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

SMILES

O(C1C=CC(O)=CC=1)[C@@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O |&1:8,9,10,12,14,r|

CAS DataBase Reference

84380-01-8(CAS DataBase Reference)

Safety Information

WGK Germany 

3

HS Code 

2938.90.0000

alpha-Arbutin Usage And Synthesis

Description

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. It also has antioxidant properties, which protect the skin from potential sun damage. Along with Retinol, it is a fairly common ingredient in anti-ageing products to treat age spots, fine lines and wrinkles.

Chemical Properties

It is a glycosylated hydroquinone molecule, meaning a sugar molecule that has replaced one of the hydroxyl (-OH) groups on hydroquinone. Hydroquinone 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.1,2 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.

Chemical Properties

alpha-Arbutin is White Solid

Uses

α-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.

Uses

alpha-Arbutin is a component used in the skin-whitening cosmetics.

Uses

more stable analog of b-Arbutin

Definition

Alpha arbutin, also called Hydroquinone β-D-glucopyranoside, is a naturally occurring antioxidant and skin brightener that is naturally found in the bearberry plant. It reduces melanin formation, improving the appearance of age spots, freckles, melasma, and post-inflammatory pigmentation.

Definition

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. Arbutin gives quicker results than vitamin C. Arbutin acts as hydroquinone, which means it has depigmenting factors. Vitamin C is not easily absorbed into the skin, whereas arbutin absorbs quickly into the skin.

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.

General Description

α-Arbutin is a glycosylated hydroquinone and an anomer of naturally occurring arbutin. It is a potent inhibitor of tyrosinase, a vital enzyme involved in epidermal melanin biosynthesis. α-Arbutin finds extensive application as a powerful skin-lightening agent in cosmetic industries.

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.

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. It 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. It is suitable for topical use but when it comes in contact with an exposed wound, it causes unbearable irritation.

Synthesis

In a 100 ml reaction flask, add (1.21 g, 2.5 mmol)P-acetoxyphenyl-2,3,4,6-tetra-O-acetyl-|?-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%.

alpha-Arbutin(84380-01-8)Related Product Information

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