Cosmetic raw material with whitening effect——Arbutin

arbutin powder

What is Arbutin

 Arbutin, auch bekannt als Arbutin, hat die chemische Bezeichnung 4-Hydroxyphenyl-D-glucopyranosid und eine relative Molekularmasse von 272,25. Es ist ein natürlich vorkommendes Glykosid, das aus grünen Pflanzen gewonnen wird und Bestandteil vieler resistenter gefriergetrockneter Pflanzen wie Weizen, Birnen und Bärentrauben aus der Familie der Rhododendrongewächse ist, die reich an gelösten Stoffen sind. Sie erscheinen als weiße, nadelförmige Kristalle oder Pulver. Sie sind leicht löslich in heißem Wasser, Methanol, Ethanol, Propylenglykol und Glycerin und unlöslich in Ether, Chloroform und Petroleum. Lösungsmittel wie Ether.

 Arbutin can be divided into α-type and β-type according to different structures.  The chemical name of α-arbutin is 4-hydroxyphenyl-α-D-glucopyranoside, and the chemical name of β-arbutin is 4-hydroxyphenyl-β-D-glucopyranoside.  α-Arbutin is the epimer of β-arbutin, and the direction of its glycosidic bond in space is opposite to that of β-arbutin (see figure for details)

α arbutin β arbutin

The whitening mechanism of arbutin

 Der Gehalt und die Verteilung von Melanin sind die wichtigsten Faktoren, die die Tiefe der Hautfarbe bestimmen. Melanin wird in Melanozyten in der Basalschicht der Epidermis der Haut gebildet. Es wird schließlich aus Tyrosin unter der Einwirkung von Tyrosinase durch eine Reihe komplexer biochemischer Reaktionen gebildet. Es wird von der Basalschicht über Synapsen von innen nach außen auf die äußere Schicht der Epidermis übertragen. Färben Sie die Haut.

 Tyrosinase hat eine Tyrosin-Hydroxylase-Aktivität (katalysiert Tyrosin zur Herstellung von Dopa) und eine Dopa-Oxidase-Aktivität (katalysiert Dopa zur Herstellung von Dopaquinon). Im Prozess der Melaninbildung ist sie das wichtigste geschwindigkeitsbeschränkende Enzym. Seine Aktivität bestimmt die Menge des gebildeten Melanins.

 Arbutin ist ein Tyrosinase-Inhibitor, der die Tyrosinase-Aktivität wirksam hemmen kann, ohne die Konzentration der Zellproliferation zu beeinträchtigen. Es konkurriert um die Bindung von Dopa durch seine direkte Bindung an die Tyrosinase. Site, blockiert die Synthese von Dopa und Dopaquinon, wodurch mit Melanozyten stören und hemmt die Produktion von Melanin. Gleichzeitig hat es auch die Funktion, gebildetes Melanin zu verdünnen, den Abbau und die Ausscheidung von Melanin zu beschleunigen, die Pigmentierung der Haut zu verringern und Flecken und Sommersprossen zu entfernen.

Preparation method of Arbutin

natural plant extraction method

 This method mainly uses plant leaves of the genus Ursi as raw materials, and uses organic solvent extraction, extraction, column chromatography and other separation and purification methods to obtain arbutin extract. As early as 1930, it was reported that arbutin is contained in the leaves of rock cabbage. Subsequent studies have confirmed that arbutin is also found in the leaves of black rice tree, bilberry, bearberry and pear tree. glycosides.

 Since the content of arbutin in plants is very low, the extraction process is relatively complex, and the purity of the extract is not high, so with the development of other preparation methods, the plant extraction method has gradually lost its competitive advantage.

plant tissue culture

 The plant tissue culture method utilizes the glycosylation ability of plant cells to convert hydroquinone into arbutin. Compared with plant extraction methods, the efficiency of obtaining arbutin using plant tissue culture methods is much higher. When applying this method, selecting an efficient plant tissue culture medium and determining appropriate culture conditions are key.

 The raw materials used in the plant tissue culture method are clean, the conversion rate is high, and the production is pollution-free. However, the production cycle is long, the separation and purification is complicated, and the industrial development is relatively immature. Further understanding the growth mechanism of plant cells, clarifying the key influencing factors of the synthesis process, shortening the production cycle, and improving yield are the key issues that need to be solved in the application of this method.

enzyme synthesis method

 The enzyme synthesis method mainly uses glycosyltransferase or glycosidase as a catalyst to catalyze glycosyl transfer and reverse hydrolysis reactions to synthesize glycosides, that is, arbutin is obtained from hydroquinone and glucose under the catalysis of glycosidase.

 The enzyme synthesis method has a simple process, high synthesis efficiency, and very optimistic development prospects. With in-depth research on this method in recent years, more and more suitable zymogens have been discovered, and the synthesis rate of arbutin is also getting higher and higher. It is believed that this method will be one of the main research directions for the synthesis of arbutin in the future. one.

chemical synthesis

 Generally, chemical synthesis of arbutin uses glucose and hydroquinone as raw materials. After the two are appropriately protected, they undergo a glycosidation reaction and then remove the protecting group. The chemical synthesis method has become the most important method for preparing arbutin due to its advantages of better synthetic product quality and lower production cost, and has achieved industrial production at home and abroad.

 At present, in China, anhydrous glucose is generally used as raw material, and β-arbutin is produced through acylation protection, catalytic condensation, and alkaline hydrolysis. With the continuous development of synthesis technology, in recent years, the steps for domestic synthesis of arbutin have been gradually simplified, the synthesis rate has been continuously improved, and the quality has reached the international advanced level. However, due to the poor stereoselectivity of the product in chemical synthesis, more in-depth research is still needed to find an efficient and specific chemical synthesis method for preparing α-arbutin.

() ()