计算溶液所需的质量、体积或浓度。
| 活性类型 | Relation | Activity value | Units | Action Type | 期刊 | PubMed Id | doi | Assay Aladdin ID |
|---|
有货
为什么选择此级别
Moligand™ 级 提供 ≥98% 纯度，适用于对基线干扰要求严格的色谱和分析工作流程。
储存与运输
2-8°C储存,充氩。低温运输 。请查阅批次 COA 获取详细规格。
质量文档
SDS、COA、产品数据表及规格说明书均可下载。可通过批号查询获取批次 COA。
文献证明
在色谱分析、有机合成和交叉偶联反应领域已被 30 篇同行评审文献引用。
概述
一种糖基化的氢醌，用于研究褪黑素生物合成和作为识别、区分和鉴定酪氨酸酶的抑制剂。
An inhibitor to identify, differentiate and characterize tyrosinase(s).
规格
别名
4-羟基苯基-β- D -吡喃葡萄糖苷, p -熊果苷, 对苯二酚 β- D -吡喃葡萄糖苷 | 熊果酚甙 | 熊果素 | 熊果叶甙 | 楊梅葉甘
英文别名
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 |
规格或纯度
Moligand™, ≥98%
英文名称
Arbutin
储存条件
2-8°C储存,充氩
运输条件
低温运输
作用类型
抑制剂
纯度
≥98%
名称和识别符
PubChem SID
EC号
207-850-3
分子类型
小分子
IUPAC Name
(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(4-hydroxyphenoxy)oxane-3,4,5-triol
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
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
分子量
272.25
Beilstein号
89673
Reaxy-Rn
22933063
Reaxys-RN link address
https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=22933063&ln=
技术文档
高级数据
系统学分类
分类树（Taxonomy Tree）
| 界（kingdom) | 有机化合物 |
|---|---|
| 超类（Superclass) | 有机氧化合物 |
| 类（Class) | 有机氧化合物 |
| 亚类（Subclass） | 碳水化合物和碳水化合物结合物 |
| 中间层级节点（Intermediate Tree Nodes） | 糖基化合物 |
| 直接上位类(Direct Parent) | 酚苷类 |
| 其他上位类（Alternative Parents） | 己糖 O-糖基化合物 4-烷氧基苯酚 苯氧基化合物 酚醚 1-羟基-2-未取代苯类化合物 氧烷 仲醇 多元醇 氧环化合物 缩醛 伯醇 碳氢化合物衍生物 |
| 分子骨架（Molecular Framework) | 芳香族杂单环化合物 |
| 取代基（Substituents） | 1-羟基-2-未取代苯环化合物 - 4-烷氧基苯酚 - 乙醛酸 - 羟基苯甲酸酯 - 芳香族杂单环化合物 - 苯基化合物 - 己糖单糖 - 烃衍生物 - 单环苯基基团 - 单糖 - O-羧基化合物 - 有机杂环化合物 - 氧杂环 - 氧杂环丁烷 - 苯酚 - 苯酚醚 - 苯酚糖苷 - 苯氧基化合物 - 多醇 - 初级醇 - 醛基 |
| 描述（Description） | 该化合物属于酚类糖苷类有机化合物。这类化合物具有酚类结构，并连接有糖基片段。酚类结构的例子包括木脂素和黄酮类化合物。天然糖苷中常见的糖单元包括D-葡萄糖、L-果糖和L-鼠李糖。 |
| 外部描述符（External Descriptors） | beta-D-glucoside - monosaccharide derivative |
三维结构
交互式化学结构模型
产品属性
| ALogP | -0.7 |
|---|
关联靶点（人）
TYR
Tclin
Tyrosinase
(717 活性数据)
ACHE
Tclin
Acetylcholinesterase
(18204 活性数据)
PTGS2
Tclin
Cyclooxygenase-2
(13999 活性数据)
Homo sapiens
(32628 活性数据)
Hs68
(138 活性数据)
HaCaT
(4069 活性数据)
HMV-2 cell line
(109 活性数据)
SMAD3
Tchem
Mothers against decapentaplegic homolog 3
(68039 活性数据)
SLCO1B1
Tchem
Solute carrier organic anion transporter family member 1B1
(2672 活性数据)
SLCO1B3
Tchem
Solute carrier organic anion transporter family member 1B3
(2517 活性数据)
IDH1
Tclin
Isocitrate dehydrogenase [NADP] cytoplasmic
(40980 活性数据)
TAS2R16
Tchem
Taste receptor type 2 member 16
(102 活性数据)
关联靶点（其它种属）
Hdac6
Histone deacetylase 6 (222 活性数据)
Pseudomonas aeruginosa (123386 活性数据)
Escherichia coli (133304 活性数据)
Bacillus subtilis (32866 活性数据)
Trichomonas vaginalis (2376 活性数据)
Mus musculus (284745 活性数据)
B16 (5829 活性数据)
P388 (20296 活性数据)
B16-F10 (4610 活性数据)
rep
Replicase polyprotein 1ab (378 活性数据)
BCHE
Cholinesterase (8742 活性数据)
Trichophyton mentagrophytes (4846 活性数据)
B16-F1 (104 活性数据)
Melan-a (81 活性数据)
SARS-CoV-2 (38078 活性数据)
作用机制
| 作用机制 | Action Type | target ID | Target Name | Target Type | Target Organism | Binding Site Name | 参考文献 |
|---|
化学和物理性质
溶解性
Soluble in water (50 mg/ml), methanol and dimethyl sulfoxide.
密度
1.556
敏感性
对空气及湿度敏感
比旋光度
-65.5 ° (C=4, H2O)
熔点
198°C
分子量
272.250 g/mol
XLogP3
-0.700
氢键供体数Hydrogen Bond Donor Count
5
氢键受体数Hydrogen Bond Acceptor Count
7
可旋转键计数Rotatable Bond Count
3
精确质量Exact Mass
272.09 Da
单同位素质量Monoisotopic Mass
272.09 Da
拓扑极表面积Topological Polar Surface Area
120.000 Ų
重原子数Heavy Atom Count
19
形式电荷Formal Charge
0
复杂度Complexity
279.000
同位素原子数Isotope Atom Count
0
定义的原子立体中心计数Defined Atom Stereocenter Count
5
未定义的原子立体中心计数Undefined Atom Stereocenter Count
0
定义的键立体中心计数Defined Bond Stereocenter Count
0
未定义的键立体中心计数Undefined Bond Stereocenter Count
0
所有立体化学键的总数The total count of all stereochemical bonds
0
共价键合单元计数Covalently-Bonded Unit Count
1
安全和危险性（GHS）
WGK Germany
3
Merck Index
773
个人防护装备
Eyeshields,Gloves,type N95 (US),type P1 (EN143) respirator filter
质检证书（CoA,COO,BSE/TSE 和分析图谱)
C of A & Other Certificates(BSE/TSE, COO):
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分析证书 | A106856 |
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显示更多⌵
技术文档和文章
Tyrosinase: a key regulatory enzyme in melanin synthesis and its biological and applied significance
目录： 技术文章
Mechanistic Analysis of Topical Glutathione in Skincare: Cellular Redox Regulation, Skin Delivery Challenges, and SLN-Based Delivery Strategies
目录： 技术文章
Mechanism of Kojic Acid in Reducing Hyperpigmentation: From Tyrosinase Inhibition to Melanin Production Regulation
目录： 技术文章
Analysis of Hydrolyzed Pearl as a Cosmetic Raw Material: Preparation Process, Active Components, and Skincare Formulation Applications
目录： 技术文章
The Dual-Targeted Skin-Brightening Mechanism of 4-MSK: Inhibiting Melanin Production and Reducing Epidermal Pigment Retention
目录： 技术文章
Phenylethyl Resorcinol (377): Structural Characteristics, Melanogenesis-Regulating Mechanisms, and Related Applications in Formulation Research
目录： 技术文章
Mechanism of Action of Tranexamic Acid in Pigmentation Care: From the Plasmin System to Regulation of Inflammation-Driven Pro-Melanogenic Signaling
目录： 技术文章
此产品的引用文献
引用文献
| 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, [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, [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, [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, [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, [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, [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, [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, [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, [PMID:33821640] [10.1021/acs.jafc.0c07379] |
| 13. Hao Huang, Tarun Belwal, Xingyu Lin, Jarukitt Limwachiranon, Ligen Zou, Zisheng Luo. (2020) 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, [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, [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, [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, [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). [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). [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, [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). [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, [PMID:26440479] [10.1021/acsami.5b06711] |
| 23. Ting Liu, Zhentao Cheng, Derong Song, Erpeng Zhu, Hui Li, Rutao Lin, Zhiling Wan, Shunxing Liu, Zeguang Gong, Chunlan Shan. (2024) Arbutin alleviates Mycoplasma gallinarum-induced damage caused by pulmonary fibrosis via the JAK2/STAT3 pathway. POULTRY SCIENCE, [PMID:39467406] [10.1016/j.psj.2024.104434] |
| 24. Ying Xu, Tingting Zhang, Shimei Mu, Yanqun Peng, Duanpu Wu, Li Yang, Qing Li, Zengxue Wu, Jian Zhang. (2025) Discovery of Arbutin as Novel Potential Antiviral Agent Against Tomato Yellow Leaf Curl Virus. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, [PMID:39918282] [10.1021/acs.jafc.4c11365] |
| 25. Jian Ouyang, Na Hu, Honglun Wang. (2024) Petanin Potentiated JNK Phosphorylation to Negatively Regulate the ERK/CREB/MITF Signaling Pathway for Anti-Melanogenesis in Zebrafish. INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 25 (11): (5939). [PMID:38892131] [10.3390/ijms25115939] |
| 26. Rongrong Wang, Jiaqi Yang, Jihong Qiang, Qingxia Li, Geng Wang, Canqi Ping, Kesheng Liu, Ruili Wang, Bin Zheng, Guolian Ren, Shuqiu Zhang. (2025) Glucose-functionalized redox-responsive dihydroartemisinin prodrug nanosystem for targeted malaria therapy. International Journal of Pharmaceutics-X, [PMID:40809063] [10.1016/j.ijpx.2025.100370] |
| 27. Wenqingqing Kang, Henry H. Y. Tong, Shu Li. (2025) Discovery of Potential Tyrosinase Inhibitors via Machine Learning and Molecular Docking with Experimental Validation of Activity and Skin Permeation. ACS Omega, [PMID:40918329] [10.1021/acsomega.5c04807] |
| 28. Fukang Deng, Kangchun Li, Hao Luo, Fangxue Hang, Debao Niu, Kedi Yang, Fuchuan Huang, Kai Li. (2025) Amphiphilic Arbutin Derivatives as Renewable Bio-Lubricants with Efficient Antibacterial Activity and Low Cytotoxicity. ACS Sustainable Chemistry & Engineering, [10.1021/acssuschemeng.5c05878] |
| 29. Qing-Pu Zhang, Hua-Wen Peng, Hui Ma, Yu-Ling Sun, Qiang Zhao, Chuan-Feng Chen, Chun Zhang. (2024) Porous triptycene network nanofilms with high molecular sieving accuracy for antibiotics separation. JOURNAL OF MEMBRANE SCIENCE, [10.1016/j.memsci.2024.123060] |
| 30. Zhuanzhuan Liu, Yulu Ma, Yaoyao Xiang, Yusi Shen, Longxiang Liao, Xiuwen Zhu, Zhen Shi, Yanxia Wei, Yanbo Kou, Yugang Wang. (2025) The phytochemical arbutin exerts potent anti-Toxoplasma effects through activation of cell-autonomous defense mechanisms while attenuating inflammation. PLoS Neglected Tropical Diseases, 19 (12): (e0013815). [PMID:41379884] [10.1371/journal.pntd.0013815] |
溶液计算器
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