An internal standard for the quantification of arbutin
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Unlabeled Version(s)
26407Arbutin
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Arbutin-d4

Item No. 33289

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(4-hydroxyphenoxy-2,3,5,6-d4)tetrahydro-2H-pyran-3,4,5-triol
Synonyms
  • β-Arbutin-d4
Molecular Formula
C12H12D4O7
Formula Weight
276.3
Purity
≥99% deuterated forms (d1-d4)
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Water: soluble
SMILES
OC[C@H]1O[C@@H](OC2=C([2H])C([2H])=C(O)C([2H])=C2[2H])[C@H](O)[C@@H](O)[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/i1D,2D,3D,4D
InChi Key
BJRNKVDFDLYUGJ-LNJODBDSSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $401

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    Product Description

    Arbutin-d4 is intended for use as an internal standard for the quantification of arbutin (Item No. 26407) by GC- or LC-MS. Arbutin is a glycosylated hydroquinone that has been found in Arctostaphylos plants and has diverse biological activities, including tyrosinase inhibitory, antioxidant, and anti-inflammatory properties.1,2 It inhibits human tyrosinase activity in crude tyrosinase solution isolated from human melanocytes (IC50s = 5.7 and 18.9 mM using L-tyrosine and L-DOPA as substrates, respectively) as well as in intact melanocytes (IC50 = 0.5 mM).3 Arbutin (50 μM) inhibits hemolysis induced by the free radical generator AAPH (Item No. 82235) in sheep erythrocytes and inhibits AAPH-induced decreases in cell viability in cultured human skin fibroblasts when used at concentrations greater than 125 μM.2 In an LPS-induced rat model of acute lung injury, arbutin (50 mg/kg) prevents increases in IL-1β, IL-6, and TNF-α levels in lung tissue and serum.4 Formulations containing arbutin have been used in the treatment of hyperpigmentation disorders.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Seo, D.-H., Jung, J.-H., Lee, J.-E., et al. Biotechnological production of arbutins (α- and β-arbutins), skin-lightening agents, and their derivatives. Appl. Microbiol. Biotechnol. 95(6), 1417-1425 (2012).

    2. Takebayashi, J., Ishii, R., Chen, J., et al. Reassessment of antioxidant activity of arbutin: Multifaceted evaluation using five antioxidant assay systems. Free Radic. Res. 44(4), 473-478 (2010).

    3. Maeda, K., and Fukuda, M. Arbutin: Mechanism of its depigmenting action in human melanocyte culture. J. Pharmacol. Exp. Ther. 276(2), 765-769 (1996).

    4. Ye, J., Guan, M., Lu, Y., et al. Arbutin attenuates LPS-induced lung injury via Sirt1/ Nrf2/ NF-κBp65 pathway. Pulm. Pharmacol. Ther. 54, 53-59 (2019).