New compounds and gelling agents

Abstract

To provide a compound capable of forming an organogel.SOLUTION: The compound is represented by the structural formula in the figure, where A represents hydrogen or OR, and each R is independently selected from the group consisting of hydrogen, a C10-22 linear alkyl group, an acyl group derived from a C10-22 linear saturated fatty acid, and an acyl group derived from a γ-amino butyric acid derivative.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a novel compound, in particular to a novel compound having the ability to gel liquids other than water. The present invention also relates to a gelling agent, in particular to a gelling agent for liquids other than water. [Background technology]

[0002] Gelling agents are used to thicken or solidify liquids, and 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 for preparing aqueous gels are known, but although there are various liquids other than water (organic solvent systems), the types of gelling agents for preparing organic solvent gels are limited. For example, Patent Document 1 and Non-Patent Document 1 disclose that a compound in which a certain type of monosaccharide skeleton is ester-bonded to a linear fatty acid can gel various organic solvents. In addition, Non-Patent Document 2 discloses that 4-(N-tetradecanoyl)aminohydroxybutanoic acid has the ability to gel organic solvents. [Prior art documents] [Patent documents]

[0003] [Patent Document 1] JP 2019-89719 A [Non-patent literature]

[0004] [Non-Patent Document 1] ChemPlusChem 2020, 85, 701-710. [Non-Patent Document 2] J. Physical Chem., B 2014, 118, 12112-12120. Summary of the Invention [Problem to be solved by the invention]

[0005] On the other hand, the compounds described in Patent Document 1 and Non-Patent Document 1 have the drawback that the gel formed has low transparency and low hardness and viscosity, and the compound described in Non-Patent Document 2 lacks variety, so there is still a demand for compounds that have excellent properties regarding the properties of the gel formed and the types of organic solvents that can gel. Therefore, an object of the present invention is to provide a compound capable of forming an organogel. [Means for solving the problem]

[0006] As a result of intensive research aimed at solving the above problems, the present inventors have found that a compound of the following formula (1) and a compound of the following formula (4) containing a partial structure thereof have the ability to gel liquids other than water, and have completed the present invention. That is, the present invention provides the following compounds and gelling agents. [1] Formula (1): [ka] (1) (A represents hydrogen or OR, Each R is independently selected from hydrogen, a linear alkyl group having 10 to 22 carbon atoms, an acyl group derived from a linear saturated fatty acid having 10 to 22 carbon atoms, and a group represented by the following formula: [ka] wherein n is 8 to 18, and at least one of R is an acyl group derived from the γ-aminobutyric acid derivative represented by the formula: Compound. [2] Formula (2) or (3): [ka] (2) [ka] (3) (The definition of each R is as described in [1] above.) The compound according to the above item [1], represented by the formula: [3] The compound according to [1] or [2] above, wherein R has one or less hydrogen atoms. [4] The compound according to any one of the above [1] to [3], wherein all of R are simultaneously an acyl group derived from the γ-aminobutyric acid. [5] The compound according to any one of the above [1] to [4], wherein n is 10 to 16. [6] A composition comprising the compound according to any one of [1] to [5] above. [7] Formula (1): [ka] (1) (A represents hydrogen or OR, Each R is independently selected from hydrogen, a linear alkyl group having 10 to 22 carbon atoms, an acyl group derived from a linear saturated fatty acid having 10 to 22 carbon atoms, and a group represented by the following formula: [ka] wherein n is 8 to 18, and at least one of R is an acyl group derived from the γ-aminobutyric acid derivative represented by the formula: or Formula (4): [ka] (4) (n is 8 to 11 or 13 to 18) A gelling agent comprising a compound of formula (I). [8] A gel composition comprising the gelling agent according to [7] above and at least one liquid other than water. [9] A method for producing the compound according to any one of the above [1] to [5], comprising the steps of: Formula (5): [ka] (5) (A' represents hydrogen or OH) of the formula: [ka] (n is 8 to 18) or an acid halide, acid anhydride or ester thereof to esterify at least one of the hydroxyl groups of the compound of formula (5).

[10] The production method according to [9] above, further comprising a step of etherifying a portion of the hydroxyl groups of the compound of formula (5) to form an ether structure having a linear alkyl group having 10 to 22 carbon atoms, and / or a step of esterifying a portion of the hydroxyl groups of the compound of formula (5) to form an ester structure having an acyl group derived from a linear saturated fatty acid having 10 to 22 carbon atoms. Effect of the Invention

[0007] According to the present invention, a novel compound and a novel gelling agent are provided that have the ability to gel liquids other than water, thus increasing the selection of compounds that can form organogels. [Brief description of the drawings]

[0008] [Figure 1] 1 shows a scanning electron microscope (SEM) image of a gel formed by a compound of the present invention (magnification 45,000). [Diagram 2] 1 shows an SEM image of a gel formed by a conventional compound (magnification 40,000). DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0009] The present invention will now be described in further detail. The present invention relates to a compound represented by formula (1): [ka] (1) In formula (1), A represents hydrogen or OR, and the compound of the present invention is a derivative of 1,5-anhydroglucitol or glucopyranose or a stereoisomer thereof.

[0010] Each R is independently selected from hydrogen, a linear alkyl group having 10 to 22 or 12 to 18 carbon atoms, an acyl group derived from a linear saturated fatty acid having 10 to 22 or 12 to 18 carbon atoms, and a group represented by the following formula: [ka] wherein n is 8 to 18, and at least one of R is an acyl group derived from the GABA derivative. In the acyl group derived from the GABA derivative, n is preferably 10 to 16. When n is in this range, the compound of the present invention can form a gel having higher hardness and higher transparency in a wider variety of organic solvents.

[0011] As described above, the compound of the present invention has an amide bond portion and a linear alkyl portion in R. Without being bound by a particular theory, it is believed that the compound can be linked in a fibrous form by hydrogen bonds formed between molecules at the amide bond portion, and has lipophilicity due to the linear alkyl portion, and therefore can form a fibrous network structure in various organic solvents to form an organogel.

[0012] In one embodiment, the compound of the present invention has formula (2) or (3): [ka] (2) [ka] (3) In particular, since 1,5-AG has a non-reducing and chemically stable structure, unwanted reactions are unlikely to occur during its synthesis, and the problem of unintended coloration of the product is unlikely to occur.

[0013] In one embodiment, the compound of the present invention has one or less hydrogen as R. Preferably, the compound does not have hydrogen as R, that is, each R is independently selected from the group consisting of a linear alkyl group having 10 to 22 carbon atoms, an acyl group derived from a linear saturated fatty acid having 10 to 22 carbon atoms, and an acyl group derived from the GABA derivative, and at least one of R is an acyl group derived from the GABA derivative. In a specific embodiment, all of R are simultaneously acyl groups derived from the GABA derivative. Compounds with fewer hydrogens as R are more hydrophobic and more likely to crystallize, so that the target compound can be easily isolated by simply crystallizing and filtering, reducing the purification burden.

[0014] In another aspect, the present invention also relates to a composition comprising the compound of formula (1). Since the compound of formula (1) has a gelling ability, the composition of the present invention is useful as a gelling agent.

[0015] In another aspect, the present invention also relates to a gelling agent. The gelling agent of the present invention has the formula (1): [ka] (1) (A represents hydrogen or OR, Each R is independently selected from hydrogen, a linear alkyl group having 10 to 22 carbon atoms, an acyl group derived from a linear saturated fatty acid having 10 to 22 carbon atoms, and a group represented by the following formula: [ka] wherein n is 8 to 18, and at least one of R is an acyl group derived from the γ-aminobutyric acid derivative represented by the formula: or Formula (4): [ka] (4) (n is 8 to 11 or 13 to 18) The gelling agent of the present invention can gel liquids other than water. The amount of the compound of formula (1) or the compound of formula (4) used is not particularly limited, but may be, for example, about 0.5 to about 20% by mass based on the total mass of the liquid to be gelled.

[0016] 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 undergoes phase separation from water or an organic solvent that does not undergo phase separation from water. For example, the liquid may be a hydrocarbon organic solvent such as liquid paraffin, squalane, hydrogenated polyisobutene, or petrolatum; an ester oil such as pentaerythrityl tetraisostearate, isopropyl myristate, ethylhexyl palmitate, tri(caprylic / capric)glyceryl, trioctanoate, diisostearyl malate, or polyglyceryl-2 triisostearate; a higher fatty acid such as capric acid or lauric acid; an oil or fat such as olive oil, canola oil, soybean oil, or castor oil; a wax such as candelilla wax or jojoba oil; an alcohol such as octyldodecanol or hydrous ethanol; a silicone oil such as diphenylsiloxyphenyl trimethicone; an ester organic solvent such as ethyl acetate; an aromatic hydrocarbon organic solvent such as toluene; or a halogen-based organic solvent such as chloroform.

[0017] The compound of formula (1) and the compound of formula (4) can gel various liquids other than water, so the composition or gelling agent of the present invention can be used in various fields.For example, in the food field, the composition or gelling agent of the present invention can be used for preparing swallowing food, solidifying liquid oil, preventing liquid oil from separating from food (such as peanut butter), and improving the shape retention of food (such as chocolate and whipped cream); in the cosmetics field, it can be used for pencil-shaped cosmetics such as lipstick, lip gloss, concealer, antiperspirant stick, ointment, lip liner, and eyeliner; in the pharmaceutical field, it can be used for ointments and transdermal absorbents; and in the environmental conservation field, it can be used for gelling waste oil to prevent water pollution.

[0018] In another aspect, the present invention also relates to a gel composition comprising the gelling agent and at least one liquid other than water, that is, the gel composition of the present invention is formed by the gelling agent and has good hardness and transparency.

[0019] The composition, gelling agent, or gel-like 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 also relates to a method for producing the compound of formula (1). The means employed in the production method of the present invention can be any means commonly used in the art, without particular limitation. For example, the production method of the present invention can be a method for producing a compound of formula (5): [ka] (5) (A' represents hydrogen or OH) of the formula: [ka] (n is 8 to 18) or its acid halide, acid anhydride or ester to esterify at least one of the hydroxyl groups of the compound of formula (5). If this esterification reaction is allowed to proceed completely, a compound of formula (1) in which all R are acyl groups derived from the GABA derivative is obtained, but if this esterification reaction is allowed to proceed incompletely to leave unreacted hydroxyl groups or if some of the hydroxyl groups of the compound of formula (5) are protected in advance with a protecting group or the like, a compound of formula (1) in which some R are hydrogen is obtained.

[0021] The compound of formula (5) may be 1,5-anhydroglucitol or glucopyranose or a stereoisomer thereof. Examples of the GABA derivatives include 4-[(1-oxodecyl)amino]butanoic acid, 4-[(1-oxoundecyl)amino]butanoic acid, 4-[(1-oxododecyl)amino]butanoic acid, 4-[(1-oxotridecyl)amino]butanoic acid, 4-[(1-oxotetradecyl)amino]butanoic acid, 4-[(1-oxopentadecyl)amino]butanoic acid, and the like. Examples of the acid halide of the GABA derivative include 4-[(1-oxohexadecyl)amino]butanoic acid, 4-[(1-oxoheptadecyl)amino]butanoic acid, 4-[(1-oxooctadecyl)amino]butanoic acid, 4-[(1-oxononadecyl)amino]butanoic acid, and 4-[(1-oxoeicosyl)amino]butanoic acid. The acid halide of the GABA derivative is not particularly limited, and may be, for example, a chloride, a bromide, or an iodide. The ester of the GABA derivative is not particularly limited, but may be, for example, an ester with a lower alcohol (having 1 to 5 carbon atoms) such as methanol or ethanol.

[0022] The reaction conditions of the compound of formula (5) and the GABA derivative or its acid halide, acid anhydride or ester are not particularly limited, but may be, for example, in an organic solvent, the compound of formula (5) and the GABA derivative or its acid halide, acid anhydride or ester are mixed at a molar ratio of about 1:3 or more, preferably about 1:4 to about 1:10, and the mixture is kept at a temperature of room temperature to 100° C. As the organic solvent, those commonly used in the art may be used without any particular limitation, and may be, for example, dichloroethane, N,N-dimethylformamide, toluene, N-methyl-2-pyrrolidone, or dichloromethane.

[0023] The reaction step of the compound of formula (5) with the GABA derivative or its acid halide, acid anhydride or ester may be carried out in the presence of, for example, a basic compound and / or a condensing agent. The basic compound and the condensing agent may be any of those commonly used in the art, without any particular limitations. For example, the basic compound may be 4-dimethylaminopyridine, pyridine, or triethylamine. The condensing agent may be diisopropylcarbodiimide, dicyclohexylcarbodiimide, or 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride.

[0024] The reaction of the compound of formula (5) with the GABA derivative or its acid halide, acid anhydride or ester is known as an acylation reaction. The compound of formula (1) can also be produced by other reactions known per se. For example, the compound of formula (5) and the GABA derivative are directly reacted at high temperature using an acidic compound as a catalyst; the compound of formula (5) and the ester of the GABA derivative are reacted in an organic solvent such as N,N-dimethylformamide using potassium carbonate as a catalyst; the compound of formula (5) is dissolved in propylene glycol, glycerin, water, etc., and a mixture of the ester of the GABA derivative is added with soap to obtain a microemulsion, which is then transesterified under reduced pressure with a small amount of catalyst; the compound of formula (5) and the ester of the GABA derivative can also be produced by transesterification using an enzyme such as lipase.

[0025] In one embodiment, the method of the present invention further includes a step of preparing the GABA derivative or its acid halide, acid anhydride, or ester. The GABA derivative or its acid halide, acid anhydride, or ester can be appropriately prepared by a conventional acylation reaction or amidation reaction. For example, GABA may be reacted with a linear saturated fatty acid having 10 to 20 carbon atoms or its acid halide, acid anhydride, or ester. The reaction conditions are not particularly limited, but for example, GABA and the linear saturated fatty acid or its acid halide, acid anhydride, or ester may be mixed in an aqueous solution at a molar ratio of about 1:1 or more, preferably about 1:1 to about 1:3, and the mixture may be kept at a temperature of 0°C to 80°C to react. As the aqueous solution, any solution commonly used in the art may be used without any particular limitation, but the aqueous solution may be a basic aqueous solution such as an aqueous potassium hydroxide solution.

[0026] In one embodiment, the production method of the present invention may further include a step of etherifying a portion of the hydroxyl groups of the compound of formula (5) to form an ether structure having a linear alkyl group having 10 to 22 carbon atoms, and / or a step of esterifying a portion of the hydroxyl groups of the compound of formula (5) to form an ester structure having an acyl group derived from a linear saturated fatty acid having 10 to 22 carbon atoms. In this case, the hydroxyl groups not involved in the etherification or esterification may be appropriately protected with a protecting group or the like.

[0027] The present invention will be specifically described below with reference to examples, but the scope of the present invention is not limited to these examples. EXAMPLES

[0028] 〔method〕 Compounds were prepared according to the preparation examples described below, and their chemical structures and properties were confirmed by nuclear magnetic resonance (NMR) method, mass spectrometry (MS), optical rotation measurement, and melting point measurement. Specifically, the prepared compounds were dissolved in deuterated chloroform or a mixture of deuterated chloroform and deuterated methanol, and analyzed at 300 K using an Avance 400 spectrometer (Bruker BioSpin). 1 H NMR (400.13MHz) and 13 C NMR (100.61 MHz) was measured. Tetramethylsilane was used as the internal standard (0 ppm) (s = singlet, d = doublet, t = triplet, m = multiplet). Accurate mass measurements were performed using an ESI-Orbitrap-MS (Thermo Fisher Scientific Inc. VELOS PRO). Optical rotation measurements were performed at room temperature by dissolving each compound in chloroform:methanol = 10:1 using a P-1020-GT (JASCO). Melting point measurements were performed while observing the sample on a temperature controller (Mettler FP82 hot stage, linked to Mettler FP90, 0.4°C accuracy) with a microscope (OLYMPUS BX51).

[0029] The gelling ability of the compound was confirmed by gel hardness measurement and turbidity measurement. Specifically, the hardness of a gel composition (thickness about 10 mm) to which a test compound was added and left to stand overnight was measured using RHEONER II (YAMADEN RE2-33005C). A spherical plunger of 5 mmφ was inserted at a speed of 60 mm / min, and the maximum stress until it was inserted 2.5 mm was taken as the gel hardness. Turbidity measurement was performed by placing the above preparation in a glass container and measuring the absorbance at 660 nm with a spectrophotometer (Beckman DU650). Water was measured as a blank and set to 0. In addition, the surface of some gels was osmium coated using an osmium deposition device, and SEM images were observed using a JSM-7600F (JEOL, SEM).

[0030] [Preparation Example 1] 4-[(1-oxododecyl)amino]butanoic acid (Compound 1; C 12 GABA), 4-[(1-oxotetradecyl)amino]butanoic acid (compound 2; C 14 GABA), 4-[(1-oxohexadecyl)amino]butanoic acid (compound 3; C 16 GABA), 4-[(1-oxooctadecyl)amino]butanoic acid (compound 4; C 18 Synthesis of GABA [ka]

[0031] GABA is reacted with various fatty acid chlorides (dodecanoic acid chloride, tetradecanoic acid chloride, palmitic acid chloride, or stearic acid chloride) by a conventional method (see International Publication No. 2013 / 148991, etc., if necessary), to obtain C 12 GABA (yield 76%), C 14 GABA (yield 17%), C 16 GABA (yield 37%) and C 18 GABA (80% yield) was synthesized. The NMR of the synthesized compounds was measured and confirmed to match the known NMR chart.

[0032] [Preparation Example 2] Synthesis of 1,5-AG bound to GABA containing linear saturated fatty acid [ka]

[0033] (2-1) 1,5-anhydro-2,3,4,6-tetra-O-{4-[(1-oxododecyl)amino]butanoyl}-D-glucitol, compound 5; C 12 Synthesis of GABA-AG 1,5-AG crystals (24 mg, 0.146 mmol) were dissolved in 100 μL of water and dried with a vacuum pump to make it amorphous. Compound 1 (250 mg, 0.876 mmol) and 4-(dimethylamino)pyridine (DMAP; 214 mg, 1.75 mmol) were added thereto, and suspended in 1,2-dichloroethane (20 mL). After heating to 60 ° C and dissolving, N,N'-diisopropylcarbodiimide (DIC; 275 μL, 1.76 mmol) was added and reacted at 60 ° C for 1.5 hours. After confirming the completion of the reaction, 60 mL of methanol was added and stirred at room temperature for 1.5 hours. The reaction solution was concentrated under reduced pressure and purified by silica gel column chromatography (chloroform:methanol = 20:1). It was crystallized with 80% methanol to obtain highly pure compound 5 (63.81 mg, yield 35%). The results of the optical rotation measurement and melting point measurement, as well as the results of the NMR method and MS measurement, are shown below.

[0034] TIFF0007670311000021.tif119156

[0035] (2-2) 1,5-anhydro-2,3,4,6-tetra-O-{4-[(1-oxotetradecyl)amino]butanoyl}-D-glucitol, compound 6; C 14 Synthesis of GABA-AG High-purity compound 6 (94.20 mg, 48% yield) was obtained in the same manner as in (2-1) above, except that compound 2 (275 mg, 0.877 mmol) was used instead of compound 1, and that crystals were generated when methanol was added after the reaction was completed, and the crystals were filtered with filter paper without silica gel column chromatography. The results of optical rotation measurement and melting point measurement, as well as the results of NMR and MS measurement are shown below.

[0036] TIFF0007670311000022.tif104156

[0037] (2-3) 1,5-anhydro-2,3,4,6-tetra-O-{4-[(1-oxohexadecyl)amino]butanoyl}-D-glucitol, compound 7; C 16 Synthesis of GABA-AG High-purity compound 7 (193.10 mg, 91% yield) was obtained in the same manner as in (2-2) above, except that compound 3 (300 mg, 0.878 mmol) was used instead of compound 2. The results of optical rotation measurement and melting point measurement, as well as the results of NMR and MS measurements, are shown below.

[0038] TIFF0007670311000023.tif119156

[0039] (2-4) 1,5-anhydro-2,3,4,6-tetra-O-{4-[(1-oxooctadecyl)amino]butanoyl}-D-glucitol, compound 8; C 18 Synthesis of GABA-AG Highly pure compound 8 (154.86 mg, 67% yield) was obtained in the same manner as in (2-2) above, except that compound 4 (324 mg, 0.877 mmol) was used instead of compound 2. The results of optical rotation measurement and melting point measurement, as well as the results of NMR and MS measurements, are shown below.

[0040] TIFF0007670311000024.tif109156

[0041] [Preparation Example 3] Synthesis of D-glucopyranose (Glc) bound to GABA containing linear saturated fatty acid [ka] (*When the reaction temperature was changed to room temperature, the yield of compound 9 became 44%.)

[0042] (3-1) 1,2,3,4,6-penta-O-{4-[(1-oxododecyl)amino]butanoyl}-D-glucopyranoside, compound 9; C 12 Synthesis of GABA-Glc Glc crystals (20 mg, 0.111 mmol) were dissolved in 100 μL of water and dried with a vacuum pump to make it amorphous. Compound 1 (238 mg, 0.834 mmol) and DMAP (203 mg, 1.66 mmol) were added thereto and suspended in 1,2-dichloroethane (20 mL). After heating to 60 °C to dissolve, DIC (261 μL, 1.67 mmol) was added and reacted at 60 °C for 1.5 hours. After confirming the completion of the reaction, 30 mL of methanol was added and stirred at room temperature for 1.5 hours. The reaction solution was concentrated under reduced pressure and purified by silica gel column chromatography (chloroform:methanol = 20:1). It was crystallized from 80% methanol to obtain highly pure compound 9 (12.08 mg, yield 7%, α:β = 0.13:0.87). When the reaction was carried out at room temperature instead of 60° C., the yield was 44% (α:β=0.13:0.87). The melting point measurement results, as well as the NMR and MS measurement results, are shown below.

[0043] TIFF0007670311000026.tif101156

[0044] (3-2) 1,2,3,4,6-penta-O-{4-[(1-oxotetradecyl)amino]butanoyl}-D-glucopyranoside, compound 10; C 14 Synthesis of GABA-Glc Compound 2 (261 mg, 0.833 mmol) was used instead of compound 1, and crystals were generated when methanol and water were added after the reaction was completed. Therefore, the crystals were filtered with filter paper without silica gel column chromatography. High-purity compound 10 (28.66 mg, 16% yield, α:β=0.15:0.85) was obtained in the same manner as in (3-1) above. The melting point measurement results and the NMR and MS measurement results are shown below.

[0045] TIFF0007670311000027.tif106156

[0046] (3-3) 1,2,3,4,6-penta-O-{4-[(1-oxohexadecyl)amino]butanoyl}-D-glucopyranoside, compound 11; C 16 Synthesis of GABA-Glc High-purity compound 11 (87.67 mg, 44% yield, α:β=0.48:0.52) was obtained in the same manner as in (3-2) above, except that compound 3 (284 mg, 0.832 mmol) was used instead of compound 2. The melting point measurement results, as well as the NMR and MS measurement results, are shown below.

[0047] TIFF0007670311000028.tif117156

[0048] (3-4) 1,2,3,4,6-penta-O-{4-[(1-oxooctadecyl)amino]butanoyl}-D-glucopyranoside, compound 12; C 18 Synthesis of GABA-Glc High-purity compound 12 (103.48 mg, 48% yield, α:β=0.51:0.49) was obtained in the same manner as in (3-2) above, except that compound 4 (307 mg, 0.831 mmol) was used instead of compound 2. The melting point measurement results, as well as the NMR and MS measurement results, are shown below.

[0049] TIFF0007670311000029.tif117156

[0050] [Test Example 1] Liquid paraffin #350 (LP#350) or triethylhexanoin (TIO) was placed in a screw cap vial, and any of compounds 1 to 12 was added thereto so as to have a concentration of 1% by mass, and dissolved on a hot plate at 100 to 150°C. The resulting solution was then left at room temperature for 12 hours or more, and the formation of a gel was observed. If the fluidity of the solution was lost and the contents did not flow out even when the screw cap vial was inverted, it was determined that a gel had formed, and the hardness of the formed gel was measured. The results are shown in Table 1.

[0051] [Table 1]

[0052] Most of the compounds 1 to 12 were able to gel both LP#350 and TIO at a concentration of 1% by mass. In particular, compound 6 was able to form a gel with high hardness with both LP#350 and TIO. Even for compounds that could not form a gel at a concentration of 1% by mass, an increase in viscosity was observed, and a gel could be formed by increasing the concentration to about 5% by mass. Note that 1,5-AG cannot be dissolved in liquid paraffin or TIO, and cannot form a gel.

[0053] [Test Example 2] Various organic solvents were placed in screw tubes, and Compound 6 or a known compound (1,5-anhydro-2,3,4,6-tetrapalmitoyl-D-glucitol; C 16 A solution of 1% by mass of AG was added to the bottle and dissolved on a hot plate at 100 to 150°C. The resulting solution was then left to stand at room temperature for 12 hours or more, and the formation of a gel was observed. If the fluidity of the solution was lost and the contents did not flow out even when the screw-top vial was turned upside down, it was determined that a gel had formed, and the hardness of the gel that had formed was measured. The turbidity of the contents of the screw-top vial was also measured. The results are shown in Table 2.

[0054] [Table 2]

[0055] C 16 AG was unable to form gels in isopropyl myristate and 80% aqueous ethanol. On the other hand, compound 6 was able to form gels in all organic solvents tested and showed excellent gel formation in most of them. 16 The gel formed by compound 6 had a higher hardness than the gel formed by AG. In the case of olive squalane and 2-octyl-1-dodecanol, the hardness of the gel formed by compound 6 was C 16 The gels formed by compound 6 were comparable to those formed by AG, but were less turbid and more transparent.

[0056] [Test Example 3] Liquid paraffin #350 (LP#350) was placed in a screw cap vial, and compound 6 or C was added thereto. 16 AG was added to a concentration of 1% by mass and dissolved on a hot plate at 100 to 150° C. The resulting solution was left at room temperature for 12 hours or more to form a gel. The gel was placed in hexane and left for 2 days to remove oil, and then observed with a scanning electron microscope.

[0057] SEM images of the gel formed by compound 6 (Fig. 1) and C 16 Comparing the SEM image of the gel formed by AG (Figure 2), it was found that the former formed a thinner fiber structure. In the gel formed by compound 6, the fibers constituting the gel are thinner, so C 16 It is considered that the gel formed by CAG is more transparent than that formed by AG. 16 AG forms a fiber structure by weak hydrogen bonds between the oxygen atom of the carbonyl group and the hydrogen atom of the alkyl group, but this fiber structure is not very stable, so it is believed that multiple fibers gather together to form a thick fiber structure and reach a stable state. On the other hand, the compound of the present invention forms a stable fiber structure by strong hydrogen bonds formed at the amide bond moiety, so it is believed that the compound can disperse in the organic solvent as it is with a thin fiber structure and form a highly transparent gel.

[0058] From the above, it was found that the compounds and gelling agents of the present invention can form gels with high hardness and transparency, and can gel various organic solvents, thereby increasing the options for compounds that can form organogels.

Claims

1. Formula (1): 【Chemistry 1】 （１） A represents hydrogen or OR; Each R is independently selected from hydrogen, a linear alkyl group having 10 to 22 carbon atoms, an acyl group derived from a linear saturated fatty acid having 10 to 22 carbon atoms, and a group represented by the following formula: 【Chemistry 2】 wherein n is 8 to 18, and at least one of R is an acyl group derived from the γ-aminobutyric acid derivative represented by the formula: Compound.

2. Formula (2) or (3): 【Chemistry 3】 （２） 【Chemistry 4】 （３） (The definition of each R is as set forth in claim 1.) The compound according to claim 1 ,

3. 3. The compound of claim 1 or 2 having not more than one hydrogen as R.

4. The compound according to any one of claims 1 to 3, wherein all of R are simultaneously acyl groups derived from said γ-aminobutyric acid.

5. The compound according to any one of claims 1 to 4, wherein n is 10 to 16.

6. A composition comprising a compound according to any one of claims 1 to 5.

7. Formula (1): 【Chemistry 5】 （１） A represents hydrogen or OR; Each R is independently selected from hydrogen, a linear alkyl group having 10 to 22 carbon atoms, an acyl group derived from a linear saturated fatty acid having 10 to 22 carbon atoms, and a group represented by the following formula: 【Chemistry 6】 wherein n is 8 to 18, and at least one of R is an acyl group derived from the γ-aminobutyric acid derivative represented by the formula: A gelling agent comprising a compound of formula (I).

8. A gel composition comprising the gelling agent of claim 7 and at least one liquid other than water.

9. A method for producing the compound according to any one of claims 1 to 5, comprising the steps of: Formula (5): 【Chemistry 7】 （５） (A' represents hydrogen or OH) The compound of the formula: 【Chemistry 8】 (n is 8 to 18) or an acid halide, an acid anhydride or an ester thereof to esterify at least one of the hydroxyl groups of the compound of formula (5).

10. The method according to claim 9, further comprising the steps of etherifying a portion of the hydroxyl groups of the compound of formula (5) to form an ether structure having a linear alkyl group having 10 to 22 carbon atoms, and / or esterifying a portion of the hydroxyl groups of the compound of formula (5) to form an ester structure having an acyl group derived from a linear saturated fatty acid having 10 to 22 carbon atoms.

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