α-Arbutin - analytical standard , CAS No.84380-01-8

CAS: 84380-01-8 Cat. No.: A140113 Formula: C₁₂H₁₆O₇ Peso molecolare: 272.25 Numero EC: 440-470-8

GRADE & PURITY Analytical standard

Synonyms

a-Arbutin | 4-hydroxyphenyl-D-lucopyranoside | FS-2928 | DTXSID20233358 | alpha-Arbutoside | f inverted question mark-Arbutin | P-HYDROXYPHENYL-.ALPHA.-D-GLUCOPYRANOSIDE | AC1L4KBI | s5112 | ALPHA-ARBUTIN [INCI] | P-HYDROXYPHENYL-alpha-D-GLUCOPYRANOSIDE |

Storage

Store at 2-8°C

Shipped In

Wet ice

Specifications

Sinonimi

a-Arbutin | 4-hydroxyphenyl-D-lucopyranoside | FS-2928 | DTXSID20233358 | alpha-Arbutoside | f inverted question mark-Arbutin | P-HYDROXYPHENYL-.ALPHA.-D-GLUCOPYRANOSIDE | AC1L4KBI | s5112 | ALPHA-ARBUTIN [INCI] | P-HYDROXYPHENYL-alpha-D-GLUCOPYRANOSIDE |

Specifiche e purezza

analytical standard

Meccanismi biochimici e fisiologici

Glycosylated hydroquinone that inhibits tyrosinase and thus prevents the formation of melanin. Used in the skin-whitening cosmetics.

Condizioni di conservazione di stoccaggio

Store at 2-8°C

Spedito in

Wet ice

Questo prodotto richiede spedizione a catena fredda. I servizi di terra e altri servizi economici non sono disponibili.

Grado

Standard analitico

Tipo di azione

INHIBITOR

Nota

Unstable; make up solutions fresh and use immediately. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Nomi e identificatori

• Sorrisi canonici: C1=CC(=CC=C1O)OC2C(C(C(C(O2)CO)O)O)O
• IUPAC Name: (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-(4-hydroxyphenoxy)oxane-3,4,5-triol
• InChIKey: BJRNKVDFDLYUGJ-ZIQFBCGOSA-N
• INCHI: 1S/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
• Isomeri SMILES: C1=CC(=CC=C1O)O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
• WGK Germania: 3
• Peso molecolare: 272.25
• Reaxy-Rn: 22933063
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=22933063&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Classe Organooxygen compounds
      • Subclass Carbohydrates and carbohydrate conjugates
        • Level5 Glycosyl compounds
          • Level6 Phenolic glycosides

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Classe: Organooxygen compounds
• Subclass: Carbohydrates and carbohydrate conjugates
• Intermediate Tree Nodes: Glycosyl compounds
• Direct Parent: Phenolic glycosides
• Alternative Parents: Hexoses O-glycosyl compounds 4-alkoxyphenols Phenoxy compounds Phenol ethers 1-hydroxy-2-unsubstituted benzenoids Oxanes Secondary alcohols Polyols Oxacyclic compounds Acetals Primary alcohols Hydrocarbon derivatives
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Phenolic glycoside - Hexose monosaccharide - O-glycosyl compound - 4-alkoxyphenol - Phenoxy compound - Phenol ether - 1-hydroxy-2-unsubstituted benzenoid - Phenol - Monocyclic benzene moiety - Monosaccharide - Benzenoid - Oxane - Secondary alcohol - Acetal - Oxacycle - Organoheterocyclic compound - Polyol - Alcohol - Primary alcohol - Hydrocarbon derivative - Aromatic heteromonocyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.
• External Descriptors: glycoside

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Meccanismi d'azione

Proprietà chimiche e fisiche

• Peso molecolare: 272.250 g/mol
• XLogP3: -0.700
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 272.09 Da
• Monoisotopic Mass: 272.09 Da
• Topological Polar Surface Area: 120.000 Ų
• Heavy Atom Count: 19
• Formal Charge: 0
• Complexity: 279.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 5
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Riferimenti

1. Hui-Ting Cao, Tiansheng Zhao, Wei Liu, Cai-Ying Xu, Yi-Jing Liao, Xi-Luan Yan, Xi Mai, Na Li.  (2023)  Smartphone-assisted ratiometric fluorescence sensor for sensitive and portable α-glucosidase activity detection and inhibitor screening.  MICROCHEMICAL JOURNAL,      [PMID:] [10.1016/j.microc.2023.109723]

2. Yi-Chi Chen, Yang-Yang Liu, Liqiang Chen, Dong-Mei Tang, YunLi Zhao, Xiao-Dong Luo.  (2023)  Antimelanogenic Effect of Isoquinoline Alkaloids from Plumula Nelumbinis.  JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY,      [PMID:37856847] [10.1021/acs.jafc.3c03784]

3. Li Jing, Li Ziyi, Gong Hui, Ma Mengyi, Li Shuolei, Yang Huilin, Zhang Hailin, Liu Jianguo.  (2023)  Identification and characterization of a novel high-activity amylosucrase from Salinispirillum sp. LH10-3-1.  APPLIED MICROBIOLOGY AND BIOTECHNOLOGY,  107  (5): (1725-1736).  [PMID:36795143] [10.1007/s00253-023-12430-6]

4. Chunxing Pan, Xiaoying Liu, Yating Zheng, Zejun Zhang, Yongliang Li, Biao Che, Guangrong Liu, Lanyue Zhang, Changzhi Dong, Haji Akber Aisa, Zhiyun Du, Zhengqiang Yuan.  (2022)  The mechanisms of melanogenesis inhibition by glabridin: molecular docking, PKA/MITF and MAPK/MITF pathways.  Food Science and Human Wellness,      [PMID:] [10.1016/j.fshw.2022.07.011]

5. Shi-Wei Zhao, Qian Zhou, Neng-Bing Long, Rui-Feng Zhang.  (2022)  Preparation and characterization of a novel 3D polymer support for the immobilization of cyclodextrin glucanotransferase and efficient biocatalytic synthesis of α-arbutin.  BIOCHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.bej.2022.108519]

6. Peng Shu, Yuan Wang, Lanyue Zhang.  (2024)  The Effect of α-Arbutin on UVB-Induced Damage and Its Underlying Mechanism.  MOLECULES,  29  (9): (1921).  [PMID:38731413] [10.3390/molecules29091921]

7. Xiang-Yi He, Qian-Wen Shen, Chao-Jie Zhu, Shuo Hao, Kai-Yu Tan, Qing Li.  (2025)  Crosstalk-free dual-mode biosensing in a single MOF for α-glucosidase activity monitoring and inhibitor screening.  TALANTA,      [PMID:40795569] [10.1016/j.talanta.2025.128693]