JPH06135985A - Benzophenone derivative and ultraviolet absorber containing the same - Google Patents

Abstract

(57) [Summary] [Structure] General formula (1) (In the formula, A represents a hydrogen atom or a (meth) acryloyl group, G represents a sugar residue having no protective group, R ¹ represents a hydrogen atom or a methyl group, and R ² represents a hydrogen atom or a methyl group. Or a benzophenone derivative represented by an alkoxy group having 1 to 8 carbon atoms, n represents a number of 2 to 6, and m represents 0 or 1, and an ultraviolet absorber containing the benzophenone derivative. [Effect] The benzophenone derivative (1) of the present invention is hydrophilic and has an excellent ultraviolet absorbing action. Therefore, the ultraviolet absorber of the present invention containing this,
It can be easily incorporated into many aqueous preparations including cosmetics.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a novel benzophenone derivative and an ultraviolet absorber containing the same.

[0002]

2. Description of the Related Art In recent years,
Ultraviolet rays are drawing attention as one of the causes of skin diseases, and it is becoming clear that ultraviolet rays are deeply involved in skin diseases such as sunburn, aging, and skin cancer. Against this background, it is important to protect the skin from ultraviolet rays, and many cosmetics such as sunscreen preparations, skin care, foundations, etc., containing an ultraviolet protective substance as a component are on the market. Further, an ultraviolet absorber is added to various polymer materials in order to prevent deterioration of the polymer due to ultraviolet rays and fading of dyes and pigments.

Ultraviolet rays are long wavelength ultraviolet rays (UV-A; 32).
0-400 nm), medium wavelength ultraviolet (UV-B; 290-3)
20-nm) and short-wavelength ultraviolet (UV-C; ~ 290 nm), among which UV-A and UV-B reaching the surface of the earth
Has been shown to be harmful to the skin, and many UV protection substances have been developed to protect these UV rays.

For example, as UV-A protective substances, inorganic compounds such as titanium oxide, iron oxide and zinc oxide, and oil-soluble organic compounds such as 4-t-butyl-4'-methoxydibenzoylmethane are known. U.S.A., U-shaped particles, ultrafine particles, hydrophobized surface treatment, composite with other substances, etc.
Various efforts have been made to enhance the VA protection effect and to make the material usable as a cosmetic material according to the purpose.

As UV-B protective substances, paraaminobenzoic acid, salicylic acid, methoxycinnamic acid, benzophenone and the like and their derivatives are known and used as cosmetic materials.

However, since most of these UV protective substances are insoluble powders or oil-soluble substances which are poorly soluble in water, it has been extremely difficult to incorporate them in aqueous preparations such as lotions and lotions. Therefore, a hydrophilic ultraviolet absorber having an excellent ultraviolet absorbing action has been desired.

[0007]

Under the circumstances, the inventors of the present invention have conducted diligent research and found that the benzophenone derivative represented by the general formula (1) described below is hydrophilic and has an excellent ultraviolet absorbing action. The present invention has been completed.

That is, the present invention is based on the general formula (1)

[0009]

[Chemical 2]

(In the formula, A represents a hydrogen atom or a (meth) acryloyl group, G represents a sugar residue having no protecting group,
R ¹ represents a hydrogen atom or a methyl group, R ² represents a hydrogen atom,
A benzophenone derivative represented by a methyl group or an alkoxy group having 1 to 8 carbon atoms, n represents a number of 2 to 6, and m represents 0 or 1; and an ultraviolet absorber containing the same. is there.

The benzophenone derivative of the present invention is represented by the above general formula (1). In the formula, the sugar residue represented by G is a monosaccharide or oligosaccharide having 1 to 10, particularly 1 to 5 sugar units. Sugars are preferable, for example, glucose, mannose, galactose, glucosamine, mannosamine, hexoses such as galactosamine, arabinose, xylose,
Pentaccharoses such as ribose, maltose, lactose, trehaltose, cellobiose, isomaltose, gentiobiose, melibiose, laminaribiose, chitobiose, xylobiose, mannobiose, sophorose and other disaccharides, mantotriose, isomalttriose,
Maltotetraose, maltopentaose, mannotriose, manninotriose, etc., and hydrolysates of starch, cellulose, chitin, chitosan etc. Can be mentioned.

These benzophenone derivatives (1) are
For example, as shown below, it can be produced by reacting a 2,4-dihydroxybenzophenone derivative (2) with a halogenated sugar (3).

[0013]

[Chemical 3]

(In the formula, R ¹ , R ² , G, n and m have the same meanings as described above, X represents a halogen atom, and A ′ represents a (meth) acryloyl group.)

That is, first, in the general formula (1), the benzophenone derivative (1a) in which A is a hydrogen atom is prepared by subjecting the 2,4-dihydroxybenzophenone derivative (2) and the halogenated sugar (3) to 0- It can be obtained by reacting at 80 ° C. for 5 to 12 hours. Here, it is preferable to use the halogenated sugar (3) whose hydroxyl group is protected by a protective group such as an acetyl group. In this case, the deprotection reaction may be carried out by a usual method after the above reaction.
As the solvent, for example, dichloromethane, 1,2-dichloroethane, chloroform, benzene, toluene, xylene, N, N-dimethylformamide, tetrahydrofuran, 1,4-dioxane, ethyl ether, ethyl acetate and the like can be used. The ratio of the 2,4-dihydroxybenzophenone derivative (2) and the halogenated sugar (3) used is particularly preferably 1.2: 1.

Further, in the general formula (1), the benzophenone derivative (1b) in which A is a (meth) acryloyl group is obtained by further adding the benzophenone derivative (1a) obtained as described above to a halogenated (meth) acryloyl group. It can be obtained by reacting. The reaction is -5 to 5 in the presence of a solvent.
It may be carried out at 5 ° C. for 4 to 15 hours, and examples of the solvent include dichloromethane, 1,2-dichloroethane, chloroform, benzene, toluene, xylene, N, N-dimethylformamide, tetrahydrofuran, 1,4-dioxane, ethyl ether, Ethyl acetate or the like can be used. The ratio of the benzophenone derivative (1a) to the halogenated (meth) acryloyl used is particularly preferably 1: 1. By this reaction, the (meth) acryloyl group can be introduced into each hydroxyl group of the sugar, but the one introduced with the (meth) acryloyl group at the 6-position of the sugar is mainly the one introduced into other hydroxyl groups. Obtained as a mixture containing some.

In any case, after the completion of the reaction, the intended product can be obtained by washing, drying, treating with a silica gel column and the like by a usual method.

The benzophenone derivative (1) of the present invention thus obtained is useful as a UV absorber because it has an excellent UV absorbing action.

In the ultraviolet absorbent of the present invention, one kind or two or more kinds of the above-mentioned benzophenone derivative (1) can be used as it is, and further, within a range not impairing the ultraviolet absorbing action of the benzophenone derivative (1), Other components such as preservatives, fragrances, colorants, surfactants, metal salts and the like can also be added.

[0020]

The benzophenone derivative of the present invention (1)
Is hydrophilic and has an excellent ultraviolet absorbing action. Therefore, the ultraviolet absorbent of the present invention containing the same can be easily blended into many aqueous preparations including cosmetics. Further, among the benzophenone derivatives of the present invention, those having a (meth) acryloyl group containing a radically polymerizable double bond in the molecule can also be copolymerized with other radically polymerizable hydrophilic monomers, For example, when it is applied to a hydrophilic contact lens or an intraocular lens material, it is possible to remove glare and ultraviolet rays that are harmful to the retina.

[0021]

EXAMPLES Next, the present invention will be further described with reference to examples, but the present invention is not limited to these examples.

Example 1 Synthesis of 2-hydroxy-4- [2 '-(β-D-glucopyranosyloxy) ethoxy] benzophenone methacrylate: (1) 2-hydroxy-4- (2'-hydroxyethoxy) benzophenone Synthesis of 2,4-dihydroxybenzophenone (17.1 g, 8
0 mmol) was dissolved in methanol (100 ml) and sodium hydroxide (3.2 g, 80 mmol) was added. Water (40 ml) was added to this, and then 2-bromoethanol (6.
(7 ml, 80 mmol) was added and the mixture was refluxed overnight. After removing the methanol by vacuum concentration, add water and add
The pH was adjusted to 2. This mixture was extracted with ethyl acetate,
The ethyl acetate layer was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was treated with hexane-ethyl acetate (3: 2 v / v) on a silica gel column, the fractions containing the target compound were collected and concentrated under reduced pressure to obtain the target product as needle crystals from hexane. Yield: 8.3 g (40%) Melting point: 88-89 ° C λ _max ; 287,326 nm log ε; 4.21, 4.02 Elemental analysis value; Calculated value C, 69.25; H, 5.46 Measured value C, 69.17; H, 5.49

(2) 2-hydroxy-4- [2 '-(tetra-O-acetyl-β-D-glucopyranosyloxy)
Synthesis of ethoxy] benzophenone Penta-O-acetyl-β-D-glucopyranose (7.81 g, 20 mmol) was dissolved in a very small amount of dichloromethane and a 25% solution of hydrogen bromide in glacial acetic acid (40 ml) was added. The mixture was left at room temperature for 2 hours and dissolved in chloroform. This solution was washed with 4% sodium hydrogen carbonate and water, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and then solidified by adding hexane. Yield: 6.05 g (74%) Brominated sugar obtained by the above method (1.81 g,
7 mmol) and 2-hydroxy-4- (2 'obtained in (1)
-Hydroxyethoxy) benzophenone (2.88 g,
7 mmol) was dissolved in 1,2-dichloroethane (20 ml), and silver oxide (1.71 g) was used as an acid acceptor and reacted overnight at room temperature. After removing the silver salt by filtration, the filtrate was concentrated under reduced pressure, and hexane-ethyl acetate (1:
1 v / v), the fractions containing the desired product were collected and concentrated under reduced pressure to obtain the desired product as a film. Yield: 2.93 g (71%) Melting point: 92-92 ° C λ _max ; 286,323 nm log ε; 4.21, 4.02 Elemental analysis value; Calculated value C, 59.18; H, 5.48 Measured value C, 59.04; H, 5.51

(3) 2-hydroxy-4- [2 '-(β
Synthesis of -D-glucopyranosyloxy) ethoxy] benzophenone 2-hydroxy-4- [2 '-(tetra-
O-Acetyl-β-D-glucopyranosyloxy) ethoxy] benzophenone (2.12 g, 3.6 mmol) was suspended in ethanol (80 ml), and 2N sodium hydroxide (10.8 ml) was added. The reaction mixture was stirred at room temperature for 30 minutes and concentrated under reduced pressure. Add water to the residue, then Dowe
Sodium hydroxide was adsorbed by adding x50 (H ⁺ type). After removing the ion exchange resin by filtration, the filtrate was concentrated under reduced pressure,
The precipitated crystals were collected. As a result of elemental analysis, it was confirmed that these crystals were monohydrate. Yield: 1.24 g (82%) Melting point: 136-137 ° C λ _max ; 286,326 nm log ε; 4.21, 4.02 Elemental analysis value; Calculated value C, 57.53; H, 5.98 Measured value C, 57.45; H, 6.01

(4) 2-hydroxy-4- [2 '-(β
Synthesis of -D-glucopyranosyloxy) ethoxy] benzophenone methacrylate 2-hydroxy-4- [2 '-(β-D- obtained in (3).
Glucopyranosyloxy) ethoxy] benzophenone (1.16 g, 2.8 mmol) was added to dichloromethane (10 m
l) and N, N-dimethylformamide (10 ml) dissolved in a mixed solution, and pyridine (0.91 ml, 11.2 mmol)
Was added. A dichloromethane solution of methacryloyl chloride (0.55 ml, 5.6 mmol) was gradually added dropwise to this solution while stirring under ice cooling. The reaction mixture was stirred under ice-cooling for 2 hours, left in a refrigerator overnight, and concentrated under reduced pressure. Ethyl acetate was added to the residue, washed with 1N hydrochloric acid, 4% sodium hydrogen carbonate and water, and then dried over anhydrous sodium sulfate,
It was concentrated under reduced pressure. Then, the residue was treated with hexane-ethyl acetate (gradient having a hexane content of 50-0%) on a silica gel column, and the fractions containing the target compound were collected and concentrated under reduced pressure to give an oily substance. It was confirmed that the obtained compound was a mixture of monomethacrylates containing, as a main component, one in which methacrylate was introduced at the 6-position of glucose. Yield: 0.62 g (45%) λ _max ; 284,324 nm log ε; 4.21, 4.02 Elemental analysis value: Calculated value C, 61.47; H, 5.78 Measured value C, 61.28; H, 5.88

(5) 2-hydroxy-obtained in (3)
4- [2 '-(β-D-glucopyranosyloxy) ethoxy] benzophenone and 2-hydroxy-4- [2'-(β-D-glucopyranosyloxy) ethoxy] benzophenone obtained in (4) 1 each of methacrylate
When a 0 ppm aqueous solution was used and the spectral characteristics were measured, as shown in FIGS. 1 and 2, a good ultraviolet absorption effect was exhibited particularly at 400 nm or less.

Example 2 (1) Synthesis of 2-hydroxy-4- [2 '-(hepta-O-acetyl-β-D-cellobiosyloxy) ethoxy] benzophenone: octa-O-acetylcellobiose (3.09 g, 5 mmol) Was dissolved in a mixed solvent of dichloromethane (50 ml) and ethyl acetate (6 ml), and titanium tetrabromide (2.94 g, 8 mmol) was added. Mix the mixture at room temperature 4
After stirring for 8 hours, the mixture was cooled with ice and washed twice with ice water. The organic layer was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and then solidified with hexane. Yield: 2.66 g (76%) Brominated sugar obtained by the above method (2.66 g,
3.8 mmol) and 2-hydroxy-4- (2′-hydroxyethoxy) benzophenone (1.29 g, 5 mmol) obtained in Example 1 (1) were added to 1,2-dichloroethane (2
It was dissolved in 0 ml), and silver oxide (1.22 g) was used as an acid acceptor and reacted overnight at room temperature. Purification was performed by the same method as in Example 1 (2) to obtain the desired product as an oil. Yield: 1.83g (62%)

(2) 2-hydroxy-4- [2 '-(β
Synthesis of -D-cellobiosyloxy) ethoxy] benzophenone: 2-hydroxy-4- [2'- obtained in (1).
(Tetra-O-acetyl-β-D-cellobiosyloxy)
Ethoxy] benzophenone (1.48 g, 1.8 mmol)
Was suspended in methanol (20 ml), 2N sodium hydroxide (8.6 ml) was added, and the target product was obtained as an amorphous solid by the same procedure as in Example 1 (3). 1
Fig. 3 shows the spectral characteristics of a 0 ppm aqueous solution. Yield: 0.70 g (67%) Melting point: 96-98 ° C λ _max ; 285,324 nm log ε; 4.18, 3.99 Elemental analysis value; Calculated value C, 55.66; H, 5.88 Measured value C, 55.54; H, 5.91

Example 3 (1) Synthesis of 2-hydroxy-4- [2 '-(hepta-O-acetyl-β-D-maltosiloxy) ethoxy] benzophenone: octa-O-acetyl-D-maltose (3 0.09 g, 5 mmol) was treated in the same manner as in Example 2 (1) to obtain a colorless syrup of hepta-O-acetyl-α-D-mannosyl bromide. This was dissolved in 1,2-dichloroethane (20 ml) to give 2 obtained in Example 1 (1).
-Hydroxy-4- (2'-hydroxyethoxy) benzophenone (1.29 g, 5 mmol) and silver oxide (1.22
g) was added, and the mixture was stirred at room temperature overnight. Purification was performed in the same manner as in Example 2 (1) to obtain the target product as a pale yellow film. Yield: 2.04g (50% from octa-O-acetyl-α-maltose)

(2) 2-hydroxy-4- [2 '-(β
Synthesis of -D-maltosiloxy) ethoxy] benzophenone: 2-hydroxy-4- [2'- obtained in (1).
(Tetra-O-acetyl-β-D-maltosiloxy) ethoxy] benzophenone (1.82 g, 2.2 mmol) was suspended in methanol (20 ml), 2N sodium hydroxide (12 ml) was added, and Example 1 ( By the same operation as in 3), the target product was obtained as an amorphous solid. 10 pp
The spectral characteristics of the m 2 aqueous solution are shown in FIG. Yield: 0.87 g (68%) Melting point: 74-73 ° C λ _max ; 287,318 nm log ε; 4.21, 4.06 Elemental analysis value; Calculated value C, 55.66; H, 5.88 Measured value C, 55.56; H, 5.93

Example 4 (1) Synthesis of 2-hydroxy-4- [2 '-(hepta-O-acetyl-β-D-lactosiloxy) ethoxy] benzophenone: octa-O-acetyl-D-lactose (3 0.09 g, 5 mmol) was treated in the same manner as in Example 2 (1) to obtain a colorless syrup of hepta-O-acetyl-α-D-lactosyl bromide. This was dissolved in 1,2-dichloroethane (20 ml) to give 2 obtained in Example 1 (1).
-Hydroxy-4- (2'-hydroxyethoxy) benzophenone (1.29 g, 5 mmol) and silver oxide (1.22
g) was added, and the mixture was stirred at room temperature overnight. Purification was performed in the same manner as in Example 2 (1) to obtain the target product as a pale yellow film. Yield: 2.07g (51% from octa-O-acetyl-D-lactose)

(2) 2-hydroxy-4- [2 '-(β
Synthesis of -D-lactosyloxy) ethoxy] benzophenone: 2-hydroxy-4- [2'- obtained in (1).
(Tetra-O-acetyl-β-D-lactosyloxy) ethoxy] benzophenone (1.93 g, 2.4 mmol) was suspended in methanol (20 ml), 2N sodium hydroxide (12 ml) was added, and Example 1 ( By the same operation as in 3), the target product was obtained as an amorphous solid. 10 pp
The spectral characteristics of the m 2 aqueous solution are shown in FIG. Yield: 0.84 g (60%) Melting point: 216-220 ° C λ _max ; 289,318 nm log ε; 4.10, 3.94 Elemental analysis value; Calculated value C, 55.66; H, 5.88 Measured value C, 55.61; H, 5.91

Example 5 Synthesis of 4- (D-glucosyloxy) -2-hydroxybenzophenone: 2,4-dihydroxybenzophenone (1.47 g, 6.8 mmol) was dissolved in methanol (20 ml) and 28% sodium methyl ester was added. A methanol solution (1.31 g) of the solution was gradually added dropwise. Anhydrous sodium carbonate (1.80 g, 17 mmol) was added, followed by Example 1 (2).
Tetra-O-acetyl-α-D-prepared in the same manner as
Glucopyranosyl bromide (2.35 g, 5.7 mmol)
Was added and the mixture was stirred at 80 ° C. overnight. The reaction mixture was allowed to cool, the insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. Water was added to the residue, and the pH was adjusted to 4 with 4N hydrochloric acid. The mixture was extracted twice with ethyl acetate, the ethyl acetate layers were combined, washed with saturated brine, and dried over anhydrous sodium sulfate. After concentration under reduced pressure, the desired product was crystallized from hexane. Fig. 6 shows the spectral characteristics of a 10 ppm aqueous solution. Yield: 0.53 g (25%) Melting point: 166-168 ° C λ _max ; 282,327 nm log ε; 4.20, 3.91 Elemental analysis value; Calculated value C, 60.63; H, 5.36 Measured value C, 60.56; H, 5.39

Example 6 Synthesis of 4- (D-cellobiosyloxy) -2-hydroxybenzophenone: 2,4-dihydroxybenzophenone (4.28 g, 20 mmol) was dissolved in methanol (50 ml) and 28% sodium methylate methanol was added. The solution (2.90 g) was added dropwise. Anhydrous sodium carbonate (5.
62 g) was added, hepta-O-acetyl-α-D-cellobiosyl bromide (5.52 g, 7.9 mmol) prepared in the same manner as in Example 2 (1) was added, and the mixture was stirred at 80 ° C. overnight. did. The insoluble material was filtered off, concentrated hydrochloric acid was added to adjust the pH to 4, and the mixture was concentrated under reduced pressure. A small amount of methanol was added again to the residue, the insoluble material was filtered off, and the filtrate was concentrated again under reduced pressure. The residue was dissolved in a very small amount of methanol and applied to a silica gel column, followed by chloroform-methanol (5: 1 v /
Flash column chromatography was performed using v). Collect the fractions containing the desired product, concentrate under reduced pressure,
The target product was obtained as an amorphous solid. Fig. 7 shows the spectral characteristics of a 10 ppm aqueous solution. Yield: 1.18 g (28%) Melting point: 184-189 ° C (decomposition) λ _max ; 281,324 nm log ε; 4.10, 3.81 Elemental analysis value; Calculated value C, 55.76; H, 5.62 Measured value C, 55.67; H, 5.67

Example 7 Synthesis of 4- (D-maltosiloxy) -2-hydroxybenzophenone: 2,4-dihydroxybenzophenone (2.14 g, 10 mmol), 28% sodium methylate in methanol (1.95 g), Anhydrous sodium carbonate (2.81 g) and hepta-O-acetyl-α-D-maltosyl bromide (2.45 g, 3.5 mmol) prepared in the same manner as in Example 3 (1) were used in the same manner as in Example 6. The target product was obtained as a hygroscopic amorphous solid. Fig. 8 shows the spectral characteristics of a 10 ppm aqueous solution. Yield: 0.24 g (13%) λ _max ; 280,326 nm log ε; 4.06, 3.78 Elemental analysis: Calculated C, 55.76; H, 5.62 Measured C, 55.64; H, 5.69

Example 8 Synthesis of 4- (D-lactosyloxy) -2-hydroxybenzophenone: 2,4-dihydroxybenzophenone (2.14 g, 10 mmol), 28% sodium methylate in methanol (1.95 g), Anhydrous sodium carbonate (2.81 g) and hepta-O-acetyl-α-D-lactosyl bromide (2.45 g, 3.5 mmol) prepared in the same manner as in Example 4 (1) were used in the same manner as in Example 6. And the desired product was obtained as crystals. FIG. 9 shows the spectral characteristics of a 10 ppm aqueous solution. Yield: 0.40 g (21%) Melting point: 171-175 ° C λ _max ; 282,324 nm log ε; 4.11, 3.83 Elemental analysis value; Calculated value C, 55.76; H, 5.62 Measured value C, 55.71; H, 5.62

Test Example 1 The hydrophilicity of each of the following compounds 1 to 6 prepared in the examples and compounds 7 to 8 conventionally used as an ultraviolet absorber was examined. That is, each compound was evaluated as ◯ when a 10 wt% aqueous solution was formed, as x when it could not be formed, and as Δ when it was heated. The results are shown in Table 1.

[0038]

[Chemical 4]

[0039]

[Chemical 5]

[0040]

[Table 1]

Reference Example 1 5-hydroxyethyl methacrylate (HEMA) 5 g
In contrast, the polymerization initiator azobisisobutyronitrile (AI
BN) 0.1% by weight, and 2-hydroxy-4- (2 '-(β-D-glucopyranosyloxy) obtained in Example 1
Add 0 to 5% by weight of (ethoxy) benzophenone methacrylate, put it between the slide glasses with a spacer of 0.5 mm in thickness, and put it in a test tube.
After nitrogen substitution and deaeration, polymerization was carried out at 50 ° C. for 72 hours and 70 ° C. for 48 hours. The spectral characteristics of the obtained sample are shown in FIG. Since this sample effectively removes ultraviolet rays, it can be used as an intraocular lens material.

Reference Example 2 5 g of a mixed monomer obtained by mixing 0.5 equivalent of a 50% aqueous solution of 2-glucosylethyl methacrylate (GEMA) with 1 equivalent of HEMA, 0.1 wt% of AIBN, and 2- Hydroxy-4- (2 '-(β-D-
Glucopyranosiloxy) ethoxy) benzophenone methacrylate was added in an amount of 0 to 5% by weight, and polymerization was carried out in the same manner as in Reference Example 1. The spectral characteristics of the obtained sample are shown in FIG.
Since this sample effectively removes ultraviolet rays, it can be used as an intraocular lens material.

[Brief description of drawings]

FIG. 1 is the 2-hydroxy-4 obtained in Example 1 (3).
It is a figure which shows the spectral characteristic of-[2 '-((beta) -D-glucopyranosyloxy) ethoxy] benzophenone.

FIG. 2 is the 2-hydroxy-4 obtained in Example 1 (4).
It is a figure which shows the spectral characteristic of- [2 '-((beta) -D-glucopyranosyloxy) ethoxy] benzophenone methacrylate.

FIG. 3 is the 2-hydroxy-4-obtained in Example 2.
It is a figure which shows the spectral characteristic of [2 '-((beta) -D-cellobiosyloxy) ethoxy] benzophenone.

FIG. 4 is the 2-hydroxy-4-obtained in Example 3.
It is a figure which shows the spectral characteristic of [2 '-((beta) -D-maltosiloxy) ethoxy] benzophenone.

FIG. 5: 2-hydroxy-4-obtained in Example 4
It is a figure which shows the spectral characteristic of [2 '-((beta) -D-lactosiloxy) ethoxy] benzophenone.

FIG. 6 is a diagram showing a spectral characteristic of 4- (D-glucosiloxy) -2-hydroxybenzophenone obtained in Example 5.

FIG. 7 is a diagram showing a spectral characteristic of 4- (D-cellobiosyloxy) -2-hydroxybenzophenone obtained in Example 6.

FIG. 8 is a view showing a spectral characteristic of 4- (D-maltosiloxy) -2-hydroxybenzophenone obtained in Example 7.

9 is a diagram showing a spectral characteristic of 4- (D-lactosyloxy) -2-hydroxybenzophenone obtained in Example 8. FIG.

10 is a diagram showing the spectral characteristics of the sample obtained in Reference Example 1. FIG.

11 is a diagram showing spectral characteristics of a sample obtained in Reference Example 2. FIG.

Claims (2)

[Claims] 1. A compound represented by the general formula (1): (In the formula, A represents a hydrogen atom or a (meth) acryloyl group, G represents a sugar residue having no protective group, R ¹ represents a hydrogen atom or a methyl group, and R ² represents a hydrogen atom or a methyl group. Or a benzophenone derivative represented by an alkoxy group having 1 to 8 carbon atoms, n is a number of 2 to 6, and m is 0 or 1. 2. An ultraviolet absorber containing the benzophenone derivative according to claim 1.