JP7474584B2 - Sweetener enhancer - Google Patents

Description

The present invention relates to a sweetness enhancer that enhances sweetness.

In recent years, research into the health effects of sugar has been actively conducted, and the number of foods that feature reduced sugar has been increasing. Reduced sugar foods generally use non-sugar high-intensity sweeteners instead of sugar, but technology that uses sweetness enhancers that can increase the sweetness of foods has also been proposed. For example, Patent Document 1 reports that sweetness is increased by adding two components, arachidonic acid triglyceride and plant sterol, to food and drink, and Patent Document 2 reports that oleic acid has the effect of enhancing the sweetness and richness of the aftertaste of hardened oils and fats.

On the other hand, α-linolenic acid (C18:3) is one of the ω3 highly unsaturated fatty acids, and has been reported to have anti-arteriosclerosis, anti-hypertensive, anti-allergic effects, etc. (Non-Patent Documents 1 to 3).
However, the effect of the combination of α-linolenic acid and oleic acid on sweetness is unknown.

JP 2011-223942 A International Publication No. 2010/004784

Djousse et al., Circulation. 2005, 111(22), pp. 2921-2926 Djousse et al., Hypertension. 2005, 45(3), pp. 368-373 Kunisawa et al., Sci Rep. 2015, 5, 9750

The present invention relates to providing a sweetness enhancer that enhances sweetness.

In order to solve the above problems, the inventors conducted extensive research focusing on fatty acid species and discovered that a combination of α-linolenic acid and oleic acid enhances sweetness.

That is, the present invention provides a sweetness enhancer that contains α-linolenic acid and oleic acid as active ingredients.

The sweetness enhancer of the present invention can be used in orally ingestible products to enhance their sweetness.

The α-linolenic acid (18:3) used in the present invention is a polyunsaturated fatty acid having 18 carbon atoms and having double bonds at the 3rd, 6th, and 9th positions counting from the methyl end of the carbon chain.
Oleic acid (18:1) is a monovalent unsaturated fatty acid having 18 carbon atoms and having a double bond at the ninth position counting from the methyl end of the carbon chain.
The unsaturated bonds in α-linolenic acid and oleic acid may be either trans or cis, but are preferably cis.
The α-linolenic acid and oleic acid used in the present invention are in a form other than triacylglycerol, diacylglycerol, or monoacylglycerol, and may be in a free form, a lower alkyl ester, or a salt form. Examples of lower alcohols that form esters with α-linolenic acid or oleic acid include those having 1 to 6 carbon atoms, such as methanol and ethanol. Examples of salts include alkali metal salts such as sodium and potassium, alkaline earth metal salts such as calcium, magnesium salts, and ammonium salts.
α-Linolenic acid and oleic acid can be obtained from foods and edible oils and fats that contain α-linolenic acid and oleic acid, or by hydrolyzing edible oils and fats using a high-temperature, high-pressure hydrolysis method or an enzymatic hydrolysis method. Commercially available products can also be used.

In the present invention, the ratio of α-linolenic acid to oleic acid, in terms of the mass ratio of α-linolenic acid to oleic acid [α-linolenic acid/oleic acid], is preferably 0.1 to 30, more preferably 0.2 to 20, even more preferably 0.5 to 15, even more preferably 1 to 10, even more preferably 1.5 to 8, and even more preferably 2 to 6, from the viewpoint of the sweetness enhancing effect.
In this specification, the amount of fatty acid is calculated as the amount of free fatty acid.

As shown in the Examples below, the combination of α-linolenic acid and oleic acid has the effect of enhancing sweetness, which is greater than that achieved by using α-linolenic acid or oleic acid alone.
Therefore, a combination of α-linolenic acid and oleic acid can be a sweetness enhancer that enhances sweetness, and can be used to enhance sweetness, and can also be used to produce a sweetness enhancer.
In the present invention, "enhancing sweetness" means enhancing sweetness. The presence or absence of sweetness and the degree of sweetness can be evaluated by sensory evaluation by a panel of experts. The sweetness includes monosaccharides (glucose, fructose, etc.), disaccharides (sucrose, maltose, lactose, etc.), polysaccharides (oligosaccharides, starch), sugar alcohols (maltitol, reduced maltose syrup, erythritol, xylitol, sorbitol, etc.), amino acids (glycine, alanine, etc.), natural sweeteners (licorice, stevia), synthetic sweeteners (sucralose, stevia, acesulfame potassium, etc.), etc.

The sweetener of the present invention contains α-linolenic acid and oleic acid as active ingredients, but may contain other ingredients as necessary. Ingredients other than α-linolenic acid and oleic acid include solvents, softeners, lipids, emulsifiers, preservatives, acidulants, sweeteners, bittering agents, pH adjusters, stabilizers, colorants, antioxidants, moisturizers, thickeners, flow improvers, foaming agents, flavorings, and seasonings, but from the viewpoint of sweetener enhancement effect, it is preferable that lipids other than α-linolenic acid and oleic acid are contained.

The lipids contained in the sweetener enhancer include monoacylglycerol, diacylglycerol, triacylglycerol, phospholipids, glycolipids, sterols, waxes, etc., but from the viewpoint of flavor and sweetness enhancement, diacylglycerol or triacylglycerol is preferred. Furthermore, the lipids contained in the sweetener enhancer are preferably derived from edible fats and oils.

The edible oils and fats may be either vegetable oils and fats or animal oils and fats. Examples of such oils and fats include vegetable oils and fats such as soybean oil, rapeseed oil, safflower oil, rice oil, corn oil, sunflower oil, cottonseed oil, olive oil, sesame oil, peanut oil, pearl barley oil, wheat germ oil, perilla oil, linseed oil, perilla oil, sacha inchi oil, walnut oil, kiwi seed oil, salvia seed oil, grape seed oil, macadamia nut oil, hazelnut oil, pumpkin seed oil, camellia oil, tea seed oil, borage oil, palm oil, palm olein, palm stearin, coconut oil, palm kernel oil, cacao butter, monkey fat, shea butter, and algae oil; animal oils and fats such as fish oil, seal oil, lard, beef tallow, and butter fat; and oils and fats synthesized by enzyme reaction or the like using fatty acids derived from these oils and fats as raw materials, as well as oils and fats such as interesterified oil, hydrogenated oil, partially decomposed oil, and fractionated oil. These oils may be used alone or in appropriate mixtures.

In the sweetener enhancer of the present invention, α-linolenic acid and oleic acid can be freely blended. For example, α-linolenic acid and oleic acid can be blended in a total amount of 0.001 to 100% by mass.

The mass ratio of the total amount of α-linolenic acid and oleic acid to the total lipid amount in the sweetness enhancer of the present invention [α-linolenic acid amount and oleic acid amount/total lipid amount] is preferably 0.0001 or more, more preferably 0.0003 or more, even more preferably 0.0005 or more, even more preferably 0.001 or more, even more preferably 0.002 or more, and even more preferably 0.003 or more, from the viewpoint of the sweetness enhancing effect.
Furthermore, from the standpoints of sweetness enhancing effect, flavor, and industrial production, the ratio [amount of α-linolenic acid and amount of oleic acid/total lipid amount] is preferably 0.995 or less, more preferably 0.8 or less, even more preferably 0.4 or less, even more preferably 0.2 or less, even more preferably 0.1 or less, even more preferably 0.03 or less, even more preferably 0.01 or less, and even more preferably 0.008 or less.

The sweetener enhancer of the present invention may be in any form, such as solid, semi-solid, or liquid.

The present invention can be used for anything that can be taken orally. Examples include food, medicine, contrast agents, etc., but it is preferable to use it for food. "Food" means any food or drink that can be taken orally.

Although there are no particular limitations on the type of food, it is preferable that foods whose sweetness has been enhanced by adding the sweetness enhancer of the present invention contain lipids in terms of the sweetness enhancing effect.

Examples of lipids contained in foods to which a sweetener enhancer has been added include monoacylglycerol, diacylglycerol, triacylglycerol, phospholipids, glycolipids, sterols, waxes, etc., but from the standpoint of flavor and sweetness enhancement, diacylglycerol or triacylglycerol is preferred. These lipids may be those originally contained in the food, or may be lipids contained in the sweetener enhancer of the present invention. Edible oils and fats may also be added together with the sweetener enhancer.

The total lipid content of a food to which the sweetness enhancer of the present invention has been added is, from the standpoint of flavor and sweetness enhancement, preferably 1% by mass or more, more preferably 3% by mass or more, even more preferably 5% by mass or more, even more preferably 10% by mass or more, even more preferably 20% by mass or more, even more preferably 30% by mass or more, and even more preferably 40% by mass or more.
In addition, from the standpoint of flavor and industrial production, the total lipid content of the food to which a sweetener enhancer has been added is preferably 99% by mass or less, more preferably 98% by mass or less, even more preferably 95% by mass or less, even more preferably 90% by mass or less, even more preferably 80% by mass or less, and even more preferably 70% by mass or less.

The mass ratio of the combined amount of α-linolenic acid and oleic acid to the total lipid amount of a food to which the sweetness enhancer of the present invention has been added [amount of α-linolenic acid and amount of oleic acid in food to which the sweetness enhancer has been added/total lipid amount of food to which the sweetness enhancer has been added] is, from the viewpoint of sweetness enhancement, preferably 0.00001 or more, more preferably 0.00002 or more, even more preferably 0.00005 or more, even more preferably 0.0001 or more, even more preferably 0.0002 or more, even more preferably 0.0005 or more.
In addition, from the standpoints of flavor, industrial production, and sweetness enhancement, [the amount of α-linolenic acid and the amount of oleic acid in the food to which a sweetness enhancer has been added/the total lipid amount in the food to which a sweetness enhancer has been added] is preferably 0.99 or less, more preferably 0.8 or less, even more preferably 0.5 or less, even more preferably 0.1 or less, even more preferably 0.03 or less, even more preferably 0.01 or less, even more preferably 0.008 or less, even more preferably 0.005 or less, even more preferably 0.003 or less, even more preferably 0.002 or less, even more preferably 0.0019 or less, and even more preferably 0.0018 or less.

Examples of foods that can use the sweetener of the present invention include fresh foods (vegetables, fruits, milk, etc.), processed foods, and food additives, but it is preferable to use the sweetener of the present invention in processed foods because it is easier to enjoy the effects of the present invention.

Processed foods include processed vegetables, processed fruits, processed grains, confectioneries, dairy products, processed egg products, and processed oils and fats, but it is preferable to use the compound in processed fruit products, confectioneries, dairy products, and processed oils and fats in terms of enhancing sweetness.

Examples of processed oils and fats include margarine, shortening, spreads, fillings, coffee creamer, whipped cream, powdered oils and fats, etc.

Processed fruit products include jams, fruit drinks, candied fruits, dried fruits, etc.

Examples of sweets include Japanese fresh confections such as yokan and manju, Western confections such as castella and cakes, snacks, and chocolate confections.

Dairy products include yogurt, cream, butter, cheese, ice cream, etc.

To enhance the sweetness of food, a combination of α-linolenic acid and oleic acid can be brought into contact with food during production, cooking, or oral ingestion of the food, and then ingested orally.

The amount of the sweetener enhancer of the present invention to be used may be any amount capable of enhancing the sweetness of the food, and may be appropriately determined depending on the form of use. For example, the sweetener enhancer may be used in a food in an amount such that the total amount of α-linolenic acid and oleic acid is preferably 0.0005 to 1% by mass, more preferably 0.001 to 0.8% by mass, even more preferably 0.002 to 0.5% by mass, even more preferably 0.003 to 0.4% by mass, even more preferably 0.004 to 0.3% by mass, and even more preferably 0.005 to 0.2% by mass of the total mass of the food.

[Method of analyzing fatty acid composition]
Fatty acid methyl esters were prepared according to "Preparation method of fatty acid methyl esters (2.4.1.-1996)" in "Standard Methods for the Analysis of Fats, Oils and Related Compounds" compiled by Japan Oil Chemists' Society, and the obtained samples were measured in accordance with American Oil Chemists. Society Official Method Ce 1f-96 (GLC method).
<GLC analysis conditions>
Apparatus: Agilent 7890 series (Agilent Technologies)
Column: CP-SIL88 50 m x 0.25 mm x 0.2 μm (Agilent J&W)
Carrier gas: 1.0 mL He/min
Injector: Split (1:50), T = 300 °C
Detector: FID, T = 300 ° C.
Oven temperature: 150°C for 5 min, increase at 1°C/min, increase at 160°C for 5 min, increase at 2°C/min, increase at 200°C for 10 min, increase at 10°C/min, increase at 220°C for 5 min

〔fatty acid〕
(i) Comparative Example 1
The reagent oleic acid (≧99% (GC), manufactured by Sigma-Aldrich) was used.

(ii) Comparative Example 2
Linolenic acid (≧99% (GC), manufactured by Sigma-Aldrich) was used as a reagent.

(iii) Example 1
The reagents, oleic acid and linoleic acid, were mixed in a mass ratio of 1:1 and used ([amount of α-linolenic acid and amount of oleic acid/total lipid amount]=0.994).

(iv) Example 2
The reagents, oleic acid and linoleic acid, were mixed in a mass ratio of 3:1 and used ([amount of α-linolenic acid and amount of oleic acid/total lipid amount]=0.994).

(v) Example 3
The reagents, oleic acid and linoleic acid, were mixed in a mass ratio of 1:3 ([amount of α-linolenic acid and amount of oleic acid/total lipid amount]=0.995).

(vi) Example 4
Semi-refined linseed oil (manufactured by ADM) was enzymatically hydrolyzed to obtain fatty acids, which were then winterized to reduce the saturated fatty acid content. The fatty acid was then filtered to obtain linseed oil fatty acids with a fatty acid purity of 92% by mass ([α-linolenic acid and oleic acid amount/total lipid amount]=0.746).

The analytical values of the fatty acid composition for Comparative Examples 1-2 and Examples 1-4 are shown in Table 1.

(vii) Example 5
Example 4 and refined rapeseed oil (manufactured by Nisshin Oillio; free fatty acids 0.03% by mass, of which oleic acid 55.5% by mass and linoleic acid 8.3% by mass) were mixed in a mass ratio of 1:99 ([amount of α-linolenic acid and amount of oleic acid/total lipid amount] = 0.0077).

(viii) Example 6
Example 4 and refined linseed oil (Summit Oil Mill; free fatty acids 0.03% by mass, including oleic acid 17.2% by mass and linoleic acid 52.9% by mass) were mixed in a mass ratio of 1:99 ([α-linolenic acid amount and oleic acid amount/total lipid amount] = 0.0077).

[Test Example 1: Whipped Cream]
Control: 1.8 g of white sugar and 30 g of whipped cream (Sujata Whip, Sujata Meiraku) were added to a glass vial (SV-50, Nichiden Rika Glass Co., Ltd., the same below), and the mixture was stirred for 1 minute at 8,000 rpm with a homogenizer (IKA T25-digital ULTRA TURRAX) to serve as the control.
Evaluation sample: 1.8 g of white sugar, 30 g of whipped cream (Sujata Whip), and 0.06 g of the fatty acid of Comparative Example 1, Comparative Example 2, or Example 1 were added to a glass vial (SV-50), and the mixture was stirred for 1 minute at 8,000 rpm with a homogenizer to prepare an evaluation sample. The total lipid content of this evaluation sample was 36.0 g per 100 g.
The evaluation was carried out by a four-member expert panel (A, B, C, D) which evaluated the sweetness of each sample and ranked them in order of sweetness from 1st to 4th.
The results are shown in Table 2.

As can be seen from Table 2, all panelists answered that Example 1 was the sweetest.

[Test Example 2: Whipped cream]
Control: 1.8 g of white sugar and 30 g of whipped cream (Sujata Whip, Sujata Meiraku) were added to a glass vial (SV-50), and the mixture was stirred at 10,000 rpm for 1 minute using a homogenizer (IKA T25-digital ULTRA TURRAX) to prepare the control.
Evaluation sample: 1.8 g of white sugar, 30 g of whipped cream (Sujata Whip), and 0.04 g of the fatty acid of Comparative Example 1, Example 2, or Example 3 were added to a glass vial (SV-50), and the mixture was stirred for 1 minute at 10,000 rpm with a homogenizer to prepare an evaluation sample. The total lipid content of this evaluation sample was 36.0 g per 100 g.
The evaluation was carried out by a panel of four experts (A, B, C, D) who evaluated the sweetness of each sample and ranked them in order of sweetness from 1st to 4th.
The results are shown in Table 3.

As shown in Table 3, all panelists answered that Examples 2 and 3 were sweeter than the control and Comparative Example 1, clearly indicating that the sweetness was enhanced. In addition, three out of four panelists answered that Example 3 was sweeter than Example 2.

[Test Example 3: Whipped cream]
Control: 1.8 g of white sugar and 30 g of whipped cream (Sujata Whip, Sujata Meiraku) were added to a glass vial (SV-50), and the mixture was stirred at 10,000 rpm for 1 minute using a homogenizer (IKA T25-digital ULTRA TURRAX) to prepare the control.
Evaluation sample: 1.8 g of white sugar, 30 g of whipped cream (Sujata Whip), and 0.03 g of the fatty acid of Example 4 were added to a glass vial (SV-50), and the mixture was stirred for 1 minute at 10,000 rpm with a homogenizer to prepare an evaluation sample. The total lipid content of this evaluation sample was 36.0 g per 100 g.
1.8 g of white sugar, 27 g of whipped cream (Sujata Whip), and 3 g of Example 5 were added to a glass vial (SV-50), and stirred for 1 minute at 10,000 rpm with a homogenizer to prepare an evaluation sample (mixed with rapeseed oil). The total lipid content of this evaluation sample was 41.8 g per 100 g.
The evaluation was carried out by a four-member expert panel (A, B, C, D) which evaluated the sweetness of each sample and ranked them in order of sweetness from 1st to 3rd.
The results are shown in Table 4.

As shown in Table 4, all panelists answered that Example 4 was sweeter than the control, clearly indicating that it enhanced the sweetness. In addition, three out of four panelists answered that the evaluation sample to which Example 5 was added was sweeter than the evaluation sample to which Example 4 was added.

[Test Example 4: Jam]
Control: 30 g of orange marmalade (Aohata Co., Ltd.) was added to a glass vial (SV-50) and stirred with a homogenizer (IKA T25-digital ULTRA TURRAX) at 10,000 rpm for 1 minute to prepare a control.
Evaluation sample: 30 g of orange marmalade (Aohata Co., Ltd.) and 0.005 g of the fatty acid of Example 4 were added to a glass vial (SV-50), and the mixture was stirred for 1 minute at 10,000 rpm with a homogenizer to prepare an evaluation sample. The total lipid content of this evaluation sample was 0.1 g or less per 100 g.
The evaluation was carried out by a panel of four experts (A, B, C, D) who evaluated the sweetness of each sample and ranked them in order of sweetness from 1st to 2nd.
The results are shown in Table 5.

As shown in Table 5, all panelists responded that Example 4 was sweeter than the control, clearly demonstrating that it enhanced sweetness.

[Test Example 5 Jam]
Control: 30 g of orange marmalade (Aohata Co., Ltd.) was added to a glass vial (SV-50) and stirred with a homogenizer (IKA T25-digital ULTRA TURRAX) at 10,000 rpm for 1 minute to prepare a control.
Evaluation sample: 30 g of orange marmalade (Aohata Co., Ltd.) and 0.02 g of the fatty acid of Example 4 were added to a glass vial (SV-50), and the mixture was stirred for 1 minute at 10,000 rpm with a homogenizer to prepare an evaluation sample. The total lipid content of this evaluation sample was 0.1 g or less per 100 g.
28 g of orange marmalade (Aohata Co., Ltd.) and 2 g of Example 6 were added to a glass vial (SV-50) and stirred at 10,000 rpm for 1 minute with a homogenizer to prepare an evaluation sample. The total lipid content of this evaluation sample was 6.7 g per 100 g.
The evaluation was carried out by a panel of four experts (A, B, C, D) who evaluated the sweetness of each sample and ranked them in order of sweetness from 1st to 3rd.
The results are shown in Table 6.

As seen from Table 6, all panelists answered that Example 4 was sweeter than the control, clearly demonstrating that it enhanced sweetness.
In addition, three out of four panelists answered that the evaluation sample containing Example 6 was sweeter than the evaluation sample containing Example 4.

[Test Example 6 Chocolate]
Control: 22 g of cacao mass (Daito Cacao Co., Ltd.) and 8 g of fructose glucose liquid sugar (Hi-fructose F-550, Sanwa Starch Industry Co., Ltd.) were added to a glass vial (SV-50) and dissolved at 80° C. Then, the mixture was stirred at 8,000 r/min for 3 minutes with a homogenizer (IKA T25-digital ULTRA TURRAX) and cooled in a refrigerator for 3 hours to prepare a control.
Evaluation sample: 22 g of cacao mass and 8 g of fructose glucose liquid sugar (high fructose F-550) were added to a glass vial (SV-50) and dissolved at 80 ° C. Then, 0.03 g of the fatty acid of Example 4 was added, stirred for 3 minutes at 8,000 r / min with a homogenizer, and cooled in a refrigerator for 3 hours to prepare an evaluation sample. The total lipid content of this evaluation sample was 40.1 g per 100 g.
The evaluation was carried out by a panel of four experts (A, B, C, D) who evaluated the sweetness of each sample and ranked them in order of sweetness from 1st to 2nd.
The results are shown in Table 7.

As shown in Table 7, all panelists responded that Example 4 was sweeter than the control, clearly demonstrating that it enhanced sweetness.

[Test Example 7: Yogurt]
Control: 26 g of commercially available drinking yogurt (Karada Tough Drinking Yogurt, Morinaga Milk Industry Co., Ltd.), 2 g of white sugar, and 2 g of rapeseed oil were added to a glass vial (SV-50), and the mixture was stirred at 8,000 r/min for 1 minute with a homogenizer (IKA T25-digital ULTRA TURRAX) to prepare a control.
Evaluation sample: 26 g of yogurt drink, 2 g of white sugar, and 2 g of Example 5 were added to a glass vial (SV-50), and the mixture was stirred for 1 minute at 8,000 rpm with a homogenizer to prepare an evaluation sample. The total lipid content of this evaluation sample was 7.5 g per 100 g.
A panel of four experts (A, B, C, D) evaluated the sweetness of each sample and ranked them in order of sweetness from 1st to 2nd.
The results are shown in Table 8.

As shown in Table 8, all panelists answered that the evaluation sample containing Example 5 was sweeter than the control, clearly demonstrating that the sweetness was enhanced.

Claims (6)

A sweetness enhancer containing α-linolenic acid and oleic acid as active ingredients, in which the α-linolenic acid and oleic acid are free fatty acids, their salts, or their lower alkyl esters, and the mass ratio of α-linolenic acid to oleic acid [α-linolenic acid/oleic acid] is 0.2 to 30 in terms of free fatty acid. The sweetener according to claim 1, which contains a lipid other than α-linolenic acid and oleic acid. The sweetener according to claim 1 or 2, wherein the mass ratio of the total amount of α-linolenic acid and oleic acid converted to free fatty acid to the total amount of lipids [amount of α-linolenic acid and amount of oleic acid/total amount of lipids] is 0.0001 to 0.995. The sweetener enhancer according to any one of claims 1 to 3, wherein α-linolenic acid and oleic acid are added to a food in an amount of 0.0005 to 1% by mass in total, calculated as free fatty acids, based on the total mass of the food. A food to which the sweetness enhancer according to any one of claims 1 to 4 has been added (however, excluding milk powder, milk chocolate containing said milk powder, and milk chocolate containing a product of treating soybean lecithin with phospholipase A2). The food according to claim 5, wherein the total lipid content is 1% by mass or more.