14861-16-6

Basic information

• Product Name: PHENYLETHYL-BETA-D-GALACTOSIDE
• Synonyms: PHENYLETHYL BETA-D-GALACTOPYRANOSIDE;PHENYLETHYL-BETA-D-GALACTOSIDE;phenylethyl B-D-galactopyranoside;phenethyl beta-D-galactopyranoside;2-Phenylethyl-B-D-Galactopyran-;2-Phenylethyl-beta-D-galactopyran-;phenylethyl β-d-galactopyranoside;phenylethyl-β-d-galactoside
• CAS NO: 14861-16-6
• Molecular Formula: C₁₄H₂₀O₆
• Molecular Weight: 284.3
• EINECS: 238-931-1
• Mol File: 14861-16-6.mol
• Article Data: 18

Chemical Properties

• Boiling Point: 486.8 °C at 760 mmHg
• Flash Point: 248.2 °C
• Appearance: /
• Density: 1.36 g/cm³
• Vapor Pressure: 2.73E-10mmHg at 25°C
• Refractive Index: 1.6
• Storage Temp.: −20°C
• CAS DataBase Reference: PHENYLETHYL-BETA-D-GALACTOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: PHENYLETHYL-BETA-D-GALACTOSIDE(14861-16-6)
• EPA Substance Registry System: PHENYLETHYL-BETA-D-GALACTOSIDE(14861-16-6)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 14861-16-6(Hazardous Substances Data)

Usage

General Description

Phenylethyl-beta-D-galactoside is a synthetic chemical compound that belongs to the beta-galactosides class and is commonly used in biochemical and molecular biology research. It is a glycosidic derivative of galactose with a phenylethyl group attached to the beta-position. PHENYLETHYL-BETA-D-GALACTOSIDE is frequently employed as a chromogenic substrate for detecting and quantifying beta-galactosidase activity, an important enzyme involved in lactose metabolism. Upon hydrolysis by beta-galactosidase, phenylethyl-beta-D-galactoside produces a visual or fluorescent signal, making it a valuable tool for studying enzyme kinetics, gene expression, and cellular functions. Additionally, phenylethyl-beta-D-galactoside has also been used in the field of carbohydrate chemistry as a building block for synthesizing more complex glycans. Overall, this chemical compound plays a crucial role in various scientific applications related to carbohydrates, enzymes, and biological assays.

InChI:InChI=1/C14H20O6/c15-8-10-11(16)12(17)13(18)14(20-10)19-7-6-9-4-2-1-3-5-9/h1-5,10-18H,6-8H2/t10-,11+,12+,13-,14-/m1/s1

Upstream product

• 2280-44-6 D-Glucose 
• 60-12-8 2-phenylethanol 
• 76870-86-5 2-phenylethanol 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 1464-44-4 phenyl-β-D-glucopyranoside 
• 492-62-6 alpha-D-glucopyranose 
• 103-82-2 phenylacetic acid 
• 1038587-84-6 2-phenylethyl tetra-O-benzoyl-β-D-glucopyranoside 
• 2492-87-7 4-nitrophenyl-β-D-glucoside 
• 492-61-5 β-D-glucose 
• 153-18-4 rutin 
• 83-87-4 D-glucose pentaacetate 
• 56401-20-8 α-D-Glucopyranoside 1-(disodium phosphate) 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 14218-11-2 2,3,4,6-tetra-O-benzoylglucosyl bromide 

Downstream Products

• 18997-55-2 2'-phenylethyl β-D-glucopyranosiduronic acid 
• 1436383-92-4 2-phenylethyl (2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-(1→3)-2-O-acetyl-β-D-glucopyranoside 
• 1436383-91-3 2-phenylethyl (2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-(1→3)-2-O-acetyl-4,6-O-benzylidene-β-D-glucopyranoside 
• 911817-13-5 2-phenylethyl 4,6-O-benzylidene-β-D-glucopyranoside 
• 125572-77-2 2-phenylethyl 1-O-α-L-arabinopyranosyl-(1->6)-β-D-glucopyranoside 
• 88510-13-8 phenylethyl 2,3,4-tri-O-acetyl-6-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-β-D-glucopyranoside 
• 88510-08-1 2-phenylethyl O-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside 
• 132278-39-8 phenethyl 2,3,4,2',3',4'-O-hexaacetyl-β-D-xylopyranosyl-(1->6)-β-D-glucopyranoside 
• 129932-48-5 2-phenylethyl β-primeveroside 
• 860648-10-8 phenethyl 2,3,4,2',3',4'-O-hexaacetyl-α-L-arabinopyranosyl-(1->6)-β-D-glucopyranoside 
• 860648-08-4 phenethyl 2,3,4-tri-O-acetyl-6-O-trityl-β-D-glucopyranoside 
• 860648-09-5 phenethyl 2,3,4-tri-O-acetyl-β-D-glucopyranoside 
• 860648-07-3 phenethyl 6-O-trityl-β-D-glucopyranoside 
• 60-12-8 2-phenylethanol 

Relevant articles and documents

Discovery of Salidroside-Derivated Glycoside Analogues as Novel Angiogenesis Agents to Treat Diabetic Hind Limb Ischemia

Therapeutic angiogenesis is a potential therapeutic strategy for hind limb ischemia (HLI); however, currently, there are no small-molecule drugs capable of inducing it at the clinical level. Activating the hypoxia-inducible factor-1 (HIF-1) pathway in skeletal muscle induces the secretion of angiogenic factors and thus is an attractive therapeutic angiogenesis strategy. Using salidroside, a natural glycosidic compound as a lead, we performed a structure-activity relationship (SAR) study for developing a more effective and druggable angiogenesis agent. We found a novel glycoside scaffold compound (C-30) with better efficacy than salidroside in enhancing the accumulation of the HIF-1α protein and stimulating the paracrine functions of skeletal muscle cells. This in turn significantly increased the angiogenic potential of vascular endothelial and smooth muscle cells and, subsequently, induced the formation of mature, functional blood vessels in diabetic and nondiabetic HLI mice. Together, this study offers a novel, promising small-molecule-based therapeutic strategy for treating HLI.

A Sustainable One-Pot, Two-Enzyme Synthesis of Naturally Occurring Arylalkyl Glucosides

A sustainable, convenient, scalable, one-pot, two-enzyme method for the glucosylation of arylalkyl alcohols was developed. The reaction scheme is based on a transrutinosylation catalyzed by a rutinosidase from A. niger using the cheap commercially available natural flavonoid rutin as glycosyl donor, followed by selective “trimming” of the rutinoside unit catalyzed by a rhamnosidase from A. terreus. The process was validated with the syntheses of several natural bioactive glucosides, which could be isolated in up to 75 % yield without silica-gel chromatography.

Short synthesis of the common trisaccharide core of kankanose and kankanoside isolated from Cistanche tubulosa

A short synthetic approach was developed for the synthesis of a common trisaccharide core found in kankanose, kankanoside F, H1, H 2, and I isolated from the medicinally active plant Cistanche tubulosa. All glycosylations were carried out under nonmetallic reaction conditions. Yields were very good in all intermediate steps.