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497-76-7

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Identification

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

Melting point 
195-198 °C

mp 
195-198 °C

Boiling point 
375.31°C (rough estimate)
alpha 
-64 º (c=3)
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)
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
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

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


3-10-23
HS Code 
29389000
Hazardous Substances Data
497-76-7(Hazardous Substances Data)

Hazard Information

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.
Indications
Arbutin has bactericidal, anti-inflammatory, and whitening effects and is mainly used in whitening cosmetics.
Definition
ChEBI: A monosaccharide derivative that is hydroquinone attached to a beta-D-glucopyranosyl residue at position 4 via a glycosidic linkage.
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

The ideal whitening agent of whitening cosmetics
Arbutin is an ideal whitening agent of whitening cosmetics. It is also called the hydroquinone glucoside. There are two kinds of optical isomers, namely α and ß. The ß isomer has biological activity. At room temperature, it is white with pale yellow powder. It is soluble in water, methanol, ethanol, propylene glycol and glycerin aqueous solution, and it has no precipitation after dissolved. It is insoluble in chloroform, ether and petroleum ether, etc. Arbutin is always added in a lot of whitening skin care products. Arbutin is named for that it was founded in ericaceae plants of the genus bearberry leaves. Subsequently, it is also founded in the leaves of ericaceae vaccinium bilberry, rosaceae pyrus sand pear (european pear, small yamanashi), saxifragaceae saxifrage and other plants. It is used as drug and cosmetic additives after extracted.
Arbutin can whiten skin and medicate freckle effectively. It can gradually reduce and eliminate skin freckles, melasma, hyperpigmentation, acne and age spots. It has higher security and no irritating, allergenic and other side effects. It has good compatibility with cosmetics components and ultraviolet irradiation stability. But arbutin is easily hydrolyzed, and it should be used under conditions of PH 5-7. In order to stabilize the performance, it is typically added an appropriate amount of antioxidants such as sodium bisulfate and vitamin E. Then it can get better effect of whitening, freckle, moisturizer, soft, wrinkle removal, anti-inflammatory. Arbutin can be used to eliminate swelling, promote wound healing without leaving scars. Besides, it also can inhibit the generation of dandruff.
Ursolic acid and α- arbutin
Ursolic acid is a kind of triterpene compounds that exists in the natural plant. It has many kinds of biological effects, like calm, anti-inflammatory, antibacterial, anti-diabetic, anti-ulcer and hypoglycaemic. In recent years, it is found that ursolic acid has the effect on resistance to get and promote cancer, and induction to F9 teratoma cell differentiation and anti-angiogenesis. It is likely to be low toxic and efficient new anti-cancer drugs. In addition, ursolic acid has obvious antioxidant function, so it is widely used as pharmaceutical and cosmetic ingredients.
α-Arbutin can repair damaged skin that caused by ultraviolet radiation and regain transparency of skin. It is not easy to be decomposed by the β-glycosidase enzymes on the surface of the skin. Its effect is about 10 times of β-arbutin. It can stay for a long time in every corner of the skin, and protect skin from harm. Melanin is the reason for the formation of skin dull. α-Arbutin can rapidly permeate into deep skin, and inhibit the activity of tyrosinase that exists in the depths of the cuticle of chromoplast. Then it forms a dual effect on the surface of the skin, and inhibits the generation of melanin.
Is it suitable for using during the day?
Arbutin can reduce the formation of melanin through inhibiting the activity of the enzyme tyrosinase, which can generate melanin. The action principle is similar to whitening drugs hydroquinone. But hydroquinone has side effects and need so many precautions. Hydroquinone must be used below the doctor's guidance and monitoring. But there is glucose molecule in the structure of arbutin, which is not in hydroquinone. So its irritation is low. It is free to add arbutin to skin care products, and its concentration limit can be up to 7%. Arbutin reactive molecules can penetrate base layer to lighten spots deeply. It has strong therapeutic effect on hyperpigmentation left over by chloasma, black spot, sun spot, drug allergy. But if its concentration is low, then the effect of persistence will be weakened. So, 5% is the safest and most efficient concentration to lighten spot. When its concentration is 5%, its effect is faster than vitamin C, and more persistent and stable. More important, it won't produce irritating effect on the skin. Arbutin is absorbed by the skin and reduced to hydroquinone, which raises some doubts about the safety of arbutin. They think that arbutin may have a chance to produce side effects similar to hydroquinone. The most commonly heard says that "cosmetics contains arbutin cannot be used during the day, otherwise whitening fails, but more black". In fact, do not worry about that. Tests show that only the concentration of arbutin is more than 7% that it may be photosensitive. So 7% is a safety critical point. The concentration of ingredients added in skin care products has specific provision. The highest concentration is 7%. In this concentration range, arbutin is not enough to produce light sensitivity. But it does not have to be used away from light. When arbutin is absorbed by the skin and deposed by light, it will be reduced to hydroquinone and produce whitening effect. The concentration of hydroquinone in arbutin skin care products is lower than 20 PPM (that is twenty millionths). Hydroquinone won't cause side effects, like skin dark, within the limits of such a low concentration. If just because the skin care products contain arbutin so that we are afraid to use them during the day. That doesn't need unless that the skin care products containing arbutin also are added other maintenance components which need to be away from light. In a word, choose reliable brand of skin care products. Then regardless of what is painted, good sunscreen is necessary during the day.
Uses
Diuretic and anti-infective drugs of urinary system. Color photographic developing stabilizer. Whitening, anti-freckle, hair care in cosmetics.

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