Arbutin

• CAS: 497-76-7
• Catalog Number: ACM497767-1
• Category: Material of Cosmetics
• Molecular Weight: 272.25
• Molecular Formula: C12H16O7
• Description: Arbutin is a natural active substance derived from green plants. It combines the "green plant, safe and reliable" and "high-efficiency discoloration" into a skin decolorizing component, which can quickly penetrate into the skin without affecting cell proliferation. At the same time, it can effectively inhibit the activity of tyrosinase in the skin, block the formation of melanin, and directly combine with tyrosinase to accelerate the decompositio;n and excretion of melanin, thereby reducing skin pigmentation, eliminating pigmentation and Freckles, and do not produce toxic, irritating, sensitizing and other side effects on melanocytes, as well as bactericidal and anti-inflammatory effects.
• Synonyms: 4-Hydroxyphenyl-beta-D-glucopyranosid
• IUPAC Name: (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(4-hydroxyphenoxy)oxane-3,4,5-triol
• SMILES: C1=CC(=CC=C1O)OC2C(C(C(C(O2)CO)O)O)O
• 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 Key: BJRNKVDFDLYUGJ-RMPHRYRLSA-N
• Boiling Point: 375.31 °C
• Melting Point: 195-198 °C
• Flash Point: 293.4 °C
• Density: 1.3582 g/cm³
• Solubility: Soluble in water, alcohol
• Appearance: Solid
• Storage: Inert atmosphere, room temperature
• Active Content: 95%
• Assay: 0.99
• Complexity: 279
• EC Number: 207-850-3
• Exact Mass: 272.08960285
• Isomeric SMILES: C1=CC(=CC=C1O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
• MDL Number: MFCD00016915
• Monoisotopic Mass: 272.08960285
• Packaging: 1 kg
• Physical State: Solid
• pKa: 10.10±0.15(Predicted)
• Plant Origin: leaf ot bearberry
• Refractive Index: -65.5 ° (C=4, H₂O)
• Solubility In Water: 10-15 g/100mL (20 ºC)
• Stability: Stable. Hygroscopic - store under dry nitrogen.
• Topological Polar Surface Area: 120 Ų

Case Study

Arbutin for the Treatment of Calcium Oxalate-Induced Nephrolithiasis via Activation of Nrf2 Signaling

Fang J, et al. Free Radical Biology and Medicine, 2025, 241, 868-881.

Arbutin was investigated for its protective role against calcium oxalate (CaOx)-induced kidney injury using both cellular and in vivo nephrolithiasis models. A mouse model of CaOx nephrolithiasis was established by administering a high-oxalate, calcium-deficient diet to induce renal crystal deposition. Parallel in vitro experiments employed HK-2 human renal epithelial cells exposed to CaOx crystals. Tandem mass tag (TMT)-based proteomic analysis was performed to identify molecular targets of arbutin treatment. The results demonstrated that arbutin significantly reduced CaOx crystal deposition and improved HK-2 cell viability. Molecular docking suggested stable binding of arbutin to the Nrf2-Keap1 complex. Subsequent assays confirmed increased expression of Nrf2 and phosphorylated Nrf2, accompanied by upregulation of downstream antioxidant proteins. Pharmacological inhibition of Nrf2 using ML385 or Nrf2-siRNA abolished the protective effects of arbutin, confirming that arbutin alleviates CaOx-induced oxidative injury primarily through activation of the Nrf2 signaling pathway.

Arbutin for Neuroprotection in Lipopolysaccharide-Induced Neuroinflammation

Pouramir A, et al. Neuroscience Letters, 2025, 865, 138356.

Arbutin was evaluated for its neuroprotective activity in a lipopolysaccharide (LPS)-induced mouse model of neuroinflammation. NMRI mice were divided into control, LPS, and arbutin treatment groups (25 and 50 mg/kg). Neuroinflammation was induced by LPS administration, followed by behavioral assessment using the Morris water maze to evaluate spatial learning and memory. Histological examination of hippocampal regions (CA1 and CA3) was conducted to assess neuronal damage, while NeuN immunostaining quantified neuronal survival. Astrocyte activation was evaluated using GFAP immunohistochemistry. Additionally, oxidative stress parameters, including total antioxidant capacity and lipid peroxidation levels, were measured. Arbutin administration significantly reduced escape latency and improved spatial learning performance. Histopathological analyses revealed decreased neuronal damage and reduced astrocyte activation. Biochemical assays further demonstrated enhanced antioxidant capacity and decreased lipid peroxidation. These results indicate that arbutin exerts neuroprotective effects by suppressing oxidative stress and astrocyte-mediated neuroinflammation.

Synthetic Use

Upstream Synthesis Route 1

• 6129-66-4

• 497-76-7

Reference: [1]Bulletin of the Korean Chemical Society,2010,vol. 31,p. 1825 - 1826
[2]Patent: US6339162,2002,B1 .Location in patent: Example 2
[3]Doklady Akademii Nauk SSSR,1952,vol. 86,p. 333
Chem.Abstr.,1953,p. 12262
[4]Patent: CN107216359,2017,A

Upstream Synthesis Route 2

• 380153-99-1

• 497-76-7

Reference: [1]Journal of the Chemical Society,1930,p. 2729,2732