Gelling agent, emulsifier, and novel compound

Abstract

To provide a compound capable of forming an organogel.SOLUTION: A gelling agent or an emulsifier according to the present invention contains a compound of formula (1) (R1-R3 are each independently hydrogen or an acyl group derived from a C10-22 linear saturated fatty acid; and R4 is an acyl group derived from a C10-22 linear saturated fatty acid).SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to gelling agents, particularly to gelling agents for liquids other than water. The present invention also relates to emulsifiers and novel compounds. [Background technology]

[0002] Gelling agents are used to thicken or solidify liquids. Known gels that can be formed by such gelling agents include aqueous hydrogels and organogels that use liquids other than water (so-called organic solvents) as dispersion media. Many gelling agents are known for preparing aqueous gels, but despite the existence of a variety of liquids other than water (organic solvent systems), the number of gelling agents for preparing organic solvent gels is limited. For example, Patent Documents 1 and 2 and Non-Patent Document 1 disclose that compounds in which a specific fatty acid is ester-bonded to a six-membered ring monosaccharide skeleton can gel various organic solvents. Furthermore, Non-Patent Document 2 discloses that 4-(N-tetradecanoyl)aminohydroxybutanoic acid has the ability to gel organic solvents.

[0003] Incidentally, Patent Document 3 and Non-Patent Documents 3 to 5 describe compounds prepared by esterifying the hydroxyl group at the 6-position of glucono-δ-lactone (D-glucono-1,5-lactone). However, there is no description as to whether the ester compounds have gelling ability. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] Japanese Patent Application Publication No. 2019-89719 [Patent Document 2] Japanese Patent Publication No. 2022-111433 [Patent Document 3] U.S. Patent No. 5,505,938 [Non-patent literature]

[0005] [Non-Patent Document 1] ChemPlusChem 2020, 85, 701-710. [Non-patent document 2] J. Physical Chem., B 2014, 118, 12112-12120. [Non-patent document 3] Carbohydrate Research (1995), 274, 111-121. [Non-patent document 4] Journal of Carbohydrate Chemistry (1995), 14(2), 265-270. [Non-patent document 5] Comptes Rendus Chimie (2004), 7(6-7), 607-610. Summary of the Invention [Problem to be solved by the invention]

[0006] The variety of gelling agents capable of forming organogel is limited, and compounds having such properties are still in demand. An object of the present invention is to provide a gelling agent capable of forming organogel. [Means for solving the problem]

[0007] The present inventors have conducted extensive research to solve the above problems and have found that a compound represented by the following formula (1) has the ability to gel a liquid other than water or to emulsify a hydrophilic solvent and a hydrophobic solvent, thereby completing the present invention. That is, the present invention provides the following gelling agent, gel composition, emulsifier, emulsion composition, and compound. [1] Formula (1): [ka] (1) (R 1 ~R 3are each independently a hydrogen atom or an acyl group derived from a linear saturated fatty acid having 10 to 22 carbon atoms, R 4 is an acyl group derived from a linear saturated fatty acid having 10 to 22 carbon atoms. A gelling agent comprising a compound of formula (I). [2] The compound is represented by the formula (2): [ka] (2) (R 1 ~R 4 The definition of is as described in [1] above. The gelling agent according to [1] above, represented by the formula: [3] R 1 ~R 4 The gelling agent according to [1] above, wherein one or more of the following is hydrogen. [4] R 3 is an acyl group derived from a linear saturated fatty acid having 10 to 22 carbon atoms. [5] R 1 ~R 4 are each independently an acyl group derived from a linear saturated fatty acid having 10 to 22 carbon atoms. [6] A gel composition comprising the gelling agent according to any one of [1] to [5] above and at least one liquid other than water. [7] Formula (1): [ka] (1) (R 1 ~R 3 are each independently a hydrogen atom or an acyl group derived from a linear saturated fatty acid having 10 to 22 carbon atoms, R 4 is an acyl group derived from a linear saturated fatty acid having 10 to 22 carbon atoms. An emulsifier comprising a compound of formula (I). [8] An emulsion composition comprising the emulsifier according to [7] above, a hydrophilic solvent, and a hydrophobic solvent. [9] Formula (1'): [ka] (1') (R 1 ~R 3 are each independently hydrogen or an acyl group derived from a linear saturated fatty acid having 10 to 22 carbon atoms, and R 1 ~R 3 at least one of is hydrogen, R 4 is an acyl group derived from a linear saturated fatty acid having 10 to 22 carbon atoms. Compound.

[10] Formula (2'): [ka] (2') (R 1 ~R 4 The definition of is as described in [9] above. The compound according to [9] above, represented by the formula:

[11] A method for producing the compound according to [9] or

[10] above, comprising the steps of: Formula (3): [ka] (3) The compound of formula (1'): is reacted with a source of an acyl group derived from a linear saturated fatty acid having 10 to 22 carbon atoms to obtain a compound of formula (1'): [ka] (1') (R 1 ~R 4 The definition of is as described in [9] above. A method of producing a compound of formula (I).

[12] The production method according to

[11] above, wherein the acyl group source comprises at least one selected from the group consisting of acid halides, acid anhydrides, and esters of linear saturated fatty acids having 10 to 22 carbon atoms. [Effects of the Invention]

[0008] According to the present invention, a novel gelling agent or a novel emulsifying agent is provided, thereby increasing the options for gelling agents or emulsifying agents that can form organogel or emulsion compositions. DETAILED DESCRIPTION OF THE INVENTION

[0009] The present invention will now be described in further detail. The present invention relates to a compound of formula (1): [ka] (1) The compound contained in the gelling agent of the present invention is a derivative of glucono-1,4-lactone or a stereoisomer thereof.

[0010] In formula (1), R 1 ~R 3 are each independently an acyl group derived from a linear saturated fatty acid having 10 to 22 or 12 to 18 carbon atoms. 1 ~R 3 may be hydrogen, or 3 Only R is hydrogen. 1 and R 2 may be the acyl group. 3 may be the acyl group. 3 When is the acyl group, it is believed that the stability of the five-membered ring structure of glucono-1,4-lactone is increased.

[0011] In formula (1), R 4 is an acyl group derived from a linear saturated fatty acid having 10 to 22 or 12 to 18 carbon atoms. 4 forms an ester with the hydroxyl group at position 6, which is the most reactive group in the glucono-1,4-lactone structure. 1 ~R 4 are each independently an acyl group derived from a linear saturated fatty acid having 10 to 22 or 12 to 18 carbon atoms, and in a particular embodiment, R 1 ~R 4 are all the same acyl group.

[0012] In one embodiment, the compound has the formula (2): [ka] (2) In formula (2), R 1 ~R 4 is as defined above for formula (1). More specifically, the compound may be, for example, 2,3,5,6-tetra-O-decanoyl-D-glucono-1,4-lactone (C10GL), 2,3,5,6-tetra-O-dodecanoyl-D-glucono-1,4-lactone (C12GL), 2,3,5,6-tetra-O-tetradecanoyl-D-glucono-1,4-lactone (C14GL), 2,3,5,6-tetra-O-palmitoyl-D-glucono-1,4-lactone (C16GL), 2,3,5,6-tetra-O-stearoyl-D-glucono-1,4-lactone (C18GL), 2,3,5,6-tetra-O-docosanoyl-D-glucono-1,4-lactone (C22GL), 2,3,6-tri-O-decanoyl-D-glucono-1,4-lactone (5-OH-C10GL), 2,3,6-tri-O-dodecanoyl-D-glucono-1,4-lactone (5-OH-C12GL), 2,3,6-tri-O-tetradecanoyl-D-glucono-1,4-lactone (5-OH-C14GL), 2,3,6-tri-O-palmitoyl-D-glucono-1,4-lactone (5-OH-C16GL), 2,3,6-tri-O-stearoyl-D-glucono-1,4-lactone (5-OH-C18GL), 2,3,6-tri-O-docosanoyl-D-glucono-1,4-lactone (5-OH-C22GL), 2,3,5-tri-O-decanoyl-6-O-dodecanoyl-D-glucono-1,4-lactone (6LauC10GL), and 6-O-Palmitoyl-2,3,5-tri-O-stearoyl-D-glucono-1,4-lactone (6PalC18GL) It may be at least one selected from the group consisting of:

[0013] The compound of formula (1) contained in the gelling agent of the present invention can be appropriately prepared by means commonly used in the art, for example, a compound of formula (3): [ka] (3) with a source of acyl groups derived from linear saturated fatty acids having 10 to 22 or 12 to 18 carbon atoms to obtain a compound of formula (1): [ka] (1) (R 1 ~R 4 The definition of is as above) By controlling the reaction time of this reaction, it is possible to produce a compound in which only a part of the hydroxyl groups of the compound of formula (3) is esterified, that is, a compound of formula (1) in which R 1 ~R 3 It is possible to prepare compounds in which at least one of the groups is hydrogen.

[0014] The acyl group source can be any source commonly used in the art without any particular limitation, and may include, for example, at least one selected from the group consisting of acid halides, acid anhydrides, and esters of linear saturated fatty acids having 10 to 22 or 12 to 18 carbon atoms. Since the hydroxyl groups of the compound of formula (3) have different reactivities depending on the position, when acyl group sources having different carbon numbers are reacted simultaneously or successively, ester bonds having different acyl groups depending on the position can be formed.

[0015] The gelling agent of the present invention can gel liquids other than water. The liquid to be gelled is not particularly limited as long as it is a liquid other than water, and may be an organic solvent (oil) that phase separates with water or an organic solvent that does not phase separate with water. For example, hydrocarbon organic solvents such as liquid paraffin, squalane, hydrogenated polyisobutene, and petrolatum; ester oils such as pentaerythrityl tetraisostearate, isopropyl myristate, ethylhexyl palmitate, tri(caprylic / capric)glyceryl, glyceryl trioctanoate, diisostearyl malate, and polyglyceryl-2 triisostearate; higher fatty acids such as capric acid and lauric acid; fats and oils such as olive oil, canola oil, soybean oil, and castor oil; waxes such as candelilla wax and jojoba oil; alcohols such as octyldodecanol and ethanol; or silicone oils such as diphenylsiloxyphenyl trimethicone, cyclopentasiloxane, and dimethicone.

[0016] The amount of the compound of formula (1) used is not particularly limited, but may be, for example, about 0.5 to about 20% by mass or about 1 to about 5% by mass relative to the total mass of the liquid to be gelled.

[0017] The gelling agent of the present invention can gel various liquids other than water, and therefore can be used in various fields. For example, in the food field, the gelling agent of the present invention can be used to prepare swallowable foods, solidify liquid oils, prevent separation of liquid oils from foods (peanut butter, etc.), and improve the shape retention of foods (chocolate, whipped cream, etc.), in the cosmetics field, it can be used in pencil-shaped cosmetics such as lipstick, lip gloss, concealer, antiperspirant stick, ointment, lip liner, and eyeliner, in the pharmaceutical field, it can be used in ointments and transdermal absorbents, and in the environmental conservation field, it can be used for gelling waste oil to prevent water pollution, etc.

[0018] In another aspect, the present invention provides a gel composition comprising the gelling agent described above as one aspect of the present invention and at least one liquid other than water, wherein the gel composition of the present invention is formed by the gelling agent and has good hardness and transparency.

[0019] The gelling agent or gel composition of the present invention may further contain any excipient and / or additive commonly used in the art, and may further contain other components having gelling ability, as long as the object of the present invention is not impaired.

[0020] In another aspect, the present invention relates to an emulsifier containing the compound of formula (1). The compound of formula (1) has emulsifying ability and can emulsify a hydrophilic solvent and a hydrophobic solvent. The hydrophilic solvent is not particularly limited, and may include, for example, water, glycerin, ethylene glycol, or butylene glycol. The hydrophobic solvent is not particularly limited, and may include, for example, hydrocarbon organic solvents such as liquid paraffin, squalane, hydrogenated polyisobutene, and petrolatum; ester oils such as pentaerythrityl tetraisostearate, isopropyl myristate, ethylhexyl palmitate, tri(caprylic / capric)glyceryl, glyceryl trioctanoate, diisostearyl malate, and polyglyceryl-2 triisostearate; higher fatty acids such as capric acid and lauric acid; oils and fats such as olive oil, canola oil, soybean oil, and castor oil; waxes such as candelilla wax and jojoba oil; alcohols such as octyldodecanol and ethanol; or silicone oils such as diphenylsiloxyphenyl trimethicone, cyclopentasiloxane, and dimethicone.

[0021] The amount of the compound of formula (1) used is not particularly limited, but may be, for example, about 0.1 to about 20% by mass or about 0.5 to about 5% by mass relative to the total amount of the hydrophilic solvent and hydrophobic solvent to be emulsified.

[0022] In another aspect, the present invention relates to an emulsion composition comprising the emulsifier described above as one aspect of the present invention, the hydrophilic solvent, and the hydrophobic solvent. The emulsion composition of the present invention is formed using the emulsifier. Emulsification refers to a state in which substances that are normally immiscible, such as water and oil, are uniformly mixed. Examples include the O / W (oil-in-water) type, in which oil droplets are dispersed in water, and the W / O (water-in-oil) type, in which water droplets are dispersed in oil. Generally, emulsification results in a cloudy, creamy mixture. This occurs because the mixture of liquids with different refractive indices causes diffuse reflection of light, making the mixture appear white. Simply mixing oil and water without an emulsifier may initially emulsify and become cloudy, but over time, the cloudiness disappears, and the oil and water separate into two layers, resulting in the loss of emulsion. This occurs because the dispersed phase particles move due to Brownian motion. When they come into contact, their interfaces adsorb to each other, forming a single new particle (called coalescence). This process is repeated, causing the particles to grow larger and making it impossible to maintain the emulsion state. In other words, it is important for emulsification that a cloudy cream state exists stably (cream stability) and that there is no separation of oil and water (cream water holding capacity). The compound of formula (1) dissolves in oil, eliminating the fluidity of the oil and causing it to gel. In the O / W type, the oil droplets in the dispersed phase gel, so even if the oil droplets come into contact with each other, they do not coalesce and remain stable. In the W / O type, the oil in the continuous phase gels, suppressing the Brownian motion of the water droplets and resulting in a stable state without coalescence.

[0023] Specific embodiments of the compound of formula (1) contained in the emulsifier or emulsion composition of the present invention are as described above in relation to the gelling agent of the present invention. In addition, the emulsifier or emulsion composition of the present invention may further contain any excipient and / or additive commonly used in the art, and may further contain other components having emulsifying ability, as long as the object of the present invention is not impaired.

[0024] In yet another aspect, the present invention also relates to the compound of formula (1) as described above and to a method for preparing the same. In one aspect, the compound of the present invention has the formula (1'): [ka] (1') (R 1 ~R 3 are each independently hydrogen or an acyl group derived from a linear saturated fatty acid having 10 to 22 or 12 to 18 carbon atoms, and R 1 ~R 3 at least one of is hydrogen, R 4 is an acyl group derived from a linear saturated fatty acid having 10 to 22 or 12 to 18 carbon atoms. is a compound of

[0025] Also, in one embodiment, the compound of the present invention has the formula (2'): [ka] (2') (R 1 ~R 4 is defined as above with respect to formula (1'). It is a compound represented by the formula:

[0026] The present invention will be specifically explained below with reference to examples, but the scope of the present invention is not limited to these examples. [Example]

[0027] [Synthesis Example 1] An acyl group was introduced into D-glucono-1,5-lactone according to the following scheme (see items (1) to (6) below for details), to synthesize the compound of formula (1). [ka]

[0028] (1) Synthesis of 2,3,5,6-tetra-O-decanoyl-D-glucono-1,4-lactone (C10GL; Compound 1) D-glucono-1,5-lactone (250 mg) was mixed with 4 equivalents of 4-dimethylaminopyridine (DMAP) (686 mg) and dissolved in 8 equivalents of pyridine (908 μL). 7.5 mL of toluene was added, and the mixture was stirred with a stirrer while adding 6 equivalents of decanoyl chloride (C 10H 19 OCl (1.75 mL) was added and the mixture was stirred at room temperature under a nitrogen atmosphere for 1 day. After confirming the completion of the reaction by TLC (AcOEt:toluene = 1:20), 1 mL of water was added and the mixture was stirred at room temperature for 30 minutes. After extraction with chloroform, the concentrated liquid was purified by silica gel column chromatography (toluene) to obtain 265 mg of compound 1 (C10GL) (yield 24%). The chemical structure and properties of compound 1 were confirmed by nuclear magnetic resonance (NMR), mass spectrometry (MS), and optical rotation measurement. HMBC-NMR indicated that compound 1 was the desired five-membered ring compound cyclized by 1-4. TIFF2025131148000015.tif86170

[0029] (2) Synthesis of 2,3,5,6-tetra-O-dodecanoyl-D-glucono-1,4-lactone (C12GL; Compound 2) Four equivalents of DMAP (686 mg) were added to D-glucono-1,5-lactone (250 mg) and dissolved in 8 equivalents of pyridine (908 μL). 7.5 mL of toluene was added, and then 6 equivalents of lauroyl chloride (C 12 H 23 OCl (1.95 mL) was added and stirred at room temperature under a nitrogen atmosphere for 1 day. After confirming the completion of the reaction by TLC (AcOEt:toluene = 1:20), 1 mL of water was added and stirred at room temperature for 30 minutes. After acidifying the reaction with 6 mL of 2N-HCl, the reaction mixture was crystallized by adding 30 mL of methanol and 10 mL of ethanol. The resulting crystals were filtered through filter paper and washed with methanol to obtain 803 mg of compound 2 (C12GL) (yield 63%). HMBC-NMR revealed that compound 2 was the desired five-membered ring compound cyclized by 1-4. TIFF2025131148000016.tif86170

[0030] (3) Synthesis of 2,3,5,6-tetra-O-tetradecanoyl-D-glucono-1,4-lactone (C14GL; Compound 3) Four equivalents of DMAP (686 mg) were added to D-glucono-1,5-lactone (250 mg) and dissolved in 8 equivalents of pyridine (908 μL). 7.5 mL of toluene was added, and then 6 equivalents of myristoyl chloride (C 14 H 27 OCl (2.29 mL) was added and stirred at room temperature under a nitrogen atmosphere for 1 day. After confirming the completion of the reaction by TLC (AcOEt:toluene = 1:20), 1 mL of water was added and stirred at room temperature for 30 minutes. After acidifying the reaction with 6 mL of 2N-HCl, the reaction mixture was crystallized by adding 30 mL of acetone and 10 mL of ethanol. The resulting crystals were filtered through filter paper and washed with acetone to obtain 1.098 g of compound 3 (C14GL) (77% yield). HMBC-NMR indicated that compound 3 was the desired five-membered ring compound cyclized by 1-4. TIFF2025131148000017.tif85170

[0031] (4) Synthesis of 2,3,5,6-tetra-O-palmitoyl-D-glucono-1,4-lactone (C16GL; Compound 4) Four equivalents of DMAP (1.4 g) were added to D-glucono-1,5-lactone (500 mg) and dissolved in 8 equivalents of pyridine (1.82 mL). After adding 15 mL of toluene, the mixture was stirred with a stirrer and then dissolved in 6 equivalents of palmitoyl chloride (C 16 H 31 The mixture was added with 5.10 mL of AcOEt and stirred at room temperature under a nitrogen atmosphere for 1 day. After confirming the completion of the reaction by TLC (AcOEt:toluene = 1:20), acetone (30 mL) was added for crystallization. The resulting crystals were filtered through filter paper and washed with acetone. NMR analysis revealed that DMAP remained in the crystals. Therefore, the crystals were dissolved in toluene (20 mL), and 10 mL of 2N HCl was added. The mixture was stirred at room temperature for 30 minutes. 30 mL of acetone was added and crystallization was resumed. The resulting crystals were filtered through filter paper and washed with acetone to obtain 1.923 g of compound 4 (C16GL) (61% yield). HMBC-NMR analysis indicated that compound 4 was a five-membered ring cyclized by 1-4. TIFF2025131148000018.tif89170

[0032] (5) Synthesis of 2,3,5,6-tetra-O-stearoyl-D-glucono-1,4-lactone (C18GL; Compound 5) Four equivalents of DMAP (686 mg) were added to D-glucono-1,5-lactone (250 mg) and dissolved in 8 equivalents of pyridine (908 μL). 7.5 mL of toluene was added, and then 6 equivalents of stearoyl chloride (C 18 H 35 HCl (2.84 mL) was added and stirred at room temperature under a nitrogen atmosphere for 1 day. After confirming the completion of the reaction by TLC (AcOEt:toluene = 1:20), 1 mL of water was added and stirred at room temperature for 30 minutes. After acidifying the reaction with 6 mL of 2N-HCl, the reaction mixture was crystallized by adding 20 mL of acetone / DMF (4:1). The resulting crystals were filtered through filter paper and washed with acetone / DMF (4:1), yielding 1.605 g of compound 5 (C18GL) (92% yield). HMBC-NMR indicated that compound 5 was a five-membered ring cyclized by 1-4. TIFF2025131148000019.tif84170

[0033] (6) Synthesis of 2,3,5,6-tetra-O-docosanoyl-D-glucono-1,4-lactone (C22GL; Compound 6) First, 6 equivalents of behenic acid (C 22 H 44 O2 (2.87 g) and 6 equivalents of DMF (652 μL) were dissolved in 20 mL of 1,2-dichloroethane, to which 30 equivalents of thionyl chloride (3.0 mL) was added and stirred at room temperature for 3 hours. The resulting solution was concentrated under reduced pressure and then dried in vacuo to obtain behenoyl chloride, which was then dissolved in 10 mL of toluene.

[0034] Next, 4 equivalents of DMAP (686 mg) were added to D-glucono-1,5-lactone (250 mg) and dissolved in 8 equivalents of pyridine (908 μL). After adding 7.5 mL of toluene, the mixture was stirred with a stirrer and the previously prepared behenoyl chloride (C 22 H 43The entire amount of AcOEt (OCl) was added, and the mixture was stirred at room temperature for 1 day under a nitrogen atmosphere. The reaction was monitored by TLC (AcOEt:toluene = 1:20) while stirring for an additional 4 hours at 80 °C. After confirming that the reaction was no longer proceeding, 1 mL of water was added and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was acidified with 6 mL of 2N HCl, and then crystallized with 20 mL of acetone. The resulting crystals were filtered through filter paper and washed with acetone / DMF (4:1). The crystals were purified by silica gel chromatography (toluene) to obtain 403 mg of compound 6 (C22GL) (yield 20%). HMBC-NMR analysis confirmed that compound 6 was the desired five-membered ring compound cyclized by 1-4. TIFF2025131148000020.tif85170

[0035] [Synthesis Example 2] Acyl groups were introduced into D-glucono-1,5-lactone according to the following scheme to synthesize 2,3,6-tri-O-palmitoyl-D-glucono-1,4-lactone (5-OH-C16GL; Compound 7). [ka]

[0036] Four equivalents of DMAP (0.7 g) were added to D-glucono-1,5-lactone (250 mg) and dissolved in 8 equivalents of pyridine (0.91 mL). After adding 7.5 mL of toluene, the mixture was stirred with a stirrer and then dissolved in 6 equivalents of palmitoyl chloride (C 16 H 31 OCl (2.55 mL) was added and stirred at room temperature under a nitrogen atmosphere for 16 minutes. Water (1 mL) was added to quench the reaction, followed by washing with 2N hydrochloric acid and extraction with toluene. After concentration under reduced pressure, acetone was added to the resulting solid for crystallization. The resulting crystals were filtered through filter paper, washed with acetone, and purified by open column chromatography (toluene). Toluene was added to the resulting white solid for recrystallization. The crystals thus obtained were filtered through filter paper and washed with toluene to obtain 232 mg of compound 7 (5-OH-C16GL) (yield 19%). 1 H- 1H COSY NMR showed that the hydroxyl group at the position corresponding to the 5-position of D-glucono-1,5-lactone was free, and HMBC-NMR showed that compound 7 was a five-membered ring cyclized by 1-4. TIFF2025131148000022.tif87170

[0037] [Test Example 1] Each test compound (C14GL, C16GL, C18GL, C22GL, or 5-OH-C16GL) was accurately weighed into a 2 mL screw-cap glass vial, and liquid paraffin #350 (LP#350) was added to a concentration of 5% by mass of the test compound. The vial was placed on a hot plate at 100-150°C to dissolve the compound, and then left at room temperature for 12 hours to observe the formation of a gel. If the solution lost its fluidity and the contents did not flow out even when the vial was inverted, it was determined that a gel had formed, and the hardness and transparency of the formed gel were measured.

[0038] Gel hardness was measured using a RHEONER II (RE233005C, Yamaden Corporation). Specifically, a 5 mm diameter spherical plunger was inserted into a gel formed in a 2 mL screw-capped glass bottle at a rate of 60 mm / min, and the maximum stress at 2.5 mm of insertion was recorded as gel hardness. Gel transparency was also measured using a spectrophotometer (DU650, Beckman Coulter Inc., Brea, CA, USA), with absorbance at 660 nm being determined as lower values ​​indicating greater transparency. Each gel was compared with C16AG (1,5-anhydro-2,3,4,6-tetra-O-palmitoyl-D-glutitol), an existing oil gelator.

[0039] The results are shown in Table 1. All of the test compounds were able to produce gels with higher transparency than C16AG. Furthermore, all of the gels produced using the test compounds had relatively high hardness. In particular, the gel produced using C18GL was significantly more transparent than the gel produced using C16AG, and had a hardness comparable to that of the gel produced using C16AG.

[0040] [Table 1]

[0041] [Test Example 2] Various organic solvents were placed in 2 mL screw-capped glass bottles, and C18GL was added to give a concentration of 5% by mass, followed by dissolution on a hot plate at 100 to 150°C. Gel formation and hardness of the formed gel were evaluated in the same manner as in Test Example 1. The results are shown in Table 2. C18GL was able to gel organic solvents with various physical properties.

[0042] [Table 2]

[0043] [Test Example 3] The emulsifying ability of each test compound (C14GL, C16GL, C18GL, C22GL, or 5-OH-C16GL) was compared with that of the known emulsifier Span 60 (sorbitan monostearate), and the existing oil gelling agents C16AG (1,5-anhydro-2,3,4,6-tetra-O-palmitoyl-D-glutitol) and Leopearl KL2 (dextrin palmitate). Specifically, each test sample was accurately weighed into a 2 mL screw-cap glass bottle, and liquid paraffin #350 was added to the bottle to achieve a 1% test sample concentration (total volume: approximately 500 mg). An additional 200 μL of water was added to the glass bottles, which were then placed on a hot plate at 100-150°C to dissolve the test samples. While still hot, the bottles were subjected to ultrasonic waves for 30 seconds using a hand sonicator (SMT Ultra Sonic Homogenizer UH-50), which resulted in a uniform emulsification of all the mixtures. The glass bottles were left to stand at room temperature for 5 days, and the stability and water-holding capacity of the creamy emulsions were evaluated according to the following criteria. The results are shown in Table 3. <Cream stability> ○: The creamy state is maintained as it was immediately after emulsification △: Creamy state is partially maintained ×: Creamy state is not maintained <Cream water holding capacity> ○: Water is dispersed evenly, just like immediately after emulsification △: Water is partially separated ×: Water is separated

[0044] [Table 3]

[0045] All of the tested compounds were able to form stable emulsions similar to known emulsifiers and oil gelling agents. In particular, C16GL, C18GL, C22GL, and 5-OH-C16GL were able to form emulsions with high water-holding capacity.

[0046] From the above, it was found that the compound of formula (1) has the ability to gel liquids other than water or the ability to emulsify hydrophilic and hydrophobic solvents. Therefore, a novel gelling agent or a novel emulsifying agent has been provided, and the options for gelling agents or emulsifying agents capable of forming organogel or emulsion compositions have been increased.

Claims

1. Formula (1): 【Chemical 1】 （１） (R 1 ~R 3 are each independently hydrogen or an acyl group derived from a linear saturated fatty acid having 10 to 22 carbon atoms, R 4 is an acyl group derived from a linear saturated fatty acid having 10 to 22 carbon atoms. A gelling agent comprising a compound of formula (I).

2. The compound has the formula (2): 【Chemistry 2】 （２） (R 1 ~R 4 The definitions are as set forth in claim 1. The gelling agent according to claim 1, represented by the formula:

3. R 1 ~R 4 10. The gelling agent of claim 1, wherein not more than one of

4. R 3 is an acyl group derived from a linear saturated fatty acid having 10 to 22 carbon atoms.

5. R 1 ~R 4 and each independently represent an acyl group derived from a linear saturated fatty acid having 10 to 22 carbon atoms.

6. A gel composition comprising the gelling agent according to any one of claims 1 to 5 and at least one liquid other than water.

7. Formula (1): 【Chemistry 3】 （１） (R 1 ~R 3 are each independently hydrogen or an acyl group derived from a linear saturated fatty acid having 10 to 22 carbon atoms, R 4 is an acyl group derived from a linear saturated fatty acid having 10 to 22 carbon atoms. An emulsifier comprising a compound of formula (I).

8. An emulsion composition comprising the emulsifier according to claim 7, a hydrophilic solvent, and a hydrophobic solvent.

9. Formula (1'): 【Chemistry 4】 （１’） (R 1 ~R 3 are each independently hydrogen or an acyl group derived from a linear saturated fatty acid having 10 to 22 carbon atoms, and R 1 ~R 3 at least one of is hydrogen, R 4 is an acyl group derived from a linear saturated fatty acid having 10 to 22 carbon atoms. Compound.

10. Formula (2'): 【Chemistry 5】 （２’） (R 1 ~R 4 The definition of is as set forth in claim 9. The compound according to claim 9, represented by:

11. A method for producing the compound of claim 9 or 10, comprising the steps of: Formula (3): 【Chemistry 6】 （３） is reacted with a source of an acyl group derived from a linear saturated fatty acid having 10 to 22 carbon atoms to obtain a compound of formula (1'): 【Chemistry 7】 （１’） (R 1 ~R 4 The definition of is as set forth in claim 9. A method of producing a compound of formula (I).

12. The method according to claim 11, wherein the acyl group source comprises at least one selected from the group consisting of an acid halide, an acid anhydride, and an ester of a linear saturated fatty acid having 10 to 22 carbon atoms.

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