<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-22 04:26:11 UTC</creation_date>
  <update_date>2026-05-14 19:07:53 UTC</update_date>
  <accession/>
  <common_name>Arbutin</common_name>
  <class>SmallMolecule</class>
  <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.</description>
  <categories/>
  <types>
    <type>PFAS</type>
    <type>Phytotoxin</type>
  </types>
  <synonyms>
    <synonym>(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(4-hydroxyphenoxy)oxane-3,4,5-triol</synonym>
    <synonym>hydroquinone-O-β-D-glucopyranoside</synonym>
  </synonyms>
  <chemical_formula>C12H16O7</chemical_formula>
  <average_molecular_weight>272.2512</average_molecular_weight>
  <monisotopic_moleculate_weight>272.089602866</monisotopic_moleculate_weight>
  <iupac_name>(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(4-hydroxyphenoxy)oxane-3,4,5-triol</iupac_name>
  <traditional_iupac>β-arbutin</traditional_iupac>
  <cas_registry_number>497-76-7</cas_registry_number>
  <smiles>[H][C@]1(CO)O[C@@]([H])(OC2=CC=C(O)C=C2)[C@]([H])(O)[C@@]([H])(O)[C@]1([H])O</smiles>
  <inchi>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>
  <inchikey>BJRNKVDFDLYUGJ-RMPHRYRLSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Phenolic glycosides</direct_parent>
    <alternate_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>4-alkoxyphenols</alternative_parent>
      <alternative_parent>Acetals</alternative_parent>
      <alternative_parent>Hexoses</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>O-glycosyl compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Phenol ethers</alternative_parent>
      <alternative_parent>Phenoxy compounds</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>4-alkoxyphenol</substituent>
      <substituent>Acetal</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Hexose monosaccharide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>O-glycosyl compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Phenol</substituent>
      <substituent>Phenol ether</substituent>
      <substituent>Phenolic glycoside</substituent>
      <substituent>Phenoxy compound</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>beta-D-glucoside</descriptor>
      <descriptor>monosaccharide derivative</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways>
    <pathway>
      <name>Arbutin Drug Metabolism Action Pathway</name>
      <smpdb_id>SMP0144635</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>-0.9</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.36</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.84</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>3.91e+01 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>9.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(4-hydroxyphenoxy)oxane-3,4,5-triol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>272.2512</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>272.089602866</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@]1(CO)O[C@@]([H])(OC2=CC=C(O)C=C2)[C@]([H])(O)[C@@]([H])(O)[C@]1([H])O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C12H16O7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>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</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>BJRNKVDFDLYUGJ-RMPHRYRLSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>119.61</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>62.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>25.88</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <route_of_exposure/>
  <mechanism_of_toxicity/>
  <metabolism/>
  <toxicity/>
  <lethaldose/>
  <carcinogenicity/>
  <use_source/>
  <min_risk_level/>
  <health_effects>#&lt;HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f7281fd5c00&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB11217</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>346</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>21241189</chemspider_id>
  <kegg_id/>
  <uniprot_id/>
  <omim_id/>
  <chebi_id/>
  <biocyc_id/>
  <ctd_id/>
  <stitch_id/>
  <actor_id/>
  <pdb_id/>
  <wikipidia/>
  <general_references/>
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  </targets>
</compound>
