Arbutin (CED0004334)

Record Information
Version1.0
Creation Date2016-05-22 04:26:11 UTC
Update Date2026-05-14 19:07:53 UTC
Accession NumberCHEM017529
Identification
Common NameArbutin
ClassSmall Molecule
Description
Arbutin belongs to the carbohydrates and carbohydrate conjugates, a subclass of organooxygen compounds within the organic compounds. This compound has the chemical formula $\text{C}_{12}\text{H}_{16}\text{O}_7$ and an average molecular weight of 272.25 g/mol. In biological systems, it acts as an inhibitor of the protein target tyrosinase (TYR). Industrially, arbutin is utilized as an antioxidant, a bleaching agent, and a softener and conditioner. It is found in or released from 32 recorded sources across multiple sectors. Within the electronics sector, it is associated with capacitors, cell phones, batteries, printed circuit boards, and wires and cables. In the food, food processing, and cookware sector, it is linked to food packaging, food preservation, the preparation of vinegar, the preparation of wine or sparkling wine, and fermentation processes for beer. Its presence in household cleaning and consumer products includes soap detergents, bleaching agents, perfumes within detergents and soaps, tobacco smoke filters, and non-electric simulated smoking devices. Additionally, it is found in synthetic textiles, carpets and rugs, medical devices, and building and construction materials such as sunshades awnings or outside screens. Recorded exposure routes for the compound include oral, inhalation, and touch.
Contaminant Type
  • PFAS
  • Phytotoxin
Chemical Structure
Synonyms
ValueSource
Hydroquinone-O-beta-D-glucopyranosideChEBI
p-Hydroxyphenyl beta-D-glucopyranosideChEBI
p-Hydroxyphenyl beta-D-glucosideChEBI
UrsinChEBI
UvasolChEBI
Hydroquinone-O-b-D-glucopyranosideGenerator
Hydroquinone-O-β-D-glucopyranosideGenerator
p-Hydroxyphenyl b-D-glucopyranosideGenerator
p-Hydroxyphenyl β-D-glucopyranosideGenerator
p-Hydroxyphenyl b-D-glucosideGenerator
p-Hydroxyphenyl β-D-glucosideGenerator
4-Hydroxyphenyl-b-glucopyranosideHMDB
4-Hydroxyphenyl-β-glucopyranosideHMDB
4-Hydroxyphenyl beta-D-glucopyranosideHMDB
4-Hydroxyphenyl β-D-glucopyranosideHMDB
ArbutineHMDB
ArbutosideHMDB
ArbutyneHMDB
Hydroquinone beta-D-glucopyranosideHMDB
Hydroquinone glucoseHMDB
Hydroquinone β-D-glucopyranosideHMDB
beta-ArbutinHMDB
p-ArbutinHMDB
Β-arbutinHMDB
ArbutinChEBI
Chemical FormulaC12H16O7
Average Molecular Mass272.251 g/mol
Monoisotopic Mass272.090 g/mol
CAS Registry Number497-76-7
IUPAC Name(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(4-hydroxyphenoxy)oxane-3,4,5-triol
Traditional Nameβ-arbutin
SMILES[H][C@]1(CO)O[C@@]([H])(OC2=CC=C(O)C=C2)[C@]([H])(O)[C@@]([H])(O)[C@]1([H])O
InChI IdentifierInChI=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 KeyBJRNKVDFDLYUGJ-RMPHRYRLSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPhenolic glycosides
Alternative Parents
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
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility39.1 g/LALOGPS
logP-1.4ALOGPS
logP-0.9ChemAxon
logS-0.84ALOGPS
pKa (Strongest Acidic)9.82ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area119.61 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity62.16 m³·mol⁻¹ChemAxon
Polarizability25.88 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrumsplash10-0uxr-1971000000-e8260464bad4d4a7fa0cNot AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0uxs-0940000000-9984522469f86670798fNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0r00-9750000000-b52a5d3b5fb7e98f0009Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-0090000000-a7028a3a9618849334b7Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0229-0920000000-532b692f9942a62cc7c8Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0229-0910000000-1cb0580496288b7004fcNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0950000000-4bafd0325d0163331c0aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0950000000-ffffdfe1cd448f0ea135Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-016r-0290000000-0ebc801fded534434aa5Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-016r-0390000000-5831b5a141106482d24dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0900000000-e517344bdabb66a133e9Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0900000000-315daa57d6f694ca71fbNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-1900000000-df811a65eba1be7fd68dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0900000000-4efe3ed1e7614387deb4Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-9000000000-6f8b05f1e0b20e00a25fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-9100000000-7092290163d035871936Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0900000000-a0b2ea306ed135900292Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-1900000000-26385cb99dd5b38d4f3cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0900000000-0a4c12f1e9730c4685eaNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03k9-0970000000-e87519bd2c30ca193e5eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-1900000000-f812a22889a4e7871758Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03e9-9600000000-9a8f2b8fb568a07413b4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-05fr-1890000000-cb67c77a9f0c57c986bdNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-1910000000-52b74ad8f6f3181df26dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-5900000000-45bf1851196d0254c239Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ab9-0950000000-597b2277ebb9d13fbb41Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ab9-4940000000-6a46c2768079c1935cb9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-7900000000-56f28af9a02294ffb2faNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01vk-0930000000-8dd700efcb05840db393Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ik9-2920000000-e4364592fc1d3fc0a847Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4r-9610000000-7ee135304790467dc07eNot AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
2769.0Log mg/kg[1600:4900]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
7PesticidesAgriculture & land managementNot Available
10InsecticidesAgriculture & land managementNot Available
120Wires and cablesElectrical & Electronic EquipmentNot Available
121Printed circuit boardsElectrical & Electronic EquipmentNot Available
125BatteriesElectrical & Electronic EquipmentNot Available
130SemiconductorsElectrical & Electronic EquipmentNot Available
138LubricantsEnergy, oil & gasNot Available
147Food packagingFood, food processing & cookwareNot Available
174LubricantsIndustrial manufacturing & chemical processingNot Available
233BrushesPersonal care & cosmeticsNot Available
234Medical devicesHealthcare, pharmaceuticals & veterinary productsNot Available
451Carpets and RugsTextiles, leather & furnishingsNot Available
454Synthetic textilesTextiles, leather & furnishingsNot Available
490Personal care & cosmeticsNot Available
492Cell phonesElectrical & Electronic EquipmentNot Available
493CapacitorsElectrical & Electronic EquipmentNot Available
501Sunshades Awnings Or Outside ScreensBuilding & ConstructionNot Available
502Sunshades Awnings Or Outside ScreensBuilding & ConstructionNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
527MagnetsElectrical & Electronic EquipmentNot Available
544Fermentation Processes For BeerFood, food processing & cookwareNot Available
545Food PreservationFood, food processing & cookwareNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
551Processing FishFood, food processing & cookwareNot Available
555Bleaching AgentsHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
581Paper Making MachinesIndustrial manufacturing & chemical processingNot Available
596AcaricidesAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
612Body Washing Or Cleaning ImplementsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
616Face Mask CosmeticsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
630ToysRecreation & sports surfacesNot Available
632ApparelTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
658Touch FastenersTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
1 pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureType 1 fimbrin D-mannose specific adhesinP08191Escherichia coli K-12Predicted (SEA)0.0778492
Click to view 3D structureLectinB4EH87Burkholderia cenocepacia (strain ATCC BAA-245 / DSM 16553 / LMG 16656/ NCTC 13227 / J2315 / CF5610) (Burkholderia cepacia (strain J2315))Predicted (SEA)0.0778492
Carbonic anhydrase 12 structureClick to view 3D structureCarbonic anhydrase 12O43570HumansPredicted (SEA)13.3122
Carbonic anhydrase 7 structureClick to view 3D structureCarbonic anhydrase 7P43166HumansPredicted (SEA)12.7673
Carbonic anhydrase 1 structureClick to view 3D structureCarbonic anhydrase 1P00915HumansPredicted (SEA)25.301
Click to view 3D structureTaste receptor type 2 member 16Q9NYV7HumansPredicted (SEA)0.155698
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2P00918HumansPredicted (SEA)39.8588
Carbonic anhydrase 4 structureClick to view 3D structureCarbonic anhydrase 4P22748HumansPredicted (SEA)12.4559
Click to view 3D structureTrehalose-phosphataseA8NS89Brugia malayiPredicted (SEA)0.0778492
Carbonic anhydrase 9 structureClick to view 3D structureCarbonic anhydrase 9Q16790HumansPredicted (SEA)35.7328
Click to view 3D structureN-acetyllactosaminide alpha-1,3-galactosyltransferaseP50127Sus scrofaPredicted (SEA)0.233548
Solute carrier family 28 member 3 structureClick to view 3D structureSolute carrier family 28 member 3Q9HAS3HumansPredicted (SEA)1.71268
Interleukin-2 structureClick to view 3D structureInterleukin-2P60568HumansPredicted (SEA)1.16774
Click to view 3D structurePA-I galactophilic lectinQ05097Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG12228)Predicted (SEA)0.467095
Click to view 3D structureBeta-1,4-galactosyltransferase 1P08037Bos taurusPredicted (SEA)0.622794
Sodium/glucose cotransporter 1 structureClick to view 3D structureSodium/glucose cotransporter 1P13866HumansPredicted (SEA)7.62922
Aldehyde dehydrogenase, mitochondrial structureClick to view 3D structureAldehyde dehydrogenase, mitochondrialP05091HumansPredicted (SEA)2.56902
Click to view 3D structurePeptidoglycan-N-acetylglucosamine deacetylaseQ8DP63Streptococcus pneumoniae (strain ATCC BAA-255 / R6)Predicted (SEA)0.467095
Click to view 3D structureAldo-keto reductase family 1 member B1P07943Rattus norvegicusPredicted (SEA)22.2649
Sodium/glucose cotransporter 2 structureClick to view 3D structureSodium/glucose cotransporter 2P31639HumansPredicted (SEA)9.49761
Click to view 3D structureOligo-1,6-glucosidase IMA1P53051Saccharomyces cerevisiae S288cPredicted (SEA)2.80257
Aldo-keto reductase family 1 member B1 structureClick to view 3D structureAldo-keto reductase family 1 member B1P15121HumansPredicted (SEA)37.3676
Gap junction beta-2 protein structureClick to view 3D structureGap junction beta-2 proteinP29033HumansPredicted (SEA)0.778492
Galectin-3 structureClick to view 3D structureGalectin-3P17931HumansPredicted (SEA)8.87481
Click to view 3D structureCarbonic anhydrase 5A, mitochondrialP35218HumansPredicted (SEA)124.559
Concentrations
Not Available
External Links
DrugBank IDDB11217
HMDB IDHMDB0029943
FooDB IDFDB030911
Phenol Explorer IDNot Available
KNApSAcK IDC00002638
BiGG IDNot Available
BioCyc IDHYDROQUINONE-O-BETA-D-GLUCOPYRANOSIDE
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkArbutin
Chemspider ID389765
ChEBI ID18305
PubChem Compound ID440936
Kegg Compound IDC06186
YMDB IDNot Available
ECMDB IDECMDB04019
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=15287073
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=9518563
3. Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.
4. Siegers C, Bodinet C, Ali SS, Siegers CP: Bacterial deconjugation of arbutin by Escherichia coli. Phytomedicine. 2003;10 Suppl 4:58-60.
5. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.