| Identification | More | [Name]
Arbutin | [CAS]
497-76-7 | [Synonyms]
4-HYDROXYPHENYL-BETA-D-GLUCOPYRANOSIDE
ARBUTIN
ARBUTOSIDE
B-D-GLUCOPYRANOSIDE, 4-HYDROXYPHENYL
HYDROQUINONE-BETA-D-GLUCOPYRANOSIDE
HYDROQUINONE-BETA-D-GLUCOSIDE
P-ARBUTIN
URSIN
UVASOL
4-hydroxyphenyl-beta-d-glucopyranosid
beta-arbutin
Arbutosie
Arbutus extract
Uresol
ARBUTIN CRYSTALLINE SYNTHETIC
ARBUTIN 98+%
ARBUTIN:B-D-GLUCOPYRANOSIDE, 4-HYDROXYPHENYL,
Hydroquinone glucose
.beta.-D-Glucopyranoside, 4-hydroxyphenyl
4-hydroxyphenyl-á-d-glucopyranoside | [EINECS(EC#)]
207-850-3 | [Molecular Formula]
C12H16O7 | [MDL Number]
MFCD00016915 | [Molecular Weight]
272.25 | [MOL File]
497-76-7.mol |
| Chemical Properties | Back Directory | [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
| [form ]
neat | [pka]
10.10±0.15(Predicted) | [color ]
White | [Stability:]
Stable. Hygroscopic-store under dry nitrogen. | [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 | [InChIKey]
BJRNKVDFDLYUGJ-RMPHRYRLSA-N | [LogP]
-1.350 | [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. | [CAS DataBase Reference]
497-76-7(CAS DataBase Reference) | [EPA Substance Registry System]
497-76-7(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [RTECS ]
CE8863000
| [F ]
3-10-23 | [HS Code ]
29389000 | [Hazardous Substances Data]
497-76-7(Hazardous Substances Data) |
| Hazard Information | Back Directory | [Description]
Arbutin is a hydroquinone compound derived from houyeyanbaicai 厚叶岩白菜 (Bergenia crassifolia (L.) Fritsch.). It is also distributed in wufanshu (Vaccinium bracteatum Thunb.), and xiongguo (bearberry), Pear tree, jishutiao (Viburnum opulus Linn. var.calvescens (Rehd.) Hara f. calvescens), xingxiangtuerfeng (Ainsliaea fragrans Champ.), heiguoxianleihuaqiu (Aronia melanocarpa), nvzhen (Ligustrum lucidum Ait.), juanbai (Selaginella tamariscina (Beauv.) Spring), maodadingcao (Gerbera piloselloides (L.) Cass), payanhong (Veronicastrum axillare (Sieb. and Zucc.) Yamazaki), and yueju (Vaccinium vitis-idaea Linn.) also contain this compound . In addition, it can be obtained from biotransformation, enzyme synthesis, and organic synthesis . | [Chemical Properties]
Crystalline powder | [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. | [Definition]
ChEBI: A monosaccharide derivative that is hydroquinone attached to a beta-D-glucopyranosyl residue at position 4 via a glycosidic linkage. | [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.] |
| Questions And Answer | Back Directory | [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. |
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