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4-Hydroxyphenyl-β-D-glucopyranosid

2-Hydroxymethyl-6-(4-hydroxy-phenoxy)-tetrahydro-pyran-3,4,5-triol

HCID 346
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Grundinformationen

CAS
497-76-7
Standard-SMILES
OCC1OC(Oc2ccc(O)cc2)C(O)C(O)C1O
InChIKey
BJRNKVDFDLYUGJ-UHFFFAOYSA-N
Summenformel
C12H16O7
Durchschnittliche Molmasse
272,25 g/mol
Monoisotopische Masse
272,08960285

Überblick

See also: Arbutin (annotation moved to); Alpha-Arbutin (annotation moved to).

Namen und Bezeichner

Bevorzugter Name
2-Hydroxymethyl-6-(4-hydroxy-phenoxy)-tetrahydro-pyran-3,4,5-triol
IUPAC
2-(hydroxymethyl)-6-(4-hydroxyphenoxy)oxane-3,4,5-triol
Lokaler Name
4-Hydroxyphenyl-β-D-glucopyranosid
Englischer Name
Arbutin
Summenformel
C12H16O7
Molmasse
272.25

Namen und Synonyme

2-Hydroxymethyl-6-(4-hydroxy-phenoxy)-tetrahydro-pyran-3,4,5-triolRefChem:10634364-Hydroxyphenyl hexopyranosidea-ArbutinNSC4036p-Hydroxyphenyl .beta.-D-glucosideHydroquinone .beta.-D-glucopyranosidep-Hydroxyphenyl .beta.-D-glucopyranoside.beta.-D-Glucopyranoside, 4-hydroxyphenyl4-Hydroxyphenyl-beta-D-glucopyranosid2-(hydroxymethyl)-6-(4-hydroxyphenoxy)oxane-3,4,5-triolNSC 4036
Weitere Namen anzeigen
beta-arbutinβ-ArbutinURSINUVASOLrbutinP-ARBUTINhydroquinone O-β-D-glucopyranoside4-HYDROXYPHENYL-BETA-D-GLUCOPYRANOSIDE
b-Arbutins5112.beta.-ArbutinSCHEMBL36352MLS006012040CHEMBL79041hexopyranoside, 4-hydroxyphenylorb1990082

Datenbank-Bezeichner

CAS
497-76-7
PubChem CID
346
DTXSID
DTXSID20859416
ChEMBL
CHEMBL79041

Eigenschaften

Berechnete Struktureigenschaften

XLogP
-0,7
Polarare Oberfläche (TPSA)
120 Ų
H-Brücken-Donoren
5
H-Brücken-Akzeptoren
7
Frei drehbare Bindungen
3
Schwere Atome
19
Formalladung
0
Komplexität
279

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals
CosmeticsAntioxidant; Skin conditioning

Physikochemische Eigenschaften

Schmelzpunkt
195 · 195-198 °C
Siedepunkt
375.31 °C · 375.31°C (rough estimate)
Dichte
1.3582 · 1.3582 (rough estimate)
Brechungsindex
-65.5 ° · -65.5 ° (C=4, H2O)
storage temp.
Inert atmosphere,Room Temperature
Löslichkeit
2 O: · H2O: 50 mg/mL hot, clear
Aggregatzustand
Solid
pka
10.1 · 10.10±0.15(Predicted)
Farbe
White
Biologische Quelle
synthetic or plant
Wasserlöslichkeit
10 · 10-15 g/100 mL at 20 ºC
Merck
14 · 14,773
BRN
89673 · 89673
Henry's Law Constant
8.2 · 8.2×1013 mol/(m3Pa) at 25℃, HSDB (2015)
Stabilität
Stable. Hygroscopic - store under dry nitrogen.
Major Application
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
-1.35 · -1.350
CAS Datenbank
497 · 497-76-7(CAS DataBase Reference)
EPA chemische Informationen
4 · .beta.-D-Glucopyranoside, 4-hydroxyphenyl (497-76-7)

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

Sicherheitsdaten

F
3-10-23
wgk
3
hs_code
29389090
RTECS-Nr.
CE8863000
risk_code
20/21/22-36/37/38
hazard_code
Xn
safety_code
22-24/25-36-26
Speicherklasse
11 - Combustible Solids
Giftige Stoffe Daten
497-76-7(Hazardous Substances Data)

Chemie und Industrie

Verwendung und Herstellung

Use ClassificationCosmetics -> Antioxidant; Skin conditioning
Anwendungen · 3 Einträge

BeschreibungArbutin 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.

HistoryArbutin 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.

VerwendenArbutin 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.

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Ergänzende Hinweise · 1 Eintrag

DefinitionChEBI: Arbutin also called Hydroquinone O-beta-D-glucopyranoside, is a monosaccharide derivative that is hydroquinone attached to a beta-D-glucopyranosyl residue at position 4 via a glycosidic linkage. It has a role as a plant metabolite and an Escherichia coli metabolite. It is a beta-D-glucoside and a monosaccharide derivative. It is functionally related to a hydroquinone.

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