Structure via PubChem · Public domain (PubChem)
arbutin
Sign in to saveAlso known as p-hydroxyphenyl beta-D-glucoside, p-hydroxyphenyl beta-D-glucopyranoside, (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(4-hydroxyphenoxy)oxane-3,4,5-triol, (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(4-hydroxyphenoxy)tetrahydropyran-3,4,5-triol, (2S,3R,4S,5S,6R)-2-(4-hydroxyphenoxy)-6-methylol-tetrahydropyran-3,4,5-triol, hydroquinone O-β-D-glucopyranoside, Hydroquinone-O-beta-D-glucopyranoside
β-Arbutin, also known by its International Nomenclature of Cosmetic Ingredients (INCI) name, arbutin, is a glycosylated derivative of hydroquinone. β-Arbutin is naturally present in the leaves and bark of a variety of plants, notably the bearberry plant, Arctostaphylos uva-ursi. Utilized as a biosynthetic active ingredient in topical treatments for skin lightening, β-arbutin is aimed at addressing hyperpigmentation issues. Its mechanism of action involves inhibiting the activity of tyrosinase, an essential enzyme for melanin synthesis in the human skin, thereby leading to a reduction in hyperp
Chemical data
- Formula
- C12H16O7
- Molecular weight
- 272.25 g/mol
- IUPAC name
- (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(4-hydroxyphenoxy)oxane-3,4,5-triol
- SMILES
- C1=CC(=CC=C1O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
- InChIKey
- BJRNKVDFDLYUGJ-RMPHRYRLSA-N
- XLogP
- -0.7
- Polar surface area
- 120 Ų
- H-bond donors
- 5
- H-bond acceptors
- 7
- Formal charge
- 0
via PubChem
Research
1,338 papers- Arbutin as a Skin Depigmenting Agent with Antimelanogenic and Antioxidant Properties.Antioxidants (Basel, Switzerland) · 2021
- GROWTH REGULATING FACTOR 7-mediated arbutin metabolism enhances rice salt tolerance.The Plant cell · 2024
- Arbutin alleviates intestinal colitis by regulating neutrophil extracellular traps formation and microbiota composition.Phytomedicine : international journal of phytotherapy and phytopharmacology · 2024
- Arbutin: Occurrence in Plants, and Its Potential as an Anticancer Agent.Molecules (Basel, Switzerland) · 2022
- Arbutin ameliorated depression by inhibiting neuroinflammation and modulating intestinal flora.Phytomedicine : international journal of phytotherapy and phytopharmacology · 2025
via PubMed
Wikidata facts
- Mass
- 272.089603
Show 5 more facts
- chemical formula
- C₁₂H₁₆O₇
- Commons category
- Arbutin
- melting point
- 198
- canonical SMILES
- C1=CC(=CC=C1O)OC2C(C(C(C(O2)CO)O)O)O
- isomeric SMILES
- C1=CC(=CC=C1O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
via Wikidata · CC0
~5 min read
Article
12 sectionsContents
- Properties
- Occurrence and preparation
- Uses
- Herbal medicine
- Mechanism of action
- Regulation of melanin synthesis
- Decomposition into hydroquinone
- Safety and regulation
- Skin-lightening agent
- Risks
- See also
- References
β-Arbutin, also known by its International Nomenclature of Cosmetic Ingredients (INCI) name, arbutin, is a glycosylated derivative of hydroquinone. β-Arbutin is naturally present in the leaves and bark of a variety of plants, notably the bearberry plant, Arctostaphylos uva-ursi. Utilized as a biosynthetic active ingredient in topical treatments for skin lightening, β-arbutin is aimed at addressing hyperpigmentation issues. Its mechanism of action involves inhibiting the activity of tyrosinase, an essential enzyme for melanin synthesis in the human skin, thereby leading to a reduction in hyperpigmentation. It is important to distinguish β-arbutin from its structurally similar stereoisomer, α-arbutin, which exhibits similar effects in clinical applications.
== Properties == Arbutin is a compound where a glucose molecule, specifically -glucose, is chemically bound to hydroquinone. In aqueous solutions, glucose can exist in one of three stereoisomeric forms: α, β, or γ, with the β-anomer being the predominant form. The standard known form of arbutin, β-Arbutin, has a molecular formula of C12H16O7 and a molecular weight of 272.25g/mol. Its stereoisomers, α-arbutin and γ-arbutin, share the same molecular formula and weight but are distinct in their atoms' spatial arrangement.