A glycosylated hydroquinone with diverse biological activities
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Isomer(s)
26407Arbutin
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α-Arbutin

Item No. 35386

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-hydroxyphenyl α-D-glucopyranoside
CAS Number
84380-01-8
Synonyms
  • Hydroquinone α-Glucoside
  • Hydroquinone O-α-D-Glucopyranoside
  • 4'-Hydroxyphenyl α-Glucoside
  • 4-Hydroxyphenyl α-Glucopyranoside
Molecular Formula
C12H16O7
Formula Weight
272.3
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMSO: 15 mg/mlEthanol: 1 mg/mlPBS (pH 7.2): 5 mg/ml
λmax
224 nm
SMILES
O[C@@H]1[C@@H](O)[C@@H](OC2=CC=C(O)C=C2)O[C@H](CO)[C@H]1O
InChi Code
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-ZIQFBCGOSA-N
Origin
Fermentation (species not specified)
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 g

    $41

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    10 g

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    25 g

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    50 g

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    Product Description

    α-Arbutin is a glycosylated hydroquinone that has been found in Ericaceae and has diverse biological activities.1,2,3,4,5 It inhibits tyrosinase in a cell-free assay (IC50 = 0.48 mM for the mouse enzyme) and the production of melanin in HMV-II melanoma cells when used at a concentration of 0.5 mM.1,2 α-Arbutin (100 µM) prevents increases in reactive oxygen species (ROS) induced by rotenone (Item No. 13995) in SH-SY5Y neuroblastoma cells.3 It decreases locomotor deficits in a parkin-null transgenic Drosophila model of Parkinson’s disease. α-Arbutin (30 mM) reduces postprandial plasma glucose levels in mice.4 It has also been used in the synthesis of α-glucosidase inhibitors.5 Formulations containing α-arbutin have been used in cosmetic products as skin lightening agents.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Funayama, M., Arakawa, H., Yamamoto, R., et al. Effects of α- and β-arbutin on activity of tyrosinases from mushroom and mouse melanoma. Biosci. Biotechnol. Biochem. 59(1), 143-144 (1995).

    2. Sugimoto, K., Nishimura, T., Nomura, K., et al. Inhibitory effects of α-arbutin on melanin synthesis in cultured human melanoma cells and a three-dimensional human skin model. Biol. Pharm. Bull. 27(4), 510-514 (2004).

    3. Ding, Y., Kong, D., Zhou, T., et al. α-Arbutin protects against Parkinson’s disease-associated mitochondrial dysfunction in vitro and in vivo. Neuromolecular Med. 22(1), 56-67 (2020).

    4. Takii, H., Matsumoto, K., Kometani, T., et al. Lowering effect of phenolic glycosides on the rise in postprandial glucose in mice. Biosci. Biotechnol. Biochem. 61(9), 1531-1535 (1997).

    5. Hakamata, W., Yamamoto, E., Muroi, M., et al. Design and synthesis of α-glucosidase inhibitor having DNA cleaving activity. J. Appl. Glycosci. 53(4), 255-260 (2006).