84380-01-8 Usage
Description
Alpha-Arbutin is a naturally occurring compound found in plant sources such as Bearberry, Cranberry, and Mulberry. It is a more stable analog of beta-Arbutin and is chemically synthesized for use as a topical skin brightening agent. Alpha-Arbutin effectively prevents the formation of melanin, the pigment responsible for skin color, and is used to treat sun spots, pigmentation, and scars caused by sun damage and breakouts. Additionally, it possesses antioxidant properties, which protect the skin from potential sun damage. It is commonly used in combination with Retinol in anti-aging products to treat age spots, fine lines, and wrinkles.
Uses
Used in Cosmetics Industry:
Alpha-Arbutin is used as a skin-whitening agent for its ability to reduce melanin production, resulting in a brighter and more even skin tone. It is particularly effective in treating sun spots, pigmentation, and scars caused by sun damage and breakouts.
Used in Skincare Products:
Alpha-Arbutin is used as an active ingredient in anti-aging products, where it works synergistically with Retinol to treat age spots, fine lines, and wrinkles. Its antioxidant properties also help protect the skin from potential sun damage.
Used in Analytical Chemistry:
Alpha-Arbutin may be used as an analytical reference standard for the determination of the analyte in cosmetics by high-performance liquid chromatography with UV detection (HPLC-UV) method. This allows for accurate measurement and quality control of cosmetic products containing Alpha-Arbutin.
benefits
Ensures an even skin tone after only one month;Reduces the degree of skin tanning after UV exposure;Helps to minimize the appearance of liver spots.
Biological Functions
Alpha arbutin acts as a tyrosinase competitive inhibitor and also slows melanosome maturation (the organelles that synthesize and store melanin or pigment).3 This is significant because it works on two different mechanisms of pigmentation. Melanin is derived from the amino acid tyrosine and this conversion is regulated by the enzyme tyrosinase. Alpha arbutin is similar in structure to tyrosine, which fits into tyrosinase, needed for melanogenesis. This means that alpha arbutin is reversibly competing with tyrosine for a spot on the enzyme and not inhibiting cell viability, so therefore is not cytotoxic. By targeting tyrosinase, the rate-limiting enzyme in melanin formation, as well as slowing production of the organelles that produce melanin, alpha arbutin is a potent skin brightening agent.
Mechanism of action
Alpha arbutin is frequently marketed as a safer alternative to hydroquinone (a popular skin-lightening ingredient that has been banned in Europe and Australia). It has similar results in brightening skin but without the dangerous bleaching process. Instead, it reduces skin’s pigment production by suppressing the enzymes that stimulate melanin. This also slows down the process by which UV light causes pigmentation, so it both prevents and treats pigmentation issues.
Synthesis
In a 100 ml reaction flask, add (1.21 g, 2.5 mmol)P-acetoxyphenyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 6,Add 36 ml of anhydrous methanol to dissolve, magnetically stir, add a catalytic amount of 0.06 g of sodium methoxide, react at 25 ° C for 2 hours, add acidic resin to neutralize to system pH = 7,The resin was recovered by filtration, and the filtrate was concentrated to dryness under reduced pressure.Beta-arbutinWhite solid 0.65 g,The yield was 96%.
Check Digit Verification of cas no
The CAS Registry Mumber 84380-01-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 8,4,3,8 and 0 respectively; the second part has 2 digits, 0 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 84380-01:
(7*8)+(6*4)+(5*3)+(4*8)+(3*0)+(2*0)+(1*1)=128
128 % 10 = 8
So 84380-01-8 is a valid CAS Registry Number.
InChI:InChI=1/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
84380-01-8Relevant articles and documents
Chemical synthetic method for beta-arbutin
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Paragraph 0006; 0009; 0013; 0018, (2019/01/08)
The invention provides a chemical synthetic method for beta-arbutin, which includes: 1) performing a reaction to pentaacetyl-beta-D-glucose with a 70% hydrofluoric acid pyridine solution at 10-30 DEGC to obtain tetraacetyl-alpha-fluoroglucose; 2) performing a reaction to the tetraacetyl-alpha-fluoroglucose with p-hydroxyacetophenone in a mixed solvent under catalysis of tetrabutylammonium bromidewith Ca(OH)2 being an accelerant at 20-30 DEG C to prepare p-acetylphenyl-2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside; 3) performing a reaction to the p-acetylphenyl-2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside with 40% peroxyacetic acid in an organic solvent at 5-20 DEG C to obtain p-acetoxylphenyl-2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside; 4) performing a reaction to the p-acetoxylphenyl-2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside at 15-25 DEG C in the presence of anhydrous methanol-sodium methoxide to obtain the beta-arbutin. The method is high in yield, low in cost, gentle in conditions and less in emission of waste liquid, waste gas and waste solids, and is suitable for industrial production.
Enzymatic Glycosylation of Phenolic Antioxidants: Phosphorylase-Mediated Synthesis and Characterization
De Winter, Karel,Dewitte, Griet,Dirks-Hofmeister, Mareike E.,De Laet, Sylvie,Pelantová, Helena,K?en, Vladimír,Desmet, Tom
, p. 10131 - 10139 (2016/02/03)
Although numerous biologically active molecules exist as glycosides in nature, information on the activity, stability, and solubility of glycosylated antioxidants is rather limited to date. In this work, a wide variety of antioxidants were glycosylated using different phosphorylase enzymes. The resulting antioxidant library, containing α/β-glucosides, different regioisomers, cellobiosides, and cellotriosides, was then characterized. Glycosylation was found to significantly increase the solubility and stability of all evaluated compounds. Despite decreased radical-scavenging abilities, most glycosides were identified to be potent antioxidants, outperforming the commonly used 2,6-bis(1,1-dimethylethyl)-4-methylphenol (BHT). Moreover, the point of attachment, the anomeric configuration, and the glycosidic chain length were found to influence the properties of these phenolic glycosides.
Purification, characterization, and gene identification of an α-glucosyl transfer enzyme, a novel type α-glucosidase from Xanthomonas campestris WU-9701
Sato, Toshiyuki,Hasegawa, Nobukazu,Saito, Jun,Umezawa, Satoru,Honda, Yuki,Kino, Kuniki,Kirimura, Kohtaro
experimental part, p. 20 - 27 (2012/09/05)
The α-glucosyl transfer enzyme (XgtA), a novel type α-glucosidase produced by Xanthomonas campestris WU-9701, was purified from the cell-free extract and characterized. The molecular weight of XgtA is estimated to be 57 kDa by SDS-PAGE and 60 kDa by gel filtration, indicating that XgtA is a monomeric enzyme. Kinetic properties of XgtA were determined for α-glucosyl transfer and maltose-hydrolyzing activities using maltose as the α-glucosyl donor, and if necessary, hydroquinone as the acceptor. The Vmax value for α-glucosyl transfer activity was 1.3 × 10-2 (mM/s); this value was 3.9-fold as much as that for maltose-hydrolyzing activity. XgtA neither produced maltooligosaccharides nor hydrolyzed sucrose. The gene encoding XgtA that contained a 1614-bp open reading frame was cloned, identified, and highly expressed in Escherichia coli JM109 as the host. Site-directed mutagenesis identified Asp201, Glu270, and Asp331 as the catalytic sites of XgtA, indicating that XgtA belongs to the glycoside hydrolase family 13.
