4-Hydroxyphenyl-β-D-glucopyranosid
beta-arbutin · β-Arbutin · URSIN · b-Arbutin · UVASOL · rbutin · P-ARBUTIN · hydroquinone O-β-D-glucopyranoside
Identifikatoren & physikalische Daten
| CAS No. | 497-76-7 |
|---|---|
| Summenformel | C12H16O7 |
| Durchschnittliche Molmasse | 272,25 g/mol |
| Monoisotopische Masse | 272,08960285 g/mol |
| SMILES | OCC1OC(Oc2ccc(O)cc2)C(O)C(O)C1O |
| InChIKey | BJRNKVDFDLYUGJ-UHFFFAOYSA-N |
| PubChem CID | 346 |
| ChEMBL | CHEMBL79041 |
| DTXSID | DTXSID20859416 |
| Lokaler Name | 4-Hydroxyphenyl-β-D-glucopyranosid |
Chemische & physikalische Eigenschaften
| XLogP | -0,7 |
|---|---|
| Polarare Oberfläche (TPSA) | 120 |
| H-Brücken-Donoren | 5 |
| H-Brücken-Akzeptoren | 7 |
| Frei drehbare Bindungen | 3 |
| Schwere Atome | 19 |
| Formalladung | 0 |
| Komplexität | 279 |
| Arzneimittel | Pharmaceuticals |
| Kosmetika | AntioxidantSkin conditioning |
| Schmelzpunkt | 195-198 °C |
| Siedepunkt | 375.31°C (rough estimate) |
| Dichte | 1.3582 (rough estimate) |
| Brechungsindex | -65.5 ° (C=4, H2O) |
| Lagerbedingungen | Inert atmosphere,Room Temperature |
| Löslichkeit | H2O: 50 mg/mL hot, clear10-15 g/100 mL at 20 ºC |
| Aggregatzustand | Solid |
| pKa (Säurekonstante) | 10.10±0.15(Predicted) |
| Farbe | White |
| Biologische Quelle | synthetic or plant |
| Merck | 14,773 |
| BRN | 89673 |
| Henry-Konstante | 8.2×1013 mol/(m3Pa) at 25℃, HSDB (2015) |
| Stabilität | Stable. Hygroscopic - store under dry nitrogen. |
| Hauptanwendungen | food and beverages |
| Kosmetik-Inhaltsstoffe Funktionen | ANTIOXIDANTSKIN CONDITIONING - MISCELLANEOUSBLEACHING |
| 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 |
| InChIKey | BJRNKVDFDLYUGJ-RMPHRYRLSA-N |
| SMILES | OC[C@H]1O[C@@H](Oc2ccc(O)cc2)[C@H](O)[C@@H](O)[C@@H]1O |
| LogP (Verteilungskoeffizient) | -1.350 |
| CAS Datenbank | 497-76-7(CAS DataBase Reference) |
| EPA chemische Informationen | .beta.-D-Glucopyranoside, 4-hydroxyphenyl (497-76-7) |
Sicherheit & Vorschriften
| F | 3-10-23 |
|---|---|
| Wassergefährdungsklasse (WGK) | 3 |
| Zollcode | 29389090 |
| RTECS-Nr. | CE8863000 |
| R-Sätze (R) | 20/21/22-36/37/38 |
| Gefahrensymbole | Xn |
| Sicherheitshinweise (S) | 22-24/25-36-26 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrstoffdaten | 497-76-7(Hazardous Substances Data) |
Anwendungen & Verwendung
Beschreibung
Arbutin is a β-D-glucopyranoside HQ derivative and a plant-derived compound found in the dried leaves of several plant species, including blueberry, cranberry, bearberry, and pear trees. It suppresses tyrosinase activity without altering RNA expression.
History
Arbutin is a hydroquinone compound with two epimers, α and β arbutin. The sources of α-arbutin and β-arbutin are completely different. β-arbutin can be prepared by plant extraction, plant cell culture, and artificial synthesis. Arbutin can relieve cough and asthma and has whitening effect. The Japanese cosmetics company Shiseido developed the arbutin as a whitening agent in the 1990s. Arbutin can not only reduce skin freckles, senile plaques, and chloasma but also relieve acne and improve healing after skin burns. Arbutin is the epimer of β-arbutin, and the spatial orientation of their glycosidic bonds is just the opposite. Alpha arbutin is generally prepared by different microbial enzymes. A molecule of glucose and a molecule of hydroquinone combine to form a molecule α-arbutin . Alpha arbutin improves ultraviolet burn scar. α-Arbutin can be used in a variety of skin whitening cosmetics since it is chemically stable.
Verwenden
Arbutin is a glycosylated hydroquinone extracted from bearberry plant. Arbutin is a known inhibitor of tyrosinase, which in turn prevents the formation of melanin. Arbutin is often used as a skin-ligh tening agent in cosmetic products.