α-Arbutin
alpha-Arbutin
CAS: 84380-01-8
Molecular Formula: C12H16O7
α-Arbutin - Names and Identifiers
| Name | alpha-Arbutin |
| Synonyms | α-Arbutin a-Arbutin alpha-Arbutin alpha-arbutin Alpha Arbutin Powder Hydroquinone O-α-D-Glucopyranoside 4-Hydroxyphenyl a-D-glucopyranoside 4-Hydroquinone-alpha-D-glucopyranoside 4-hydroquinone-alpha-d-glucopyranoside 4-hydroxyphenyl alpha-D-glucopyranoside (2R,3S,4S,5R,6S)-2-(HYDROXYMETHYL)-6-(4-HYDROXYPHENOXY)TETRAHYDROPYRAN-3,4,5-TRIOL |
| CAS | 84380-01-8 |
| EINECS | 209-795-0 |
| InChI | InChI=1/C12H16O7/c13-5-8-9(15)10(16)11(17)12(19-8)18-7-3-1-6(14)2-4-7/h1-4,8-17H,5H2/t8-,9-,10+,11-,12+/m1/s1 |
| InChIKey | BJRNKVDFDLYUGJ-ZIQFBCGOSA-N |
α-Arbutin - Physico-chemical Properties
| Molecular Formula | C12H16O7 |
| Molar Mass | 272.25 |
| Density | 1.556±0.06 g/cm3(Predicted) |
| Melting Point | 195-196°C |
| Boling Point | 561.6±50.0 °C(Predicted) |
| Flash Point | 293.4°C |
| Solubility | Soluble in methanol, ethanol, DMSO and other organic solvents |
| Vapor Presure | 1.9E-13mmHg at 25°C |
| Appearance | White crystalline powder |
| Color | White to Off-White |
| BRN | 89675 |
| pKa | 10.10±0.15(Predicted) |
| Storage Condition | 2-8°C |
| Refractive Index | 1.65 |
| MDL | MFCD09838262 |
| Physical and Chemical Properties | Melting point 195-196°C |
α-Arbutin - Risk and Safety
| WGK Germany | 3 |
α-Arbutin - Reference
| Reference Show more | 1. Teng Xinfeng, Li Zhong, Liu Longyuan, et al. Determination of apparent oil-water partition coefficient and dissociation constant of α-arbutin equilibrium solubility [J]. Chinese patent medicine 2016 38(11):2366-2366. 2. Li Xiaoyu, Xia Yuanyuan, Shen Wei, etc. Characterization of Leuconostoc sp. Sucrose phosphorylase and its application in catalytic synthesis of α-arbutin [J]. Journal of Biological Engineering, 202036, no.8, 1546-1555, MEDLINE ISTIC PKU CSCD CA, 2020. 3. Fu Shi Peng, Chen Jianbo. Study on the interaction between α-arbutin and human serum albumin by multi-spectroscopic and molecular docking methods [J]. Spectroscopy and spectral analysis, 2018, 38(011):3489-3494. 4. Li Xiaoyu, Xia Yuanyuan, Shen Wei, Yang Haiquan, Cao Yu, Chen Xianzhong. Characterization of Leuconostoc sp. Sucrose phosphorylase and its application in catalytic synthesis of α-arbutin [J]. Chinese Journal of bioengineering, 2020,36(08):1546-1555. 5. Tang, Xiaoqing, Weixi Cai, and Baojun, Bruce Xu. "Comparison of the chemical profiles and antioxidant and antidiabetic activities of extracts from two Ganoderma species (Agaricomycetes)." International journal of medicinal mushrooms 18.7 (2016).10.1615/IntJ 6. [IF=9.783] Huiping Bi et al."Biosynthesis of a rosavin natural product in Escherichia coli by glycosyltransferase rational design and artificial pathway construction."Metab Eng. 2022 Jan;69:15 7. [IF=2.629] Ding Yaqi et al."α-Arbutin Protects Against Parkinson's Disease-Associated Mitochondrial Dysfunction In Vitro and In Vivo."Neuromol Med. 2020 Mar;22(1):56-67 8. [IF=5.645] Jing Xie et al."Chemical compounds, anti-aging and antibacterial properties of Rosa rugosa Purple branch."Ind Crop Prod. 2022 Jul;181:114814 9. [IF=6.312] Wei Wang et al."Kojic Acid Showed Consistent Inhibitory Activity on Tyrosinase from Mushroom and in Cultured B16F10 Cells Compared with Arbutins."Antioxidants-Basel. 2022 Mar;11(3):502 |
α-Arbutin - Reference Information
| Overview | arbutin is a hydroquinone glycoside compound, chemical name for 4-hydroxyphenyl-d-glucopyranoside (y), exists in bear fruit, bilberry and other plants, is a new non-irritating, non-allergic, natural whitening active substances with strong compatibility. Arbutin has two structural and functional functional groups in its molecular structure: one is a glucose residue; The other is a phenolic hydroxyl group. The physical state of α-arbutin appears as a white to light gray powder, which is more soluble in water and ethanol. |
| efficacy | α-arbutin has a better therapeutic effect on scars caused by UV Burns, has a better anti-inflammatory, repair and whitening effect. Can inhibit the production and deposition of melanin, remove spots and freckles. |
| mechanism of action | The whitening mechanism of α-arbutin directly inhibits tyrosinase activity, thereby reducing the production of melanin, rather than reducing melanin production by inhibiting cell growth or tyrosinase gene expression. As α-Arbutin is a more efficient and safer whitening active substance, many cosmetic companies at home and abroad have adopted α-arbutin instead of β-arbutin as a whitening additive. |
| Application | alpha-Arbutin is a chemical that is similar to arbutin, can inhibit the production and deposition of melanin, remove spots and freckles. The results show that arbutin can inhibit the activity of tyrosinase at relatively low concentration, and its inhibitory effect on tyrosinase is better than that of arbutin. alpha-arbutin can be used as a whitening agent in cosmetics. |
| purification and identification | the sample obtained by the reaction was first extracted with ethyl acetate, then extracted with n-butanol, the samples were collected by evaporation on a rotary evaporator and centrifuged. The supernatant was analyzed by HPLC and compared with the HPLC chromatogram of α-arbutin, whether the sample and α-arbutin have the same retention time is compared, and whether the sample contains α-Arbutin is preliminarily inferred. The product after extraction and purification was identified by positive ion mode of LC-ESI-MS/MS. By comparing the relative molecular mass of α-bear fruit with the relative molecular mass of α-arbutin standard, it can be determined whether the product is α-arbutin. |
| Usage | α-arbutin can inhibit tyrosinase activity at relatively low concentration, its inhibitory effect on tyrosinase is better than that of arbutin |
Last Update：2024-04-09 20:13:35
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