Arbutin Chemical Properties

Melting point:

195-198 °C

alpha 

-64 º (c=3)

Boiling point:

375.31°C (rough estimate)

Density 

1.3582 (rough estimate)

refractive index 

-65.5 ° (C=4, H2O)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

H₂O: 50 mg/mL hot, clear

pka

10.10±0.15(Predicted)

form 

Solid

color 

White

optical activity

[α]/D -64.0±2.0°, c = 3 in H2O

Water Solubility 

10-15 g/100 mL at 20 ºC

Sensitive 

Hygroscopic

Merck 

14,773

BRN 

89673

Stability:

Stable. Hygroscopic - store under dry nitrogen.

InChIKey

BJRNKVDFDLYUGJ-RMPHRYRLSA-N

LogP

-1.350

CAS DataBase Reference

497-76-7(CAS DataBase Reference)

EPA Substance Registry System

.beta.-D-Glucopyranoside, 4-hydroxyphenyl (497-76-7)

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22-36/37/38

Safety Statements 

22-24/25-36-26

WGK Germany 

3

RTECS 

CE8863000

F 

3-10-23

HS Code 

29389090

Hazardous Substances Data

497-76-7(Hazardous Substances Data)

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Arbutin Usage And Synthesis

Skin Whitening

Arbutin, which is derived from the leaves of ericaceae plants such as bearberry and bilberry, is a popular ingredient in whitening skin care products. It is a safe and effective whitening agent that can help reduce and eliminate skin freckles, acne, hyperpigmentation, and age spots without causing irritation or other side effects. However, arbutin is susceptible to hydrolysis and should be used in a pH range of 5 to 7 and with appropriate antioxidants such as sodium bisulfate and vitamin E for improved stability and efficacy. In addition to its whitening properties, arbutin also has moisturizing, softening, anti-inflammatory, healing, and anti-dandruff effects.

Ursolic acid vs α- arbutin

Ursolic acid is a triterpene compound naturally found in plants. It has various biological effects, including calming, anti-inflammatory, antibacterial, anti-diabetic, anti-ulcer, and hypoglycemic properties.
Alpha-arbutin is a skin-repairing agent that can improve the transparency of damaged skin caused by UV radiation. It is not easily decomposed by enzymes present on the skin surface and is ten times more effective than beta-arbutin. It can penetrate deeply into the skin, inhibit tyrosinase activity, and prevent melanin production, thereby resulting in brighter, more even-toned skin. 

Photosensitivity

Arbutin can reduce melanin formation by inhibiting the activity of tyrosinase, an enzyme that generates melanin. Its action principle is similar to hydroquinone, a whitening drug. Arbutin concentration above 7% may cause photosensitivity, so 7% is considered a safety critical point. Skincare products have provisions for ingredient concentration, with a maximum 7% concentration for arbutin. This concentration range is safe from light sensitivity, although direct light exposure should still be avoided. When absorbed by the skin, arbutin reacts to light, breaking down into hydroquinone for a whitening effect. Hydroquinone concentration in arbutin skincare is usually less than 20 PPM, which is too low to cause side effects such as skin darkening.

Uses

Diuretic and anti-infective drugs of urinary system. Color photographic developing stabilizer. Whitening, anti-freckle, hair care in cosmetics.

Description

Arbutin is a glycosylated hydroquinone that has been found in Arctostaphylos plants and has diverse biological activities, including tyrosinase inhibitory, antioxidant, and anti-inflammatory properties. It inhibits human tyrosinase activity in crude tyrosinase solution isolated from human melanocytes (IC₅₀s = 5.7 and 18.9 mM using L-tyrosine and L-DOPA as substrates, respectively) as well as in intact melanocytes (IC₅₀ = 0.5 mM). Arbutin (50 μM) inhibits hemolysis induced by the free radical generator AAPH in sheep erythrocytes and inhibits AAPH-induced decreases in cell viability in cultured human skin fibroblasts when used at concentrations greater than 125 μM. In an LPS-induced rat model of acute lung injury, arbutin (50 mg/kg) prevents increases in IL-1β, IL-6, and TNF-α levels in lung tissue and serum. Formulations containing arbutin have been used in the treatment of hyperpigmentation disorders.

Description

Arbutin is a β-D-glucopyranoside HQ derivative and a plant-derived compound found in the dried leaves of several plant species, including blueberry, cranberry, bearberry, and pear trees. It suppresses tyrosinase activity without altering RNA expression.

Chemical Properties

Arbutin is also known as hydroquinone glucoside and has two optical isomers, α and ?, with the latter having biological activity. At room temperature, it appears as a white powder with a slight yellowish tint that is soluble in water, methanol, ethanol, propylene glycol, and glycerin aqueous solutions without precipitation. However, it is insoluble in chloroform, ether, and petroleum ether.

Physical properties

Appearance: white powder. Solubility: soluble in hot water. Melting point: 198–201?°C

History

Arbutin is a hydroquinone compound with two epimers, α and β arbutin. The sources of α-arbutin and β-arbutin are completely different. β-arbutin can be prepared by plant extraction, plant cell culture, and artificial synthesis. Arbutin can relieve cough and asthma and has whitening effect.
The Japanese cosmetics company Shiseido developed the arbutin as a whitening agent in the 1990s. Arbutin can not only reduce skin freckles, senile plaques, and chloasma but also relieve acne and improve healing after skin burns. Arbutin is the epimer of β-arbutin, and the spatial orientation of their glycosidic bonds is just the opposite. Alpha arbutin is generally prepared by different microbial enzymes. A molecule of glucose and a molecule of hydroquinone combine to form a molecule α-arbutin . Alpha arbutin improves ultraviolet burn scar. α-Arbutin can be used in a variety of skin whitening cosmetics since it is chemically stable.

Uses

veterinary drug

Uses

arbutin is used primarily for its anti-oxidant and bleaching properties. Arbutin is the active constituent of bearberry, and found in other plant sources, including wheat. It acts as a tyrosinase inhibitor by converting to hydroquinone, and thus can prevent melanin formation.

Uses

Arbutin is a glycosylated hydroquinone extracted from bearberry plant. Arbutin is a known inhibitor of tyrosinase, which in turn prevents the formation of melanin. Arbutin is often used as a skin-ligh tening agent in cosmetic products.

Uses

Antibacterial; tyrosinase inhibitor, depigmentor, antitussive

Definition

ChEBI: Arbutin also called Hydroquinone O-beta-D-glucopyranoside, is a monosaccharide derivative that is hydroquinone attached to a beta-D-glucopyranosyl residue at position 4 via a glycosidic linkage. It has a role as a plant metabolite and an Escherichia coli metabolite. It is a beta-D-glucoside and a monosaccharide derivative. It is functionally related to a hydroquinone.

Indications

Arbutin has bactericidal, anti-inflammatory, and whitening effects and is mainly used in whitening cosmetics.

Pharmacology

Arbutin could effectively inhibit the activity of tyrosinase in skin cells and block the formation of melanin without affecting cell proliferation . Furthermore, it could accelerate the decomposition and excretion of melanin and thereby reduce skin pigmentation and eliminate freckles. In addition, arbutin shows no toxicity, irritation, sensitization, and other side effects . Alpha arbutin is safer and has a stronger inhibitory effect on tyrosinase. At present the whitening cosmetics market in the developed countries has been almost monopolized by arbutin.

Clinical Use

Arbutin is mainly used in high-level cosmetics and has been formulated into skin cream, freckle cream, and senior pearl cream. Arbutin is a major component of medicine for treating burn and scald, characterized by rapid elimination of pain and swelling and fast healing, leaving no scars. Arbutin can also be used as raw materials for intestinal anti-inflammatory drug, with sterilization, anti-inflammatory effect, and nontoxic side effects.

Purification Methods

The glycoside from Protea exima is purified by recrystallisation from H2O or moist EtOAc (as monohydrate), after chromatography through silica Gel using EtOAc/MeOH. Crystallisation from EtOH/CHCl3 gives crystals m 199-200o with intermediate melting at 164o and resolidifying. The pentaacetate crystallises from EtOH in fine needles with m 145-146o, [] D 20 -28.2o (c 2, Me2CO). [Robinson & Waters J Chem Soc 2729 1930, IR, NMR, MS: Perold et al. J Chem Soc, Perkin Trans 1 239 1979, Beilstein 17/7 V 110.]

Arbutin(497-76-7)Related Product Information

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