JP2003221397A - 2-methoxy-4-glucosaminomethylphenol - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To obtain a glycoside with low odor having a high water solubility, a tyrosinase inhibiting activity, an active oxygen scavenging activity, an antibacterial activity and little side effects on the human body, and also to provide a method for producing the glycoside at a low cost with a high industrial productivity. <P>SOLUTION: 2-Methoxy-4-glucosaminomethylphenol of formula (I) and a Shiff base compound of formula (II) are provided. A method for producing 2-methoxy-4-glucosaminomethylphenol which reduces a Shiff base compound of formula (II) and a method for producing the Shiff base compound by reacting D-glucosamine of formula (III) with vanillin are also provided. In addition, uses of the 2-methoxy-4-glucosaminomethylphenol, such as a cosmetic containing the compound, are also provided. <P>COPYRIGHT: (C)2003,JPO

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to 2-methoxy-4.
-Glucosaminomethylphenol. More specifically, whitening agents, antioxidants, antibacterial agents, fragrances, cosmetics such as whitening cosmetics, various pharmaceuticals, quasi drugs, foods,
2-methoxy-4-glucosaminomethylphenol which can be suitably used for beverages and the like, and a method for producing the same, and 2
TECHNICAL FIELD The present invention relates to a Schiff base compound which is an intermediate for producing methoxy-4-glucosaminomethylphenol and a method for producing the same.

[0002]

2. Description of the Related Art Women always want to be beautiful regardless of age. And, as can be seen as the "white-fish-like hand," it is an eternal task for women to have white and delicate skin.

In order to solve this problem, various studies have been conducted so far. For example, it is considered that the cause of skin darkening due to exposure to ultraviolet rays and the formation of spots and freckles is due to melanin produced by melanocytes of skin tissues. In this melanocyte, tyrosine, which is an amino acid, is oxidized, and melanin is finally produced through the pathways of dopa, dopaquinone, dopachrome, and dihydroxyindole.

All of these chemical reactions are oxidation reactions, and as a substance acting as an in-vivo catalyst for the reaction,
Tyrosinase active enzyme and active oxygen in the body are known.

Arbutin, kojic acid and the like are known as substances that inhibit this tyrosinase active enzyme. Also, as substances that trap active oxygen in the body, catechins, polyphenols represented by flavonoids, capsaicin, which is the hot taste component of capsicum, ferulic acid, which is often contained in rice bran, and eugenol extracted from clove buds. Substances that exhibit an active oxygen scavenging effect such as and isoeugenol are known.

These compounds have some things in common. The common point is, for example, that it has many phenolic hydroxyl groups or hydroxyl groups similar thereto. Usually, phenolic hydroxyl groups are reductive and have the ability to form a copper ion complex that greatly affects the inhibition of tyrosinase-activating enzyme, so they are expected to be effective in both inhibiting tyrosinase-activating enzyme and eliminating active oxygen in the body. ing.

The efficacy of arbutin is due to the hydroquinone in the structure. Hydroquinone itself has the effect of bleaching the skin, but its efficacy is too strong,
Since it has low solubility in water, it is used after hydroquinone has been converted into a glycoside.

Also, ferulic acid and eugenol are difficult to dissolve in water like arbutin, and therefore, it has been proposed to use them as glycosides (Japanese Patent Laid-Open No. 06-06206).
-256137, JP 2000-96O78).

However, glycosides of these compounds having a phenolic hydroxyl group are usually biosynthesized by microorganisms or enzymes that relax toxins, or synthesized using γ-halogenated glucose obtained through several steps. Since the synthetic method is adopted, it is not suitable for mass production and has a drawback of high cost.

[0010]

DISCLOSURE OF THE INVENTION The present invention has been made in view of the above-mentioned prior art and has good water solubility,
Tyrosinase active enzyme inhibition, active oxygen scavenging, excellent antibacterial and low odor properties, and has few side effects on the human body.
It is an object to provide a glycoside having a phenolic hydroxyl group in the molecule. Another object of the present invention is to provide a method capable of inexpensively producing a glycoside having a phenolic hydroxyl group in the molecule with high industrial productivity.

It is an object of the present invention to provide a production intermediate which can be suitably used for the production of glycoside having a phenolic hydroxyl group in the molecule and a production method thereof. The present invention further relates to various uses in which a glycoside having a phenolic hydroxyl group in the molecule is used.

[0012]

The present invention provides (1) formula (I):

[0013]

[Chemical 12]

2-methoxy-4-glucosaminomethylphenol represented by: (2) Formula (II):

[0015]

[Chemical 13]

2-methoxy-4 represented by the formula (I), which is characterized by reducing the Schiff base compound represented by
-Glucosaminomethylphenol production method, (3) Formula (II)
A Schiff base compound represented by (4) formula (III):

[0017]

[Chemical 14]

D-glucomican represented by the formula (IV):

[0019]

[Chemical 15]

A method for producing a Schiff base compound represented by the formula (II), which comprises reacting with vanillin represented by the formula (5): 2-methoxy-4-gluco represented by the formula (I) Cosmetics containing Saminomethylphenol, (6) Antioxidant consisting of 2-methoxy-4-glucosaminomethylphenol represented by Formula (I), (7) Represented by Formula (I) The present invention relates to an antibacterial agent comprising 2-methoxy-4-glucosaminomethylphenol, and (8) a fragrance comprising 2-methoxy-4-glucosaminomethylphenol represented by the formula (I).

[0021]

BEST MODE FOR CARRYING OUT THE INVENTION 2 represented by the formula (I) of the present invention
Methoxy-4-glucosaminomethylphenol (hereinafter,
2-methoxy-4-glucosaminomethylphenol) is a Schiff base compound represented by the formula (II) as a production intermediate thereof (hereinafter simply referred to as Schiff base compound).
Can be manufactured by using.

The Schiff base compound represented by the formula (II) includes a D-glucominsan represented by the formula (III) (hereinafter simply referred to as D-glucominsan) and a vanillin represented by the formula (IV) ( Hereinafter, simply referred to as vanillin).

Both D-glucominsan and vanillin are readily available compounds. Alternatively, D-glucominsan hydrochloride may be used in place of D-glucominsan, and D-glucominsan hydrochloride may be reacted with a base such as sodium hydroxide in water to generate D-glucominsan.

The reaction between D-glucominsan and vanillin is carried out by reacting the amino group of D-glucominsan with the aldehyde group of vanillin. Therefore, the amount of D-glucominsan and vanillin is stoichiometrically such that the amino group of D-glucominsan and the aldehyde group of vanillin are equimolar, but usually from the viewpoint of reducing the amount of unreacted compound. Therefore, the amount of the aldehyde group of vanillin is 1 mol of the amino group of D-glucominsan.
It may be about 0.8 to 1.2 mol.

The reaction between D-glucominsan and vanillin can be usually carried out in a solvent.

As the solvent, for example, water; methanol,
Alcohols such as ethanol; ketones such as acetone and methyl ethyl ketone; ethers such as diethyl ether and tetrahydrofuran; aromatic compounds such as benzene, toluene and xylene; acetic acid esters such as methyl acetate and ethyl acetate. Can be used alone or in admixture of two or more. Of these, water and ethanol can be preferably used in the present invention.

The amount of the solvent is not particularly limited, but usually D
-The total amount of glucominsan and vanillin is 100 to 1000 parts by volume, preferably about 300 to 600 parts by volume, relative to 100 parts by volume.

The reaction temperature is from the viewpoint of accelerating the reaction.
It is desirable that the temperature is 10 ° C. or higher, preferably 20 ° C. or higher. However, if the temperature is too high, it causes coloring, so 100 ° C. or lower, preferably 50 ° C. or lower.

The atmosphere during the reaction is not particularly limited. Such an atmosphere may be atmospheric air or an inert gas such as nitrogen gas or argon gas.

The reaction time is not particularly limited, but is usually 0.
It takes about 5 to 6 hours. The end point of the reaction can be easily confirmed by, for example, disappearance of raw materials by high performance liquid chromatography (HPLC) or gas chromatography.

Thus, a reaction solution containing the Schiff base compound is obtained. When the obtained Schiff base compound is isolated from the reaction solution, the Schiff base compound may be precipitated by distilling the solvent from the reaction solution, and the precipitated Schiff base compound may be recovered by filtration.

Since the obtained Schiff base compound is contained in the reaction solution, 2-methoxy-4-glucosaminomethylphenol is produced without isolating the Schiff base compound from the reaction solution. In order to do so, the reaction solution may be subjected to reduction as it is. This method is preferable from the viewpoint of obtaining 2-methoxy-4-glucosaminomethylphenol in good yield.

As described above, the Schiff base compound can be suitably used as an intermediate for the production of 2-methoxy-4-glucosaminomethylphenol of the present invention.

The 2-methoxy-4-glucosaminomethylphenol of the present invention can be easily produced by reducing a Schiff base compound.

The reduction of the Schiff base compound is carried out, for example, by a hydrogen reduction method in which hydrogen gas is blown into a solution in which the Schiff base compound is dissolved or suspended in a solvent, or in a solution in which a reducing compound is dissolved or suspended in the solvent. It can be easily carried out by a method of dropping a solution prepared by dissolving or suspending a Schiff base compound in a solvent.

When the reduction is carried out by the former method, a palladium catalyst, a platinum catalyst, a Raney nickel catalyst or the like can be used as a catalyst. When the reduction is carried out by the latter method, as the reducing compound, for example, sulfur dioxide, sodium hydrogen sulfite, sodium sulfite, acetaldehyde derivative, sodium borohydride, sodium cyanoborohydride, alkylaluminum compound and the like can be used. it can. The amounts of these catalysts and reducing compounds differ depending on their types and so cannot be determined unconditionally. Usually, the amount of catalyst and reducing compound is above the theoretical amount required to reduce the Schiff base compound.

As the solution in which the Schiff base compound is dissolved or suspended in a solvent, a reaction solution of D-glucominsan and vanillin can be used, or the Schiff base compound is dissolved or suspended in the above-mentioned solvent. Different solutions can be used. From the viewpoint of accelerating the reduction reaction, the amount of the solvent used in such a solution is usually about 300 to 5000 parts by weight, preferably about 500 to 1500 parts by weight, relative to 100 parts by weight of the Schiff base compound. .

The liquid temperature of the solution during the reduction is 10 to 80 ° C., preferably 30 to 50 ° C., from the viewpoint of promoting the reduction reaction efficiently.
Is desirable.

The time required for the reduction reaction of the Schiff base compound cannot be unconditionally determined because it depends on the amount of the Schiff base compound, the liquid temperature of the solution, etc.
~ 40 hours.

The termination of the reduction reaction can be carried out, for example, by confirming the disappearance of the Schiff base compound by high performance liquid chromatography (HPLC) or the like.

Thus, 2-methoxy-4-glucosaminomethylphenol can be obtained. Since the reaction solution contains a solvent and the like, it can be removed, washed and purified by a conventional method. desirable.

As described above, according to the production method of the present invention, a Schiff base compound can be easily prepared by reacting D-glucomysan with vanillin, and from the obtained Schiff base compound. The desired compound, 2-methoxy-4-glucosaminomethylphenol, can be easily produced by a simple operation.

Therefore, the production method of the present invention has an advantage that 2-methoxy-4-glucosaminomethylphenol can be easily produced on an industrial scale and economically.

The 2-methoxy-4-glucosaminomethylphenol of the present invention has good water solubility, is excellent in tyrosinase active enzyme inhibition, active oxygen scavenging, antibacterial property and low odor, and moreover, is suitable for human body. It exhibits excellent physical properties with few side effects.

Therefore, the 2-methoxy-4-of the present invention
Glucosaminomethylphenol can be used alone as a whitening agent, an antioxidant, an antibacterial agent, a fragrance, etc., as well as cosmetics such as whitening cosmetics, various pharmaceuticals such as skin external medicines, and skin medications. It can also be suitably used for various quasi drugs such as quasi drugs, foods, beverages and the like. Especially, 2-methoxy-4-glucosaminomethylphenol of the present invention can be preferably used for cosmetics.

Examples of the form of the cosmetics include various types of lotion such as astringent lotion; various lotions such as after-shave lotion; milky lotion; various creams such as massage cream and nutrition cream; paste-like wash-off packs and peel-off types. Examples include various pack agents such as pack agents, but the present invention is not limited to such examples.

When the 2-methoxy-4-glucosaminomethylphenol of the present invention is used for these purposes,
The amount of the 2-methoxy-4-glucosaminomethylphenol cannot be unconditionally determined because it varies depending on its application. Therefore, such 2-methoxy-4
-The amount of glucosaminomethylphenol may be appropriately determined according to its application. As an example thereof, 2 of the present invention
When -methoxy-4-glucosaminomethylphenol is used in cosmetics, for example, the content in the cosmetics is
It is desirable to adjust the amount to about 0.1 to 50% by weight, preferably about 3 to 30% by weight.

In using the 2-methoxy-4-glucosaminomethylphenol of the present invention for these purposes, for example, an emulsifier, a gelling agent,
It can be used in combination with a surfactant, an antioxidant, a fragrance, an antiseptic, a pigment, a fatty substance, a vitamin, a nutrient, a moisturizer, an anti-UV agent and the like.

[0049]

EXAMPLES Next, the present invention will be described in more detail based on examples and prescription examples, but the present invention is not limited to such examples and prescription examples.

Example 1 A 1000-mL five-flask flask equipped with a reflux condenser, a dropping funnel, a thermometer, a nitrogen gas introducing tube, and a stirring device,
10 g (46.4 mol) of D-glucosamine hydrochloride and 1.88 g (46.4 mol) of sodium hydroxide were added, the contents were mixed with a stirrer, and water was added so that the component concentration would be 70% by weight. Thereby, an aqueous solution of D-glucomysan was obtained.

Next, 7.1 g of vanillin was added to the obtained aqueous solution.
Dissolve (46.4mol) in 7.1g of ethanol and add the solution,
After stirring at room temperature for 6 hours, a precipitate of pale yellow crystals was obtained. 11.4 mg of the obtained precipitate was collected by filtration (yield 80%).

The obtained precipitate had the following physical properties and was confirmed to be a Schiff base compound represented by the formula (II).

Melting point: 170.6 ° C. Elemental analysis Measured value C: 53.20%, H: 5.85%, N: 4.30% Theoretical value C: 53.67%, H: 6.11%, N: 4.47%

Example 2 10 mg of the Schiff base compound obtained in Example 1 was added to 500 m of purified water.
After being dispersed in L, 0.6 g of palladium carbon was added to the dispersion. After that, the Schiff base compound was reduced by stirring at 50 ° C. for 48 hours while blowing hydrogen gas into the solution.

The completion of the reduction reaction was confirmed by the disappearance of the peak due to the Schiff base compound by liquid chromatography.

Next, the obtained reaction solution was dried by spray drying to obtain 9.0 mg of pale yellow to dark brown crystals (yield
90%).

Since the obtained crystal had the following physical properties, it was confirmed to be 2-methoxy-4-glucosaminomethylphenol represented by the formula (I).

Melting point: 122.8 ° C. Elemental analysis measured value C: 50.50%, H: 6.17%, N: 6.09% Theoretical value C: 53.33%, H: 6.71%, N: 4.44% MS: 316, 302, 293, 179 , 137, 124, 112, 99,
65

¹ H-NMR (δ: ppm): 3.02-3.067 (m, m, 2H, -C
H ₂ -OH), 3.680 (s, 3H, -OC H ₃ ), 4.036 (m, 2H, -NH-C H ₂
-), 5.019 (s, 1H , - NH -CH 2 -), 6.648 (d, 1H, Ph), 7.07
2 (m, 1H, Ph), 7.150 (m, 1H, Ph), 9.271 (s, 1H, Ph- O
H )

Next, the physical properties of the obtained 2-methoxy-4-glucosaminomethylphenol were examined by the following methods.

(1) 20% of water-soluble 2-methoxy-4-glucosaminomethylphenol
When dissolved in water at ℃ to prepare a 10 wt% aqueous solution,
2-Methoxy-4-glucosaminomethylphenol was quickly dissolved in water to obtain a transparent aqueous solution. From this, it can be seen that 2-methoxy-4-glucosaminomethylphenol is excellent in water solubility.

(2) Tyrosinase-activating enzyme inhibition A 10 mmol / L aqueous solution of DL-tyrosine was prepared, and 20 mg of the obtained aqueous solution was charged with 0.5 mg of tyrosinase enzyme, and 2-methoxy-4-glucosaminomethylphenol was added thereto. 6
3.2 mg (0.2 mmol) was added to obtain a sample.

On the other hand, in order to compare with the sample, DL-
A 10 mmol / L aqueous solution of tyrosine was prepared and the resulting aqueous solution 20
After adding 0.5 mg of tyrosinase enzyme to mL, add 2-
A control sample without the addition of methoxy-4-glucosaminomethylphenol was obtained.

Next, 20 mL of each of the sample and the control sample was placed in a 50 mL colorimetric tube and kept at 36 ° C. for 24 hours.

As a result, the color of the sample was lighter than that of the control sample. From this, 2-methoxy-
Since 4-glucosaminomethylphenol inhibits tyrosinase-activating enzyme, it can be seen that it can be preferably used as a tyrosinase inhibitor.

(3) Odor The odor of 2-methoxy-4-glucosaminomethylphenol was examined by the sense of smell. As a result, it was confirmed that 2-methoxy-4-glucosaminomethylphenol continuously expresses a sweet odor like vanillin. From this,
2-methoxy-4-glucosaminomethylphenol is
It can be seen that it can be suitably used as a vanillin flavor.

Formulation Example 1 (whitening cream) A whitening cream (vanishing cream) was obtained by mixing the following components at room temperature (about 20 ° C) with stirring.

[0068] Composition (% by weight) Stearic acid 8.0 Stearyl alcohol 4.0 N-Butyl stearate 6.0 Propylene glycol 5.0 Glycerin monostearate 2.0 2-Methoxy-4-glucosaminomethylphenol powder 10.0 Potassium hydroxide 1.0 Preservative Suitable amount Antioxidant Appropriate amount Fragrance suitable amount Deionized water balance (Total) 100.0

Formulation 2 (whitening lotion) A whitening lotion (emollient lotion) was obtained by mixing the following components at room temperature (about 20 ° C) with stirring.

[0070] Composition (% by weight) Cetyl alcohol 1.0 Beeswax 0.5 Vaseline 2.0 Squalane 6.0 Dimethyl polysiloxane 2.0 Ethanol 5.0 Glycerin 4.0 1,3-butylene glycol 4.O Polyoxyethylene (10) monooleate 1.0 Glycerol monostearate 1.0 2-Methoxy-4-glucosaminomethylphenol powder 15.0 Quinceseed extract (5% aqueous solution) 20.0 Preservative Suitable amount Antioxidant Appropriate amount Fragrance suitable amount Deionized water balance (Total) 100.0

Prescription Example 3 (Whitening pack mask) The following components were mixed at room temperature (about 20 ° C) with stirring to obtain a whitening pack mask (jelly-like peel-off type pack).

[0072] Composition (% by weight) Polyvinyl alcohol 15.0 Carboxymethyl cellulose 5.0 1,3-butylene glycol 5.0 Ethanol 12.0 2-Methoxy-4-glucosaminomethylphenol powder 15.O Polyoxyethylene oleyl alcohol ether 0.5 Preservative Suitable amount Buffering agent Antioxidant Appropriate amount Fragrance suitable amount Deionized water balance (Total) 100.0

Formulation Example 4 (Whitening pack mask) The following components were mixed at room temperature (about 20 ° C) with stirring to obtain a whitening pack mask (paste peel-off type pack mask).

[0074] Composition (% by weight) Polyvinyl acetate emulsion 15.0 Polyvinyl alcohol 10.0 Sorbitol 5.O Polyethylene glycol 400 5.0 Jojoba oil 2.0 Squalane 2.0 Polyoxyethylene sorbitan monostearate 1.0 Titanium oxide 5.0 Talc 10.0 Ethanol 8.0 2-Methoxy-4-glucosaminomethylphenol powder 15.0 Preservative Suitable amount Fragrance suitable amount Deionized water balance (Total) 100.0

Comparative Prescription Example 1 Whitening cream was prepared in the same manner as in Prescription Example 1, except that 10.0 wt% of kojic acid was used instead of 10.0 wt% of 2-methoxy-4-glucosaminomethylphenol. (Vanishing cream) was obtained.

Comparative Formulation Example 2 Whitening lotion was prepared in the same manner as in Formulation Example 2 except that 15.0% by weight of kojic acid was used in place of 15.0% by weight of 2-methoxy-4-glucosaminomethylphenol. (Emollient lotion).

Comparative Prescription Example 3 Whitening pack in the same manner as in Prescription Example 3 except that 15.0 wt% of kojic acid was used instead of 15.0 wt% of 2-methoxy-4-glucosaminomethylphenol in Prescription Example 3. (Jelly-like peel-off type pack) was obtained.

Comparative Prescription Example 4 Whitening pack in the same manner as in Prescription Example 4 except that 15.0 wt% of kojic acid was used in place of 15.0 wt% of 2-methoxy-4-glucosaminomethylphenol in Prescription Example 4. (Paste peel-off type pack) was obtained.

Test Examples 20 subjects (female) who randomly selected each of the cosmetics obtained in Formulation Examples 1 to 4 and Comparative Formulation Examples 1 to 4 respectively
A sensory test was conducted on the whitening effect and skin irritation.

The conditions for applying each cosmetic are as follows. Prescription Example 1 and Comparative Prescription Example 1: Morning (after waking up) on the entire face
And, at night (before going to bed), the operation of applying the cream once each is performed for one week. Prescription Example 2 and Comparative Prescription Example 2: Whole face, morning (after waking up)
And at night (before going to bed), apply the lotion once each for one week. Prescription Examples 3 to 4 and Comparative Prescription Examples 3 to 4: A pack is applied to the entire face once at night, and after 10 minutes, the pack is peeled off for one week.

One week after the start of use, each subject was evaluated according to the following evaluation method.

[Evaluation Method] (a) Whitening Effect (Evaluation Criteria) 5 points: Dullness disappeared as compared with before use, and the skin was clearly white and bright. 3 points: Skin became slightly whiter than before use. 0 point: No change from before use.

(B) Irritation 5 points: There is no tingling sensation or itching on the skin. 3 points: There is a tingling sensation on the skin. 0 points: I feel pain in the skin.

Next, for each evaluation item, the scores of 20 persons were totaled to obtain a total score, and the following ranking was performed.
The results are shown in Table 1.

[0085] A: Total score is 90 points or more B: Total score of 80-89 C: Total score 70-79 D: Total score 60-69 E: Total score is 59 points or less

[0086]

[Table 1]

From the results shown in Table 1, the cosmetics obtained in Formulation Examples 1 to 4 all showed an excellent whitening effect,
Moreover, it can be seen that it is safe without irritation (side effects) to the skin.

On the other hand, the cosmetics obtained in Comparative Formulation Examples 1 to 4 all show an excellent whitening effect,
It can be seen that the irritation to the skin is strong and side effects are a concern.

[0089]

INDUSTRIAL APPLICABILITY The 2-methoxy-4-glucosaminomethylphenol of the present invention has good water solubility, is excellent in tyrosinase active enzyme inhibition, active oxygen scavenging, antibacterial property and low odor, and has a human health effect. It has the effect of few side effects. Therefore, 2-methoxy-4-glucosaminomethylphenol of the present invention includes whitening agents, antioxidants, antibacterial agents, fragrances, cosmetics such as whitening cosmetics, various pharmaceuticals, quasi drugs, foods, It can be suitably used for beverages and the like.

Further, according to the production method of the present invention, 2-methoxy-4-glucosaminomethylphenol can be produced at low cost and with good industrial productivity by using a Schiff base compound which can be easily produced.

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Claims (8)

[Claims] 1. Formula (I): 2-Methoxy-4-glucosaminomethylphenol represented by: 2. Formula (II): A Schiff base compound represented by the formula (I) characterized by reducing: A method for producing 2-methoxy-4-glucosaminomethylphenol represented by: 3. Formula (II): embedded image A Schiff base compound represented by. 4. Formula (III): And D-glucomysan represented by the formula (IV): The formula characterized by reacting with vanillin represented by
(II): [Chemical 7] A method for producing a Schiff base compound represented by. 5. Formula (I): embedded image A cosmetic comprising 2-methoxy-4-glucosaminomethylphenol represented by: 6. Formula (I): embedded image An antioxidant consisting of 2-methoxy-4-glucosaminomethylphenol represented by: 7. Formula (I): embedded image An antibacterial agent consisting of 2-methoxy-4-glucosaminomethylphenol represented by: 8. Formula (I): embedded image A fragrance composed of 2-methoxy-4-glucosaminomethylphenol represented by: