Arbutin

• CAS: 497-76-7
• Catalog Number: ACM497767
• 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
• Canonical 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

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