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Showing Compound Arbutin (FDB001221)

Record Information
Version1.0
Creation date2010-04-08 22:04:53 UTC
Update date2025-11-18 22:29:11 UTC
Primary IDFDB001221
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameArbutin
DescriptionArbutin, also known as arbutoside or beta-arbutin, 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. Arbutin is an extremely weak basic (essentially neutral) compound (based on its pKa). Arbutin is a bitter tasting compound. Arbutin is found, on average, in the highest concentration within a few different foods, such as bilberries, quinces, and pears. Arbutin has also been detected, but not quantified in, several different foods, such as sweet marjorams, apples, pomes, yali pears, and milk (cow). This could make arbutin a potential biomarker for the consumption of these foods.
CAS Number497-76-7
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
4-Hydroxyphenyl b-D-glucopyranoside, 9ci, 8ciHMDB
4-Hydroxyphenyl beta-D-glucopyranosideHMDB
4-Hydroxyphenyl-beta-D-glucopyranosideHMDB
ArbutinumHMDB
ArbutosideHMDB
beta -D-Glucopyranoside, 4-hydroxyphenylHMDB
beta-ArbutinHMDB
EricolinHMDB
Hydroquinone beta -D-glucopyranosideHMDB
Hydroquinone beta-D-glucopyranosideHMDB
Hydroquinone O-beta-D-glucopyranosideHMDB
Hydroquinone-glucoseHMDB
Hydroquinone-O-beta-D-glucopyranosideHMDB
p-ArbutinHMDB
p-Hydroxyphenyl beta -D-glucopyranosideHMDB
p-Hydroxyphenyl beta -D-glucosideHMDB
p-Hydroxyphenyl beta-D-glucopyranosideHMDB
p-Hydroxyphenyl beta-D-glucosideHMDB
UrsinHMDB
UvasolHMDB
β-D-Glucopyranoside, 4-hydroxyphenylbiospider
4-Hydroxyphenyl b-D-glucopyranoside, 9CI, 8CIdb_source
4-hydroxyphenyl beta-D-glucopyranosidebiospider
Beta-arbutinbiospider
Hydroquinone β-d-glucopyranosidebiospider
Hydroquinone beta-d-glucopyranosidebiospider
Hydroquinone o-beta-d-glucopyranosidebiospider
Hydroquinone-o-beta-d-glucopyranosidebiospider
P-arbutinbiospider
P-hydroxyphenyl β-d-glucopyranosidebiospider
P-hydroxyphenyl β-d-glucosidebiospider
P-hydroxyphenyl beta-d-glucopyranosidebiospider
P-hydroxyphenyl beta-d-glucosidebiospider
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
Polarizability25.92 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC12H16O7
IUPAC name2-(hydroxymethyl)-6-(4-hydroxyphenoxy)oxane-3,4,5-triol
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
InChI KeyBJRNKVDFDLYUGJ-UHFFFAOYSA-N
Isomeric SMILESOCC1OC(OC2=CC=C(O)C=C2)C(O)C(O)C1O
Average Molecular Weight272.2512
Monoisotopic Molecular Weight272.089602866
Classification
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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 52.94%; H 5.92%; O 41.14%DFC
Melting PointMp 142-143°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logP-1.35HANSCH,C ET AL. (1995)
Experimental pKa10
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]18D -60.34 (H2O)DFC
Spectroscopic UV Data[neutral] lmax 294 () (EtOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSArbutin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0w29-5950000000-b06dd9542fa7bbd667f2Spectrum
Predicted GC-MSArbutin, 5 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-014i-2201239000-2f42b1022552b40a482eSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03k9-0970000000-7f1103faf15e6a9062522015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0900000000-f96f8a574fa0e00ad3232015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-9800000000-5ea8ff882118ae29ef232015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05fr-1790000000-08eaec414aecf42a9f902015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1910000000-51e3a547305d558284672015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-4900000000-481f6d878e6db1bc8f7c2015-04-25View Spectrum
NMRNot Available
ChemSpider ID339
ChEMBL IDCHEMBL79041
KEGG Compound IDC06186
Pubchem Compound ID440936
Pubchem Substance IDNot Available
ChEBI ID18305
Phenol-Explorer ID659
DrugBank IDNot Available
HMDB IDHMDB29943
CRC / DFC (Dictionary of Food Compounds) IDBWQ88-O:BWQ88-O
EAFUS IDNot Available
Dr. Duke IDARBUTIN
BIGG IDNot Available
KNApSAcK IDC00002638
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDArbutin
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
AllelochemicA chemical released by plants that interacts with other organisms, influencing their behavior or growth. Its biological role involves plant defense and communication. Therapeutically, allelochemics have anti-inflammatory, antimicrobial, and antioxidant properties, with applications in managing anxiety, pain, and infections, as well as potential anticancer uses.DUKE
Anti bacterial33282 An agent that inhibits the growth of or destroys bacteria, playing a crucial role in preventing and treating infections. Therapeutically, it is used to combat bacterial infections, with key medical applications including treating pneumonia, tuberculosis, and skin infections, as well as preventing surgical site infections and sepsis.DUKE
Anti-edemicAn agent that relieves or prevents edema, reducing abnormal fluid accumulation in tissues or the circulatory system, commonly used to treat conditions such as swelling, inflammation, and water retention.DUKE
Anti-melanogenic35610 An agent that inhibits melanin production, reducing skin pigmentation. It plays a biological role in regulating melanogenesis, and has therapeutic applications in treating hyperpigmentation disorders, such as melasma and freckles, and key medical uses in skin whitening and depigmentation treatments.DUKE
Anti septic33281 An agent that prevents or reduces the growth of microorganisms, such as bacteria, fungi, or viruses, to promote wound healing and prevent infection. Therapeutically, anti septics are used to treat minor cuts, scrapes, and burns, and are commonly applied topically to reduce the risk of infection and promote tissue repair. Key medical uses include wound care, surgical site preparation, and skin infection management.DUKE
Anti-streptococcic33282 An agent that targets and combats Streptococcus bacteria, reducing infection and inflammation. Therapeutically, it is used to treat streptococcal infections, such as strep throat and skin infections, and to prevent complications like rheumatic fever.DUKE
Anti-tussive52217 An agent that suppresses coughing, reducing the frequency and severity of coughs. It works by targeting the brain's cough center, providing therapeutic relief for dry, irritating coughs. Key medical uses include managing coughs associated with colds, flu, and other respiratory conditions.DUKE
ArtemicideAn herbicidal agent that targets and eliminates weeds of the Artemisia genus, with potential therapeutic applications in allergy management and anti-inflammatory uses, particularly for conditions exacerbated by Artemisia allergens.DUKE
CandidicideAn agent that kills Candida species, such as Candida albicans, reducing fungal infections. Therapeutically, it is used to treat candidiasis, with key medical applications in managing oral thrush, vaginal yeast infections, and other fungal diseases.DUKE
Diuretic35498 An agent that increases urine production, helping remove excess fluids and salts from the body. It plays a key biological role in regulating fluid balance and blood pressure. Therapeutically, diuretics are used to treat conditions such as hypertension, edema, and heart failure, helping reduce swelling and lower blood pressure.DUKE
Insulin-sparingAn agent that reduces the dose of insulin required to achieve a given level of glycemic control, used therapeutically to manage diabetes, improving insulin sensitivity and reducing insulin resistance.DUKE
Mycoplasma inhibitorAn agent that inhibits growth of Mycoplasma bacteria, used therapeutically to treat Mycoplasma infections, with applications in managing respiratory and urogenital diseases.DUKE
Pesticide25944 An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.DUKE
Tyrosinase inhibitor59997 An agent that blocks the activity of tyrosinase, an enzyme involved in melanin production, reducing skin pigmentation. Therapeutically used to treat hyperpigmentation disorders, such as melasma and vitiligo, and as a skin-lightening agent in dermatology.DUKE
Urinary antisepticAn agent that prevents the growth of microorganisms in urine, reducing the risk of urinary tract infections (UTIs). Therapeutically, it helps manage and prevent UTIs, commonly used to treat conditions such as cystitis and pyelonephritis.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.