JP2001097858A - Vitamin a derivative-containing composition - Google Patents
Vitamin a derivative-containing compositionInfo
- Publication number
- JP2001097858A JP2001097858A JP27949799A JP27949799A JP2001097858A JP 2001097858 A JP2001097858 A JP 2001097858A JP 27949799 A JP27949799 A JP 27949799A JP 27949799 A JP27949799 A JP 27949799A JP 2001097858 A JP2001097858 A JP 2001097858A
- Authority
- JP
- Japan
- Prior art keywords
- vitamin
- derivative
- fat
- oil
- palmitate
- 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.)
- Pending
Links
- 150000004347 all-trans-retinol derivatives Chemical class 0.000 title claims abstract description 23
- 239000000203 mixture Substances 0.000 title claims abstract description 15
- 229940042585 tocopherol acetate Drugs 0.000 claims abstract description 10
- ZAKOWWREFLAJOT-CEFNRUSXSA-N D-alpha-tocopherylacetate Chemical compound CC(=O)OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-CEFNRUSXSA-N 0.000 claims abstract description 9
- ZAKOWWREFLAJOT-UHFFFAOYSA-N d-alpha-Tocopheryl acetate Natural products CC(=O)OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229920006395 saturated elastomer Polymers 0.000 claims abstract 2
- VYGQUTWHTHXGQB-FFHKNEKCSA-N retinyl palmitate group Chemical group C(CCCCCCCCCCCCCCC)(=O)OC\C=C(\C=C\C=C(\C=C\C1=C(CCCC1(C)C)C)/C)/C VYGQUTWHTHXGQB-FFHKNEKCSA-N 0.000 claims description 17
- VYGQUTWHTHXGQB-UHFFFAOYSA-N Retinol hexadecanoate Natural products CCCCCCCCCCCCCCCC(=O)OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C VYGQUTWHTHXGQB-UHFFFAOYSA-N 0.000 claims description 9
- 229940108325 retinyl palmitate Drugs 0.000 claims description 9
- 235000019172 retinyl palmitate Nutrition 0.000 claims description 9
- 239000011769 retinyl palmitate Substances 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 4
- 230000000087 stabilizing effect Effects 0.000 claims description 4
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical class OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 abstract description 13
- FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 abstract description 11
- FPIPGXGPPPQFEQ-BOOMUCAASA-N Vitamin A Natural products OC/C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-BOOMUCAASA-N 0.000 abstract description 9
- 235000019155 vitamin A Nutrition 0.000 abstract description 9
- 239000011719 vitamin A Substances 0.000 abstract description 9
- 229940045997 vitamin a Drugs 0.000 abstract description 9
- -1 vitamin A palmitic ester Chemical class 0.000 abstract description 4
- 230000003647 oxidation Effects 0.000 abstract 2
- 238000007254 oxidation reaction Methods 0.000 abstract 2
- 239000003925 fat Substances 0.000 description 9
- 239000003921 oil Substances 0.000 description 8
- 235000019198 oils Nutrition 0.000 description 8
- 239000002385 cottonseed oil Substances 0.000 description 5
- 235000012343 cottonseed oil Nutrition 0.000 description 5
- 230000003078 antioxidant effect Effects 0.000 description 4
- 229940088594 vitamin Drugs 0.000 description 4
- 229930003231 vitamin Natural products 0.000 description 4
- 235000013343 vitamin Nutrition 0.000 description 4
- 239000011782 vitamin Substances 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical group 0.000 description 3
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 3
- 229960000984 tocofersolan Drugs 0.000 description 3
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 3
- 150000003722 vitamin derivatives Chemical class 0.000 description 3
- 239000002076 α-tocopherol Substances 0.000 description 3
- 235000004835 α-tocopherol Nutrition 0.000 description 3
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 150000004667 medium chain fatty acids Chemical class 0.000 description 2
- 229960003471 retinol Drugs 0.000 description 2
- 235000020944 retinol Nutrition 0.000 description 2
- 239000011607 retinol Substances 0.000 description 2
- 229960000342 retinol acetate Drugs 0.000 description 2
- QGNJRVVDBSJHIZ-QHLGVNSISA-N retinyl acetate Chemical compound CC(=O)OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C QGNJRVVDBSJHIZ-QHLGVNSISA-N 0.000 description 2
- 235000019173 retinyl acetate Nutrition 0.000 description 2
- 239000011770 retinyl acetate Substances 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 235000001809 DL-alpha-tocopherylacetate Nutrition 0.000 description 1
- 239000011626 DL-alpha-tocopherylacetate Substances 0.000 description 1
- 208000003556 Dry Eye Syndromes Diseases 0.000 description 1
- 206010013774 Dry eye Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 208000001140 Night Blindness Diseases 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 230000004300 dark adaptation Effects 0.000 description 1
- 230000007850 degeneration Effects 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 150000002168 ethanoic acid esters Chemical class 0.000 description 1
- 230000004438 eyesight Effects 0.000 description 1
- 235000021323 fish oil Nutrition 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000003780 keratinization Effects 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 235000014593 oils and fats Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
Landscapes
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】 本発明は、ビタミンA誘導体を
安定化した組成物及びビタミンA誘導体の安定化方法に
関するものである。TECHNICAL FIELD The present invention relates to a composition in which a vitamin A derivative is stabilized and a method for stabilizing a vitamin A derivative.
【０００２】[0002]
【従来技術】ビタミンＡは、視覚ことに暗順応を高める
作用を有し、また、粘膜の異常乾燥と変性、角化、損
傷、眼球乾燥症を改善する脂溶性ビタミンである。ビタ
ミンAは極めて不安定であるため、通常は、エステル体
として投与されることが多いが、エステルとしても安定
性は十分ではない。ビタミンA誘導体を、安定に保存又
は使用するには、例えば、抗酸化剤を添加したり、容器
中に全満又は窒素置換し冷所に保存する等の方法が取ら
れている。2. Description of the Related Art Vitamin A is a fat-soluble vitamin that has an action of enhancing dark adaptation to vision and improves abnormal drying and degeneration of mucous membranes, keratinization, damage, and dry eye. Since vitamin A is extremely unstable, it is usually administered as an ester form, but the stability is not sufficient even as an ester. In order to store or use the vitamin A derivative stably, for example, a method of adding an antioxidant, or replacing the container completely or with nitrogen in a container and storing it in a cold place is used.
【０００３】[0003]
【発明が解決しようとする課題】ビタミンAは、食品か
らの摂取量が不足しがちであるため、医薬品として補給
する場合があり、その安定化を図ることは極めて重要な
課題である。本発明者は、この課題を解決すべく鋭意検
討した結果、以下に示す手段により解決できることを見
出し本発明を完成した。Problems to be Solved by the Invention Vitamin A is liable to be replenished as a medicament because the intake from food tends to be insufficient, and stabilizing it is an extremely important task. As a result of intensive studies to solve this problem, the present inventor has found that it can be solved by the following means, and has completed the present invention.
【０００４】[0004]
【課題を解決するための手段】本発明は、ビタミンＡ誘
導体及び酸化されにくい油脂からなるビタミンA誘導体
を安定化した組成物である。本発明は、また、ビタミン
A誘導体に酸化されにくい油脂を添加することによるビ
タミンA誘導体の安定化方法である。SUMMARY OF THE INVENTION The present invention is a composition comprising a vitamin A derivative and a vitamin A derivative comprising a hardly oxidizable oil or fat. The invention also relates to vitamins
This is a method for stabilizing a vitamin A derivative by adding a fat or oil that is hardly oxidized to the A derivative.
【０００５】ビタミンAは、レチノール又はアキセロフ
トールとも称され、肝油、魚油等に多く含まれる脂溶性
ビタミンである。ビタミンＡは動物の発育、夜盲症など
の眼症状の予防、治療に用いられるほか、総合ビタミン
剤の成分としても用いられる。本発明におけるビタミン
A誘導体としては、例えば、ビタミンA（レチノール）の
酢酸エステル、パルミチン酸エステルを挙げることがで
きる。ビタミンＡ酢酸エステルは、酢酸レチノールとし
て日本薬局方に記載されており、パルミチン酸エステル
は、通常、日本薬局方記載のビタミンＡ油として入手で
きる。[0005] Vitamin A, also called retinol or axelophthol, is a fat-soluble vitamin that is often contained in liver oil, fish oil and the like. Vitamin A is used for the prevention and treatment of ocular symptoms such as animal growth and night blindness, and is also used as a component of a multivitamin preparation. Vitamin in the present invention
Examples of the A derivative include acetate and palmitate of vitamin A (retinol). Vitamin A acetate is described as retinol acetate in the Japanese Pharmacopoeia, and palmitate is usually available as a vitamin A oil described in the Japanese Pharmacopoeia.
【０００６】本発明における酸化されにくい油脂とは、
通常の保存条件において容易に酸化を受けない油脂を意
味し、例えば、オクチルデシルトリグリセリド等の中鎖
飽和脂肪酸のトリグリセリド、ジグリセリド、ビタミン
E酢酸エステル、プロピレングリコールジカプリン酸エ
ステル等のプロピレングリコールと中鎖脂肪酸のジエス
テル又はモノエステル、流動パラフィン等を挙げること
ができる。ビタミンＥ酢酸エステルは、より具体的に
は、酢酸ｄｌ−α−トコフェロール、酢酸ｄ−α−トコ
フェロール、酢酸ｌ−α−トコフェロール等があるが特
に限定されない。The hardly oxidized fats and oils in the present invention are:
Means fats and oils that are not easily oxidized under normal storage conditions, for example, triglycerides of medium-chain saturated fatty acids such as octyldecyl triglyceride, diglycerides, vitamins
E Diesters or monoesters of propylene glycol and medium-chain fatty acids such as acetic acid ester and propylene glycol dicapric acid ester, and liquid paraffin can be exemplified. More specifically, the vitamin E acetate includes, but is not particularly limited to, dl-α-tocopherol acetate, d-α-tocopherol acetate, 1-α-tocopherol acetate, and the like.
【０００７】本発明におけるビタミンＡ誘導体の混合物
中の濃度は、２０重量％以下であり、好ましくは１０重
量％以下である。即ち、ビタミンA誘導体と酸化されに
くい油脂との混合比率は、ビタミンＡ誘導体1重量部に
対し、酸化されにくい油脂４重量部以上、好ましくは９
重量部以上である。本発明にかかる組成物を製造するに
は、ビタミンＡ誘導体と酸化されにくい油脂を混合して
製することができる。[0007] The concentration of the vitamin A derivative in the mixture of the present invention is 20% by weight or less, preferably 10% by weight or less. That is, the mixing ratio of the vitamin A derivative and the hard-to-oxidize fat is 4 parts by weight or more, preferably 9 to 10 parts by weight of the vitamin A derivative.
More than parts by weight. In order to produce the composition according to the present invention, a vitamin A derivative and a hardly oxidizable fat can be mixed.
【０００８】[0008]
【発明の効果】ビタミンＡパルミチン酸エステル百万単
位を、中鎖脂肪酸トリグリセリドであるオクチルデシル
トリグリセリド（ＯＤＯ）で２０倍に希釈し、ガラス瓶
に充填し、開放下４５℃で６０日間保存し、経時的にビ
タミンＡパルミチン酸エステルの残存量を測定した。対
照として綿実油を用いて同様に希釈した試料及びビタミ
ンＡパルミチン酸エステルを用い残存量を測定した。結
果を表１に示した。EFFECT OF THE INVENTION One million units of vitamin A palmitate is diluted 20-fold with octyldecyl triglyceride (ODO) which is a medium-chain fatty acid triglyceride, filled in a glass bottle, stored at 45 ° C. under open condition for 60 days, and stored over time. The residual amount of vitamin A palmitate was measured. As a control, the remaining amount was measured using a sample similarly diluted using cottonseed oil and vitamin A palmitate. The results are shown in Table 1.
【０００９】[0009]
【表１】 [Table 1]
【００１０】表１よりビタミンＡパルミチン酸エステル
及び酸化されやすい油脂である綿実油で希釈したビタミ
ンＡパルミチン酸エステルは極めて安定性が悪いが、酸
化されにくい油脂であるＯＤＯで希釈したものはビタミ
ンＡパルミチン酸エステルの安定性が顕著に増大するこ
とが分かる。From Table 1, it can be seen that vitamin A palmitate and vitamin A palmitate diluted with cottonseed oil, which is an easily oxidizable oil and fat, have extremely poor stability. It can be seen that the stability of the acid ester is significantly increased.
【００１１】次にビタミンＡパルミチン酸エステルを酢
酸ｄ−α−トコフェロール、ＯＤＯで希釈し、ビタミン
Aパルミチン酸エステルの濃度がそれぞれ１〜２０重量
％とし、ガラス瓶に充填し開放下４５℃で保存して、ビ
タミンＡパルミチン酸エステルの残存量を測定した。対
照として綿実油及びｄ−α−トコフェロールを用い同様
に希釈、測定した。結果を表２に示した。なお、本試験
に用いたビタミンAパルミチン酸エステル（表中パルミ
チン酸ＶＡと略）はロッシュ社製、ｄ−α−トコフェロ
ール（表中ＶＥと略）及び酢酸ｄ−α−トコフェロール
（表中酢酸ＶＥと略）はタマ生化学製、ＯＤＯは日清精
油製、綿実油は岡村油脂製である。Next, vitamin A palmitate is diluted with d-α-tocopherol acetate and ODO,
The concentration of A palmitate was set to 1 to 20% by weight, filled in a glass bottle, stored at 45 ° C. under open condition, and the residual amount of vitamin A palmitate was measured. The same measurement was performed using cottonseed oil and d-α-tocopherol as controls. The results are shown in Table 2. The vitamin A palmitate ester (abbreviated as palmitic acid VA in the table) used in this test was manufactured by Roche, d-α-tocopherol (abbreviated as VE in the table) and d-α-tocopherol acetate (VE in the table). ) Is manufactured by Tama Seikagaku, ODO is manufactured by Nisshin Essential Oil, and cottonseed oil is manufactured by Okamura Yushi.
【００１２】[0012]
【表２】 [Table 2]
【００１３】表２より、酸化されにくい油脂である酢酸
ｄ−α−トコフェロール、ＯＤＯを用いるとビタミンＡ
パルミチン酸エステルの安定性が顕著に増大することが
明らかである。ビタミンＡ誘導体が、抗酸化作用を有す
る油脂により何故安定化されるのかは明らかではない。
表２の対照例より明らかなように、抗酸化作用を有する
ｄ−α−トコフェロールでは安定化されないため、抗酸
化作用によるものではなく、また、綿実油によっても安
定化されないため、油脂による酸素との接触抑制でもな
い。本発明は、意外にも、ＯＤＯ、ビタミンＥ酢酸エス
テル等の酸化されにくい油脂との組成物がビタミンＡ誘
導体の安定化を有することを見出し完成したものである
が、本発明により、従来極めて不安定で取扱の難しかっ
たビタミンＡ誘導体の保存、製剤化が極めて容易に行え
るようになる。From Table 2, it can be seen that when d-α-tocopherol acetate and ODO which are hardly oxidized oils and fats are used, vitamin A
It is clear that the stability of the palmitate ester is significantly increased. It is not clear why vitamin A derivatives are stabilized by fats and oils having an antioxidant effect.
As is clear from the control example in Table 2, d-α-tocopherol having an antioxidant effect is not stabilized, and is not due to an antioxidant effect, and is not stabilized by cottonseed oil. Neither is contact suppression. The present invention has been surprisingly found out that a composition with a hardly oxidizable oil or fat such as ODO or vitamin E acetate has stabilization of a vitamin A derivative. The storage and formulation of a stable and difficult-to-handle vitamin A derivative can be performed very easily.
Claims (5)
からなるビタミンA誘導体を安定化した組成物。1. A composition comprising a vitamin A derivative and a vitamin A derivative comprising a hardly oxidizable oil or fat.
添加することによるビタミンA誘導体の安定化方法。2. A method for stabilizing a vitamin A derivative by adding a fat or oil which is hardly oxidized to the vitamin A derivative.
リセリド又はビタミンE酢酸エステルである請求項1記載
の組成物。3. The composition according to claim 1, wherein the oil or fat that is hardly oxidized is a saturated medium-chain fatty acid glyceride or a vitamin E acetate.
ン酸エステルである請求項1記載の組成物。4. The composition according to claim 1, wherein the vitamin A derivative is vitamin A palmitate.
重量％以下である請求項１記載の組成物。5. The composition according to claim 1, wherein the content of the vitamin A derivative is 20.
The composition according to claim 1, which is less than or equal to weight percent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP27949799A JP2001097858A (en) | 1999-09-30 | 1999-09-30 | Vitamin a derivative-containing composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP27949799A JP2001097858A (en) | 1999-09-30 | 1999-09-30 | Vitamin a derivative-containing composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2001097858A true JP2001097858A (en) | 2001-04-10 |
| JP2001097858A5 JP2001097858A5 (en) | 2006-05-18 |
Family
ID=17611882
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP27949799A Pending JP2001097858A (en) | 1999-09-30 | 1999-09-30 | Vitamin a derivative-containing composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2001097858A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009044854A1 (en) | 2007-10-03 | 2009-04-09 | Asahi Breweries, Ltd. | Granule, tablet, and their production methods |
| JP2013256462A (en) * | 2012-06-12 | 2013-12-26 | Rohto Pharmaceutical Co Ltd | Water-based composition including vitamin a group |
| JP2016216509A (en) * | 2016-09-26 | 2016-12-22 | ロート製薬株式会社 | Aqueous composition containing vitamins A |
| JP2018168168A (en) * | 2018-06-12 | 2018-11-01 | ロート製薬株式会社 | Aqueous composition containing vitamins A |
| JP2020105222A (en) * | 2020-03-31 | 2020-07-09 | ロート製薬株式会社 | Aqueous composition containing vitamin A |
-
1999
- 1999-09-30 JP JP27949799A patent/JP2001097858A/en active Pending
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009044854A1 (en) | 2007-10-03 | 2009-04-09 | Asahi Breweries, Ltd. | Granule, tablet, and their production methods |
| JP2012072190A (en) * | 2007-10-03 | 2012-04-12 | Asahi Group Holdings Ltd | Granule, tablet, and method for producing the same |
| JP2013256462A (en) * | 2012-06-12 | 2013-12-26 | Rohto Pharmaceutical Co Ltd | Water-based composition including vitamin a group |
| JP2016216509A (en) * | 2016-09-26 | 2016-12-22 | ロート製薬株式会社 | Aqueous composition containing vitamins A |
| JP2018168168A (en) * | 2018-06-12 | 2018-11-01 | ロート製薬株式会社 | Aqueous composition containing vitamins A |
| JP2020105222A (en) * | 2020-03-31 | 2020-07-09 | ロート製薬株式会社 | Aqueous composition containing vitamin A |
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