| Identification | More | [Name]
alpha-Arbutin | [CAS]
84380-01-8 | [Synonyms]
4-hydroquinone-alpha-d-glucopyranoside
alpha-arbutin | [EINECS(EC#)]
209-795-0 | [Molecular Formula]
C12H17O7 | [MDL Number]
MFCD09838262 | [Molecular Weight]
273.259 | [MOL File]
84380-01-8.mol |
| Chemical Properties | Back Directory | [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) |
| Hazard Information | Back Directory | [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]
alpha-Arbutin is White Solid
| [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. | [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%. |
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