (m,
1H), 0.96 (s, 3H), 0.94 (s, 3H).
[0070] Step 2: To a stirred solution of picolinaldehyde (0.6 ml,
5.28 mmol) and NaOMe in Tetrahydrofuran (50 ml) and
1-(2-hydroxy-4-isobutoxyphenyl)ethanone in 5 ml THF was added at
room temperature. The mixture was stirred at room temperature for 5
h, 1N HCl was added until pH=7. The aqueous layer was extracted
3.times. with EtOAc. The organic layers combined, washed with
water, brine and dried (Na.sub.2SO.sub.4). The solvent was removed
in vacuo and the residue chromatographed on silica gel (25% EtOAc
in Hex) to give 0.8 g (51%) of yellow solid.
[0071] .sup.1H NMR (300 MHz, CDCl.sub.3): .delta. 13.37 (s, 1H),
8.72 (d, J=5.1 Hz, 1H), 8.22 (d, J=15.0 Hz, 1H), 7.97 (d, J=9.0 Hz,
1H), 7.84 (d, J=15.0 Hz, 1H), 7.77 (d, d, J=1.8, 7.2 Hz, 1H), 7.50
(d, J=8.1 Hz, 1H), 7.33 (d, d, J=4.8, 7.8 Hz, 1H), 6.51 (d, d,
J=2.4, 9.0 Hz, 1H), 6.47 (d, J=2.7 Hz, 1H), 3.80 (d, J=6.6 Hz, 2H),
2.20-2.07 (m, 1H), 1.60 (s, 3H), 1.05 (s, 3H).
[0072] Step 3: In a 200 mL round-bottomed flask,
(E)-1-(2-hydroxy-4-isobutoxyphenyl)-3-(pyridin-2-yl)prop-2-en-1-one
(1.08 g, 3.63 mmol) and 80 mg of 10% Pd/C was mixted together in
wet EtOAc (50 ml). Hydrogenation was conducted at atmospheric
pressure room temperature until the starting material was gone. The
catalyst was filtered and the crude was purified by chromatography
on silica gel (25% EtOAc/hexane) to provide 0.92 g of final
compound (82%) as off white solid.
[0073] .sup.1H NMR (300 MHz, CDCl.sub.3): .delta. 12.73 (s, 1H),
8.52 (d, J=4.8 Hz, 1H), 7.72 (d, J=9.0 Hz, 1H), 7.61(d, d, d,
J=2.4, 7.8, 9.6 Hz, 1H), 7.25 (d, J=7.8 Hz, 1H), 7.13 (d, d, d,
J=1.5, 4.8, 6.0 Hz, 1H), 6.43 (d, d, J=2.1, 8.4 Hz, 1H), 6.39 (d,
J=2.7 Hz, 1H), 3.75 (d, J=7.2 Hz, 2H), 3.46 (t, J=7.2 Hz, 2H), 3.23
(t, J=6.9 Hz, 2H), 2.16-2.02 (m, 1H), 1.02 (d, d, J=7.2 Hz,
6H).
EXAMPLE 13
1-(4-cyclopropylmethoxy)-2-hydroxyphenyl)-3-(pyridine-2-yl)propan-1-one
[0074] The title compound was synthesized using the same procedure
as described in example 11.
[0075] .sup.1H NMR (300 MHz, CDCl.sub.3): .delta. 12.61 (s, 1H),
8.42 (d, J=5.7 Hz, 1H), 7.52 (d, d, d, J=1.8, 7.8, 9.6 Hz, 1H),
7.16 (d, J=7.5 Hz, 1H), 7.04 (d, d, J=4.8, 7.2 Hz, 1H), 6.34 (d, d,
J=2.7, 9.0 Hz, 1H), 6.28 (d, J=2.4 Hz, 1H), 3.73 (d, J=6.9 Hz, 2H),
3.37 (t, J=7.2 Hz, 2H), 3.13 (t, J=7.5 Hz, 2H), 1.24-1.11 (m, 1H),
0.59-0.53 (m, 2H), 0.29-0.23 (m, 2H).
EXAMPLE 14
1-(4-(cyclopentyloxy)-2-hydroxyphenyl)-3-(pyridine-2-yl)propan-1-one
[0076] The title compound was synthesized using the same procedure
as described in example 11.
[0077] .sup.1H NMR (300 MHz, CDCl.sub.3): .delta. 12.74 (s, 1H),
8.53 (d, J=4.8 Hz, 1H), 7.74-7.70 (m, 1H), 7.62 (d, d, d, J=2.1,
8.1, 9.9 Hz, 1H), 7.26 (d, J=7.8 Hz, 1H), 7.14 (d, d, d, J=1.2,
4.8, 7.5 Hz, 1H), 6.41-6.37 (m, 2H), 4.80-4.76 (m, 1H), 3.47 (t,
J=7.5 Hz, 2H), 3.23 (t, J=7.5 Hz, 2H), 2.01-1.78 (m, 8H).
EXAMPLE 15
1-(4-hydroxybenzo[d][1,3]dioxol-5-yl)-3-(pyridin-2-yl)propan-1-one
##STR00012##
[0079] Step 1
[0080] 1-(4-hydroxybenzo[d][1,3]dioxol-5-yl)ethanone (1.8 g, 9.99
mmol) was dissolved in THF (40 ml) to give a colorless solution.
Sodium methanolate 30% (5 g, 27.8 mmol) was added. Reaction mixture
became dark green colored. After 15 min. stirring at room
temperature 1.1 g (10 mmol) of picolinaldehyde dissolved in 10 ml
THF was added dropwise during 10 min. The addition was started at
22.degree. C. and was slightly exothermic. Stirring at room
temperature was continued for another 3 hrs. Mixture was diluted
with diethyl ether and the pH was adjusted to pH 6 with a
concentrated hydrochloric acid solution while vigorously stirring.
The color changes from dark green to orange/red. After 5 minutes
the formed solids were filtered. Solids were stirred with 100 mL of
methanol and the remaining solids (mainly NaCl) were filtered
again. The filtrate was evaporated and the residue was taken up in
a mixture of diethylether and methanol. Solids were filtered and
dried to yield 1.7 g of an orange powder. To remove the small
amounts of impurities the orange product was stirred with
chloroform for 10 minutes, filtered and dried to yield 1.5 g (47%)
of the
(E)-1-(4-hydroxybenzo[d][1,3]dioxol-5-yl)-3-(pyridin-2-yl)prop-2-en-1-one-
.
[0081] 1H-NMR in DMSO-d6: 6.17(2H, O--CH2-O, s), 6.72(1H,
CO--CH.dbd., d), 7.60(1H, aromatic, m),
[0082] 7.83(1H, aromatic, d), 7.94(1H, CO--CH.dbd.CH--, d),
8.09-8.13(2H, aromatic, m),
[0083] 8.35(1H, aromatic, d), 8.75(1H, aromatic N--CH, d), 9.83(1H,
OH, s)
[0084] The 1-(4-hydroxybenzo[d][1,3]dioxol-5-yl)ethanone was
prepared by the reaction of trihydroxy acetophenone with
diiodomethane.
[0085] Step 2
[0086]
(E)-1-(4-hydroxybenzo[d][1,3]dioxol-5-yl)-3-(pyridin-2-yl)prop-2-en-
-1-one (0.5 g, 1.857 mmol) was added to methanol (50 ml) to give a
yellow solution. Palladium on carbon (0.05 g) was added. Product
was hydrogenated while stirring till conversion was completed
(checked by TLC). The reaction mixture was filtered, evaporated and
the solid residue was washed with diethylether, and dried to yield
0.3 g (57%) of the title compound.
[0087] 1H-NMR in DMSO-d 6: 3.11(2H, CH2-C.dbd.N, t), 3.49(2H,
CO--CH2-, t), 6.13(2H, O--CH2-O, s),
[0088] 6.64(1H, aromatic, d), 7.19(1H, aromatic, m), 7.33(1H,
aromatic, d), 7.67-7.70(2H, aromatic, m),
[0089] 8.44(1H, aromatic N--CH, d), 9.83(1H, OH, s)
EXAMPLE 16
1-(2-methoxyphenyl)-3-(pyridin-2-yl)propan-1-one
##STR00013##
[0091] 1-(2-methoxyphenyl)ethanone (3 g, 19.98 mmol),
pyridin-2-ylmethanol (2.180 g, 19.98 mmol), and potassium hydroxide
(1.121 g, 19.98 mmol) were added to dioxane (50 ml) to give a
yellow suspension. RuCl2(Me2SO)4 (0.2 g) was added. Reaction
mixture was heated at 80.degree. C. for 1 hour.
[0092] Reaction mixture was filtered through Silicagel to remove
catalyst and KOH. The filtrate was evaporated and the residue was
purified by column chromatography.
[0093] Eluent:ethylacetate:heptane=3:1. 0.2 g (4%) of the title
compound was obtained.
[0094] 1H-NMR in chloroform,d: 3.20(2H, CO--CH2-, t), 3.47(2H,
--CH2-Ar, t), 3.87(3H, --OCH3, s),
[0095] 6.95(2H, aromatic, m), 7.1(1H, aromatic, m), 7.23(1H,
aromatic, d), 7.45(1H, aromatic, m)
[0096] 7.58(1H, aromatic, m), 7.70(1H, aromatic, d), 8.50(1H,
aromatic N--CH.dbd., d)
EXAMPLE 17
[0097] Testing of Compounds
[0098] Various compounds prepared in the previous examples were
tested.
[0099] Two solutions were prepared:
[0100] A: a solution of 0.3% NaCl,
[0101] B: a solution of 0.3% NaCl and 2 ppm compound as per Table
1.
[0102] The samples were tasted by a trained sensory panel composed
of 20 women aged between 30 and 60.
TABLE-US-00001 TABLE 1 Compound Taste description
1-(2-hydroxy-4-methylphenyl)-3-(pyridin-2-yl)propan-1-one Umami,
sweet, licorice, savoury
1-(2-hydroxy-4-methoxyphenyl)-3-(pyridin-2-yl)propan-1-one umami,
sweet, salty, longlasting savouryness
1-(2-hydroxyphenyl)-3-(5-methylpyridin-2-yl)propan-1-one Slightly
umami, some green aftertaste, floral
1-(4-ethoxy-2-hydroxyphenyl)-3-(pyridine-2-yl)propan-1-one Umami,
floral 1-(4-cyclopropylmethoxy)-2-hydroxyphenyl)-3-(pyridine-2-
Umami yl)propan-1-one
1-(2-hydroxy-4-isobutoxyphenyl)-3-(pyridine-2-yl)propan-1-one
Umami, sweet, salty, bouillon, lingering, intense
1-(2-hydroxy-4,5-dimethylphenyl)-3-(pyridine-2-yl)propan-1-one
Umami, sweet, savoury, salty
1-(2-methoxyphenyl)-3-(pyridin-2-yl)propan-1-one Umami, slightly
bitter 1-(2-hydroxyphenyl)-3-(3-methylpyridin-2-yl)propan-1-one
Slightly umami, savoury, meaty
1-(4-hydroxybenzo[d][1,3]dioxol-5-yl)-3-(pyridin-2-yl)propan-1-
Clearly umami, slightly yeasty, bouillon one
1-(2-hydroxy-3,5-dimethylphenyl)-3-(pyridine-2-yl)propan-1-one
Umami
1-(4-(cyclopentoxy)-2-hydroxyphenyl)-3-(pyridine-2-yl)propan-1-
Umami one
1-(2-hydroxy-5-methylphenyl)-3-(pyridine-2-yl)propan-1-one Umami
1-(2-methoxyphenyl)-3-(pyridine-2-yl)propan-1-one Umami, slightly
bitter 1-(5-ethyl-2-hydroxyphenyl)-3-(pyridine-2-yl)propan-1-one
Umami, slightly bitter
1-(2-hydroxy-3,5-dimethylphenyl)3-(pyridine-2- Umami
yl)propan-1-one.
EXAMPLE 18
[0103] Comparative Test with MSG
[0104] Two solutions were prepared:
[0105] A: a solution of 0.3% NaCl and 0.03% MSG,
[0106] B: a solution of 0.3% NaCl, 0.03% MSG and 5 ppm of
1-(4-hydroxybenzo[d][1,3]dioxol-5-yl)-3-(pyridin-2-yl)propan-1-one.
[0107] The samples were tasted by a trained sensory panel composed
of 20 women aged between 30 and 60.
[0108] Solution A: salty, umami.
[0109] Solution B: salty, umami, more bouillon-like, more complex,
less sweet.
EXAMPLE 19
[0110] Tomato Soup Formulation
[0111] A tomato soup mix was prepared from 9.4 g sodium chloride, 1
g MSG, 0.08 g ribonucleotides (ex yeast), 32 g tomato powder (ex
Spreda), 25.1 g glucose, 21 g starch (Ultrasperse.TM. 5 ex National
Starch), 5 g palm fat powder, 3 g yeast powder, 1 g onion powder,
0.15 g carrot powder, 0.05 g ground white pepper, 0.3 g celery
extract powder, 0.05 g ground laurel leaf powder, and 1.85 g
sucrose. 25 g of the well-mixed ingredients was added to 250 g of
boiling water and stirred until completely dissolved, to give a
reference soup.
[0112] The reference soup was compared with a batch of the same
soup containing 1.5 ppm of
1-(2-hydroxy-4-isobutoxyphenyl)-3-(pyridine-2-yl)propan-1-one. A
small group of flavourists (2 male, 2 female) tasted the soups and
agreed that the test soup was more umami, had a clear lingering
effect, was more salty and was more complex than the reference
soup.
EXAMPLE 20
[0113] Potato Chips
[0114] Plain potato chips were prepared.
[0115] One part was flavoured with 1.2% sodium chloride (sample
A),
[0116] One part was flavoured with 1.2% sodium chloride and 0.3%
MSG (sample B),
[0117] One part was flavoured with 1.2% sodium chloride and 2 ppm
of 1-(2-hydroxy-4-methylphenyl)-3-(pyridin-2-yl)propan-1-one
(sample C).
[0118] The samples were tasted by a trained sensory panel composed
of 20 women aged between 30 and 60.
[0119] The panel preferred sample C over the other two samples.
[0120] Sample A was described as salty, sample B as salty and umami
and sample C as salty, strong umami, long lasting, savoury,
bouillon.
Example 21
[0121] Tomato Ketchup
[0122] A tomato ketchup was prepared from 19% tomato paste (28-30%
dry weight), 8% vinegar (15%), 3% sodium chloride, 20% sugar and
50% water.
[0123] To one-half of the batch was added 2 ppm of
1-(2-hydroxy-4-methoxyphenyl)-3-(pyridin-2-yl)propan-1-one.
[0124] A small group of flavourists (2 male, 2 female) tasted the
ketchups and agreed that the test ketchup tasted clearly more
umami, more salty and had a pleasant savoury note compared with
that of the ketchup without the compound.
EXAMPLES 22-24
[0125] The following compositions are made and tested. Using a
bench-top tasting panel (consisting of 10 panelists--flavorists,
application experts), panelists were asked to record the sensory
attribute differences (umami) between the samples. All samples were
tasted blind and ranked on umami.
EXAMPLE 22
[0126] Commercial Organic Chicken Broth (Swanson's Certified
Organic Chicken Broth--No added MSG, contains about 0.4%
sugars)
[0127] Control
TABLE-US-00002 Ingredient % (by weight) Commercial Organic Chicken
Broth 100 (550 mg Na/240 mL serving)
[0128] Reference
TABLE-US-00003 Ingredient % (by weight) MSG 0.05 Commercial Organic
Chicken Broth Balance to 100 (550 mg Na/240 mL serving)
[0129] Ingredient
1-(2-hydroxy-4-methylphenyl)-3-(pyridin-2-yl)propan-1-one
TABLE-US-00004 Ingredient % (by weight)
1-(2-hydroxy-4-methylphenyl)-3-(pyridin- 0.001 2-yl)propan-1-one;
Commercial Organic Chicken Broth Balance to 100 (550 mg Na/240 mL
serving)
[0130] Sensory findings: Panelists preferred 0.001% of
1-(2-hydroxy-4-methylphenyl)-3-(pyridin-2-yl)propan-1-one in this
base. In a blind ranking of 6 different samples MSG was the highest
umami with
1-(2-hydroxy-4-methylphenyl)-3-(pyridin-2-yl)propan-1-one finishing
2.sup.nd and Control finishing 5.sup.th.
[0131] Ingredient
1-(2-hydroxy-4-isobutoxyphenyl)-3-(pyridine-2-yl)propan-1-one
TABLE-US-00005 Ingredient % (by weight)
1-(2-hydroxy-4-isobutoxyphenyl)-3- 0.002
(pyridine-2-yl)propan-1-one Commercial Organic Chicken Broth
Balance to 100 (550 mg Na/240 mL serving)
[0132] Sensory findings: Panelists preferred 0.002% of
1-(2-hydroxy-4-isobutoxyphenyl)-3-(pyridine-2-yl)propan-1-one in
this base. In a blind ranking of 6 different samples MSG was the
highest umami with
1-(2-hydroxy-4-isobutoxyphenyl)-3-(pyridine-2-yl)propan-1-one
finishing 3.sup.rd and Control finishing 5.sup.th.
[0133] Ingredient
1-(2-hydroxy-4-methoxyphenyl)-3-(pyridin-2-yl)propan-1-one
TABLE-US-00006 Ingredient % (by weight)
1-(2-hydroxy-4-methoxyphenyl)-3- 0.002 (pyridin-2-yl)propan-1-one
Commercial Organic Chicken Broth Balance to 100 (550 mg Na/240 mL
serving)
[0134] Sensory findings: Panelists preferred 0.002% of
1-(2-hydroxy-4-methoxyphenyl)-3-(pyridin-2-yl)propan-1-one in this
base. In a blind ranking of 6 different samples MSG was the highest
umami with
1-(2-hydroxy-4-methoxyphenyl)-3-(pyridin-2-yl)propan-1-one
finishing 4.sup.th and Control finishing 5.sup.th.
EXAMPLE 23
[0135] Model Chicken Broth--no MSG Added, no Sugar Added
[0136] The model chicken broth powder was prepared from 11.9 g
chicken fat, 23.81 g salt, 14.29 g sugar, 0.95 g onion powder,
49.01 g chicken powder, 0.04 g turmeric powder. To prepare the
model chicken broth 2.0 g of powder was mixed 98.0 g hot water.
[0137] Control
TABLE-US-00007 Ingredient % (by weight) Model Chicken Broth 100
(653 mg Na/240 mL serving)
[0138] Reference
TABLE-US-00008 Ingredient % (by weight) MSG 0.05 Model Chicken
Broth Balance to 100 (653 mg Na/240 mL serving)
[0139] Ingredient
1-(2-hydroxy-4-methylphenyl)-3-(pyridin-2-yl)propan-1-one
TABLE-US-00009 Ingredient % (by weight)
1-(2-hydroxy-4-methylphenyl)-3-(pyridin- 0.0005 2-yl)propan-1-one
Model Chicken Broth Balance to 100 (653 mg Na/240 mL serving)
[0140] Sensory findings: Panelists preferred 0.0005% of
1-(2-hydroxy-4-methylphenyl)-3-(pyridin-2-yl)propan-1-one in this
base. In a blind ranking of 6 different samples MSG was the highest
umami with
1-(2-hydroxy-4-methylphenyl)-3-(pyridin-2-yl)propan-1-one finishing
3.sup.rd and Control finishing 5.sup.th.
[0141] Ingredient
1-(2-hydroxy-4-isobutoxyphenyl)-3-(pyridine-2-yl)propan-1-one
TABLE-US-00010 Ingredient % (by weight)
-(2-hydroxy-4-isobutoxyphenyl)-3- 0.001 (pyridine-2-yl)propan-1-one
Model Chicken Broth Balance to 100 (653 mg Na/240 mL serving)
[0142] Sensory findings: Panelists preferred 0.001% of
-(2-hydroxy-4-isobutoxyphenyl)-3-(pyridine-2-yl)propan-1-one in
this base. In a blind ranking of 6 different samples MSG was the
highest umami with
-(2-hydroxy-4-isobutoxyphenyl)-3-(pyridine-2-yl)propan-1-one
finishing 4.sup.th and Control finishing 5.sup.th.
[0143] Ingredient
1-(2-hydroxy-4-methoxyphenyl)-3-(pyridin-2-yl)propan-1-one
TABLE-US-00011 Ingredient % (by weight)
1-(2-hydroxy-4-methoxyphenyl)-3- 0.001 (pyridin-2-yl)propan-1-one
Model Chicken Broth Balance to 100 (653 mg Na/240 mL serving)
[0144] Sensory findings: Panelists preferred 0.001% of
1-(2-hydroxy-4-methoxyphenyl)-3-(pyridin-2-yl)propan-1-one in this
base. In a blind ranking of 6 different samples MSG was the highest
umami with
1-(2-hydroxy-4-methoxyphenyl)-3-(pyridin-2-yl)propan-1-one
finishing 2.sup.nd and Control finishing 5.sup.th.
EXAMPLE 24
[0145] Model Chicken Broth--no MSG Added, 0.3% Sugar Added
[0146] The model chicken broth powder was prepared from 11.9 g
chicken fat, 23.81 g salt, 14.29 g sugar, 0.95 g onion powder,
49.01 g chicken powder, 0.04 g turmeric powder. To prepare the
model chicken broth 2.0 g of powder was mixed 98.0 g hot water.
[0147] Control
TABLE-US-00012 Ingredient % (by weight) Model Chicken Broth - sugar
added 100 (653 mg Na/240 mL serving)
[0148] Reference
TABLE-US-00013 Ingredient % (by weight) MSG 0.05 Model Chicken
Broth - sugar added Balance to 100 (653 mg Na/240 mL serving)
[0149] Ingredient
1-(2-hydroxy-4-methylphenyl)-3-(pyridin-2-yl)propan-1-one
TABLE-US-00014 Ingredient % (by weight)
1-(2-hydroxy-4-methylphenyl)-3-(pyridin- 0.0010 2-yl)propan-1-one
Model Chicken Broth - sugar added Balance to 100 (653 mg Na/240 mL
serving)
[0150] Sensory findings: Panelists preferred 0.001% of
1-(2-hydroxy-4-methylphenyl)-3-(pyridin-2-yl)propan-1-one in this
base. In a blind ranking of 6 different samples MSG was the highest
umami with
1-(2-hydroxy-4-methylphenyl)-3-(pyridin-2-yl)propan-1-one finishing
5.sup.th and Control finishing 6.sup.th.
[0151] Ingredient:
1-(2-hydroxy-4-isobutoxyphenyl)-3-(pyridine-2-yl)propan-1-one
TABLE-US-00015 Ingredient % (by weight)
1-(2-hydroxy-4-isobutoxyphenyl)-3- 0.002
(pyridine-2-yl)propan-1-one Model Chicken Broth - sugar added
Balance to 100 (653 mg Na/240 mL serving)
[0152] Sensory findings: Panelists preferred 0.002% of compound
1-(2-hydroxy-4-isobutoxyphenyl)-3-(pyridine-2-yl)propan-1-one in
this base. In a blind ranking of 6 different samples MSG was the
highest umami with
1-(2-hydroxy-4-isobutoxyphenyl)-3-(pyridine-2-yl)propan-1-one
finishing 4.sup.th and Control finishing 6.sup.th.
[0153] Ingredient
1-(2-hydroxy-4-methoxyphenyl)-3-(pyridin-2-yl)propan-1-one
TABLE-US-00016 Ingredient % (by weight)
1-(2-hydroxy-4-methoxyphenyl)-3- 0.002 (pyridin-2-yl)propan-1-one
Model Chicken Broth - sugar added Balance to 100 (653 mg Na/240 mL
serving)
[0154] Sensory findings: Panelists preferred 0.002% of
1-(2-hydroxy-4-methoxyphenyl)-3-(pyridin-2-yl)propan-1-one in this
base. In a blind ranking of 6 different samples MSG was the highest
umami with
1-(2-hydroxy-4-methoxyphenyl)-3-(pyridin-2-yl)propan-1-one
finishing 3.sup.rd and Control finishing 6.sup.th.
[0155] Ingredient
1-(2-hydroxy-4,5-dimethylphenyl)-3-(pyridine-2-yl)propan-1-one
TABLE-US-00017 Ingredient % (by weight)
1-(2-hydroxy-4,5-dimethylphenyl)-3- 0.002
(pyridine-2-yl)propan-1-one Model Chicken Broth - sugar added
Balance to 100 (653 mg Na/240 mL serving)
[0156] Sensory findings: Panelists preferred 0.002% of
1-(2-hydroxy-4,5-dimethylphenyl)-3-(pyridine-2-yl)propan-1-one in
this base. In a blind ranking of 6 different samples MSG was the
highest umami with
1-(2-hydroxy-4,5-dimethylphenyl)-3-(pyridine-2-yl)propan-1-one
finishing 2.sup.nd and Control finishing 6.sup.th.--in this base at
this level.
1-(2-hydroxy-4,5-dimethylphenyl)-3-(pyridine-2-yl)propan-1-one
performed well when evaluating for umami.
[0157] In certain embodiments there is provided a compound
(including salts thereof) according to Formula I
##STR00014## [0158] in which [0159] R.sup.1 comprises H, methyl or
ethyl; [0160] R.sup.2 comprises H, OH, fluorine, C.sub.1-C.sub.4
linear or branched alkyl, C.sub.1-C.sub.6 alkoxy wherein the alkyl
group is linear or branched, or a C.sub.3-C.sub.5 cycloalkyl
moiety; [0161] R.sup.3 comprises H, methoxy, methyl or ethyl;
[0162] or R.sup.2 and R.sup.3 together form a bridging moiety
--O--CH.sub.2--O-- between the phenyl carbon atoms to which they
are connected; [0163] R.sup.4 comprises OH or methoxy; and [0164]
R.sup.5 and R.sup.6 independently comprise H or methyl; [0165]
R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are such
that, [0166] (i) when R.sup.2 and R.sup.3 together form a bridging
moiety --O--CH.sub.2--O-- between the phenyl carbon atoms to which
they are connected, R.sup.1, R.sup.5, R.sup.6 are H, and R.sup.4 is
OH; and [0167] (ii) when R.sup.4 is OH and R.sup.1-R.sup.3 are H,
at least one of R.sup.5 or R.sup.6 is methyl.
[0168] In a particular embodiment, R.sup.3 is selected from H and
methoxy.
[0169] In a particular embodiment, R.sup.2 comprises H, OH,
fluorine, methyl, C.sub.1-C.sub.6 alkoxy wherein the alkyl group is
linear or branched, or a C.sub.3-C.sub.5 cycloalkyl moiety.
[0170] In other particular embodiments, R.sup.2 consists of a
C.sub.3-C.sub.5 cycloalkyl moiety.
[0171] In other particular embodiments, R.sup.1 comprises H or
methyl, R.sup.2 comprises methyl, methoxy or isobutyloxy, R.sup.3
is H, R.sup.4 is OH, and R.sup.5 and R.sup.6 are H.
[0172] These compounds confer desirable umami taste sensations on
compositions intended to be taken orally, as disclosed above.
[0173] Although the embodiments have been described in detail
through the above description and the preceding examples, these
examples are for the purpose of illustration only and it is
understood that variations and modifications can be made by one
skilled in the art without departing from the scope of the
disclosure. It should be understood that the embodiments described
above are not only in the alternative, but can be combined.
* * * * *