알부틴 C화학적 특성, 용도, 생산
개요
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.
화학적 성질
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.
물리적 성질
Appearance: white powder. Solubility: soluble in hot water. Melting point: 198–201?°C
역사
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.
용도
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.
Indications
Arbutin has bactericidal, anti-inflammatory, and whitening effects and is mainly used in whitening cosmetics.
정의
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.
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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