Food or edible material: processes – compositions – and products – Products per se – or processes of preparing or treating... – Flavor or flavor adjunct – acidulant or condiment
Reexamination Certificate
2002-08-20
2004-03-23
Wong, Leslie (Department: 1761)
Food or edible material: processes, compositions, and products
Products per se, or processes of preparing or treating...
Flavor or flavor adjunct, acidulant or condiment
C426S534000, C426S650000
Reexamination Certificate
active
06709691
ABSTRACT:
BRIEF SUMMARY OF THE INVENTION
The present invention relates to the flavor industry. It concerns more particularly a process for producing a washed citrus oil flavor, which comprises treating a citrus oil with a mixture of propylene glycol and an alkanol from C
1
to C
4
. The invention also relates to clear beverages flavored with citrus washed oils as formulated by the process of the invention.
BACKGROUND OF THE INVENTION
The importance in the flavor industry of various citrus oils has resulted in intensive research directed towards processing methods, compositional analyses, quality and utilization.
Detailed compositional data concerning the commercially important citrus oils can be found in several reviews. Extensive lists of various chemical compounds identified as components of orange, grapefruit, tangerine, lemon, and lime oils have been described.
The flavoring characteristics of the citrus oils are a function of the properties of certain components identified in the oils. Furthermore, d-limonene, which is the main component present in citrus oils, acts as a carrier of flavor for other oxygenated compounds mainly responsible for the citrus flavor characteristics.
The extraction from a citrus oil of the oxygenated compounds which are responsible for the citrus flavor is therefore a field of huge interest for the flavor industry. It is well known in the art that flavoring agents may be prepared by extracting from folded oils the oxygenated compounds desired in an extracted or washed flavor profile.
The formulation of washed oil flavors disclosed in the prior art uses water or propylene glycol as solvents for the extraction of useful flavor compounds from a citrus oil. For instance, U.S. Pat. No. 3,809,757 describes the preparation of a flavoring extract from orange oil by selective extraction, using propylene glycol and a hydrocarbon solvent.
The quality of an extract or a wash is mainly characterized by the selectivity of the extracted compounds. The scope sought in the flavor industry when formulating a wash from a citrus oil, is therefore to selectively obtain the key citrus flavor compounds i.e., the oxygenated compounds such as neral, geranial, neral acetate, geranial acetate, decanal, nootkatone, etc. Other requirements such as clearness or flash point requirements are necessary for obtaining an optimized washed oil product.
DETAILED DESCRIPTION OF THE INVENTION
Now, we have been able to find a novel process for the preparation of a citrus washed oil flavor, combining propylene glycol usually utilized for the extraction of oxygenated compounds, with an alkanol from C
1
to C
4
. This process makes it possible to obtain a surprisingly selective wash of the key flavor compounds present in a citrus oil, which further meets all the requirements of quality and security needed for such a product. The present invention is thus related to a process for producing a citrus washed oil flavor, which comprises treating a citrus oil with a mixture of propylene glycol and an alkanol from C
1
to C
4
. In a preferred embodiment the alkanol is selected from the group consisting of ethanol and isopropanol.
The process of the invention advantageously allows to obtain citrus washed oil flavors which meet the clarity, flash point and usage level objectives required in the art. The washes obtained by the process according to the invention have a flash point greater than 100° F. (38° C.) (i.e. they belong to the Class I liquids), cut clear in water and have a light, clean profile with the hint of fruit flavor from 0.05 to 0.2%, preferably at a 0.1% use level. Moreover, analyses of the washed citrus oil flavors formulated respectively with and without the use of an alkanol from C
1
to C
4
, clearly indicate that washes produced with the use of some alkanol are superior to those made with propylene glycol on its own. This result will be demonstrated in the comparative tables below, in the case of ethanol.
Unexpectedly, and besides the fact that alkanols from C
1
to C
4
suffer from the standpoint of their low flash point, we have now been able to optimize the formulation of citrus washed oils using the alkanol at the right level to extract the oxygenated compounds while meeting the flash point limitations.
The proportion of alkanol used in the extracting mixture with propylene glycol can vary in a certain range of values. Typically it can be comprised between 3 and 10% and is preferably comprised between 5 and 7% of the total weight of the composition comprising the citrus oil, propylene glycol and the alkanol.
As mentioned above, among the alkanols from C
1
to C
4
, ethanol and isopropanol are preferred.
The starting product for the process of the invention may be any commercially available citrus oil, in the form of a cold pressed oil, or a folded oil, for instance. Non limiting examples of citrus oils which can be used for the process of the invention include lemon, berry, orange, grapefruit, tangerine, lime, kumquat, mandarin, bergamot and other essential oils or a mixture thereof.
The selectivity of the extraction system may be demonstrated by the comparison between citrus washes made with some ethanol, and washed oil flavors made with 75% propylene glycol: 25% flavor oil, i.e. ethanol free.
The following tables compare the washes obtained with propylene glycol combined with ethanol, and those obtained with propylene glycol on its own.
Table 1 reports the results for a lemon wash while Table 2 reports the results for a grapefruit wash.
TABLE 1
Percent
Lemon wash
−83% PG
Lemon wash
Lemon
−6% EtOH
−75% PG
compounds
Oil*
−11% Oil
−25% Oil
Phellandrene
0.75
0.39
0.36
&agr; Pinene
3.32
2.10
1.52
Camphene
0.17
Sabinene
2.30
1.80
&bgr; Pinene
19.68
16.10
10.43
Myrcene
2.45
1.56
1.61
Limonene
52.70
56.41
57.26
(Iff)oximene
0.48
0.37
0.42
&ggr;-Terpinene
10.67
8.43
7.86
a-Terpinolene
0.67
0.56
0.53
Nonanal
0.27
0.29
0.15
Linalol
0.11
0.23
1.84
Citronellal
0.11
&agr;-Terpineol
0.22
0.35
3.31
Decanal
0.12
Neral
1.53
0.61
0.68
Geranial
2.49
0.59
0.30
Undecanal
<0.05
Citronellyl acetate
0.06
Neryl acetate
1.25
1.14
0.66
Geranyl acetate
0.75
0.60
0.30
Caryophyllene
0.46
Neral/pg acetal
1.48
2.31
A sesquiterpene
0.70
Neral/pg acetal
0.95
1.50
Geranial/pg acetal
3.29
4.23
Geranial/pg acetal
2.26
2.92
&bgr;-Bisabolene
1.00
*Origin: Firmenich Citrus Center, Florida, U.S.A.
TABLE 2
Percent
Grapefruit wash
−83% PG
Grapefruit wash
Grapefruit
−6% EtOH
−75% PG
compounds
Oil*
−11% Oil
−25% Oil
&agr;-Pinene
0.52
2.08
Sabinene
0.31
Myrcene
2.51
Limonene
75.04
80.55
Iffocimene
0.51
0.71
Nonanal
0.35
0.39
Linalol
0.68
0.85
Limonene oxide
0.31
Citronellal
0.51
&agr;-Terpineol
2.13
2.51
39.74
Decanal
2.62
3.14
Octyl acetate
0.58
0.47
Neral
0.40
Geranial
0.47
Neryl acetate
0.08
Geranyl acetate
0.37
&agr;-Copaene
0.96
&bgr;-Cubebene
0.89
Caryophyllene
2.60
0.84
&agr;-Humulene
0.43
Pg acetal
0.90
&dgr;-Cadinene
0.88
Nootkatone
2.86
3.40
&agr;-Coumarin
0.69
2.10
60.26
&agr;-Benzopyranone
3.31
2.05
*Origin Firmenich Citrus Center, Florida, U.S.A.
It can be easily concluded from the results reported in the above tables that the use of some ethanol is advantageous in extracting the key flavor compounds (i.e. oxygenated compounds such as neral, geranial, neral acetate, geranial acetate, decanal, nootkatone, etc.) from a citrus oil.
The invention also relates to a method to impart, improve, enhance or modify the flavoring properties of a flavoring composition or a flavored product, which comprises adding to said composition or product a citrus washed oil flavor produced by the process of the invention.
Another object of the invention is a flavoring composition or a flavored product such as a clear beverage, comprising a citrus washed oil flavor as an active flavoring ingredient, the proportion of the latter being comprised between 0.05 and 0.2% of the total weight of the composition or product.
The invention will now be illustrated in a more detailed manner in the following example wherein the temperatures are indicated in degrees centigrade and the abbre
Firmenich SA
Winston & Strawn LLP
Wong Leslie
LandOfFree
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