JPH05294989A - Novel sterol derivative and its production - Google Patents

Abstract

PURPOSE:To obtain the subject derivative having both a skin roughness- improving effect and a surface-active performance and useful as a base agent for cosmetics, toiletry products or medicines, etc., reacting a sterol with an alkenyl succinic acid anhydride or alkoxysuccinic acid anhydride. CONSTITUTION:A sterol (e.g. cholesterol) is reacted with an alkylsuccinic acid anhydride or alkenylsuccinic acid anhydride (e.g. n-hexadecenylsuccinic acid anhydride) at 160 deg.C in a stream of nitrogen gas, and the reaction product is purified by a silica gel column chromatography to obtain the new objective sterol derivativer of formula I [R<1> is the residue (the H atom is removed from the hydroxyl group) of a natural sterol having the hydroxyl group or its hydrogenation product; the group of formula II is a group bonded to the O of the hydroxyl group of the sterol; R<2> is a group of formula III (R<3> is 6-20C alkenyl, alkyl); M is H, alkali (ne earth) metal, ammonium, etc.,].

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel sterin derivative having a rough skin improving effect and a surface activity and useful as a base for cosmetics, toiletry products or pharmaceuticals, and a process for producing the same.

[0002]

2. Description of the Related Art It has been conventionally known that moisture in the stratum corneum is important for moisturizing and softening the skin. Recently, it has been found that lipids existing between corneocytes form a lamellar structure in the presence of water and play an important role in water retention in the stratum corneum (G.Imokawa, M. Hattori, J. Invest.Der
matol., 84 , 282 (1985)]. In addition, among the intercellular lipids, especially ceramide and cholesterol ester have been found to have a high effect of improving rough skin when applied to the skin (G. Imokawa et al, Arch. Dermatol. Res., 281 , 45).
(1989)]. Furthermore, an artificial intercellular lipid composed of a substance similar to the intercellular lipid component of keratin has been attempted to moisturize and soften the skin, and a relatively high improvement effect has been recognized [Genji Imagawa, FRAGRANCE JOURNAL, 4 , 2
6 (1990) and Genji Imokawa et al., “Functional Cosmetics”, 235,
CMC (1990)].

However, when the artificial intercellular lipid is applied to the skin, the water-retaining ability of the stratum corneum is improved, and the effect of preventing or healing rough skin is observed to some extent, but it is at the same level as that of perfectly healthy skin. I couldn't recover until now, and I wasn't satisfied. Therefore, it is possible to fundamentally improve the water-retaining ability of the stratum corneum of rough skin, restore the function to a level equal to or higher than that of a healthy living body, and to give the skin moisture and flexibility. The development of a base has been eagerly awaited.

[0004]

[Means for Solving the Problems] In view of such a situation,
In order to solve the above problems, the present inventors have made diligent studies focusing on the intermolecular interactions of keratinocyte-lipid components, and found that the ceramide-containing intercellular lipid components have a lamellar liquid crystal structure in the presence of water. It was found that, when applied to rough skin, the effect of improving the rough skin is remarkably improved by the formation, and as a result of further investigation, the sterin derivative represented by the general formula (I) described later shows that the rough skin itself has high rough skin. It has an improving effect and is highly effective in stabilizing the lamellar liquid crystal structure formed by intercellular lipids. Surprisingly, among the sterin derivatives represented by the general formula (I), lamellae by itself are used. When forming a liquid crystal and used as an emulsifier, W
The present invention was completed by discovering that some of them have high surface activity, such as stabilizing / O type emulsion. That is, the present invention provides a novel sterin derivative represented by the following general formula (I) and a method for producing the same.

[0005]

[Chemical 4]

[In the formula, the residue remaining after removing the hydrogen atom of the hydroxyl group of natural sterin or a hydrogenated product thereof (hereinafter referred to as sterins) having R ¹ : 1 hydroxyl group is shown.

[0007]

[Chemical 5]

It is a group that is bonded to an oxygen atom to which a hydrogen atom of a hydroxyl group of sterins is bonded. Where R ₂ is

[0009]

[Chemical 6]

(R ³ represents a linear or branched alkenyl group or alkyl group having 6 to 20 carbon atoms), M is a hydrogen atom, an alkali metal or an alkaline earth metal. , Ammonium, alkanolammonium having 2 to 9 carbon atoms, alkylammonium or alkenylammonium having 1 to 22 carbon atoms, pyridinium substituted with an alkyl or alkenyl group having 1 to 18 carbon atoms, or a basic amino acid. The sterin derivative of the present invention has a remarkably high effect of improving skin roughness itself, can stabilize the lamellar liquid crystal structure formed by intercellular lipids in the presence of water in the presence of water, and further has good surfactant activity and is used as an emulsifier or the like. In terms of what can be done, esters of sterins and monocarboxylic acids that have been used as a base for external use of skin for the purpose of improving rough skin (Japanese Patent Publication No. 59-2332).
No. 0, JP-A-58-140007, JP-A-1-242690, and JP-A-2-191208).

In the sterin derivative represented by the general formula (I), R ¹ is a natural sterin having one hydroxyl group (for example, cholesterol, stigmasterol, sitosterol, lanosterol, ergosterol, etc.) or its hydrogenated product. It is a residue that remains after the hydrogen atom of the hydroxyl group is removed, and is preferably a cholesterol residue.

Further, in the sterin derivative represented by the general formula (I), R ³ is a linear or branched alkenyl group having 6 to 20 carbon atoms or an alkyl group, for example, linear or branched 2 -Hexenyl group, 2-octenyl group, 2-
Deceter group, 2-dodecenyl group, 2-tetradecenyl group, 2-hexadecenyl group, 2-octadecenyl group, 2
-Eicosenyl group, hexyl group, octyl group, decyl group, dodecyl group, tetradecyl group, hexadecyl group, octadecyl group, eicosyl group and the like are exemplified, and among them, 2-tetradecenyl group, 2-hexadecenyl group, 2-octadecenyl group, 2 -Eicosenyl group, tetradecyl group, hexadecyl group, octadecyl group and eicosyl group are preferable.

The sterin derivative of the present invention can be widely used in cosmetics, toiletry products, pharmaceuticals and the like by utilizing its rough skin improving effect and surface activity. Further, the sterin derivative represented by the general formula (I) provided by the present invention (hereinafter abbreviated as sterin derivative (I))
Can be obtained by reacting sterins with an alkenylsuccinic anhydride or an alkylsuccinic anhydride and, if necessary, neutralizing with an alkaline substance. Also R ¹ group, R ³
For those having no unsaturated double bond in the group, it is also possible to react the sterins with an alkenylsuccinic anhydride or an alkylsuccinic anhydride and then hydrogenate by a usual method using a noble metal catalyst or the like. can get.

As a result of intensive studies on the synthesis method of the sterin derivative (I), the present inventors have found that sterins and alkenylsuccinic anhydrides or alkylsuccinic anhydrides in a solvent containing substantially no water or alcohol. By reacting with, preferably in the presence of an acidic substance or an alkaline substance, the corresponding sterin derivative (I)
Was found to be obtained in good yield, and the production method of the present invention was completed. A specific example of this reaction is as follows.

[0015]

[Chemical 7]

In the reaction of the present invention, first, as a solvent, an organic solvent substantially free of water and alcohol, for example, benzene, toluene, xylene, dimethylformamide (DMF), dimethylsulfoxide (DMSO), dioxane, 1,2- Dichloroethane, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, etc. can be used, but the raw material sterins are easily dissolved, and they are stable even in the presence of acidic or alkaline substances used as reaction catalysts, and coloring is unlikely to occur. Toluene and xylene are preferable. Further, as an acidic substance used as a reaction catalyst, p-toluenesulfonic acid (P
TS), formic acid, acetic acid, hydrochloric acid, sulfuric acid and the like can be used, but p-toluenesulfonic acid (PTS), which is less likely to cause coloring of the product, is preferable. As the alkaline substance used as the reaction catalyst, pyridine, triethylamine, caustic potash, caustic soda, or the like can be used, but pyridine and triethylamine are preferable from the viewpoint of solubility in a solvent. Further, the reaction can be carried out in the absence of a solvent, a reaction catalyst consisting of an acidic substance or an alkaline substance, but first, in the absence of a solvent, the reaction must be carried out at a high temperature above the melting point of sterins, As a result, a side reaction such as formation of a diester in which both carbonyl groups of the reaction reagent alkenyl succinic anhydride or alkyl succinic anhydride is esterified easily proceeds, so it is preferable to use a solvent. Further, in the absence of a reaction catalyst composed of an acidic substance or an alkaline substance, the reaction progresses slowly, so the reaction temperature must be extremely high or the reaction time must be lengthened, and as a result, in the absence of a solvent. Since a side reaction such as a diester is likely to proceed similarly to the reaction, it is preferable to use an acidic substance or an alkaline substance as a reaction catalyst.

It is more preferable to use an acidic substance as the reaction catalyst rather than an alkaline substance because coloring is less likely to occur. The addition amount of alkenyl succinic anhydride or alkyl succinic anhydride or a mixture thereof which is a reaction reagent is preferably 1 to 1.5 times mol relative to sterins. The reaction temperature is preferably 40 to 180 ° C, more preferably 60 to 150 ° C. When the reaction temperature exceeds 180 ° C., side reactions such as formation of diester become remarkable, which is not preferable. Although the reaction time depends on the reaction temperature and the addition amount of the acidic substance or the alkaline substance, 30 minutes to 20 hours is sufficient. The amount of the acidic substance added is about 0.01 to 10% by weight, more preferably 0.1 to 2% by weight with respect to the reaction reagents sterins.
It may be added by weight%. When an alkaline substance is added as a reaction catalyst, the molar ratio is about 0.1 to 2.0 times, more preferably 1.0 to 1.5 times that of the reaction reagent such as alkenylsuccinic anhydride, alkylsuccinic anhydride, or a mixture thereof. It may be added twice.

As described above, the solvent, the reaction catalyst comprising an acidic substance or an alkaline substance, and the amount of the alkenylsuccinic anhydride, the alkylsuccinic anhydride or a mixture thereof, the reaction time and the reaction temperature are arbitrarily set, The desired sterin derivative (I) can be obtained. Sterin derivative (I) thus obtained
When an alkaline substance is used as a reaction catalyst, it is a carboxylic acid type or an alkali neutralized salt type or a mixture thereof depending on the amount used. In order to obtain the desired group in the M group in the general formula (I), if necessary, (A) an alkaline substance is further added to form a completely alkali-neutralized salt, or (B) an acidic substance is added. It can be used in the form of a completely carboxylic acid type or (C) another alkaline neutralized salt by adding an alkaline substance to the carboxylic acid type sterin derivative. When (D) an acidic substance is added, or when neither an acidic substance nor an alkaline substance is added, the obtained sterin derivative is in the acid form after the reaction, and if necessary, an alkaline substance is added, It can be used as a completely alkali-neutralized salt type or a mixture of an alkali-neutralized salt type and an acid type (hereinafter,
The steps (A) to (D) are collectively called a neutralization / counterion exchange step. ).

Alkaline substances used in the neutralization / counterion exchange step include sodium hydroxide, potassium hydroxide, lithium hydroxide, barium hydroxide, sodium hydrogen carbonate,
Inorganic alkalis such as sodium carbonate and potassium carbonate, or monoethanolamine, diethanolamine, triethanolamine, decylamine, dodecylamine, tetradecylamine, hexadecylamine, octadecylamine, basic amino acids and the like can be mentioned. Alternatively, it can be used as a solution of an organic solvent or a mixed solution thereof. As the acidic substance used in the neutralization / counterion exchange step, hydrochloric acid, sulfuric acid, formic acid, acetic acid, propionic acid, etc. can be mentioned.
These can be used as an aqueous solution, a solution of an organic solvent, or a mixed solution thereof. The neutralization / counterion exchange step was obtained by the above reaction with the alkaline substance or acidic substance or its aqueous solution used in the above neutralization / counterion exchange step, a solution of an organic solvent or a mixed solution of water and an organic solvent. 80 with sterin derivative (I)
It suffices to stir at a temperature below 0 ° C for about 1 hour.

The solvent present in the thus-obtained mixture containing sterin derivative (I) is first heated under reduced pressure to be distilled off (desolvation step), and then the remaining inorganic salts and organic salts are removed. Removal by electrodialysis, adsorption with ion-exchange resin, adsorbent, etc., or washing with water, recrystallization, etc. (desalting process)
can do. Further, if necessary, it can be purified (purification step) by column chromatography or the like, but depending on the application, the above neutralization / counterion exchange step, desolvation step, desalting step, and purification step can be omitted. ..

[0021]

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

Example 1 A reaction vessel having a capacity of 500 ml equipped with a thermometer and a stirrer was charged with 109.1 g (282 mmol) of cholesterol and heated to 160 ° C. in an oil bath under aeration of nitrogen gas to dissolve cholesterol. .. Then n-hexadecenyl succinic anhydride 90.9
g (282 mmol) was added, and the mixture was heated at 160 ° C. for 10 minutes with stirring, cooled to 130 ° C., and further stirred for 1 hour.
The reaction was cooled to room temperature, yielding 200 g of a pale yellow, viscous pasty material. This was purified by column chromatography using silica gel (mobile phase; hexane / ethyl acetate = 4/1), and a colorless, translucent paste-like n-hexadecenylsuccinic acid cholesteryl monoester was obtained.
178.4 g (yield 89.2%) was obtained. Table 1 shows measured and theoretical values of the acid value, saponification value and hydroxyl value of the obtained n-hexadecenylsuccinic acid cholesteryl monoester.

[0023]

[Table 1]

The IR spectrum and ¹ H-NM of the obtained n-hexadecenyl succinic acid cholesteryl monoester were also obtained.
The R spectrum is as follows, and the elemental analysis values are as shown in Table 2. The ¹³ C-NMR spectrum is shown in FIG. From FIG. 1, it was found that the product was a mixture of isomers (I-1 and I-2) having different substitution positions of n-hexadecenyl group in a ratio of about 1: 1 (weight ratio). IR spectrum (Ekimakuho) 2960,2926,2854,1740 (C = O stretching), 1710 (C = O stretching), 1470,1380cm ^{-1 1} H-NMR spectrum ([delta], ppm) in CDCl ₃ a; 0.70 (S, 3H) b; 0.75 to 2.40 (m, 55H) c; 0.80 (d, 6H) d; 0.93 (d, 3H) e; 1.00 (s, 3H) f; 2.40 to 3.0 (m, 3H) g 4.65 (m, 1H) h; 5.35 (m, 3H) i; 11.5 (m, 1H)

[0025]

[Chemical 8]

[0026]

[Table 2]

Example 2 500 ml capacity equipped with a thermometer, reflux condenser and stirrer
52.4 g of cholesterol (136 mmol), n-
Octadecenyl succinic anhydride 47.6 g (136 mmol), p-
Toluenesulfonic acid monohydrate 0.5 g and toluene 200
Charged ml. The mixture was heated to reflux for 3 hours while stirring under a nitrogen gas atmosphere. To the reaction mixture, 500 ml of ethyl acetate was added, washed with about 100 ml of ion-exchanged water three times using a separating funnel, and dried with about 30 g of anhydrous sodium sulfate.
Then, the solvent was distilled off by heating under reduced pressure to obtain 93.2 g (yield 93.2%) of a pale yellow and hard paste of n-octadecenylsuccinic acid cholesteryl monoester. Obtained n
Table 3 shows measured and theoretical values of the acid value, saponification value, hydroxyl value and water content of octadecenyl succinic acid cholesteryl monoester.

[0028]

[Table 3]

The IR spectrum and ¹ H-NM of the obtained n-octadecenyl succinic acid cholesteryl monoester were also obtained.
The R spectrum is as follows, and the elemental analysis values are as shown in Table 4. The ¹³ C-NMR spectrum is shown in FIG. From FIG. 2, it was found that the product was a mixture of isomers (I-3 and I-4) having different substitution positions of the n-octadecenyl group in a ratio of about 1: 1 (weight ratio). IR spectrum (Ekimakuho) 2960,2925,2850,1742 (C = O stretching), 1713 (C = O stretching), 1460,1380cm ^{-1 1} H-NMR spectrum ([delta], ppm) in CDCl ₃ a; 0.68 (S, 3H) b; 0.75 to 2.40 (m, 59H) c; 0.80 (d, 6H) d; 0.95 (d, 3H) e; 1.00 (s, 3H) f; 2.40 to 3.0 (m, 3H) g 4.60 (m, 1H) h; 5.40 (m, 3H) i; 11.3 (m, 1H)

[0030]

[Chemical 9]

[0031]

[Table 4]

Example 3 59.2 g (153 mmol) of cholesterol, n in a reaction vessel of 1 liter capacity equipped with a thermometer, a reflux condenser and a stirrer
40.8 g (153 mmol) of dodecenyl succinic anhydride and 500 ml of pyridine were charged. Under nitrogen gas bubbling, the mixture was heated under stirring for 2 hours and refluxed. After completion of the reaction, excess pyridine was heated under reduced pressure to distill off, and 13.8 g (223 mmol) of acetic acid was added to neutralize. The remaining brown solid was dissolved in 500 ml of ethyl acetate, washed 3 times with about 100 ml of deionized water using a separating funnel, and dried with about 30 g of anhydrous sodium sulfate. Then, the solvent was distilled off to obtain 87.3 g of a pale yellow glassy substance.
This was purified by column chromatography using silica gel (mobile phase; hexane / ethyl acetate = 4/1) to obtain 37.9 g (yield 37.9%) of colorless and transparent glassy n-dodecenylsuccinic acid cholesteryl monoester. It was
Table 5 shows the measured and theoretical values of the acid value, saponification value, hydroxyl value and water content of the obtained n-dodecenyl succinic acid cholesteryl monoester.

[0033]

[Table 5]

The IR spectrum and ¹ H-NMR spectrum of the obtained n-dodecenylsuccinic acid cholesteryl monoester are as follows, and the elemental analysis values are as shown in Table 6. In addition, from the ¹³ C-NMR spectrum, the product was n-
About 1: of two isomers having different substitution positions of dodecenyl group
It was found to be a mixture of 1 (weight ratio). IR spectrum (Ekimakuho) 2955,2920,2850,1740 (C = O stretching), 1710 (C = O stretching), 1467,1380cm ^{-1 1} H-NMR spectrum ([delta], ppm) in CDCl ₃ a; 0.65 (S, 3H) b; 0.75 to 2.40 (m, 47H) c; 0.81 (d, 6H) d; 0.93 (d, 3H) e; 1.05 (s, 3H) f; 2.40 to 3.0 (m, 3H) g 4.60 (m, 1H) h; 5.40 (m, 3H) i; 11.0 (m, 1H)

[0035]

[Chemical 10]

[0036]

[Table 6]

Example 4 50 equipped with a thermometer, a reflux condenser, a stirrer and a dropping funnel
48.5 g of n-hexadecenyl succinic acid cholesteryl monoester synthesized in Example 1 in a 0 ml reaction vessel.
(68.4 mmol) and 300 ml of isopropanol were charged. 30 ml of an aqueous solution containing 5.75 g (67.6 mmol) of sodium hydrogen carbonate
Was charged into the above reaction vessel from a dropping funnel at room temperature over about 30 minutes. After the dropping was completed, the mixture was further stirred at room temperature for 30 minutes.
Water and isopropanol were heated and distilled off under reduced pressure from the reaction product. The remaining white solid was washed with a large amount of hexane and dried under reduced pressure to obtain 47.5 g of a white powder of n-hexadecenylsuccinic acid cholesteryl monoester sodium salt (yield:
95.0%). Table 7 shows the measured and theoretical values of the acid value, saponification value, and water content of the obtained sodium salt of n-hexadecenyl succinic acid cholesteryl monoester.

[0038]

[Table 7]

The IR spectrum of the obtained sodium salt of n-hexadecenylsuccinic acid cholesteryl monoester is as follows, and the elemental analysis values are as shown in Table 8. IR spectrum (liquid film method) 3406 (OH stretching), 2926, 2854, 1731 (C = O stretching), 15
75 and 1407 (C = O expansion / contraction), 1380cm ^-1

[0040]

[Table 8]

Test Example 1 Structures of n-hexadecenyl succinic acid cholesteryl monoester and n-octadecenyl succinic acid cholesteryl monoester synthesized in Example 1 and Example 2 at room temperature (phase state) ) Was examined by X-ray.
CuKα ray (λ = 1.54Å) was used as the X-ray. The X-ray diffraction patterns thereof are shown in FIGS. 3 and 4. As a result, the n-hexadecenylsuccinic acid cholesteryl monoester (FIG. 3) showed that the x-ray diffraction pattern (d =
43.7Å: 21.1Å: 13.8Å: 10.2Å: 8.2Å≈1: 1 /
2: 1/3: 1/4: 1/5) and no clear diffraction peak was observed in the wide-angle region, indicating that lamellar liquid crystal was formed at room temperature. Similarly, n-octadecenyl succinic acid cholesteryl monoester (Fig. 4) also has an X-ray diffraction pattern (d = 43.0Å: 21.0Å:
14.0Å: 10.6Å: 8.5 Å = 1: 1/2: 1/3: 1 /
4: 1/5) and the diffraction pattern in the wide-angle region showed that the lamellar liquid crystal was present.

Test Example 2 Table 10 shows n-octadecenylsuccinic acid cholesteryl monoester synthesized in Example 2 and beef brain ceramide (manufactured by Funakoshi Chemical Co., Ltd.) represented by the following formula (II). The oil-in-water emulsion cosmetic (the external preparation for skin containing the present invention) formulated as described above was produced, and a known method for comparison (Japanese Patent Publication No.
59-23320), an oil-in-water emulsion cosmetic (isotopic preparation containing comparative product) containing isostearic acid cholesteryl ester as shown in Table 10 was used to measure skin conductance and rough skin according to the following methods. evaluated. The results are shown in Table 10.

[0043]

[Chemical 11]

(In the formula, R ⁴ and R ⁵ each represent a linear or branched, saturated or unsaturated hydrocarbon group having 8 to 26 carbon atoms, which may be substituted with one or more hydroxyl groups.) <Test method> 20-50 with rough skin on cheeks in winter
10 year old women are used as subjects, and different samples are applied to the left and right cheeks once a day for 2 weeks. On the day after the application for 2 weeks was completed, the following items were tested. (1) Skin conductance After washing the face with warm water of 37 ℃, leave it in a room with a temperature of 20 ℃ and humidity of 40%.
After resting for a minute, the water content of the stratum corneum was measured with a skin conductance meter (IBS). The smaller the conductance value is, the rougher the skin is, and when the conductance value is 5 or less, the skin is severely rough. On the other hand, if this value is 20 or more, almost no rough skin is observed. (2) Rough skin score Rough skin was visually observed and judged according to the criteria shown in Table 9. The score was shown by the average value +/- standard deviation.

[0045]

[Table 9]

[0046]

[Table 10]

From the above test results, it was found that the external preparation for skin containing the n-octadecenyl succinic acid cholesteryl monoester of the present invention has a better effect on improving rough skin than that containing the isostearic acid cholesteryl ester. did.

Test Example 3 N-hexadecenyl succinic acid cholesteryl monoester synthesized in Example 1 was used as an emulsifier in an amount of 5% by weight, dissolved in 30 g of liquid paraffin, and 70 g of water was added under stirring to give 70%.
Emulsified at ℃, the resulting water-in-oil emulsion at room temperature
It was allowed to stand for a week and the state of phase separation was observed. For comparison,
A similar study was conducted using isostearic acid cholesteryl ester as an emulsifier. The results are shown in Table 11.

[0049]

[Table 11]

From the above test results, it was found that the n-hexadecenylsuccinic acid cholesteryl monoester of the present invention has an excellent emulsifying ability as compared with isostearic acid cholesteryl ester.

[0051]

INDUSTRIAL APPLICABILITY The sterin derivative (I) of the present invention has a high effect of improving skin roughness when applied to the skin itself, and can stabilize the lamellar liquid crystal structure formed by intercellular lipids in the presence of water, Further, since it has good surface activity, it can be widely used as a base for external use on skin, an emulsifier, etc. in cosmetics, toiletry products, pharmaceuticals and the like.

[Brief description of drawings]

1 is a ¹³ C-NMR spectrum of the compound obtained in Example 1. FIG.

FIG. 2 is a ¹³ C-NMR spectrum of the compound obtained in Example 2.

FIG. 3 is a view showing an X-ray diffraction pattern at room temperature of n-hexadecenylsuccinic acid cholesteryl monoester.

FIG. 4 is a view showing an X-ray diffraction pattern at room temperature of n-octadecenylsuccinic acid cholesteryl monoester.

Claims (4)

[Claims] 1. A sterin derivative represented by the general formula (I). [Chemical 1] [In the formula, R ¹ represents a residue remaining after removing a hydrogen atom of a hydroxyl group of natural sterin having one hydroxyl group or a hydrogenated product thereof (hereinafter referred to as sterins). [Chemical 2] It is a group that is bonded to an oxygen atom to which a hydrogen atom of a hydroxyl group of sterins is bonded. Here, R ₂ is (R ³ represents a linear or branched alkenyl group or alkyl group having 6 to 20 carbon atoms.), M
Is a hydrogen atom, alkali metal, alkaline earth metal, ammonium, alkanolammonium having 2 to 9 carbon atoms, alkylammonium or alkenylammonium having 1 to 22 carbon atoms, alkyl group or alkenyl group having 1 to 18 carbon atoms. A substituted pyridinium or basic amino acid is shown. ] 2. The sterin derivative according to claim 1, wherein the natural sterin is cholesterol, stigmasterol, sitosterol, lanosterol or ergosterol. 3. In the general formula (I), R ¹ is a residue remaining after removing a hydrogen atom of a hydroxyl group of cholesterol, and R ³ is a linear alkenyl group or alkyl group having 6 to 20 carbon atoms. The sterin derivative according to claim 1. 4. The method for producing a sterin derivative represented by the general formula (I) according to claim 1, which comprises reacting sterins with an alkenylsuccinic anhydride or an alkylsuccinic anhydride.