31427-08-4

Basic information

• Product Name: 4-Hydroxy-2-methoxyphenyl β-D-glucopyranoside
• Synonyms: 4-Hydroxy-2-methoxyphenyl β-D-glucopyranoside;Isotachioside;4-hydroxy-2-methoxyphenyl 1-O-beta-D-glucopyranoside
• CAS NO: 31427-08-4
• Molecular Formula: C₁₃H₁₈O₈
• Molecular Weight: 302.27722
• Mol File: 31427-08-4.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 579.9±50.0 °C(Predicted)
• Appearance: /
• Density: 1.519±0.06 g/cm3(Predicted)
• PKA: 9.76±0.20(Predicted)
• CAS DataBase Reference: 4-Hydroxy-2-methoxyphenyl β-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Hydroxy-2-methoxyphenyl β-D-glucopyranoside(31427-08-4)
• EPA Substance Registry System: 4-Hydroxy-2-methoxyphenyl β-D-glucopyranoside(31427-08-4)

Safety Data

• Hazardous Substances Data: 31427-08-4(Hazardous Substances Data)

Usage

Definition

ChEBI: A monosaccharide derivative that consists of 2-methoxybenzene-1,4-diol attached to a beta-D-glucopyranosyl residue at position 1 via a glycosidic linkage. It is isolated from Acacia mearnsii.

Upstream product

• 6195-80-8 2,4-bis(benzyloxy)phenol 
• 74808-10-9 O-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl)trichloroacetimidate 
• 251921-28-5 2,4-dihydroxyphenyl-tetra-O-acetyl-β-D-glucopyranoside 
• 251921-27-4 1-O-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)-2,4-dibenzyloxybenzene 
• 824-46-4 methoxyhydroquinone 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 

Downstream Products

• 824-46-4 methoxyhydroquinone 

Relevant articles and documents

Chemical synthesis and tyrosinase-inhibitory activity of isotachioside and its related glycosides

Isotachioside (1) and its related natural product 2 are isolated from Isotachis japonica and Protea neriifolia, respectively, and are categorized as analogs of arbutin (3), a tyrosinase inhibitor for practical use. Both of the natural products and several derivatives such as glucoside 4, xyloside 5, cellobioside 6, and maltoside 7 were synthesized via Schmidt glycosylation as a key step, and their tyrosinase inhibitory activity was evaluated. The half maximal inhibitory concentration (IC50) of 1–3 could not be determined even when the concentration was increased to 1000 μM. Contrastingly, glycosides 4–7, missing methyl and benzoyl groups, acted as tyrosinase inhibitors with IC50s of 417 μM, 852 μM, 623 μM, and 657 μM, respectively. Among these novel inhibitors, derivative 4 was the most potent, indicating that the structural combination of resorcinol and glucose was significant for inducing the inhibitory effect.