Arbutin
[CAS# 497-76-7]

Identification

• Classification: Biochemical >> Amino acids and their derivatives >> Proline derivatives
• Name: Arbutin
• Synonyms: 4-Hydroxyphenyl-beta-D-glucopyranoside; p-Arbutin
• Molecular Formula: C₁₂H₁₆O₇
• Molecular Weight: 272.25
• CAS Registry Number: 497-76-7
• EC Number: 207-850-3
• SMILES: C1=CC(=CC=C1O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O

Properties

• Solubility: 50 mg/mL (hot water), 46 mg/mL (CH3OH) (Expl.)
• Density: 1.6±0.1 g/cm³, Calc.^*
• Melting point: 195-198 °C (Expl.)
• Index of Refraction: 1.65, Calc.^*
• Boiling Point: 561.6±50.0 °C (760 mmHg), Calc.^*
• Flash Point: 293.4±30.1 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315

Discovery and Applications

Arbutin is a naturally occurring glycoside compound found in various plant species, including bearberry (Arctostaphylos uva-ursi), blueberry, cranberry, and pear. It is a derivative of hydroquinone, with a glucose molecule attached to the hydroxyl group of hydroquinone. The compound is commonly used in the cosmetic and pharmaceutical industries due to its skin-brightening properties and antioxidant activity.

The discovery of arbutin dates back to the early 19th century when it was first isolated from the leaves of the bearberry plant. The compound gained attention for its therapeutic properties, particularly its potential as a natural alternative to hydroquinone in skin lightening formulations. Arbutin works by inhibiting the activity of tyrosinase, an enzyme responsible for the production of melanin in the skin. This makes it effective in treating hyperpigmentation, such as age spots, freckles, and melasma.

In addition to its cosmetic applications, arbutin has been studied for its potential medicinal benefits. It has been used as a urinary antiseptic, as it is metabolized into hydroquinone in the body, which has antibacterial properties. Arbutin's ability to release hydroquinone has also led to its investigation in the treatment of urinary tract infections and other related conditions.

The most common form of arbutin used in cosmetics is beta-arbutin, which is synthesized through the glycosylation of hydroquinone. Alpha-arbutin, a more stable form of the compound, is also used in some formulations. Both forms of arbutin are valued in the skincare industry for their skin-lightening and anti-aging effects, as they help reduce the appearance of dark spots and promote a more even skin tone. Arbutin is typically incorporated into creams, serums, and lotions designed for skin brightening and treatment of hyperpigmentation.

Arbutin is generally considered safe for topical use in cosmetic products, although it is important to note that excessive use or misuse of products containing hydroquinone, the active ingredient released by arbutin, can lead to skin irritation or other adverse effects. As a result, the use of arbutin is carefully regulated in many countries to ensure consumer safety.

In summary, arbutin is a naturally derived compound widely used in cosmetics for its skin-brightening and anti-pigmentation effects. Its discovery in the 19th century and subsequent application in the treatment of hyperpigmentation has made it a valuable ingredient in the skincare industry.

References

2024. Pharmacological and biochemical insights into lead-induced hepatotoxicity: Pathway interplay and the protective effects of arbutin via the oral and intraperitoneal routes in silico and in vivo. International Immunopharmacology, 141.
DOI: 10.1016/j.intimp.2024.112968

2024. Arbutin alleviates Mycoplasma gallinarum-induced damage caused by pulmonary fibrosis via the JAK2/STAT3 pathway. Poultry Science, 103(12).
DOI: 10.1016/j.psj.2024.104434

2024. Valorisation of Environmental Menace “Water Hyacinth” Biomass for Extraction of Valuable Metabolites and as High-Performance Adsorbent. Waste and Biomass Valorization, 15(12).
DOI: 10.1007/s12649-024-02827-3