JPH0446191A - Kojic acid derivative - Google Patents
Kojic acid derivativeInfo
- Publication number
- JPH0446191A JPH0446191A JP15052590A JP15052590A JPH0446191A JP H0446191 A JPH0446191 A JP H0446191A JP 15052590 A JP15052590 A JP 15052590A JP 15052590 A JP15052590 A JP 15052590A JP H0446191 A JPH0446191 A JP H0446191A
- Authority
- JP
- Japan
- Prior art keywords
- kojic acid
- formula
- glucose
- culture
- anhydrous
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- BEJNERDRQOWKJM-UHFFFAOYSA-N kojic acid Chemical class OCC1=CC(=O)C(O)=CO1 BEJNERDRQOWKJM-UHFFFAOYSA-N 0.000 title claims abstract description 13
- 239000000126 substance Substances 0.000 claims description 2
- 229960004705 kojic acid Drugs 0.000 abstract description 20
- WZNJWVWKTVETCG-UHFFFAOYSA-N kojic acid Natural products OC(=O)C(N)CN1C=CC(=O)C(O)=C1 WZNJWVWKTVETCG-UHFFFAOYSA-N 0.000 abstract description 20
- 150000001875 compounds Chemical class 0.000 abstract description 12
- -1 Kojic acid glucoside Chemical class 0.000 abstract description 11
- 229930182478 glucoside Natural products 0.000 abstract description 10
- 230000002401 inhibitory effect Effects 0.000 abstract description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract description 9
- 230000000694 effects Effects 0.000 abstract description 9
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 abstract description 6
- 239000008103 glucose Substances 0.000 abstract description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract description 4
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 abstract description 3
- 239000002253 acid Substances 0.000 abstract description 3
- 230000002378 acidificating effect Effects 0.000 abstract description 3
- 239000003456 ion exchange resin Substances 0.000 abstract description 3
- 229920003303 ion-exchange polymer Polymers 0.000 abstract description 3
- 238000002360 preparation method Methods 0.000 abstract description 3
- 239000007787 solid Substances 0.000 abstract description 3
- 239000004480 active ingredient Substances 0.000 abstract description 2
- 239000002537 cosmetic Substances 0.000 abstract description 2
- 239000007788 liquid Substances 0.000 abstract description 2
- 239000011259 mixed solution Substances 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- XUMBMVFBXHLACL-UHFFFAOYSA-N Melanin Chemical compound O=C1C(=O)C(C2=CNC3=C(C(C(=O)C4=C32)=O)C)=C2C4=CNC2=C1C XUMBMVFBXHLACL-UHFFFAOYSA-N 0.000 abstract 2
- 102000003425 Tyrosinase Human genes 0.000 abstract 1
- 108060008724 Tyrosinase Proteins 0.000 abstract 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 239000002609 medium Substances 0.000 description 9
- 230000008099 melanin synthesis Effects 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000000862 absorption spectrum Methods 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 201000001441 melanoma Diseases 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000002054 inoculum Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 239000001888 Peptone Substances 0.000 description 2
- 108010080698 Peptones Proteins 0.000 description 2
- 238000012136 culture method Methods 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 2
- 235000019796 monopotassium phosphate Nutrition 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 235000019319 peptone Nutrition 0.000 description 2
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 2
- 239000012488 sample solution Substances 0.000 description 2
- RVUXIPACAZKWHU-UHFFFAOYSA-N sulfuric acid;heptahydrate Chemical compound O.O.O.O.O.O.O.OS(O)(=O)=O RVUXIPACAZKWHU-UHFFFAOYSA-N 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- 241000228212 Aspergillus Species 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 238000005273 aeration Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 229940099112 cornstarch Drugs 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000012091 fetal bovine serum Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000010903 husk Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 238000009630 liquid culture Methods 0.000 description 1
- WRUGWIBCXHJTDG-UHFFFAOYSA-L magnesium sulfate heptahydrate Chemical compound O.O.O.O.O.O.O.[Mg+2].[O-]S([O-])(=O)=O WRUGWIBCXHJTDG-UHFFFAOYSA-L 0.000 description 1
- 229940061634 magnesium sulfate heptahydrate Drugs 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000001965 potato dextrose agar Substances 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 238000011218 seed culture Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
Landscapes
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Saccharide Compounds (AREA)
Abstract
Description
【発明の詳細な説明】 〔産業上の利用分野〕 本発明は、新規なコウジ酸誘導体に関するものである。[Detailed description of the invention] [Industrial application field] The present invention relates to novel kojic acid derivatives.
２−ヒドロキンメチル−５−ヒドロキシ−４Ｈ−ピラン
−４−オンはコウジ酸として公知の化合物である。2-Hydroquinemethyl-5-hydroxy-4H-pyran-4-one is a compound known as kojic acid.
そして、このコウジ酸の２位のヒドロキシ基をアンル化
した化合物としては２−アルキルカルポニルオキンメチ
ル−５−ヒドロキン−４Ｈビラン−４−オン（特開昭５
４−９２６３２号公報）、２−ペンソイルオキソメチル
−５−ヒドロキン−４８−ピラン−４−オン、２−／ン
ナモイルオキンメチルー５−ヒドロキン−４Ｈ−ピラン
４−オン、２−フェノキシメチル−５−ヒドロキン−４
Ｈ−ピラン−４−オン（特開昭５９−３Ｂ２Ｏ３号公報
）が知られており、また、式（式中Ｒは、２−ピロリド
ン−５−イル基又はピリジル基を示す）
で示されるコウジ酸誘導体く特開昭６０−２３３０７１
号公報）も知られている。As a compound in which the hydroxy group at the 2-position of kojic acid is anlated, 2-alkylcarponyloquinemethyl-5-hydroquine-4H bilan-4-one (JP-A-5
4-92632), 2-pensoyloxomethyl-5-hydroquine-48-pyran-4-one, 2-/nnamoyloxomethyl-5-hydroquine-4H-pyran-4-one, 2-phenoxymethyl- 5-Hydroquine-4
H-pyran-4-one (JP-A-59-3B2O3) is known, and H-pyran-4-one (in which R represents a 2-pyrrolidon-5-yl group or a pyridyl group) is known. Acid derivatives JP-A-60-233071
No. 2) is also known.
本発明は、タイロシネース活性阻害により顕著なメラニ
ン生成抑制作用を有し、色白化粧料などの外用剤として
有用な新規化合物を提供することにある。An object of the present invention is to provide a novel compound that has a remarkable melanin production inhibiting effect by inhibiting tylosinase activity and is useful as an external preparation for fairing skin cosmetics and the like.
本発明の化合物は、式
で表される文献未載の新規化合物であるコウジ酸グルコ
シドくα−グルコピラノジルコウジ酸）であり、下記の
物性を有するものである。The compound of the present invention is kojic acid glucoside (α-glucopyranojirkojic acid), which is a novel compound not described in any literature and is represented by the formula, and has the following physical properties.
分子量；３０４．２５
融点 ；１７２〜１７７℃（分解）
溶解性：水に溶は易く、ブタノールに溶ける元素分析値
・ＣＩ２ Ｈ＋ ６０９ として実測値： Ｃ４７，５
１％、８５．１７％計算値： Ｃ４７，３７％、８５．
３０％ＦｅＣｌ！、 テスト：腸性
本発明の新規化合物であるコウジ酸グルコ／ドは、コウ
ジ酸を原料として固体培地、および液体培地のいずれか
による培養法、合成法によっても合成することができる
。Molecular weight: 304.25 Melting point: 172-177°C (decomposition) Solubility: Easily soluble in water, soluble in butanol Elemental analysis value / Actual value as CI2 H+ 609: C47.5
1%, 85.17% Calculated value: C47, 37%, 85.
30% FeCl! , Test: Intestinal The kojic acid gluco/do, which is a novel compound of the present invention, can also be synthesized using kojic acid as a raw material by a culture method using either a solid medium or a liquid medium, or by a synthesis method.
製造例１ （液体培養法）
ｉ！［ｌＬａ：して、アスペルギルス・アルバスＮｏ、
６を用い、これをペプトン０．２％添加ポテトデキスト
ロース寒天（栄研化学■製）斜面培地に接種し、３０℃
で１週間培養を行った。Production example 1 (liquid culture method) i! [lLa: Aspergillus albus No.
6 was used to inoculate a potato dextrose agar supplemented with 0.2% peptone (manufactured by Eiken Chemical Co., Ltd.) onto a slanted medium and incubated at 30°C.
Culture was performed for one week.
種母培地として、ブドウ糖４％、コーンスターチ４％、
ペプトン０．５％、リン酸２水素カリウム０．１５％、
硫酸マグネシウム・７水塩０．０５％およびニラコール
ＢＣ−１０７Ｘ （日光ケミカルズ■製の商品名）０
．１％の水溶液形態をｐＨ４に調製したものを用いて、
これを２０００ｒｒ＋Ａフラスコに１０００ ｍβ充填
し、１２１℃で１５分間殺菌して室温まで冷却したのち
、前記種菌を接種した。培養は温度３２℃、振盪回数１
２０回／分、振幅５ｃｍで４８時間振盪培養し、種母を
調製した。As a seed medium, 4% glucose, 4% cornstarch,
Peptone 0.5%, potassium dihydrogen phosphate 0.15%,
Magnesium sulfate heptahydrate 0.05% and Niracol BC-107X (trade name manufactured by Nikko Chemicals ■) 0
．． Using a 1% aqueous solution prepared to pH 4,
A 2000rr+A flask was filled with 1000 mβ of this, sterilized at 121° C. for 15 minutes, cooled to room temperature, and then inoculated with the inoculum. Culture at a temperature of 32°C and shaking 1 time.
A seed mother was prepared by culturing with shaking 20 times/min and an amplitude of 5 cm for 48 hours.
本培養の培地として、種母培地と同様に調製したものを
用いて、これを３０１容ジヤーフγ−メンター（■丸菱
理化学研究所製）３連の８槽に２０ｐずつ充填し、１２
１℃で１５分間殺菌して室温まで冷却したのち、前記種
菌を接種した。培養は３２℃、通気量２０〜Ｌ／分およ
び回転速度３５０〜４００ｒｐｍで１２０時間培養した
。培養液中のコウジ酸グルコシド濃度は１％であった。As a medium for the main culture, a medium prepared in the same manner as the seed medium was used, and 20 p each of this was filled into 3 series of 8 tanks of 301 volumes of JAF γ-mentor (manufactured by Marubishi Rikagaku Kenkyusho).
After sterilizing at 1° C. for 15 minutes and cooling to room temperature, the seed culture was inoculated. Culture was carried out for 120 hours at 32°C, aeration rate of 20-L/min, and rotation speed of 350-400 rpm. The concentration of kojic acid glucoside in the culture solution was 1%.
＊造例２（固体培養法）
種菌トして、アスベルギス・アルバスＮｏ６より単胞子
分離をし、紫外線照射によってコウジ酸生産能を向上さ
せた変異菌株を用い、固体培養を行った。種菌培養は！
ｉ！造例造出１様にして行った。*Creation Example 2 (Solid-state culture method) A seed strain was used, monospores were isolated from Asbergus albus No. 6, and solid-state culture was performed using a mutant strain whose kojic acid production ability was improved by ultraviolet irradiation. Inoculum culture!
i! This was done in the same way as Example Production 1.
本培養の培地として、とうもろこしく飼料用）１５％、
もみがら１％、ブドウ糖１％、リン酸２水素カリウム０
．０５％、硫酸マグ不ンウム７水塩０．０２％および水
８２％を用い、これに前記種菌母胞子Ｖ、濁液を接種し
、３０℃で７２時間培養した。As a medium for main culture, corn feed) 15%,
Rice husk 1%, glucose 1%, potassium dihydrogen phosphate 0
．． Using 0.05% magunium sulfate heptahydrate, 0.02% magunium sulfate heptahydrate, and 82% water, the inoculum mother spores V and the suspension were inoculated and cultured at 30° C. for 72 hours.
コウジ酸ゲルコンド濃度は固体培養物１ｇ当たり１００
ｍｇであった。The concentration of kojic acid gelcond is 100 per gram of solid culture.
It was mg.
製造例３（合成法）
無水アセトニトリル５０ｍＡ’および無水〜、Ｎ−ジメ
チルホルムアミド５０ｍβの混合溶液にコウジ酸０．０
５ ｇ、ブドウ糖６，４ｇおよび強酸性イオン交換樹脂
５ｇを加え、撹拌しながら２４時間還流する。反応後、
強酸性イオン交換樹脂を加熱ろ過により除去し、ろ液を
減圧留去する。残渣からＯＤＳカラムによりコウジ酸グ
ルコシドを精製する。ＯＤＳカラムの溶媒には、７％ア
セトニトリル水溶液（塩酸でｐＨ２，５に調整したもの
）を用いる。収量０．４３ｇ（収率４０％）かくしで得
られた本発明の新規化合物であるコウジ酸ゲルコンドの
赤外線吸収スペクトル、紫外線吸収スペクトル、核磁気
共鳴スペクトル、マススペクトルをそれぞれ第１ないし
第４図として示す。Production Example 3 (Synthesis method) 0.0 kojic acid was added to a mixed solution of 50 mA' of anhydrous acetonitrile and 50 mβ of anhydrous to N-dimethylformamide.
5 g of glucose, 6.4 g of glucose, and 5 g of a strongly acidic ion exchange resin were added, and the mixture was refluxed for 24 hours with stirring. After the reaction,
The strongly acidic ion exchange resin is removed by hot filtration, and the filtrate is distilled off under reduced pressure. Kojic acid glucoside is purified from the residue using an ODS column. A 7% acetonitrile aqueous solution (adjusted to pH 2.5 with hydrochloric acid) is used as the solvent for the ODS column. The infrared absorption spectrum, ultraviolet absorption spectrum, nuclear magnetic resonance spectrum, and mass spectrum of kojic acid gelcond, which is a new compound of the present invention obtained in a yield of 0.43 g (yield 40%), are shown in Figures 1 to 4, respectively. show.
本発明の化合物は、強いタイロシネース活性抑制効果、
および培養Ｂ１６マウスメラノ一マ細胞白色化効果を示
し、これを有効成分とする化Ｍｌｌは、人体に対して好
ましくない副作用を有さす、人体皮膚内に存在するタイ
ロシネースの活性を阻止し、すぐれたメラニン生成抑制
作用を示す。The compound of the present invention has a strong tylosinase activity inhibiting effect,
and cultured B16 mouse melanoma cells, and Mll containing this as an active ingredient inhibits the activity of tylosinase present in the human skin, which has unfavorable side effects on the human body, and has an excellent effect. Shows an inhibitory effect on melanin production.
（タイロシネース活性抑制効果）
本発明のコウジ酸グルコシドのインビトロでのタイロシ
ネース活性抑制効果を調べた。試料液としてコウジ酸グ
ルコシド（実施例１のもの）を水に溶解し、３９ｍＭの
水溶液を調製した。酵素液（８１６マウスメラノーマ細
胞３０．０ＯＯＧ上清）１００ μ！ 、１０ａ＋Ｍ
ｄｏｐａ溶液３３３ ｐ ｊ’ 、１００ｍＭ リン
酸緩衝液（ｐ）！ ６．８＞ ５５７μｍ、５４２μ
！および試料液１０μｌ、２５μｌを３７℃でインキュ
ベートし、１分ごとに４１５ｎｍ の吸光度を測定した
結果を第１表に示す。(Inhibitory effect on tylosinase activity) The in vitro inhibitory effect of kojic acid glucoside on tylosinase activity was investigated. As a sample solution, kojic acid glucoside (from Example 1) was dissolved in water to prepare a 39 mM aqueous solution. Enzyme solution (816 mouse melanoma cell 30.0OOG supernatant) 100μ! , 10a+M
dopa solution 333 p j', 100 mM phosphate buffer (p)! 6.8>557μm, 542μm
! Table 1 shows the results of incubating 10 μl and 25 μl of the sample solution at 37° C. and measuring the absorbance at 415 nm every minute.
（培ｌｌＢ１６マウスメラノーマ細胞白色化効果）本発
明のコウジ酸グルコシドのメラニン生成抑制効果を培＃
Ｂ１６マウスメラノーマ細胞を用いて調べた。コウジ酸
グルコシド３．０７ｍｇをイーグルＭＥＭ １．０．８
ｍ 矛に溶解し、９．３ｍＭ溶液とした。(B16 mouse melanoma cell whitening effect in culture) The melanin production inhibiting effect of kojic acid glucoside of the present invention was
This was investigated using B16 mouse melanoma cells. Kojic acid glucoside 3.07mg in Eagle MEM 1.0.8
It was dissolved in a 9.3mM solution.
この溶液を１０％ウシ胎児血清を含むイーグルＭＥＭに
添加した。培地中のコウジ酸グルコシドの濃度を１．２
．２．３．４．７ｍＭとしてメラニン生成抑制効果を調
べたところ、２．３および４．７ｍＭの濃度でメラニン
生成の抑制を認めた。This solution was added to Eagle MEM containing 10% fetal bovine serum. The concentration of kojic acid glucoside in the medium was 1.2.
．． When the inhibitory effect on melanin production was investigated at concentrations of 2.3 and 4.7mM, inhibition of melanin production was observed at concentrations of 2.3 and 4.7mM.
第１図は、本発明のコウジ酸グルコシドの赤外線吸収ス
ペクトルを示す図である。
第２図は、同化合物の紫外線吸収スペクトルを示す図で
ある。
第３図は、同化合物の核磁気共鳴スペクトルを示す図で
ある。
第４図は、同化合物のマススペクトルを示す図である。
第
図
第
図
第
図
第
図FIG. 1 is a diagram showing an infrared absorption spectrum of kojic acid glucoside of the present invention. FIG. 2 is a diagram showing the ultraviolet absorption spectrum of the same compound. FIG. 3 is a diagram showing a nuclear magnetic resonance spectrum of the same compound. FIG. 4 is a diagram showing the mass spectrum of the same compound. Figure Figure Figure Figure Figure
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15052590A JP2933682B2 (en) | 1990-06-08 | 1990-06-08 | Kojic acid derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15052590A JP2933682B2 (en) | 1990-06-08 | 1990-06-08 | Kojic acid derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0446191A true JPH0446191A (en) | 1992-02-17 |
| JP2933682B2 JP2933682B2 (en) | 1999-08-16 |
Family
ID=15498774
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15052590A Expired - Fee Related JP2933682B2 (en) | 1990-06-08 | 1990-06-08 | Kojic acid derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2933682B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100486921B1 (en) * | 2002-11-08 | 2005-05-03 | 주식회사 바이오랜드 | New preparation method of kojic acid derivative |
-
1990
- 1990-06-08 JP JP15052590A patent/JP2933682B2/en not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100486921B1 (en) * | 2002-11-08 | 2005-05-03 | 주식회사 바이오랜드 | New preparation method of kojic acid derivative |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2933682B2 (en) | 1999-08-16 |
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