4-Hydroxyphenyl-β-D-glucopyranosid

Bezeichnung:4-Hydroxyphenyl-β-D-glucopyranosid

CAS-Nr497-76-7

Englisch Name:Arbutin

CBNumberCB6670456

SummenformelC12H16O7

Molgewicht272.25

MOL-Datei497-76-7.mol

Synonyma

4-Hydroxyphenyl-β-D-glucopyranosid

4-Hydroxyphenyl-β-D-glucopyranosid physikalisch-chemischer Eigenschaften

Schmelzpunkt	195-198 °C
Siedepunkt	375.31°C (rough estimate)
alpha	-64 º (c=3)
Dichte	1.3582 (rough estimate)
Brechungsindex	-65.5 ° (C=4, H2O)
storage temp.	Inert atmosphere,Room Temperature
Löslichkeit	H₂O: 50 mg/mL hot, clear
pka	10.10±0.15(Predicted)
Farbe	White
Optische Aktivität	[α]/D -64.0±2.0°, c = 3 in H2O
Wasserlöslichkeit	10-15 g/100 mL at 20 ºC
Sensitive	Hygroscopic
Merck	14,773
BRN	89673
Stabilität	Stable. Hygroscopic - store under dry nitrogen.
InChIKey	BJRNKVDFDLYUGJ-RMPHRYRLSA-N
LogP	-1.350
CAS Datenbank	497-76-7(CAS DataBase Reference)
EPA chemische Informationen	.beta.-D-Glucopyranoside, 4-hydroxyphenyl (497-76-7)

Sicherheit

Kennzeichnung gefährlicher	Xn
R-Sätze:	20/21/22-36/37/38
S-Sätze:	22-24/25-36-26
WGK Germany	3
RTECS-Nr.	CE8863000
F	3-10-23
HS Code	29389090
Giftige Stoffe Daten	497-76-7(Hazardous Substances Data)

Gefahreninformationscode (GHS)

Arbutin Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R20/21/22:Gesundheitsschädlich beim Einatmen,Verschlucken und Berührung mit der Haut.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S22:Staub nicht einatmen.
S24/25:Berührung mit den Augen und der Haut vermeiden.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
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.
Beschreibung
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. 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). Arbutin (50 μM) inhibits hemolysis induced by the free radical generator AAPH in sheep erythrocytes and inhibits AAPH-induced decreases in cell viability in cultured human skin fibroblasts when used at concentrations greater than 125 μM. 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. Formulations containing arbutin have been used in the treatment of hyperpigmentation disorders.
Chemische Eigenschaften
Arbutin is also known as hydroquinone glucoside and has two optical isomers, α and ?, with the latter having biological activity. At room temperature, it appears as a white powder with a slight yellowish tint that is soluble in water, methanol, ethanol, propylene glycol, and glycerin aqueous solutions without precipitation. However, it is insoluble in chloroform, ether, and petroleum ether.
Physikalische Eigenschaften
Appearance: white powder. Solubility: soluble in hot water. Melting point: 198–201?°C
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
veterinary drug
Verwenden
arbutin is used primarily for its anti-oxidant and bleaching properties. Arbutin is the active constituent of bearberry, and found in other plant sources, including wheat. It acts as a tyrosinase inhibitor by converting to hydroquinone, and thus can prevent melanin formation.
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.
Verwenden
Antibacterial; tyrosinase inhibitor, depigmentor, antitussive
Definition
ChEBI: 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.
Indications
Arbutin has bactericidal, anti-inflammatory, and whitening effects and is mainly used in whitening cosmetics.
Pharmakologie
Arbutin could effectively inhibit the activity of tyrosinase in skin cells and block the formation of melanin without affecting cell proliferation . Furthermore, it could accelerate the decomposition and excretion of melanin and thereby reduce skin pigmentation and eliminate freckles. In addition, arbutin shows no toxicity, irritation, sensitization, and other side effects . Alpha arbutin is safer and has a stronger inhibitory effect on tyrosinase. At present the whitening cosmetics market in the developed countries has been almost monopolized by arbutin.
Clinical Use
Arbutin is mainly used in high-level cosmetics and has been formulated into skin cream, freckle cream, and senior pearl cream. Arbutin is a major component of medicine for treating burn and scald, characterized by rapid elimination of pain and swelling and fast healing, leaving no scars. Arbutin can also be used as raw materials for intestinal anti-inflammatory drug, with sterilization, anti-inflammatory effect, and nontoxic side effects.
läuterung methode
The glycoside from Protea exima is purified by recrystallisation from H2O or moist EtOAc (as monohydrate), after chromatography through silica Gel using EtOAc/MeOH. Crystallisation from EtOH/CHCl3 gives crystals m 199-200o with intermediate melting at 164o and resolidifying. The pentaacetate crystallises from EtOH in fine needles with m 145-146o, [] D 20 -28.2o (c 2, Me2CO). [Robinson & Waters J Chem Soc 2729 1930, IR, NMR, MS: Perold et al. J Chem Soc, Perkin Trans 1 239 1979, Beilstein 17/7 V 110.]

4-Hydroxyphenyl-β-D-glucopyranosid Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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