| SKU | Size | Availability | Price | Qty |
|---|---|---|---|---|
| A106857-250mg | 250mg | In stock | $69.90 |
Naturally occurring beta-D-glucopyranoside of hydroquinone. Competitive inhibitor of tyrosinase.
| Synonyms | NCGC00095599-01 | SpecPlus_000314 | CHEBI:18305 | NCGC00166076-09 | (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(4-hydroxyphenoxy)tetrahydropyran-3,4,5-triol | Arbutin - Uva - p-Arbutin | BSPBio_002706 | Prestwick3_001026 | SMP1_000028 | KS-5252 | MLS002207046 | |
|---|---|
| Specifications & Purity | analytical standard, ≥99% |
| Biochemical and Physiological Mechanisms | Naturally occurring beta-D-glucopyranoside of hydroquinone. Isolated from the leaves of Bearberry ( Arctostaphylos ). Competitive inhibitor of tyrosinase in melanocytes. Inhibits melanin biosynthesis. |
| Shipped In | Normal |
| Grade | analytical standard |
| Action Type | INHIBITOR |
| Mechanism of action | Tyrosinase inhibitor |
| Note | Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details. |
| ALogP | -0.7 |
|---|
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| Mechanism of Action | Action Type | target ID | Target Name | Target Type | Target Organism | Binding Site Name | References |
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| IUPAC Name | (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(4-hydroxyphenoxy)oxane-3,4,5-triol |
|---|---|
| INCHI | InChI=1S/C12H16O7/c13-5-8-9(15)10(16)11(17)12(19-8)18-7-3-1-6(14)2-4-7/h1-4,8-17H,5H2/t8-,9-,10+,11-,12-/m1/s1 |
| InChi Key | BJRNKVDFDLYUGJ-RMPHRYRLSA-N |
| Canonical SMILES | C1=CC(=CC=C1O)OC2C(C(C(C(O2)CO)O)O)O |
| Isomeric SMILES | C1=CC(=CC=C1O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O |
| WGK Germany | 3 |
| PubChem CID | 440936 |
| Molecular Weight | 272.25 |
| Beilstein | 89673 |
Enter Lot Number to search for COA:
| Specific Rotation[α] | -65.5 ° (C=4, H2O) |
|---|---|
| Melt Point(°C) | 198°C |
| WGK Germany | 3 |
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| Merck Index | 773 |
| 1. Jing Wu, Funa Zhang, Haixia Yu, Shimei Qi, Yu Wu, Weihua Xiao. (2023) Anti-Melanogenic and Antioxidant Activity of Bifidobacterium longum Strain ZJ1 Extracts, Isolated from a Chinese Centenarian. INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 24 (16): (12810). [PMID:37628988] [10.3390/ijms241612810] |
| 2. Zhengming Xu, Shuang Liu, Huining Lai, Lijun You, Zhengang Zhao. (2023) Green-Efficient Enzymatic Synthesis and Characterization of Liposoluble 6′/6″-O-Lauryl Phenolic Glycosides with Enhanced Intestinal Permeability. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 71 (20): (7689–7702). [PMID:37167604] [10.1021/acs.jafc.3c00527] |
| 3. Wei Wang, Lijuan Yang, Weiwei Wang, Jianyong Zhang, Ulrich H. Engelhardt, Heyuan Jiang. (2023) Inhibitory Activities of Samples on Tyrosinases Were Affected by Enzyme Species and Sample Addition Methods. INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 24 (7): (6013). [PMID:37046986] [10.3390/ijms24076013] |
| 4. Hui Jiang, Fei Wu, Xi Jiang, Yun-Feng Pu, Li-Rong Shen, Cui-Yun Wu, Hong-Jin Bai. (2022) Antioxidative, cytoprotective and whitening activities of fragrant pear fruits at different growth stages. Frontiers in Nutrition, 9 (1020855). [PMID:36245497] [10.3389/fnut.2022.1020855] |
| 5. Tang Han, Du Han, Kuang Xielan, Huang Hao, Zeng Jingshu, Long Chongde, Zhu Binbin, Fu Licheng, Wang Hua, Zhang Qingjiong, Lin Shuibin, Yan Jianhua, Shen Huangxuan. (2022) Arbutin Protects Retinal Pigment Epithelium Against Oxidative Stress by Modulating SIRT1/FOXO3a/PGC-1α/β Pathway. Frontiers in Genetics, 13 (1763). [PMID:36051689] [10.3389/fgene.2022.922807] |
| 6. Tingting Lin, Ben Chen, Liqun Fang, Haibo You, Chu Chu, Qingsong Shao, Shengqiang Tong. (2022) Solvent strength of organic phase for two biphasic solvent systems in high speed countercurrent chromatography. JOURNAL OF CHROMATOGRAPHY A, 1680 (463422). [PMID:36037578] [10.1016/j.chroma.2022.463422] |
| 7. Jiaodi Li, Chenxi Wang, Xiaoling Chen, Minghui Huang, Qian Fu, Rongjie Li, Yilin Wang, Chunyan Li, Pengcheng Zhao, Yixi Xie, Junjie Fei. (2022) A non-enzymatic photoelectrochemical sensor based on g-C3N4@CNT heterojunction for sensitive detection of antioxidant gallic acid in food. FOOD CHEMISTRY, 389 (133086). [PMID:35526285] [10.1016/j.foodchem.2022.133086] |
| 8. Luo Yiyuan, Wang Juan, Li Shuo, Wu Yue, Wang Zhirui, Chen Shaojun, Chen Hongjiang. (2022) Discovery and identification of potential anti-melanogenic active constituents of Bletilla striata by zebrafish model and molecular docking. BMC Complementary Medicine and Therapies, 22 (1): (1-14). [PMID:34996448] [10.1186/s12906-021-03492-y] |
| 9. Peijie Wu, Ling Qiao, Han Yu, Hui Ming, Chao Liu, Wenjun Wu, Baixue Li. (2021) Arbutin Alleviates the Liver Injury of α-Naphthylisothiocyanate-induced Cholestasis Through Farnesoid X Receptor Activation. Frontiers in Cell and Developmental Biology, 9 (758632). [PMID:34926449] [10.3389/fcell.2021.758632] |
| 10. Zilong Chen, Hongdong Liu, Jie Chen, Weifeng Zhu, Yong Liu, Jianxin Min, Xiaotian Chen, Bin Li, Xin Yang. (2021) Separation and enrichment of sibiskoside from Sibiraea angustat with magnetic surface dummy template molecularly imprinted polymers. JOURNAL OF CHROMATOGRAPHY B-ANALYTICAL TECHNOLOGIES IN THE BIOMEDICAL AND LIFE SCIENCES, 1178 (122767). [PMID:34224966] [10.1016/j.jchromb.2021.122767] |
| 11. Kunkun Guo, Xin Wang, Baolin Huang, Xiaoyun Wu, Shuimei Shen, Zimin Lin, Jie Zhao, Zheng Cai. (2021) Comparative study on the intestinal absorption of three gastrodin analogues via the glucose transport pathway. EUROPEAN JOURNAL OF PHARMACEUTICAL SCIENCES, 163 (105839). [PMID:33852971] [10.1016/j.ejps.2021.105839] |
| 12. Haixia Xu, Xiaofeng Li, Xuan Xin, Lan Mo, Yucong Zou, Guanglei Zhao, Yigang Yu, Kebing Chen. (2021) Antityrosinase Mechanism and Antimelanogenic Effect of Arbutin Esters Synthesis Catalyzed by Whole-Cell Biocatalyst. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 69 (14): (4243–4252). [PMID:33821640] [10.1021/acs.jafc.0c07379] |
| 13. Hao Huang, Tarun Belwal, Xingyu Lin, Jarukitt Limwachiranon, Ligen Zou, Zisheng Luo. (2021) Novel bind-then-release model based on fluorescence spectroscopy analysis with molecular docking simulation: New insights to zero-order release of arbutin and coumaric acid. FOOD HYDROCOLLOIDS, 112 (106356). [PMID:] [10.1016/j.foodhyd.2020.106356] |
| 14. Saipeng Huang, Wenshuai Li, Xin Zhou, Mengyao Xie, Qing Luo, Huiyun Wen, Yane Luo, Weiming Xue. (2020) One-step synthesis of levodopa functionalized carbon quantum dots for selective detection of tyrosinase and inhibitor screening. MICROCHEMICAL JOURNAL, 159 (105456). [PMID:] [10.1016/j.microc.2020.105456] |
| 15. Hao Huang, Tarun Belwal, Halah Aalim, Li Li, Xingyu Lin, Songbai Liu, Caixia Ma, Qunhe Li, Ying Zou, Zisheng Luo. (2019) Protein-polysaccharide complex coated W/O/W emulsion as secondary microcapsule for hydrophilic arbutin and hydrophobic coumaric acid. FOOD CHEMISTRY, 300 (125171). [PMID:31330369] [10.1016/j.foodchem.2019.125171] |
| 16. Hui Chen, Wei Song, Kun-Kun Sun, He-Wei Du, Shu-Dong Wei. (2018) Structure Elucidation and Evaluation of Antioxidant and Tyrosinase Inhibitory Effect and Mechanism of Proanthocyanidins from Leaf and Fruit of Leucaena Leucocephala. JOURNAL OF WOOD CHEMISTRY AND TECHNOLOGY, [PMID:] [10.1080/02773813.2018.1533975] |
| 17. Ge Zhang, Xiu-Han Guo, Shi-Sheng Wang, Yue-Qing Li, Guang-Zhe Li, Wei-Jie Zhao. (2017) Screening and identification of natural ligands of tyrosinase from Pueraria lobata Ohwi by a combination of ultrafiltration and LC-MS. Analytical Methods, 9 (33): (4858-4862). [PMID:] [10.1039/C7AY00851A] |
| 18. Yi Tao, Dandan Su, Yingshan Du, Weidong Li, Baochang Cai, Liuqing Di, Liyun Shi, Lihong Hu. (2016) Magnetic solid-phase extraction coupled with HPLC-Q-TOF-MS for rapid analysis of tyrosinase binders from San-Bai decoction by Box–Behnken statistical design. RSC Advances, 6 (111): (109730-109741). [PMID:] [10.1039/C6RA22045B] |
| 19. Jianmin Chen, Xiaojing Yu, Yufeng Huang. (2016) Inhibitory mechanisms of glabridin on tyrosinase. SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 168 (111). [PMID:27288962] [10.1016/j.saa.2016.06.008] |
| 20. Li Zhu, Hai-Long Wu, Li-Xia Xie, Huan Fang, Shou-Xia Xiang, Yong Hu, Zhi Liu, Tong Wang, Ru-Qin Yu. (2016) A chemometrics-assisted excitation–emission matrix fluorescence method for simultaneous determination of arbutin and hydroquinone in cosmetic products. Analytical Methods, 8 (24): (4941-4948). [PMID:] [10.1039/C6AY00821F] |
| 21. Ji Wenhua, Zhang Mingming, Gao Qianshan, Cui Li, Chen Lizong, Wang Xiao. (2016) Preparation of hydrophilic molecularly imprinted polymers via bulk polymerization combined with hydrolysis of ester groups for selective recognition of iridoid glycosides. ANALYTICAL AND BIOANALYTICAL CHEMISTRY, 408 (19): (5319-5328). [PMID:27209589] [10.1007/s00216-016-9625-6] |
| 22. Lujing Chai, Jin Zhou, Hui Feng, Cong Tang, Yuanyuan Huang, Zhaosheng Qian. (2015) Functionalized Carbon Quantum Dots with Dopamine for Tyrosinase Activity Monitoring and Inhibitor Screening: In Vitro and Intracellular Investigation. ACS Applied Materials & Interfaces, 7 (42): (23564–23574). [PMID:26440479] [10.1021/acsami.5b06711] |
| 1. Wang DD et al.. (2018) Rare ginsenoside Ia synthesized from F1 by cloning and overexpression of the UDP-glycosyltransferase gene from Bacillus\xa0subtilis: synthesis, characterization, and in\xa0vitro melanogenesis\xa0inhibition activity in BL6B16 cells.. J Ginseng Res, 42 (42-49). [PMID:29348721] |
| 2. Jing Wu, Funa Zhang, Haixia Yu, Shimei Qi, Yu Wu, Weihua Xiao. (2023) Anti-Melanogenic and Antioxidant Activity of Bifidobacterium longum Strain ZJ1 Extracts, Isolated from a Chinese Centenarian. INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 24 (16): (12810). [PMID:37628988] [10.3390/ijms241612810] |
| 3. Zhengming Xu, Shuang Liu, Huining Lai, Lijun You, Zhengang Zhao. (2023) Green-Efficient Enzymatic Synthesis and Characterization of Liposoluble 6′/6″-O-Lauryl Phenolic Glycosides with Enhanced Intestinal Permeability. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 71 (20): (7689–7702). [PMID:37167604] [10.1021/acs.jafc.3c00527] |
| 4. Wei Wang, Lijuan Yang, Weiwei Wang, Jianyong Zhang, Ulrich H. Engelhardt, Heyuan Jiang. (2023) Inhibitory Activities of Samples on Tyrosinases Were Affected by Enzyme Species and Sample Addition Methods. INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 24 (7): (6013). [PMID:37046986] [10.3390/ijms24076013] |
| 5. Hui Jiang, Fei Wu, Xi Jiang, Yun-Feng Pu, Li-Rong Shen, Cui-Yun Wu, Hong-Jin Bai. (2022) Antioxidative, cytoprotective and whitening activities of fragrant pear fruits at different growth stages. Frontiers in Nutrition, 9 (1020855). [PMID:36245497] [10.3389/fnut.2022.1020855] |
| 6. Tang Han, Du Han, Kuang Xielan, Huang Hao, Zeng Jingshu, Long Chongde, Zhu Binbin, Fu Licheng, Wang Hua, Zhang Qingjiong, Lin Shuibin, Yan Jianhua, Shen Huangxuan. (2022) Arbutin Protects Retinal Pigment Epithelium Against Oxidative Stress by Modulating SIRT1/FOXO3a/PGC-1α/β Pathway. Frontiers in Genetics, 13 (1763). [PMID:36051689] [10.3389/fgene.2022.922807] |
| 7. Tingting Lin, Ben Chen, Liqun Fang, Haibo You, Chu Chu, Qingsong Shao, Shengqiang Tong. (2022) Solvent strength of organic phase for two biphasic solvent systems in high speed countercurrent chromatography. JOURNAL OF CHROMATOGRAPHY A, 1680 (463422). [PMID:36037578] [10.1016/j.chroma.2022.463422] |
| 8. Jiaodi Li, Chenxi Wang, Xiaoling Chen, Minghui Huang, Qian Fu, Rongjie Li, Yilin Wang, Chunyan Li, Pengcheng Zhao, Yixi Xie, Junjie Fei. (2022) A non-enzymatic photoelectrochemical sensor based on g-C3N4@CNT heterojunction for sensitive detection of antioxidant gallic acid in food. FOOD CHEMISTRY, 389 (133086). [PMID:35526285] [10.1016/j.foodchem.2022.133086] |
| 9. Luo Yiyuan, Wang Juan, Li Shuo, Wu Yue, Wang Zhirui, Chen Shaojun, Chen Hongjiang. (2022) Discovery and identification of potential anti-melanogenic active constituents of Bletilla striata by zebrafish model and molecular docking. BMC Complementary Medicine and Therapies, 22 (1): (1-14). [PMID:34996448] [10.1186/s12906-021-03492-y] |
| 10. Peijie Wu, Ling Qiao, Han Yu, Hui Ming, Chao Liu, Wenjun Wu, Baixue Li. (2021) Arbutin Alleviates the Liver Injury of α-Naphthylisothiocyanate-induced Cholestasis Through Farnesoid X Receptor Activation. Frontiers in Cell and Developmental Biology, 9 (758632). [PMID:34926449] [10.3389/fcell.2021.758632] |
| 11. Zilong Chen, Hongdong Liu, Jie Chen, Weifeng Zhu, Yong Liu, Jianxin Min, Xiaotian Chen, Bin Li, Xin Yang. (2021) Separation and enrichment of sibiskoside from Sibiraea angustat with magnetic surface dummy template molecularly imprinted polymers. JOURNAL OF CHROMATOGRAPHY B-ANALYTICAL TECHNOLOGIES IN THE BIOMEDICAL AND LIFE SCIENCES, 1178 (122767). [PMID:34224966] [10.1016/j.jchromb.2021.122767] |
| 12. Kunkun Guo, Xin Wang, Baolin Huang, Xiaoyun Wu, Shuimei Shen, Zimin Lin, Jie Zhao, Zheng Cai. (2021) Comparative study on the intestinal absorption of three gastrodin analogues via the glucose transport pathway. EUROPEAN JOURNAL OF PHARMACEUTICAL SCIENCES, 163 (105839). [PMID:33852971] [10.1016/j.ejps.2021.105839] |
| 13. Haixia Xu, Xiaofeng Li, Xuan Xin, Lan Mo, Yucong Zou, Guanglei Zhao, Yigang Yu, Kebing Chen. (2021) Antityrosinase Mechanism and Antimelanogenic Effect of Arbutin Esters Synthesis Catalyzed by Whole-Cell Biocatalyst. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 69 (14): (4243–4252). [PMID:33821640] [10.1021/acs.jafc.0c07379] |
| 14. Hao Huang, Tarun Belwal, Xingyu Lin, Jarukitt Limwachiranon, Ligen Zou, Zisheng Luo. (2021) Novel bind-then-release model based on fluorescence spectroscopy analysis with molecular docking simulation: New insights to zero-order release of arbutin and coumaric acid. FOOD HYDROCOLLOIDS, 112 (106356). [PMID:] [10.1016/j.foodhyd.2020.106356] |
| 15. Saipeng Huang, Wenshuai Li, Xin Zhou, Mengyao Xie, Qing Luo, Huiyun Wen, Yane Luo, Weiming Xue. (2020) One-step synthesis of levodopa functionalized carbon quantum dots for selective detection of tyrosinase and inhibitor screening. MICROCHEMICAL JOURNAL, 159 (105456). [PMID:] [10.1016/j.microc.2020.105456] |
| 16. Hao Huang, Tarun Belwal, Halah Aalim, Li Li, Xingyu Lin, Songbai Liu, Caixia Ma, Qunhe Li, Ying Zou, Zisheng Luo. (2019) Protein-polysaccharide complex coated W/O/W emulsion as secondary microcapsule for hydrophilic arbutin and hydrophobic coumaric acid. FOOD CHEMISTRY, 300 (125171). [PMID:31330369] [10.1016/j.foodchem.2019.125171] |
| 17. Hui Chen, Wei Song, Kun-Kun Sun, He-Wei Du, Shu-Dong Wei. (2018) Structure Elucidation and Evaluation of Antioxidant and Tyrosinase Inhibitory Effect and Mechanism of Proanthocyanidins from Leaf and Fruit of Leucaena Leucocephala. JOURNAL OF WOOD CHEMISTRY AND TECHNOLOGY, [PMID:] [10.1080/02773813.2018.1533975] |
| 18. Ge Zhang, Xiu-Han Guo, Shi-Sheng Wang, Yue-Qing Li, Guang-Zhe Li, Wei-Jie Zhao. (2017) Screening and identification of natural ligands of tyrosinase from Pueraria lobata Ohwi by a combination of ultrafiltration and LC-MS. Analytical Methods, 9 (33): (4858-4862). [PMID:] [10.1039/C7AY00851A] |
| 19. Yi Tao, Dandan Su, Yingshan Du, Weidong Li, Baochang Cai, Liuqing Di, Liyun Shi, Lihong Hu. (2016) Magnetic solid-phase extraction coupled with HPLC-Q-TOF-MS for rapid analysis of tyrosinase binders from San-Bai decoction by Box–Behnken statistical design. RSC Advances, 6 (111): (109730-109741). [PMID:] [10.1039/C6RA22045B] |
| 20. Jianmin Chen, Xiaojing Yu, Yufeng Huang. (2016) Inhibitory mechanisms of glabridin on tyrosinase. SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 168 (111). [PMID:27288962] [10.1016/j.saa.2016.06.008] |
| 21. Li Zhu, Hai-Long Wu, Li-Xia Xie, Huan Fang, Shou-Xia Xiang, Yong Hu, Zhi Liu, Tong Wang, Ru-Qin Yu. (2016) A chemometrics-assisted excitation–emission matrix fluorescence method for simultaneous determination of arbutin and hydroquinone in cosmetic products. Analytical Methods, 8 (24): (4941-4948). [PMID:] [10.1039/C6AY00821F] |
| 22. Ji Wenhua, Zhang Mingming, Gao Qianshan, Cui Li, Chen Lizong, Wang Xiao. (2016) Preparation of hydrophilic molecularly imprinted polymers via bulk polymerization combined with hydrolysis of ester groups for selective recognition of iridoid glycosides. ANALYTICAL AND BIOANALYTICAL CHEMISTRY, 408 (19): (5319-5328). [PMID:27209589] [10.1007/s00216-016-9625-6] |
| 23. Lujing Chai, Jin Zhou, Hui Feng, Cong Tang, Yuanyuan Huang, Zhaosheng Qian. (2015) Functionalized Carbon Quantum Dots with Dopamine for Tyrosinase Activity Monitoring and Inhibitor Screening: In Vitro and Intracellular Investigation. ACS Applied Materials & Interfaces, 7 (42): (23564–23574). [PMID:26440479] [10.1021/acsami.5b06711] |
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