CN117242162A

CN117242162A - Compositions and methods for preventing or reducing autoxidation of fragrances and edible oils

Info

Publication number: CN117242162A
Application number: CN202280032968.5A
Authority: CN
Inventors: M·卡兰德拉; 王英; D·斯利亚拉斯尼
Original assignee: Firmenich SA
Current assignee: Firmenich SA
Priority date: 2021-05-05
Filing date: 2022-04-20
Publication date: 2023-12-15

Abstract

The present application relates to 2-oxo acids modified for use as stabilizers in non-polar applications, such as applications containing edible fats or oils, or aromatic oils.

Description

Compositions and methods for preventing or reducing autoxidation of fragrances and edible oils

Cross Reference to Related Applications

The present application claims priority from U.S. provisional application No.63/184,247 filed 5/2021 and European application No.21176136.6 filed 27/5/2021. The entire contents of these applications are expressly incorporated herein by reference.

Technical Field

The present application provides compositions and methods for controlling autoxidation in fats or oils used in foods, fragrances and cosmetics (for skin creams, lotions, etc.), as well as in terpenes and other Perfumery Raw Materials (PRMs).

Background

Autoxidation of fats and oils can lead to rancidity, while autoxidation of Perfume Raw Materials (PRMs) can lead to skin allergy problems and/or fragrance instability. Many formulated perfumes, body care products, household care products, perfumery raw materials (such as, for example, essential oils, natural extracts and synthetic ingredients) and food raw materials (such as, for example, fats and oils derived from animal or vegetable sources and derivatives thereof, including monoglycerides, diglycerides, lecithins, phosphatidylethanolamine or other phospholipids, and modified triglycerides) undergo oxidation resulting in the formation of chemicals, including peroxides, organic hydroperoxides, peroxyhemiacetals, hemiacetals, acetals, or transesterification products. The oxidation-formed chemicals may alter the organoleptic properties or appearance of the perfume ingredients, formulated perfumes, formulated body care products, formulated skin care products, formulated home care products, essential oils, food materials, formulated food products, and natural extracts or be harmful, irritating or sensitized. The high peroxide value (POV) of formulated fragrances, body care products and fragrance raw materials can lead to skin allergy problems, such as contact dermatitis. Excessive POV may result in the fragrance raw material failing the quality control test and being deemed unusable. Unacceptably high POV can result in food ingredients having an unpleasant rancid taste.

Disclosure of Invention

In the present application, the effects of autoxidation in foods, fragrances and cosmetics are mitigated by methods and compositions that result in the chemical consumption of reactive and potentially harmful organic hydroperoxides and/or rancid-smelling volatile compounds formed during autoxidation. The application can not only prevent the formation of rancidity in triglyceride fats/oils, but also reduce the degree of rancidity of fats/oils that have already been rancidity; in other words, rancidity of the fat/oil is repaired.

U.S. publication No. 2019/031274 A1 discloses the use of 2-oxo acids and related compounds as stabilizers for perfumes, raw materials and food products. Although 2-oxo acids and/or salts thereof may be effective in vegetable oils or undiluted perfume oils, solubility problems may exist in these very hydrophobic matrices due to the ionic nature of the 2-oxo acid salt. The low solubility of 2-oxoacid salts may limit their successful use.

The present application provides modifications of such compounds, allowing for use in non-polar applications, such as food fat/oil containing applications, as well as in undiluted hydrophobic perfume oils (perfume oils insoluble in typical hydroalcoholic solvents used in Eau De Toilette (EDT)).

The present application relates to the use of a formulation of a-ketoglutarate (AKG) or other 2-oxo acid dissolved in a solvent containing hydroxyl groups, in particular in a solvent having two hydroxyl groups in the 1, 2-or 1, 3-position (orientation) on the carbon chain. Non-limiting examples include 1, 2-pentanediol (1, 2-dihydroxypentane); 1, 3-butanediol (1, 3-dihydroxybutane); hexanediol (2-methyl-2, 4-pentanediol); diethyl tartrate; mono-or diglycerides; or a mono/diglyceride mixture derived from any edible oil. In cases where the solubility of such salts is problematic, these dissolved formulations provide alternatives to the 2-oxoacid salts. Surprisingly, polar 2-oxo acids, especially highly polar AKGs, are soluble in hydrophobic media by some unspecified covalent or other interactions with compounds containing polar hydroxyl groups. Combining these two components, the hydrophobicity is unexpectedly improved.

The method of controlling the autoxidation of fats/oils in food, fragrance and cosmetics according to the present application in terpenes and other Perfume Raw Materials (PRMs) comprises:

mixing and stirring the 2-oxo acid and the hydroxyl-containing compound (SOP), optionally warm and heated, until they form a clear, homogenous mixture/solution; and

the mixed and stirred SOP is added to the material to be treated (e.g., fats/oils used in foods and cosmetics, and fats/oils in terpenes and other Perfume Raw Materials (PRMs)) and mixed.

Drawings

FIG. 1 is a graph showing POV of corn oil treated with ART compound 1 over several days.

FIG. 2 is a graph showing the percentage decrease in POV in corn oil treated with ART compound 1.

FIG. 3 is a graph showing POV of pure corn oil, DET in corn oil, and AKG/DET in corn oil.

FIG. 4 is a graph showing the percent reduction in POV of corn oil treated with 5%1:10 AKG/DET.

FIG. 5 is a graph showing POV of undiluted fragrance oil and fragrance oil containing AKG-Aleen5, AKG-BG, AKG-NMDEA and AKG-DET over time.

FIG. 6 is a graph showing the percentage decrease in POV over time for undiluted fragrance oils and fragrance oils containing AKG-Aleen5, AKG-BG, AKG-NMDEA, and AKG-DET.

FIG. 7 is a graph showing POVs of untreated EDT and EDT treated with AKG-BG, AKG-diNMDEA, ADG-DET or AKG-DET at pH 7.

FIG. 8 is a graph showing POVs of untreated EDT and EDT treated with AKG-BG, AKG-diNMDEA, ADG-DET or AKG-DET at pH 5.5.

FIG. 9 is a graph showing the concentration of aldehydes (hexanal or 2-nonenal) in salad dressing treated or untreated with dimethyl decyl ammonium phenylpyruvate salt.

Fig. 10 is a graph showing the decrease in POV over time of corn oil treated with ART compound 2.

Detailed Description

The present application provides methods and compositions for preventing the formation of rancidity in triglyceride fats/oils and/or reducing the degree of rancidity of fats/oils that have already been rancid; in other words, rancidity of the fat/oil is remedied. 2-oxo acids (see U.S. patent publication No. 2019/031274) appear to act as aldehyde scavengers because volatile aldehydes are the main contributor to rancid odors in fats/oils.

As used herein, "solubilized 2-oxo acid formulation" or "SOP" refers to the 2-oxo acid/hydroxy group-containing solvent formulation of the present application.

SOPs of the present application include, but are not limited to, esters of AKG, such as:

1 (1)

2, 2

3

Wherein R is ¹ Or R is ² Is an organic moiety (alkyl or aryl) derived from/corresponding to an alcohol R-OH, and R-OH is any alcohol that is sufficiently non-polar to impart sufficient hydrophobic character to the corresponding ester relative to the unesterified carboxylate moiety such that the resulting ester has enhanced solubility in a hydrophobic matrix, such as undiluted aromatic oil or edible oil/cooking oil (e.g., sunflower seed oil). R is R ¹ Or R is ² May be any alkyl or aryl group or combination thereof, which may also contain additional functional groups/substituents including double bonds, hydroxyl groups, ethers, esters, ketones, aldehydes, amides, ketals, or acetals.

Deriving a specific R ¹ Or R is ² Non-limiting examples of partial alcohols include:

4. The method is to

5. The method is to

6. The method is to

7. The method of the application

Non-limiting examples of SOPs of the present application include: esters formed from AKG and hexanediol:

8. The method is used for preparing the product

Diester formed from AKG and hexanediol:

9. The application is applicable to

Ketals formed from diols oriented in the 1, 2-or 1, 3-position configuration, such as ketals formed from AKG with 1, 2-pentanediol:

10. The method of the application

One possible isomer of ketal and ester combinations formed from AKG with hexanediol:

11. The method of the application

One possible isomer of the ketal and diester combination formed by AKG with hexanediol:

12. Fig.

One possible isomer of an ester formed from AKG with palmitoyl monoglyceride:

13 of the group

Ketals formed from AKG with palmitoyl monoglycerides:

14, of the order of magnitude

One possible isomer of ketal and ester combinations formed from AKG with palmitoyl monoglycerides:

15 of the formula

As used herein, the term "peroxide value" or "POV" refers to the amount of oxidation potential equivalents per 1 kg of material. The POV of the material is determined by analysis. The term "POV" does not refer to a compound or group of compounds, but may be used interchangeably with the autoxidation product within a sample that causes a response during the POV test. These autoxidation products vary depending on the particular material being tested. Many classes of compounds respond during the POV test, including but not limited to organic and inorganic hydroperoxides, organic and inorganic peroxides, peroxyhemiacetals, peroxyhemiketals, and hydrogen peroxide itself.

By way of illustration, one POV test is the iodometric redox titration method. All POV-responsive compounds share a common property that they are capable of oxidizing iodide ions to molecular iodine within a time period specified by the test; in fact, the iodide oxidation reaction is the basis of the test. Thus, "POV" is a value representing the molar sum of all iodide oxidizing species in a particular sample.

For example, limonene and linalool are unsaturated terpenes, commonly found as major components in many essential oils. Both limonene and linalool are readily oxidized by atmospheric oxygen to form hydroperoxides. Hydroperoxides of limonene and linalool are known to be sensitizers capable of causing contact dermatitis. Thus, limonene and natural products containing limonene can only be used as perfume raw materials when the recommended organic hydroperoxide content is below 20 mmol/L. Also, essential oils and isolates from the Pinaceae (pinaceae) family (including Pinus) and Picea (Abies) can be used as perfume raw materials only at recommended organic hydroperoxide levels below 10 mmol/L.

As another example, fats and oils or derivatives thereof are known to undergo an autoxidation process, resulting in unpleasant and unpalatable rancidity. Without being bound to any particular theory, triglyceride hydroperoxides are intermediate chemicals in the autoxidation process that further degrade into aldehydes and ketones that produce rancid odors.

The POV of a formulated fragrance, body care product, cosmetic, home care product, perfumery raw material, flavored product or food raw material can be determined by any method readily selected by a person of ordinary skill in the art. Non-limiting examples include iodometric titration, high performance liquid chromatography, and the like. Examples of HPLC methods for determining POV of a fragrance raw material are disclosed in Flavor and Fragr.J. (2015), 30, p 121-130, by Calandra et al.

Perfume raw materials include, but are not limited to, essential oils, natural extracts, and synthetic ingredients.

The present application relates to the use of a formulation of a-ketoglutarate (AKG) or other 2-oxo acid dissolved in a solvent containing hydroxyl groups, in particular in a solvent having two hydroxyl groups in the 1, 2-or 1, 3-position (orientation) on the carbon chain. These solvents must be sufficiently hydrophobic in nature that they can be readily dissolved in the hydrophobic matrix that one seeks to treat. In other words, the solvent is highly soluble in edible oils or undiluted aromatic oils. Examples include 1, 2-pentanediol (1, 2-dihydroxypentane), 1, 3-butanediol (1, 3-dihydroxybutane), hexanediol (2-methyl-2, 4-pentanediol), diethyl tartrate, or monoglycerides derived from any edible oil. In cases where the solubility of the 2-oxoacid salt is problematic, these dissolved formulations provide alternatives to the 2-oxoacid salt. According to the present application, the POV of a formulated perfume, body care product, cosmetic, home care product, perfumery raw material, flavored product or food raw material can be reduced by treating the formulated perfume, body care product, cosmetic, home care product, perfumery raw material, flavored product or food raw material with SOP.

The present application may provide advantages over 2-oxoacid salts in a very hydrophobic matrix due to the increased solubility of SOP relative to salt. The exact nature of the interaction between AKG or other 2-oxo acid and the hydroxyl containing solvents in these SOPs is not known. However, SOP may not be an ionic salt and therefore has greater solubility in a hydrophobic matrix. Because of its better solubility, SOP should allow POV remediation treatment in triglyceride oils and derivatives thereof, as well as in many PRMs, without creating cloudy, milky suspensions, and without forming two distinct phases.

The SOP compounds according to the present application are readily reactive with organic hydroperoxides and are organoleptically and toxicologically compatible for use in food, high quality fragrance (fine fragrance) and body care applications. The hydroperoxide scavenging material containing 2-oxo acid moieties/functional groups in the SOP according to the present application must maintain reactivity towards hydroperoxides after dissolution by hydrophobic hydroxyl containing solvents.

To form the SOP of the present application, the solvent must contain a hydroxyl group or groups, typically in the 1, 2-or 1, 3-position configuration, that is capable of interacting with the 2-oxo acid in a manner that enables the solvent to dissolve the 2-oxo acid. Solvents should be readily soluble in hydrophobic media, which typically require having an extended carbon chain or ring system or some combination thereof in the solvent molecule; for example, an alkyl chain of eight to eighteen carbons works.

The SOP of the present application may be applied as a leave-in ingredient to a fragrance raw material or formulation, or as an additive in an oily food, fragrance and/or oily skin care product or an aromatised skin care product. SOP can also be used to process raw materials during manufacturing and then mix them into fully formulated flavor/fragrance oils or consumer products.

The SOP of the present application may be used in any fat/oil containing food formulation to prevent the formation of rancidity or to remedy existing rancidity, such as frying oil. SOP can also be used in any fragrance skin care product to prevent skin allergy caused by terpene hydroperoxides and, if triglyceride oils are used (e.g. in skin creams), the formation of rancidity. Thus, the present application can simultaneously perform a dual role in skin care products; the formation of rancidity is prevented by lipid hydroperoxide scavenging action and skin allergy is prevented by terpene hydroperoxide scavenging action.

In one form, the SOP comprises from about 0.01 wt% to about 10.0 wt% edible oil, aromatic oil. In another form, the SOP comprises from about 0.1 wt% to about 5.0 wt% edible oil, aromatic oil. In another form, the SOP comprises from about 0.1 wt% to about 1.0 wt% edible oil, aromatic oil.

The SOP of the present application can be used, for example, in raw materials, which are then mixed into fully formulated flavor or fragrance oils; or for consumer products such as foods and cosmetics (e.g. skin creams, lotions, etc.), oleaginous foods (e.g. frying oils, mayonnaises, margarines and salad dressings), fragrances, oleaginous skin care products or fragranced skin care products.

Examples

Example 1: corn oil treated with a 1:3 mixture of alpha-ketoglutarate and mono-and diglycerides derived from coconut oil

Corn oil treated with a 1:3 mixture of alpha-ketoglutarate and mono-and diglycerides derived from coconut oil is hereinafter referred to as ART compound 1 (anti-rancidity technical compound 1).

Preparation of ART compound 1:2.0g of Capmul MCM C8 EP/NF (caprylic acid monoglyceride/diester, ABITEC corporation) was placed in a 10mL glass vial. The semi-solid material was heated in a 35 ℃ heating zone (block) for 20 minutes to melt it. 0.669g of alpha-ketoglutaric acid was addedAfter being in the vial, the mixture was stirred at room temperature for 2 hours, yielding a white semi-solid. When the vial was again warmed to 35 ℃ for 20 minutes, the mixture melted again. The liquid was stirred at room temperature overnight and then heated to 100 ℃ for 40 minutes. All AKG eventually dissolved, giving a pale yellow liquid which remained liquid after returning to room temperature.

Treatment of corn oil with various concentrations of ART compound 1:

to 8mL of corn oil was added the following amount of ART compound 1 to produce clear solutions over a range of concentrations as shown in the following Table. The POV of these solutions was measured periodically after being placed on a laboratory bench under ambient light and temperature conditions.

TABLE 1

FIG. 1 is a graph showing POV over several days for corn oil treated with varying amounts of ART compound 1. FIG. 2 is a graph showing the percent reduction in POV in corn oil treated with varying amounts of ART compound 1. The figure shows that the POV decreases in a dose dependent manner.

Example 2: corn oil treated with a 1:10 mixture of alpha-ketoglutarate (AKG) and diethyl tartrate (DET)

0.201gm of AKG and 2.011gm of DET were placed in a 15mL glass vial. The mixture was stirred at room temperature with a small magnetic stirrer for a weekend (about 3 days). However, not all AKG was dissolved, and thus the vials were placed in a heating zone at 90 ℃ for 15 minutes, resulting in clear solutions. After cooling and standing for several days, no solids precipitated. This material (0.4 mL) was diluted into 8mL corn oil to start the experiment. Samples were also prepared with 0.4mL DET in 8mL corn oil. POV titration measurements were periodically performed on each sample with untreated corn oil.

FIG. 3 is a graph showing pure corn oil, DET in corn oil, and POV of AKG/DET in corn oil.

FIG. 4 is a graph showing the percent reduction in POV of corn oil treated with 5%, 1:10 AKG/DET.

It can be seen that DET alone (without dissolving any AKG) has some measurable activity for reducing POV of corn oil, but it is significantly lower than when AKG is included simultaneously.

Example 3: model perfume treatment and undiluted perfume oil

Model perfume oils were made using approximately the following formulation:

TABLE 2

The model perfume oil was diluted as described below and the pH was adjusted to produce two model perfumes, pH 7.0 and 5.5, respectively.

Prepared model perfume (diluted with 90:10v/v EtOH/water. Times.5):

two separate bottles (a and B) (240 mL each) were prepared as follows and p measured:

200mL of EtOH/water at 90:10v/v and 40mL of model fragrance oil were mixed and stirred to give a clear, yellowish solution with a pH of 6.16. Aromatic oil concentration: 40mL/240mL = 16.67% v/v.

The pH of the model perfume prepared above was adjusted to the desired level using the following procedure:

diethyl citrate (DEC) and triethanolamine (TEA, sigma Aldrich); d=1.124 g/mL,60mg tea=53 μl TEA. Because of the extremely high viscosity of TEA, a positive displacement pipette was used to transfer TEA.

Bottle a-EDT pH 7.0: about 53. Mu.L (60 mg) TEA was added to 240mL of model flavor to bring the pH to 7.67. The pH was adjusted to 7.03 by slow addition of DEC with continuous stirring while monitoring with a pH meter. The solution remained initially clear but appeared very slightly cloudy after standing at room temperature for several days.

B bottle-EDT at pH 5.5: about 53. Mu.L (60 mg) TEA was added to 240mL of model flavor to bring the pH to 7.77. The pH was adjusted to 5.52 by slow addition of DEC with continuous stirring while monitoring with a pH meter. As a result, the solution became slightly cloudy.

Example 4: SOP was prepared from various solvents for testing in undiluted fragrance oils and model fragrances

AKG-NMDEA salt (AKG di [ N-methyldiethanolammonium)]Salt) preparation:the compounds were tested as known effective treatments, such as Flavor&Fragrance Journal, M.Calandra and Y.Wang,2020, 35:686-694.

From diethyl tartrate (DET), 1, 3-butanediol (butanediol, BG) and 1, 2-pentanediol (A-Leen 5) SOP：

AKG-Alen 5 (1:4, mol/mol): to a vial containing AKG (2.985 g,0.02 mol) was added 1, 2-pentanediol (pentanediol, A-Leen5 from Minasolve, 8.426g,0.08mol,4 equivalents, 26.2% w/w AKG). The mixture was stirred at room temperature overnight to give a clear liquid.

AKG-BG (1:4, mol/mol): to a vial containing AKG (5.872 g,0.04 mol) was added 1, 3-butanediol (Brontide from Genomatica, 14.280g,0.16mol,4 equivalents, 29.1% w/w AKG). The mixture was stirred at room temperature overnight to give a clear liquid.

AKG-DET (1:5, w/w): diethyl tartrate (DET, 8.00g, from Sigma Aldrich,16.67% w/w AKG) was added to a vial containing AKG (1.60 g). The mixture was stirred at room temperature overnight, but no clear liquid was obtained. The mixture was then heated to 90 ℃ for 50 minutes and cooled to room temperature to give a clear liquid.

Treatment of undiluted aromatic oil:180 μl (2% v/v) of each SOP was added to an aliquot of the mixed model fragrance oil (9 mL per aliquot) in a 15mL vial, and the sample was vortexed vigorously for about 1 minute to obtain a homogeneous, clear solution (AKG-NMDEA is one exception because it is cloudy). The resulting sample was then placed on a laboratory bench top under ambient light and temperature. After addition, the POV measurements change over time; each time the vial is opened, the headspace within the vial is refreshed by the surrounding atmosphere.

As shown in fig. 5 and 6, the POV of each treated aromatic oil was reduced relative to untreated aromatic oil.

Example 5: treatment of model perfume (hydroalcoholic EDT solution)

SOPs prepared from various solvents as described above were dissolved into model perfume EDT solutions according to the table below. The weight of each SOP used was based on the% (w/w) of AKG in each SOP such that the final concentration of AKG in the treated model perfume EDT was 0.05% w/v.

TABLE 3 Table 3

As shown in fig. 7 and 8, the POV of each treated fragrance oil was reduced relative to untreated EDT.

Example 6: aldehyde scavenging Activity of AKG salts and AKG-derived SOPs

Aldehyde content in corn oil or other food products (e.g., salad dressing) was measured using DNPH derivatization and HPLC analysis methods (j.ag.food chem. Deng, F-y.et al, (2014) 62,52,12545-12552;Food Res.Internat, cao, j.et al, (2014) 64, 901-907). Alternatively, or in addition to aldehyde measurement by HPLC, sensory evaluation was also performed to assess the level of rancidity in the samples.

Treatment of salad dressing with 2-oxoacid salts

Sample: pasture salad dressing (Pepper lime flavor)

The 2-oxoacid salt used: dimethyl decyl ammonium phenylpyruvate

Dosage is as follows: about 2.7% (w/w) (0.4 g salt added to 15g salad dressing).

Storage conditions: at room temperature, loosely capped, and mixed periodically.

FIG. 9 is a graph showing the concentration of aldehydes (hexanal or 2-nonenal) in salad dressing treated or untreated with dimethyl decyl ammonium phenylpyruvate salt. As shown, the aldehyde content in the treated salad dressing was lower.

For this salad dressing, the salad dressing had a moderate rancid smell before treatment, but the degree of rancidity after treatment was significantly reduced.

Example 7 Performance of SOP

SOP performance is monitored by POV titration, e.g. Flavor&Fragrance Journal, M.Calandra and Y.Wang,2020,35:107-113 or according to the IFRA POV method (seewww.ifraorg.org)。

SOP is effective in reducing POV (hydroperoxide removal) in PRM, fully formulated perfume oils and triglyceride fats/oils. In some cases, rancid volatile compounds are also removed from the triglyceride fat/oil. The SOPs described herein are capable of forming clear solutions in hydrophobic media (e.g., edible oils and typical model undiluted aromatic oils).

Example 8-corn oil treated with a 1:5 mixture of phenylpyruvate and coconut oil derived mono-and diglycerides

Note that: for convenience, this material is hereinafter referred to as ART compound 2 (anti-acid-decay technical compound 2).

Preparation of ART compound 2:2.0g of Capmul MCM C8 EP/NF (caprylic acid monoglyceride/diester, ABITEC corporation) was placed in a 10mL glass vial. The semi-solid, partially crystalline material was heated to 35 ℃ in the heating zone for 20 minutes until melted into a transparent liquid. After the addition of 0.404g of phenylpyruvate (PPA), the vial was stirred at room temperature for 10 minutes to give a white cloudy mixture.When the vial was warmed to 35 ℃ for an additional 20 minutes, the turbid liquid became transparent. This was stirred at room temperature for a further 2 hours to give a clear, pale yellow liquid.

Example 9: treatment of corn oil with different concentrations of ART compound 2

To 16mL of corn oil was added the following amount of ART compound 2 to produce a series of clear solutions as shown in the following table. After ART compound 2 was added to the oil, the mixture was stirred at room temperature for 5 minutes. The sample was completely dissolved and no solid precipitation or layer separation was observed. The POV of these solutions was measured periodically after being placed on a laboratory bench under ambient light and temperature conditions. See fig. 10.

TABLE 4 Table 4

/>

Claims

1. A composition comprising a solubilized 2-oxo acid preparation (SOP) and a perfume oil.

2. A composition comprising a solubilized 2-oxo acid preparation (SOP) and an edible oil.

3. The composition according to claim 1 or 2, wherein the SOP is selected from the group consisting of:

(a)

1 (1)

(b)

2, 2

(c)

3

Wherein R is ¹ And R is ² May be the same or different and are independently selected from the group consisting of: any alkyl or aryl groups and combinations thereof;

and wherein R is ¹ And R is ² Additional functional groups/substituents may also be included, including double bonds, hydroxyl groups, ethers, esters, ketones, aldehydes, amides, ketals, or acetals.

4. The composition according to claim 1 or 2, wherein the SOP is selected from the group consisting of:

(i)

8. The method is used for preparing the product

(ii)

9. The application is applicable to

(iii)

10. The method of the application

(iv)

11. The method of the application

(v)

12. Fig.

(vi)

13 of the group

(vii)

14, of the order of magnitude

(viii)

15 of the formula

And combinations thereof.

5. A method of preventing rancidity formation and/or reducing the degree of fat or rancidity that has already been rancid in a triglyceride fat or oil comprising mixing the triglyceride fat or oil with a dissolved 2-oxo-acid formulation (SOP).

6. A method for reducing the peroxide value (POV) of a fragrance oil comprising mixing a dissolved 2-oxo acid formulation (SOP) with the fragrance oil.

7. A method for reducing the peroxide value (POV) of an edible oil comprising mixing a dissolved 2-oxo acid formulation (SOP) with a perfume oil.

8. A consumer product comprising the SOP of any one of claims 1-4.

9. Use of the dissolved 2-oxo acid preparation (SOP) according to any one of claims 1,3 or 4 for reducing POV of aromatic oil.

10. Use of the dissolved 2-oxo acid preparation (SOP) according to any one of claims 2 to 4 for reducing POV of an edible oil.