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ALPHA-ARBUTIN

Alpha-Arbutin, is a glycosylated hydroquinone, and an anomer of the naturally occurring arbutin. 
Alpha-Arbutin is used in the cosmetic and pharmaceutical industries for its skin lightening effects, treatment of hyperpigmentation, and as a safer alternative to hydroquinone.
Alpha-Arbutin is a water-based serum specifically designed to even skin tone and minimize the appearance of dark spots. 

CAS:    84380-01-8
MF:    C12H16O7
MW:    272.25
EINECS:    209-795-0

Synonyms
Alpha Arbutin Powder;4-hydroquinone-alpha-d-glucopyranoside;alpha-arbutin;a-Arbutin;Hydroquinone O-α-D-Glucopyranoside;4-Hydroxyphenyl a-D-glucopyranoside;(2R,3S,4S,5R,6S)-2-(HYDROXYMETHYL)-6-(4-HYDROXYPHENOXY)TETRAHYDROPYRAN-3,4,5-TRIOL;4-;hydroxyphenyl alpha-D-glucopyranoside;alpha-Arbutin;84380-01-8;4-Hydroxyphenyl a-D-glucopyranoside;alpha arbutin;a-Arbutin;4-hydroxyphenyl alpha-D-glucopyranoside;(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-(4-hydroxyphenoxy)oxane-3,4,5-triol;UNII-72VUP07IT5;72VUP07IT5;ORISTAR AAT;a-D-Glucopyranoside, 4-hydroxyphenyl;alpha-D-Glucopyranoside, 4-hydroxyphenyl;CHEBI:29710;DTXSID20233358;(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-(4-hydroxyphenoxy)tetrahydro-2H-pyran-3,4,5-triol;MFCD09838262;AC1L4KBI;Alpha Arbutine;Alfa Arbutina;I+/--Arbutin;4-Hydroxyphenyl-alpha-D-glucopyranoside;PubChem16460;.ALPHA.-ARBUTIN;|A-Arbutin (Standard);SCHEMBL435261;CHEMBL226495;ALPHA-ARBUTIN [WHO-DD];Derma Pella Intimate Brightening;f inverted question mark-Arbutin;HY-N3002R;DTXCID20155849;BJRNKVDFDLYUGJ-ZIQFBCGOSA-N;alpha-Arbutin, analytical standard;HY-N3002;s5112;AKOS015905235
;CCG-267174;DB14109;(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-(4-hydroxyphenoxy)tetrahydropyran-3,4,5-triol;1ST40211;AC-34884;AS-15466;A3284;CS-0022901
;NS00120412;P-HYDROXYPHENYL-alpha-D-GLUCOPYRANOSIDE;EN300-7406351;P-HYDROXYPHENYL-.ALPHA.-D-GLUCOPYRANOSIDE;4-HYDROXYPHENYL-.ALPHA.-D-GLUCOPYRANOSIDE;W-203913;Q27110235

This dark spot correcting serum combines a potent concentration of purified alpha arbutin, a well-known skin brightening ingredient, with hyaluronic acid.
This high-strength formula offers effective results yet is easy to use and well-tolerated. Alpha-Arbutin can be used daily in any regimen to support a more even-looking skin tone and reduce the look of dark spots. 
Alpha-Arbutin also improves overall skin radiance for a brighter-looking complexion.
Alpha-Arbutin is naturally found in plant sources such as Bearberry, Cranberry and Mulberry, which essentially prevents the formation of melanin (the pigment that creates skin colour). 
The chemically synthesised version of this plant extract is known as Alpha-Arbutin which is used as a topical skin brightening agent to treat sun spots, pigmentation and scars caused by sun damage and breakouts. 
Alpha-Arbutin also has antioxidant properties, which protect the skin from potential sun damage. 
Along with Retinol, Alpha-Arbutin is a fairly common ingredient in anti-ageing products to treat age spots, fine lines and wrinkles.

Alpha arbutin, also called Hydroquinone β-D-glucopyranoside, is a naturally occurring antioxidant and skin brightener that is naturally found in the bearberry plant. 
Alpha-Arbutin reduces melanin formation, improving the appearance of age spots, freckles, melasma, and post-inflammatory pigmentation.
Alpha-Arbutin is the best as compared to vitamin c because it has fewer side effects and more benefits like reducing dark spots, age spots, ageing, etc. 
Alpha-Arbutin gives quicker results than vitamin C. 
Alpha-Arbutin acts as hydroquinone, which means it has depigmenting factors. 
Alpha-Arbutin is not easily absorbed into the skin, whereas arbutin absorbs quickly into the skin.

Alpha-Arbutin is a glycosylated hydroquinone and an anomer of naturally occurring arbutin. 
Alpha-Arbutin is a potent inhibitor of tyrosinase, a vital enzyme involved in epidermal melanin biosynthesis. 
Alpha-Arbutin finds extensive application as a powerful skin-lightening agent in cosmetic industries.
Arbutin or alpha-arbutin is a natural product. 
Alpha-Arbutin is a hydroquinone glucoside with antioxidant properties. 
Alpha-Arbutin is widely used in cosmetics as depigmenting agent, acting as an inhibitor of tyrosinase in melanocytes. 
Alpha-Arbutin acts by supressing the enzymes that stimulate these melanocytes without killing or fully inhibiting them. 
As a consequence, melanin production is decreased to avoid hyperpigmentation that might be caused by an excess of UV radiation or a higher activity of tyrosinases.

Alpha-Arbutin is a plant-derived or synthetic ingredient that helps to brighten, fade discolorations, protect skin from oxidative stress and promote a more even skin tone. 
Alpha-Arbutin is made from hydroquinone and the alpha form of the sugar molecule, glucose.
Its mechanism of action on skin isn’t fully understood; however, Alpha-Arbutin’s believed to work by interrupting or limiting the ability of an enzyme in skin (known as tyrosinase) from making too much melanin. 
This in turn helps reduce the size and appearance of surface discolorations. 
As an antioxidant, Alpha-Arbutin can help neutralize skin-damaging free radicals and also help boost skin’s natural antioxidant defenses.
Alpha-Arbutin was once thought that alpha-arbutin works because it breaks down to hydroquinone on skin, but now we know that the amount of hydroquinone produced from alpha-arbutin is likely too low to play a role in its discoloration-fading benefits. 
Interestingly, Alpha-Arbutin seems microorganisms on skin’s surface and/or exposure to UV light are the triggers that release some of the hydroquinone used to create alpha-arbutin.

Alpha-Arbutin, also called Hydroquinone β-D-glucopyranoside, is a naturally occurring antioxidant and skin brightener that is naturally found in the bearberry plant. 
Alpha-Arbutin reduces melanin formation, improving the appearance of age spots, freckles, melasma, and post-inflammatory pigmentation. 
Alpha-Arbutin is a glycosylated hydroquinone molecule, meaning a sugar molecule that has replaced one of the hydroxyl (-OH) groups on hydroquinone. 
Alpha-Arbutin is seen as the gold standard of skin lightening, but there are concerns surrounding this well-studied tyrosinase inhibitor, such as skin sensitization, melanocytotoxicity from oxidative byproducts, and exogenous ochronosis (blue-black splotchy pigmentation) as a result of long-term application.
Alpha-Arbutin is a more tolerable alternative to hydroquinone and is sometimes referred to as “natural hydroquinone.” 
Alpha-Arbutin functions similarly to hydroquinone, due to its molecular structure, but with reduced irritation and melanocytotoxicity. 
Alpha-Arbutin does not pose a risk in regards to exogenous ochronosis and poses minimal irritation and sensitization risk, making it a more tolerable alternative to hydroquinone.

Biological Functions    
Alpha-Arbutin acts as a tyrosinase competitive inhibitor and also slows melanosome maturation (the organelles that synthesize and store melanin or pigment).
Alpha-Arbutin is significant because it works on two different mechanisms of pigmentation. 
Alpha-Arbutin 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). 
Alpha-Arbutin has similar results in brightening skin but without the dangerous bleaching process. 
Instead, Alpha-Arbutin 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 Alpha-Arbutin both prevents and treats pigmentation issues.

Alpha-Arbutin's mechanism of action as a skin lightening agent is primarily through the competitive enzymatic inhibition of tyrosinase, leading to a decrease in melanin production without affecting the mRNA gene expression of tyrosinase. 
Alpha-Arbutin is more potent an inhibitor of tyrosinase than arbutin.
Alpha-Arbutin directly inhibits the enzymatic activity of tyrosinase, which is essential for melanin synthesis. 
Tyrosinase catalyzes the first two steps in melanin production: the hydroxylation of tyrosine to l-DOPA and the oxidation of l-DOPA to dopaquinone.
By inhibiting tyrosinase, Alpha-Arbutin reduces the formation of melanin in melanocytes.

Alpha-Arbutin does not affect the gene expression of tyrosinase mRNA. 
This means that while α-arbutin inhibits the activity of the tyrosinase enzyme, Alpha-Arbutin does not decrease the enzyme's production at the genetic level.
This reduction in melanin leads to lighter skin tones and can help in the treatment of hyperpigmentation disorders. 
The efficacy of α-arbutin in reducing melanin synthesis was demonstrated in cultured human melanoma cells and a three-dimensional human skin model, where Alpha-Arbutin effectively reduced melanin synthesis.

Alpha-Arbutin Chemical Properties
Melting point: 195-196°C
Boiling point: 561.6±50.0 °C(Predicted)
Density: 1.556±0.06 g/cm3(Predicted)
Storage temp.: 2-8°C
Solubility: DMSO (Slightly), Methanol (Slightly)
Form: Solid
pka: 10.10±0.15(Predicted)
Color: White to Off-White
BRN: 89675
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+/s3
InChIKey: BJRNKVDFDLYUGJ-ZIQFBCGOSA-N
CAS DataBase Reference: 84380-01-8(CAS DataBase Reference)

Alpha-Arbutin is a glycosylated hydroquinone molecule, meaning a sugar molecule that has replaced one of the hydroxyl (-OH) groups on hydroquinone. 
Alpha-Arbutin is seen as the gold standard of skin lightening, but there are concerns surrounding this well-studied tyrosinase inhibitor, such as skin sensitization, melanocytotoxicity from oxidative byproducts, and exogenous ochronosis (blue-black splotchy pigmentation) as a result of long-term application.
Alpha-Arbutin is a more tolerable alternative to hydroquinone and is sometimes referred to as “natural hydroquinone.” 

Alpha-Arbutin functions similarly to hydroquinone, due to its molecular structure, but with reduced irritation and melanocytotoxicity. 
Alpha-Arbutin does not pose a risk in regards to exogenous ochronosis and poses minimal irritation and sensitization risk, making it a more tolerable alternative to hydroquinone.
Alpha-Arbutin is a synthetic substance that can be produced by enzymatic glycosylation of hydroquinone in the presence of α-amylase and dextrin. 
In one example, this has been done in recombinant Escherichia coli, using amylase of Bacillus subtilis and sucrose phosphorylase of Leuconostoc mesenteroides.
Structurally Alpha-Arbutin is the α-anomer of arbutin (β-arbutin), and like the β-form it is an enzyme inhibitor of human tyrosinase.

Uses    
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.
Alpha-Arbutin is a component used in the skin-whitening cosmetics.
Alpha-Arbutin is used in the cosmetic and pharmaceutical industries for its skin lightening effects, treatment of hyperpigmentation, and as a possibly safer alternative to hydroquinone. 
Alpha-Arbutin may also possess antioxidant properties, which can protect the skin from free radical damage.
Alpha-Arbutin is used in products aimed at fading solar lentigo, freckles, melasma, and other forms of hyperpigmentation where excess melanin is a concern, providing a more even skin complexion.
For Alpha-Arbutin, concentrations of up to 2% α-arbutin are found in face creams and serums and 0.5% in body creams.

Alpha-Arbutin showed a significant reduction in melanin synthesis in cultured human melanoma cells and a three-dimensional human skin model, with melanin synthesis reduced to 40% of the control, indicating its potency as a skin lightening agent without affecting cell viability.

Side effects    
Alpha-Arbutin is an active compound. 
Using too many active agents together can cause harshness to your skin.
For sensitive skin, using too much product containing Alpha-Arbutin can cause a burning sensation on your face or skin.
Using moisturisers just after applying alpha arbutin cream or gel may not work well on your skin. 
Alpha-Arbutin is a light compound which does not absorb well into the skin if topped over a moisturiser.
Alpha-Arbutin side effects occur when applied on cracked skin. 
Alpha-Arbutin is suitable for topical use but when it comes in contact with an exposed wound, it causes unbearable irritation.

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