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

CAS: 497-76-7 Cat. No.: A106857 Formule: C12H16O7 Poids moléculaire: 272.25 Beilstein Registry Number: 89673 Numéro CE: 207-850-3
DISPONIBLE À COMMANDE
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,Argon charged
Shipped In
Normal
★
Size
Allemagne (EU)
USA*
Price
Qty
250mg
A106857-250mg
—
5 En stock

51,11€

60,65€
Enregistrer 9,55 € (15.74%)
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Why this grade

analytical standard, ≥99% Étalon d'analyse for sensitive chromatographic and analytical workflows requiring minimal baseline interference.

🌡

Storage & shipping

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

📋

Quality documents

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

📚

Literature proof

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

Vue d’ensemble

Arbutin is a glycosylated hydroquinone used in traditional Chinese medicine (TCM). Arbutin inhibits melanin formation due to its tyrosinase inhibitory activity.

Specifications

Synonymes
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 |
Spécifications et pureté
analytical standard, ≥99%
Mécanismes biochimiques et physiologiques
Naturally occurring beta-D-glucopyranoside of hydroquinone. Isolated from the leaves of Bearberry ( Arctostaphylos ). Competitive inhibitor of tyrosinase in melanocytes. Inhibits melanin biosynthesis.
Application
Arbutin, a glycosylated hydroquinone, is used in studies on melanin biosynthesis and as an inhibitor to identify, differentiate and characterize tyrosinase(s). Biochem/physiol Actions
Conditions de stockage de stockage
Room temperature,Argon charged
Expédié en
Normal
Grade
Étalon d'analyse
Type d'action
INHIBITOR
Mécanisme d'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.
Pureté
≥99%
Propriétés du produit
ALogP
-0.7
Noms et identifiants
Pubchem Sid
Pubchem Sid Url
https://pubchem.ncbi.nlm.nih.gov/substance/504758742
Sourires canoniques
C1=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
InChIKey
BJRNKVDFDLYUGJ-RMPHRYRLSA-N
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
Isomères SMILES
C1=CC(=CC=C1O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
WGK Allemagne
3
Poids moléculaire
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.

View datasheet →

🔬 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
ClasseOrganooxygen 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
Structure 3D
Modèle de structure chimique interactif





Cibles associées (humaines)
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
Cibles associées (non humaines)
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
Mécanismes d'action
Certificats (CoA, COO, BSE/TSE et tableau d'analyse)
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.

3 results found

Lot NumberCertificate TypeDateArticle
I2628012Certificate of AnalysisOct 09, 2026 A106857
G2314025Certificate of AnalysisApr 08, 2025 A106857
J2227162Certificate of AnalysisJul 26, 2024 A106857
Propriétés chimiques et physiques
SensibilitéMoisture sensitive,Air sensitive
Rotation spécifique [α]-65.5 ° (C=4, H2O)
Point de fusion (°C)198°C
Poids moléculaire272.250 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
FAQ et articles
Tyrosinase: a key regulatory enzyme in melanin synthesis and its biological and applied significance
Mechanistic Analysis of Topical Glutathione in Skincare: Cellular Redox Regulation, Skin Delivery Challenges, and SLN-Based Delivery Strategies
Mechanism of Kojic Acid in Reducing Hyperpigmentation: From Tyrosinase Inhibition to Melanin Production Regulation
Analysis of Hydrolyzed Pearl as a Cosmetic Raw Material: Preparation Process, Active Components, and Skincare Formulation Applications
The Dual-Targeted Skin-Brightening Mechanism of 4-MSK: Inhibiting Melanin Production and Reducing Epidermal Pigment Retention
Phenylethyl Resorcinol (377): Structural Characteristics, Melanogenesis-Regulating Mechanisms, and Related Applications in Formulation Research
Mechanism of Action of Tranexamic Acid in Pigmentation Care: From the Plasmin System to Regulation of Inflammation-Driven Pro-Melanogenic Signaling
Reactions and Applications of 3,3-Difluoroallyl Sulfonium Salts (DFASs): Small-Molecule gem-Difluoroallylation, Selective Peptide Modification, and Subsequent Functionalization
How Arbutin Regulates Melanin Production: α/β Anomeric Configuration and Tyrosinase Action
Glycosidic Bond Structure and Cleavage Mechanisms—Chemical and Enzymatic Cleavage of O-, N-, S-, and C-Glycosides
Citations of This Product
Calculateurs de solution
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