Salidroside

Base Information

• Chemical Name: Salidroside
• CAS No.: 10338-51-9
• Molecular Formula: C14H20O7
• Molecular Weight: 300.309
• Hs Code.: 29389090
• European Community (EC) Number: 695-621-2
• NSC Number: 741643
• UNII: M983H6N1S9
• DSSTox Substance ID: DTXSID4049034
• Nikkaji Number: J15.618C
• Wikipedia: Salidroside
• Wikidata: Q7404463
• Pharos Ligand ID: 3R4HFSJ558W6
• Metabolomics Workbench ID: 49888
• ChEMBL ID: CHEMBL465208
• Mol file: 10338-51-9.mol

Synonyms:Rhodiola roseal.P.E;b-D-Glucopyranoside, 2-(4-hydroxyphenyl)ethyl;Glucopyranoside,p-hydroxyphenethyl (7CI);Salidroside (8CI);2-(4-Hydroxyphenyl)ethyl-b-D-glucopyranoside;4-Hydroxy-phenyl-2-ethyl-b-D-glucopyranoside;Rhodioloside;Rhodosin;Tyrosol a-(b-D-glucopyranoside);

Chemical Property of Salidroside

Chemical Property:

• Appearance/Colour: Red-brown fine powder
• Vapor Pressure: 6.54E-13mmHg at 25°C
• Melting Point: 159～160℃
• Refractive Index: 1.628
• Boiling Point: 549.5 °C at 760 mmHg
• PKA: 9.98±0.15(Predicted)
• Flash Point: 286.2 °C
• PSA: 119.61000
• Density: 1.46 g/cm³
• LogP: -1.24880
• Storage Temp.: ?20°C
• Solubility.: Methanol (Slightly), Pyridine (Slightly)
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 300.12090297
• Heavy Atom Count: 21
• Complexity: 306

Purity/Quality:

Salidroside 3-5%, Rosavins 3-5%, Rosavin 2% up ^*data from raw suppliers

Salidroside ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=CC=C1CCOC2C(C(C(C(O2)CO)O)O)O)O
• Isomeric SMILES: C1=CC(=CC=C1CCO[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)O
• General Description: Salidroside, a phenylpropanoid glycoside with neuroprotective properties, was referenced in this study as a benchmark compound for evaluating the efficacy of newly synthesized aralkyl alcoholic 2-acetamido-2-deoxy-β-D-pyranosides. While salidroside itself demonstrated protective effects against hypoglycemia and serum limitation-induced apoptosis in PC12 cells, the study highlighted that certain synthesized derivatives (e.g., compounds 4g and 4h) outperformed salidroside in attenuating cell viability loss, reducing apoptotic cell death, modulating apoptosis-related genes, and restoring mitochondrial membrane potential. These findings suggest that while salidroside remains a viable neuroprotective agent, optimized derivatives may offer superior therapeutic potential for ischemic stroke and neurodegenerative diseases.

Technology Process of Salidroside

There total 45 articles about Salidroside which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

tetraacetyl salidroside (28251-63-0) → Salidroside (10338-51-9)

Guidance literature:

With methanol; potassium carbonate;

DOI:10.1016/S0040-4020(01)89229-2

Reference yield: 97.7%

(2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(4-acetoxyphenethoxy)tetrahydro-2Hpyran-3,4,5-triyl triacetate (39032-08-1) → Salidroside (10338-51-9)

Guidance literature:

With sodium methylate; In methanol; for 1h; Ambient temperature;

DOI:10.1248/cpb.46.581

Reference yield: 94.9%

β-D-glucose (492-61-5) + p-hydroxyphenethyl alcohol (501-94-0) → Salidroside (10338-51-9)

Guidance literature:

With E_.coli (BLPad-StyAB-RostyC-SlPAR₁-UGT₈₅A₁); In aq. phosphate buffer; at 37 ℃; for 12h; pH=7.0; Reagent/catalyst; Enzymatic reaction;

DOI:10.1039/d0gc03595e

upstream raw materials:

methanol

cornoside

tetraacetyl salidroside

p-hydroxyphenethyl alcohol 1-O-β-D-(6''-O-galloyl)-glucopyranoside

Downstream raw materials:

cornoside

4-hydroxy-4-(2-hydroxyethyl)cyclohexanone

rengyoside A

(2R,3R,4S,5S,6R)-2-[2-(1-Hydroxy-4,4-dimethoxy-cyclohexyl)-ethoxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

Refernces

Synthesis and protective effects of aralkyl alcoholic 2-acetamido-2-deoxy- β-d-pyranosides on hypoglycemia and serum limitation induced apoptosis in PC12 cell

10.1016/j.bmc.2011.07.031

The study investigates the synthesis and neuroprotective effects of a series of novel aralkyl alcoholic 2-acetamido-2-deoxy-b-D-pyranosides on PC12 cells. The researchers aimed to improve neuroprotective effects for ischemic stroke treatment by synthesizing these compounds and testing their protective activities against hypoglycemia and serum limitation-induced cell death in rat pheochromocytoma cells (PC12 cells). The chemicals involved include salidroside, a phenylpropanoid glycoside known for its neuroprotective properties, and various aralkyl alcohols coupled with N-acetylglucosamine to form the target compounds. The study found that most of the synthesized compounds exhibited strong neuroprotective effects, with compounds 4g and 4h showing superior potency to salidroside. These compounds significantly attenuated cell viability loss and apoptotic cell death in PC12 cells, modulated apoptosis-related gene expression, and restored mitochondrial membrane potential, suggesting their potential as new neuroprotective agents for treating cerebral ischemic stroke and neurodegenerative diseases.