183209-56-5

Basic information

• Product Name: 2-(4-benzyloxyphenyl)ethyl β-D-glucopyranoside
• Synonyms: 2-(4-benzyloxyphenyl)ethyl β-D-glucopyranoside
• CAS NO: 183209-56-5
• Molecular Weight: 390.433
• Mol File: 183209-56-5.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2-(4-benzyloxyphenyl)ethyl β-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-benzyloxyphenyl)ethyl β-D-glucopyranoside(183209-56-5)
• EPA Substance Registry System: 2-(4-benzyloxyphenyl)ethyl β-D-glucopyranoside(183209-56-5)

Safety Data

• Hazardous Substances Data: 183209-56-5(Hazardous Substances Data)

Upstream product

• 100-39-0 benzyl bromide 
• 501-94-0 p-hydroxyphenethyl alcohol 
• 58609-13-5 4-(benzyloxy)phenylacetic acid benzyl ester 
• 156-38-7 4-hydroxyphenylacetate 
• 74808-10-9 O-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl)trichloroacetimidate 
• 61439-59-6 2-(4-benzyloxyphenyl)ethanol 
• 3947-62-4 2,3,4,5-tetra-O-acetyl-D-glucopyranose 
• 83-87-4 D-glucose pentaacetate 
• 916458-79-2 2-(4-benzyloxyphenyl)ethyl-(2,3,4,6-tetra-O-acetyl)-β-D-glucopyranoside 

Downstream Products

• 110344-59-7 2-(4-hydroxyphenyl)ethyl 4-Ο-(E)-Feruloyl-β-D-glucopyranoside 
• 955944-28-2 2-(4-benzyloxyphenyl)ethyl 2,3-di-O-benzyl-β-D-glucopyranoside 
• 955944-29-3 2-(4-benzyloxyphenyl)ethyl 2,3-di-O-benzyl-6-O-[(E)-4-O-benzylferuloyl]-β-D-glucopyranoside 
• 955944-30-6 2-(4-benzyloxyphenyl)ethyl 2,3-di-O-benzyl-4-O-[(E)-4-O-benzylferuloyl]-β-D-glucopyranoside 
• 110978-95-5 2-(4-hydroxyphenyl)ethyl 6-O-(E)-(3-methoxy-4-hydroxy)cinnamoyl β-D-glucopyranoside 
• 10338-51-9 Salidroside 
• 916458-88-3 (4-benzyloxyphenyl)ethyl (2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-(1->3)-2-O-acetyl-4-O-[(E)-3,4-di-O-benzyl]caffeoyl-6-O-tert-butyldimethylsilyl-β-D-glucopyranoside 
• 916458-87-2 (4-benzyloxyphenyl)ethyl (2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-(1->3)-2-O-acetyl-6-O-tert-butyldimethylsilyl-β-D-glucopyranoside 
• 916458-86-1 (4-benzyloxyphenyl)ethyl (2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-(1->3)-2-O-acetyl-β-D-glucopyranoside 

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.

Synthesis, biological activity of salidroside and its analogues

Salidroside is a phenylpropanoid glycoside isolated from Rhodiola rosea L., a traditional Chinese medicinal plant, and has displayed a broad spectrum of pharmacological properties. In this paper, about 18 novel salidroside analogues were prepared through Koenigs-Knorr method, the effects of these compounds over PC12 was assessed with the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) method. The novel compounds differ in the substituents attached to the benzene ring or in the glycosyl donor. According to the data, compounds (3,5-dimethoxyphenyl)methyl β-D-glucopyranoside and (3,5-dimethoxyphenyl) methyl β-D-galactopyranoside with methoxy group at 3 and 5-positions of the benzene ring were the most viability at concentration of 300 μmol/l and 60 μmol/l, respectively.

Synthesis of a benzyl-protected analog of arenarioside, a trisaccharide phenylpropanoid glycoside

A benzyl-protected analog of the phenylpropanoid glycoside arenarioside, (4-benzyloxyphenyl)ethyl α-l-rhamnopyranosyl-(1→3)-4-O-[(E)-3,4-di-O-benzyl-caffeoyl]-[β-d-xylopyranosyl-(1→6)]-β-d-glucopyranoside (22), was synthesized through two different routes from d-glucose. This is the first approach on the synthesis of a trisaccharide phenylpropanoid glycoside, although the benzyl-protecting group in the backbone of the arenarioside analog could not be removed by conventional debenzylation procedures.