Arbutin - analytical standard, ≥99% , Tyrosinase inhibitor, CAS No.497-76-7, Tyrosinase inhibitor

CAS: 497-76-7 Cat. No.: A106857 Molecular Weight: 272.25 Beilstein Registry Number: 89673 EC Number: 207-850-3
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GRADE & PURITY Analytical standard ? Analytical standard — certified-purity material for quantitative calibration. Use to prepare calibration standards and validate analytical methods. ≥99%
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 |
Storage
Room temperature
Shipped In
Normal
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Size
Status
Price
Qty
250mg
A106857-250mg
5

$58.90

$69.90
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Why this grade

analytical standard, ≥99% Analytical standard for sensitive chromatographic and analytical workflows requiring minimal baseline interference.

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Storage & shipping

Room temperature Ships Normal Check lot-specific COA for exact specifications.

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Quality documents

SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.

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Literature proof

Cited in 30 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.

Specifications

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.
Storage
Room temperature
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.
Purity
≥99%
Product Properties
ALogP-0.7
Names and Identifiers
Pubchem Sid504758742
Pubchem Sid Urlhttps://pubchem.ncbi.nlm.nih.gov/substance/504758742
Canonical SmilesC1=CC(=CC=C1O)OC2C(C(C(C(O2)CO)O)O)O
IUPAC Name(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(4-hydroxyphenoxy)oxane-3,4,5-triol
InChIKeyBJRNKVDFDLYUGJ-RMPHRYRLSA-N
INCHI1S/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
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
Molecular Weight 272.25
Beilstein 89673
Reaxy-Rn 22933063
Reaxys-RN_link_address https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=22933063&ln=

Documentation

📋 Safety Data Sheet (SDS)

Comprehensive hazard, handling, storage, and regulatory compliance document.

Download SDS →

✅ Certificate of Analysis (COA)

Lot-specific quality data. Enter your lot number to retrieve the exact COA.

Look up COA →

📊 Datasheet

Quick-reference summary of product specifications and applications.

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🔬 Specification Sheet

Full quality attributes and acceptance criteria for this grade.

View spec sheet →

Advanced Data

Taxonomic Classification

Taxonomy Tree

KingdomOrganic compounds
SuperclassOrganic oxygen compounds
ClassOrganooxygen compounds
SubclassCarbohydrates and carbohydrate conjugates
Intermediate Tree Nodes Glycosyl compounds
Direct ParentPhenolic glycosides
Alternative Parents Hexoses  O-glycosyl compounds  4-alkoxyphenols  Phenoxy compounds  Phenol ethers  1-hydroxy-2-unsubstituted benzenoids  Oxanes  Secondary alcohols  Polyols  Oxacyclic compounds  Acetals  Primary alcohols  Hydrocarbon derivatives  
Molecular FrameworkAromatic heteromonocyclic compounds
Substituents Phenolic glycoside - Hexose monosaccharide - O-glycosyl compound - 4-alkoxyphenol - Phenoxy compound - Phenol ether - 1-hydroxy-2-unsubstituted benzenoid - Phenol - Monocyclic benzene moiety - Monosaccharide - Benzenoid - Oxane - Secondary alcohol - Acetal - Oxacycle - Organoheterocyclic compound - Polyol - Alcohol - Primary alcohol - Hydrocarbon derivative - Aromatic heteromonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.
External Descriptors beta-D-glucoside - monosaccharide derivative
3D Structure
Interactive Chemical Structure Model





Associated Targets(Human)
TYR Tclin Tyrosinase (717 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ACHE Tclin Acetylcholinesterase (18204 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PTGS2 Tclin Cyclooxygenase-2 (13999 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Homo sapiens (32628 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Hs68 (138 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HaCaT (4069 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HMV-2 cell line (109 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SMAD3 Tchem Mothers against decapentaplegic homolog 3 (68039 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SLCO1B1 Tchem Solute carrier organic anion transporter family member 1B1 (2672 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SLCO1B3 Tchem Solute carrier organic anion transporter family member 1B3 (2517 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
IDH1 Tclin Isocitrate dehydrogenase [NADP] cytoplasmic (40980 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TAS2R16 Tchem Taste receptor type 2 member 16 (102 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Associated Targets(non-human)
Hdac6 Histone deacetylase 6 (222 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Pseudomonas aeruginosa (123386 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Escherichia coli (133304 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Bacillus subtilis (32866 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Trichomonas vaginalis (2376 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mus musculus (284745 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
B16 (5829 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
P388 (20296 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
B16-F10 (4610 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
rep Replicase polyprotein 1ab (378 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
BCHE Cholinesterase (8742 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Trichophyton mentagrophytes (4846 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
B16-F1 (104 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Melan-a (81 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mechanisms of Action
Certificates(CoA,COO,BSE/TSE and Analysis Chart)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:

Find and download the COA for your product by matching the lot number on the packaging.

2 results found

Lot NumberCertificate TypeDateItem
J2227162Certificate of AnalysisJul 26, 2024 A106857
G2314025Certificate of AnalysisJul 25, 2023 A106857
Chemical and Physical Properties
Specific Rotation[α]-65.5 ° (C=4, H2O)
Melt Point(°C)198°C
Molecular Weight272.250 g/mol
XLogP3-0.700
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count7
Rotatable Bond Count3
Exact Mass272.09 Da
Monoisotopic Mass272.09 Da
Topological Polar Surface Area120.000 Ų
Heavy Atom Count19
Formal Charge0
Complexity279.000
Isotope Atom Count0
Defined Atom Stereocenter Count5
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
The total count of all stereochemical bonds0
Covalently-Bonded Unit Count1
Documents & Articles
Citations of This Product
References
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,      [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,      [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,      [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,  (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,  (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,      [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,  (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,      [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,      [PMID:] [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,      [PMID:] [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]
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