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4-Hydroxyphenyl-β-D-glucopyranosid Produkt Beschreibung

Arbutin Struktur
497-76-7
CAS-Nr.
497-76-7
Bezeichnung:
4-Hydroxyphenyl-β-D-glucopyranosid
Englisch Name:
Arbutin
Synonyma:
URSIN;UVASOL;Uresol;rbutin;ARBUTIN;Arbutyne;P-ARBUTIN;Arbutosie;Ericolin);b-Arbutin
CBNumber:
CB6670456
Summenformel:
C12H16O7
Molgewicht:
272.25
MOL-Datei:
497-76-7.mol

4-Hydroxyphenyl-β-D-glucopyranosid Eigenschaften

Schmelzpunkt:
195-198 °C
alpha 
-64 º (c=3)
Siedepunkt:
375.31°C (rough estimate)
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)
Aggregatzustand
neat
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
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
3-10-23
HS Code  29389090
Giftige Stoffe Daten 497-76-7(Hazardous Substances Data)

4-Hydroxyphenyl-β-D-glucopyranosid 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 hydroquinone compound derived from houyeyanbaicai 厚叶岩白菜 (Bergenia crassifolia (L.) Fritsch.). It is also distributed in wufanshu (Vaccinium bracteatum Thunb.), and xiongguo (bearberry), Pear tree, jishutiao (Viburnum opulus Linn. var.calvescens (Rehd.) Hara f. calvescens), xingxiangtuerfeng (Ainsliaea fragrans Champ.), heiguoxianleihuaqiu (Aronia melanocarpa), nvzhen (Ligustrum lucidum Ait.), juanbai (Selaginella tamariscina (Beauv.) Spring), maodadingcao (Gerbera piloselloides (L.) Cass), payanhong (Veronicastrum axillare (Sieb. and Zucc.) Yamazaki), and yueju (Vaccinium vitis-idaea Linn.) also contain this compound . In addition, it can be obtained from biotransformation, enzyme synthesis, and organic synthesis .

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 (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. 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

Crystalline powder

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

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

tyrosinase inhibitor, depigmentor, antitussive

Verwenden

Antibacterial;Tyrosinase inhibitor

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

veterinary drug

Definition

ChEBI: A monosaccharide derivative that is hydroquinone attached to a beta-D-glucopyranosyl residue at position 4 via a glycosidic linkage.

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 Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


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

Global( 584)Lieferanten
Firmenname Telefon Fax E-Mail Land Produktkatalog Edge Rate
COSMAN CHEMICAL CO., LTD.
+8613761622051
sales@cosmanchem.com China 14 58
Hengshui Haoye Chemical Co.,Ltd.
0318-2102300
hy@chemcoms.com CHINA 224 58
Shaanxi Yikanglong Biotechnology Co., Ltd.
17791478691
yklbiotech@163.com CHINA 297 58
Chongqing Chemdad Co., Ltd
+86-13650506873
sales@chemdad.com CHINA 37282 58
Hefei TNJ Chemical Industry Co.,Ltd.
0551-65418671
0551-65418697 sales@tnjchem.com CHINA 37441 58
Wuhan Monad Medicine Tech Co.,LTD
18771942761 02768782018
sales01@whmonad.com CHINA 1000 58
Baoji Guokang Healthchem co.,ltd
09178656283
cngksw@aliyun.com CHINA 9464 58
Wuhan Shuokang Biological Technology Co.,Ltd
+8615927270571 +86-86-02787366298
tianyi@skbiology.cn CHINA 296 58
Henan DaKen Chemical CO.,LTD.
+86-371-66670886
info@dakenchem.com China 15419 58
Shanghai Bojing Chemical Co.,Ltd.
+86-21-37122233
+86-21-37127788 Candy@bj-chem.com CHINA 497 55

497-76-7(4-Hydroxyphenyl-β-D-glucopyranosid)Verwandte Suche:


  • 4-hydroxyphenyl-beta-d-glucopyranosid
  • beta-arbutin
  • Hydroquinone β-D-glucopyranoside
  • Arbutin (natural)
  • 4-HYDROXYPHENYL-BETA-D-GLUCOPYRANOSIDE
  • 4-(β-D-Glucopyranosyloxy)phenol
  • arbutin,beta-arbutin
  • 4-hydroxyphenyl β-D-galactopyranoside
  • Arbutyne
  • Uva, p-Arbutin
  • Hydroquinone-beta-D-glucoside 4-Hydroxyphenyl beta-D-Glucopyranoside
  • Arbutin (Uva, p-Arbutin)
  • β-D-Glucopyranoside, 4-hydroxyphenyl
  • Arbutin 4-Hydroxyphenyl-beta-D-glucopyranoside
  • Arbutin (p-Arbutin
  • Arbutin - Synthetic origin
  • hydroquinone O-β-D-glucopyranosidee
  • ARBUTIN
  • ARBUTOSIDE
  • B-D-GLUCOPYRANOSIDE, 4-HYDROXYPHENYL
  • HYDROQUINONE-BETA-D-GLUCOPYRANOSIDE
  • HYDROQUINONE-BETA-D-GLUCOSIDE
  • UVASOL
  • URSIN
  • P-ARBUTIN
  • Arbutosie
  • Arbutus extract
  • Uresol
  • Hydroquinone glucose
  • .beta.-D-Glucopyranoside, 4-hydroxyphenyl
  • 4-hydroxyphenyl-á-d-glucopyranoside
  • 4-hydroxyphenyl-β-d-glucopyranoside
  • ARBUTIN,98%(BULK
  • 4-hydroquinone-D-glucopyranoside
  • ARBUTIN CRYSTALLINE SYNTHETIC
  • ARBUTIN 98+%
  • ARBUTIN:B-D-GLUCOPYRANOSIDE, 4-HYDROXYPHENYL,
  • ARACHIDYL STEARATE
  • ARBUTIN (4-HYDROXYPHENYL-β-D-GLUCOPYRANOSIDE)
  • Arbutin (Hydroquinone-glucose
  • Ericolin)
  • 4-Hydroxyphenyl-β-D-glucopyranoside, p-Arbutin, Hydroquinone β-D-glucopyranoside
  • β- Arbutin (Arbutin)
  • 4-Hydroxyphenyl-β-D-glucopyranosidep
  • rbutin
  • Hydroquinone-β-D-glucoside
  • Arbutin、Arbutosie、Ursin、Uresol
  • hydroquinone O-beta-D-glucopyranoside
  • b-Arbutin
  • ARBUTIN 99.5%
  • ARBUTIN - NATURAL ORIGIN
  • β-arbutin 497-76-7
  • Arbutin CRS
  • Arbutin >
  • Arbutin retinoate
  • Natural Beta-Arbutin
  • (3S,4S,5S,6S)-2-(Hydroxymethyl)-6-(4-hydroxyphenoxy)-tetrahydro-2H-pyran-3,4,5-triol
  • Arbutin fandachem
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