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| 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 |
neat |
| 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 |
| CAS DataBase Reference |
497-76-7(CAS DataBase Reference) |
| EPA Substance Registry System |
.beta.-D-Glucopyranoside, 4-hydroxyphenyl (497-76-7) |
| Provider |
Language |
| SigmaAldrich |
English |
| ALFA |
English |
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| Arbutin Usage And Synthesis |
| 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. |
| 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. |
| 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 (Item No. 82235) 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. |
| 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. |
| 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 |
tyrosinase inhibitor, depigmentor, antitussive |
| Uses |
Antibacterial;Tyrosinase inhibitor |
| 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 |
veterinary drug |
| 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.] |
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| Arbutin Preparation Products And Raw materials |
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China (Mainland)
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